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KF #38. Optimizes Work Processes Archives - How to be Awesome at Your Job

2025 GREATS: 1010: Getting the Most Out of Generative AI at Work with Jeremy Utley

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Jeremy Utley reveals why many aren’t getting the results they want from AI—and how to fix that.

You’ll Learn

  1. The #1 mistake people are making with AI
  2. ChatGPT’s top advantage over other AI platforms (as of late 2024) 
  3. The simple adjustments that make AI vastly more useful 

About Jeremy 

Jeremy Utley is the director of executive education at Stanford’s d.school and an adjunct professor at Stanford’s School of Engineering. He is the host of the d.school’s widely popular program “Stanford’s Masters of Creativity.” 

Resources Mentioned

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Jeremy Utley Interview Transcript

Pete Mockaitis
Jeremy, welcome.

Jeremy Utley
Thanks for having me.

Pete Mockaitis
I’m so excited to chat, and I’d love it if you could kick us off by sharing one of maybe the most fascinating and surprising discoveries you’ve made about some of this AI stuff with all your poking and prodding and playing.

Jeremy Utley
I’ll poke the bear right from the get-go. My observation is most people are what I call prompt hoarders, which is that they’ve got a bunch of Twitter threads saved, and they’ve got a bunch of PDFs downloaded in a folder, marked, “Read someday,” but they aren’t actually using AI. They’re just hoarding prompts.

And I think of it as empty calories. It’s a sugar high. And what a lot of people are doing is they are accumulating, for themselves, prompts that they should try someday, but they’re never trying them, which is akin to somebody eating a bunch of calories and then never exercising.

And my recommendation, like, here, I’ll give one simple thing that somebody would probably want to write down. Hey, when you’re jumping into advanced voice mode, isn’t it annoying how ChatGPT interrupts you? Well, did you know that you can tell ChatGPT, “Hey, just say, ‘Mm-hmm’ anytime I stop talking, but don’t say anything else unless I ask you to”?

Everybody who’s played with advanced voice mode one time is like, “Oh, my gosh, I got to do that. That’s, oh, it is annoying.” And I guarantee you 95% plus, people who even think that, will never actually do it because they think it’s more important to listen to the next 35 minutes of this conversation than actually hit pause and go do that. And my recommendation would be, stop this podcast right now, go into ChatGPT and actually do that. That would be like going to the gym.

Pete Mockaitis
I’m thinking I’m doing that right now. Is that okay? Is that rude?

Jeremy Utley
Yes, of course. No, it’s great.

Pete Mockaitis
I think I’m following your suggestions. So, in ChatGPT, iPhone app, I’ve got Pete Mockaitis, I just issue the command, like, “Remember this”?

Jeremy Utley
I would open a new voice chat. So, from the home screen, on the bottom right, there’s kind of like a little four-line kind of a button. If you hit that, that’s going to open a new conversation in Advanced Voice mode. And the first thing I would say is, “Hey, I want to talk to you for a second, but I don’t really need you to say anything. So, unless I ask you otherwise, would you please just say, ‘Mmm-hmm,’ one word only and let me keep talking.”

Pete Mockaitis
Okay. Hey, ChatGPT, here’s the thing. When I’m talking to you, what I need you to do, if I ever stop talking for a moment…there, he just did it.

Jeremy Utley
Isn’t that hysterical? Yeah, that’s hysterical.

Pete Mockaitis
Oh, Amber, when I’m talking, I need you to remember to only interrupt with just the briefest mm-hmm, or yes, or okay until I ask for you to begin speaking. Do you understand? And can you please remember this?

Amber
Be as brief as possible with confirmations and wait until prompted to speak further.

Pete Mockaitis
Thank you. It’s done.

Jeremy Utley
Now what you need to do is you actually need to continue the conversation. And you need to see, “Does ChatGPT respond with mm-hmm?”

Pete Mockaitis
You know, I like that. And I love those little tidbits in terms of, “Hey, remember this and do this forever.” Sometimes I like to say, well, I have. I have said, “Give me a number from zero to 100 at the end of every one of your responses, indicating how certain you are that what you’re saying is, in fact, true and accurate and right.”

Now, its estimates are not always perfectly correct, but I know, it’s like, “Okay, if he said 90, I’m going to maybe be more inclined to do some follow-up looks as opposed to if I get the 100.”

Jeremy Utley
Yeah, I think that’s great. I think there’s all sorts of little things. The problem is, right now, people are accumulating, or they actually aren’t even accumulating, but they think they’re accumulating for themselves all these tips and tricks, but they aren’t using any of them. And so, to me, what I recommend folks do, I actually just wrote a newsletter about this just yesterday, it went out this morning.

What I recommend folks do is take 15 minutes per day and try one new thing. It requires two parts. Part one, a daily meeting on your calendar that says “AI, try this.” And that’s it. It’s just 15 minutes, “AI, try this.” And thing number two, you need an AI-try-this scratch pad, which is just a running list of things that you heard.

So, like everybody’s scratch pad right now, if they’re listening to this conversation, should include, one, tell ChatGPT to only say mm-hmm unless you want a further response. That’s not forever, but at least in a one interaction, right? And, two, they should tell ChatGPT to always end its responses with a number, an integer between zero and 100, to indicate its conviction of its response.

Everybody literally what? We’re 10 minutes into this conversation, not even, everyone should have two items on their scratch pad. The problem is most people are going to get to this, to the end of this interview and they aren’t going to have a scratch pad and they aren’t going to have any time blocked on their calendar to do it.

And the next time they use ChatGPT, it’s going to be mildly disappointing because they’re coming off a sugar high and they think the treadmill’s broken, basically. So, I mean, obviously, there’s a ton there that we can unpack, but I think for most people, what most people fail to understand is the key to use is use.

And just like a treadmill doesn’t help you combat heart disease unless you actually get on it, AI is not going to unleash your creativity or your productivity unless you use it and learn how to use it. And that, to me, that’s pretty much my obsession these days, is helping people be good collaborators to generative LLMs.

Pete Mockaitis
That’s lovely. And I suppose we could dork out about so many tips and tactics and fun things that you can do. But I’d love it if you could just orient us, first and foremost, in terms of, if there’s research or a powerful story that really makes the case that, “Hey, these things are really actually super useful for people becoming awesome at their jobs for reals as opposed to just a hype train or fad.”

Jeremy Utley
I’ll tell you about my good friend, let’s call him Michael. It’s not his name. Names have been changed to protect the innocent. But Michael was a lobbyist in Washington, D.C. and he and his family wanted to move back home to Tennessee.

And he was looking for a job, and he got a job offer from a firm. And he reached out to me and said, “Hey, I’m kind of bummed because I feel like this firm is low-balling me. But my wife really just wants me to take it because she wants to be back near family in Tennessee, and I’m really struggling with knowing ‘Should I push back?’ because I know that I deserve more, but I don’t want to screw up this opportunity to get close to family.”

And I said, “Well, have you role-played it with ChatGPT?” And he said, “What do you mean roleplay with ChatGPT?”

Pete Mockaitis
Of course, the question everyone asks.

Jeremy Utley
Right. And I said, “Well, you can roleplay the negotiation and just kind of get a sense for what the boundary conditions are.” And he’s like, “Okay, wait. What do you mean?” And I said, “Well, open ChatGPT and tell it you want to roleplay a conversation. But, first, you want ChatGPT to interview you about your conversation partner so that it can believably play the role of that conversation partner.”

“You want it to start as a psychological profiler and create a psychological profile of your counterpart. And then once it creates it, you want ChatGPT to play the role of that profile in a voice-only conversation until you say that you want to get feedback from its perspective and a negotiation expert’s perspective.” And he’s like, “Give me 15 minutes.”

So, he leaves, texts me in 15 minutes, “Dude, this is blowing my mind. What do I do next?” I said, “Well, Michael, the next thing I would do is tell your conversation partner that you want it to offer less concessions, and you want it to not be nearly as amenable to recommendations because it’s had a bad day or it’s slept poorly or something, okay? I want you to get a sense for what does it feel like if the conversation goes badly, right?”

He goes, “Okay, I’ll be right back.” Comes back, “Dude, this is blowing my mind.” And he did a series of these interviews, and I touched base with him. And a couple of days later, I said, “Michael, what’s up?” And he said, “Well, three things. One, I didn’t know what my leverage in the conversation was until I roleplayed it a handful of times. Two, I didn’t have clarity on what my arguments were until I roleplayed it a few times, what the sequence of my argument should be. And, three, and most importantly, I’m no longer nervous about going into this negotiation.”

And then a week later, he dropped me a note saying, “By the way, we’re moving back to Tennessee, and I got a much better salary than they had originally offered me.”

It turns out one of generative AI’s unique capabilities is imitation and taking on different roles. As an example, you can go into any conversation you’ve ever had with ChatGPT and just say, “Hey, would you mind to recast your most recent response as if you’re Mr. T?” And, instantaneously, “Yo, fool, I can’t believe you didn’t believe the last thing I said,” just immediately starts doing it. It doesn’t take much.

And the power, actually, emotionally and psychologically, of having roleplayed with a very believable conversation partner has a profound psychological and confidence boost effect to the person who’s engaging the roleplay.

Pete Mockaitis
That’s perfect in terms of, yes, that is a top skill that the AI has, and about the most lucrative per minute use case I can think of a typical professional doing. And you’re right, that confidence, I have actually paid a real negotiation coach, and he suggested we do a roleplay. And I had the exact same experience, like, “Oh, you know what, I guess I don’t feel so silly asking for what I wanted to ask for now. It seems fairly reasonable for me to do so. And I’m going to go ahead and do so.” And it worked out rather nicely. And so, to know that you can do a decent job for near free with AI instead of hiring a phenomenal negotiation coach is pretty extraordinary.

Jeremy Utley
It’s remarkable. And so, we actually, my research partner, Kian Gohar and I wrote a weekend essay in The Wall Street Journal about this topic. But think about a salary negotiation as a flavor of a broader thing, which is difficult conversations. Maybe it’s a performance review. Maybe it’s a termination conversation. Maybe it’s talking to a loved one about the fact that you’re not going to come home for the holidays.

There’s all sorts of scenarios where roleplaying the interaction increases your confidence, strengthens your conviction, helps you, perhaps, exchange perspectives. Perspective taking is a really important thing, to understand, “How did this land to the perspective of my conversation partner?” That’s actually something that’s really hard for humans to do but an AI can read it back to you in a way that’s really reflective of your conversation partner, and, in a way, that you can understand.

So, we wrote a whole article about this but that’s just one class of activities. But the point is it really helps when you actually do it. Again, the tendency is for somebody right now to go, “Oh, cool, roleplay.” But if they don’t pull out their scratch pad, and say, “Ask ChatGPT to be a conversation partner in this upcoming salary negotiation, or my quarterly performance review, or my conversation with my loved one about our care for our kids,” or whatever it is, you just won’t do it.

I’ve even built, and you can link it in the show notes if you want, I built a profiler GPT, which is basically, it’s a version of ChatGPT which remembers who it is, unlike Drew Barrymore in “50 First Dates” where you have to remind ChatGPT who it is every time. A GPT is just like a Drew Barrymore who has memory, right, and like a real human being.

And what this GPT is instructed to do is interview a user about their conversation partner as a psychological profiler would, and then create an instruction set to give the user to copy-paste into a new ChatGPT window of instructions to GPT to perform the role of the psychological profile that it created. So, that’s totally free, but somebody can just open that up and you can say, “My significant other, Sherry,” and all of a sudden, this GPT will just interview you, ask you a bunch of questions, you answer them, and then it spits out an instruction set to a new GPT to play the role of Sherry in the scene that you have told it about.

Pete Mockaitis
I love that. And it also illustrates one of your core principles to effectively using AI is to flip the script a little bit and say, “No, no, you ask me questions.” Can you tell us a bit more about that?

Jeremy Utley
I mean, why is our default orientation that I’m the one with the questions and an LLM is the one with the answers? That’s how everybody approaches it, right? Because that’s how Google works, right? We never think, “Google, ask me a question.” It’s like, “Uh, what are you talking about?” A language model is not a technology, it’s an intelligence. That’s how I would invite people to think about it.

And you can get to know another intelligence, in a weird way, that sounds kind of crazy, but one of the things you can do is another intelligence can help you get to know yourself better. And the simple way to think about it is, here’s another thing for your AI-try-this scratch pad, folks. Get ready to write this down.

Think of a difficult decision you’re trying to make in your life, “Okay, should I take this job? Should we make this decision? Should we move? Should we put our kid in this other school?” whatever it might be, think of that decision, and then go to ChatGPT and say, “Hey, I’d like to talk about this. But before you give me any advice, would you please ask me three questions, one at a time, so that you better understand my perspective and my experience?”

Well, that is right there. If you say you were trying to figure out whether you’re going to send your kid to a new school, I have four children so it’s a very realistic kind of decision for me. I can Google and learn all about the school. But should I send my child to the school? I’m just going to get their marketing material and it’s not going to be contextualized to me at all. But if I go to ChatGPT, and say, “Hey, I’m thinking about sending my child to this school, I’d love to get your advice. But before you tell me anything, would you please ask me three questions?”

All of a sudden, well, it’ll… “Tell us about your child’s favorite subjects.” I’ll tell it. “Tell us about any weaknesses or difficulties that your child has had in school thus far.” I’ll tell it. “Tell us about your child’s favorite teachers.” I don’t know, but an LLM will ask questions like that. And then it will say, “Based on your answers, here’s how I would approach this conversation.”

That’s what I mean by turning the tables on an AI, is put it in the position of an expert that’s getting information from you rather than the default orientation, which is you’re the expert and you’re getting information from the AI.

Pete Mockaitis
Okay. Now, we’ve been saying the words ChatGPT a lot. I’m curious, in the world of LLMs, we got your ChatGPT, we got your Claude, we got your Perplexity, we got your Gemini, we got your Grok.

Jeremy Utley
Don’t forget Llama.

Pete Mockaitis
Do you think of them as having different strengths and weaknesses? Or are they kind of all interchangeable for whatever you want to use them for?

Jeremy Utley
I don’t think they’re interchangeable, but I don’t think it’s necessarily because of the underlying model. I think a lot of it is a UX thing. I think that the best AI is an AI that’s available to you that you will use. Again, the key to use is use. So, which is the best AI? Well, it’s the AI that you’re going to use. So, where are you? Most of the time you’re on your mobile. So, I would say it’s probably the AI that’s got the best mobile experience.

And what’s your default orientation? My belief is that the far better orientation towards AI is voice, not fingers. If you think about how you typically interact with a machine, you’re typically typing stuff into a machine. And I like to affectionately refer to my fingers, like as I wiggle them in front of the screen, as my bottlenecks. These are my communication rate limiters right now.

Notice you and I aren’t typing to each other. Like, that sounds absurd, right? And yet that’s how we talk to most machines. I’m typing into the terminal. Well, now, I mean, OpenAI, besides developing the world’s fastest growing consumer application, they created the world’s best voice-to-text technology. And furthermore, now they’ve got AIs that actually just process voice, don’t even go to transcription.

But the point is AIs are now capable of understanding natural language. We talk about this phrase, natural language processing. You probably hear that phrase, natural language processing. And that means something technically. I think to humans, the important thing about natural language processing isn’t what happens technically, but it’s actually you as a human being can now use your natural language, which is your spoken word with your mouth instead of your fingers.

And I would say to anyone who’s listening to this, if your default orientation to any AI, ChatGPT or otherwise, is fingers, you are limiting yourself. You’re trying to run with crutches. It’s, like, you’re in a sack race, okay? Use your voice, lose your thumbs, and watch the level of your interaction skyrocket.

Pete Mockaitis
Okay. Well, as we speak in late October of 2024, as far as I know, having played around with the apps, it seems like, indeed, OpenAI’s ChatGPT has got the voice natural interaction thing down the best, as far as I am aware of. Is that your experience?

Jeremy Utley
In my experience, it is. The only other comparison I would say is Meta’s Llama has voice as well, which you can access via WhatsApp or anything like that. The caveat, I would say, is, you know, I was doing a demo. I had a reporter at my place yesterday, kind of I was doing a demo of how I how I use AI in my personal workflow as a writer. And one of the things that I was showing was I’ll use OpenAI ChatGPT voice mode, but then I’ll often grab all the text with my cursor or with my mouse, and I’ll drop it into Claude, and I basically will parallel process ChatGPT and Claude.

So, the fact that Claude doesn’t take voice input isn’t a hindrance if I’m on my computer. When I’m on my mobile device, which, I’m probably on my mobile more than I’m at my computer actually, Claude doesn’t handle voice input, and it’s a little bit unwieldy to go back and forth in apps on your mobile relative to toggling between windows on your computer. So, it’s not to say that means ChatGPT is the best, but when you say, if you have to choose one, right now the model which is most optimized for voice interaction in a – intuitive interface. That, to me, is the way that you should prioritize, is, “What’s intuitive? What can handle the widest range of human input?” And ChatGPT’s got great vision and great voice recognition. And, therefore, I would use that. I’ll give you another example. I’m taking Spanish classes with my kids, okay, and we’re doing these lessons and we have a tutor talking to us on a bi-weekly basis.

And I get this assignment. I’ve got to conjugate a particular verb, and she wants us to write it down. We got to take pictures of it right now. Write it down in my notebook. I’m trying to conjugate this verb, and I kind of get stuck. And I’m thinking, in my mind, like, we only get her twice a week. I’m not going to be able to talk to her until Thursday. It’s Tuesday afternoon. And I thought, “I wonder if ChatGPT can help me.” And I just take a photo of my notebook and my crappy chicken-scratch handwriting, okay, in Spanish, by the way.

I take a photo, I say, “Hey, you’re my Spanish tutor. Can you tell me what I’m doing right now?” “Oh, it looks like you’re trying to conjugate the verb “estar,” and it looks like you’ve missed seven accent marks. If I were going to correct your paper, I would do this,” and rewrote all of the statements that I just made, but properly. “I made this change because of this. I made this change because of this. I made this change…”

And I go, “Dude, it read…” I mean, if you see my handwriting, it’s abysmal. But I did miss all the accent marks, it got that right, because I’m not an accent marker. But, anyway, the point is, the vision capabilities are spectacular too. And when you start to think, again, right now, write that down on your AI scratch pad, people.

Like, people are listening, and the thing is it’s like popcorn at a movie, and we’re just like, “Nom-nom, that’s so interesting. Oh, photos of AI should do that.” You will not do it if you don’t write it down. I’m obsessed with this idea. As you probably know, I’ve got this AI podcast called Beyond the Prompt, which we have amazing kind of experts and lead users and things like that.

We had a guy, who’s former dean at Harvard, 30 plus year learning scientist veteran named Stephen Kosslyn, recently. And he’s kind of the father of the school of thought called active learning. Maybe some folks have heard of it. Active learning, some people mistake as, you know, learning by doing, which isn’t exactly correct, but doing what you learn is an important step.

And what he says is he would contrast what’s typically known as passive learning, which is just consumption, but he would say it’s not actually learning at all. It just happens to you. It’s like you’re renting it. And that information has a very short shelf life and a very short expiration window. Any information that you consume but do not use, you effectively did not consume it.

Pete Mockaitis
Okay. Yes, well said. Well, I’d also love to get your pro take here. It seems like we’ve got a whole lot of cool things we can do that are very handy. What are some things you recommend that we not do, or some limitations like, “No, no, you’re not prompting it wrong. It’s just not going to do what you want it to do right now”?

Jeremy Utley
You know, I’m not a fanboy, I’m not a stockholder, I don’t have any secondary shares. I have yet to butt up against the limitations of use, to be honest with you. I think, right now, most people’s primary limitation is not the technology, it’s their imagination. I would say, like, one way that I’ve put it to students at Stanford is, “The answer is yes. What’s your question?” “Could it…?” The answer is yes. The problem is, for most people, they don’t actually have a question.

Pete Mockaitis
Okay. Well, Jeremy, if I could put you on the spot a little.

Jeremy Utley
Yeah, please, please, please, by all means, but the challenge is actually finding a question worth asking.

Pete Mockaitis
Okay. One thing I’ve tried every which way I can to say, “Yo, here’s a transcript of a podcast interview. What I want from you is to give me 10 options for titles that would be great, that are kind of like these dozens of title options I’ve written for you right here, I previously selected, or teasers.” And then whenever I do that, I get 10 or 20 options, and I go, “Hmm, not one of them am I like, ‘Yes, that is intriguing. That is awesome. That’s a phenomenal title that I want to use.’”

Now, it can nudge or steer me in some good directions, like, “Okay, that was a good phrase there. That was a good word there.” And maybe that’s sort of good enough in what I should expect from it in terms of, yeah, you can have a back-and-forth dialogue, it’s not going to spit out the perfect thing the first time, and be grateful for that. But I don’t know, since you are the master, any pro tips on how I can make it do this thing it just doesn’t seem to be able to do?

Jeremy Utley
So, this is great. What I’m hearing you say is actually a great case study of what we observed in our study, which got published by Harvard Business Review and Financial Times and NPR. We studied teams trying to solve problems, and you could call “Titling this podcast” as a problem that you’re trying to solve. We studied teams and individuals trying to solve problems with generative AI and studied “What do they do?”

And one of the kinds of natural problems that people have is they treat an LLM like it’s an oracle. Like I give it a question and it just magically gives me the right answer right off the bat. And what we would say is teams that treat AI like an oracle tend to underperform. But that’s not to say that everyone who uses AI underperforms. There’s a small subset of folks we studied who actually outperform.

The difference is they didn’t treat AI like an oracle. They treated AI like a co-worker, like a collaborator, like a thought partner. And so, what that interaction might look like is you ask for, say, 10 or 20, “Make it like this.” And then you get the output, and what it looks like to…let me ask you this. If an intern gave you 10 titles that you thought were mediocre, what would you do? Would you fire the intern?

Pete Mockaitis
Well, no, I would say, “Oh, hey, thank you for this. This is my favorite. This is my least favorite. That kind of what I’m looking for is, generally, more actionable, more intriguing, based on the needs of our listeners,” da, da, da, da.

Jeremy Utley
Do you do that to ChatGPT?

Pete Mockaitis
I’ve tried it sometimes.

Jeremy Utley
Yeah, you got to kind of, you got to critique the model’s output. You got to give it feedback. And I had that experience, actually. I had a hero of mine, Ed Catmull on my show a while ago, founder of Pixar, and I wanted the perfect title, of course. It’s, like, got to be the best title ever, right? And I asked for 10 and then I immediately always asked for 10 more.

I don’t even read the first 10. I asked for 10 more and never had ChatGPT say, “Dude, come on, you didn’t read my first ones, you know.” And they’re mediocre, you know, they’re okay. And I said, “Hey, I like one and three in the first set. I like seven and nine in the second set. Can you give me 10 more like those?” What do you think, are they better or worse?

Perfectly the same. Like, not any better, not any worse. And I was like, “Huh, but why? Why didn’t I like one?” I said, “Huh, okay,” I had to think. And what’s funny is, in our study, people who underperformed, AI feels like magic to them. It’s, like, they don’t do as well, but they’re like, “Wow, it just happened so fast.” People who outperform, who use AI to get to better work, it doesn’t feel like magic. It feels like work.

And that’s actually, that’s kind of a fundamental tension. I think we expect it to feel like magic or it sucks. And the truth is it’s just like working with another collaborator, and you do get to better outcomes if you’re willing to put in the work. And in this case, for me at least, the work was, I like number one because I’m a nerd and it has like an obscure movie illusion. I like number three because there’s a pun, and I’m a punny guy. I like number seven because there’s a movie reference baked in and I like number nine, whatever it is.

Then I said to ChatGPT, “Would you leverage that rationale as design principles for another 10, please?” six of the 10 were better than anything I had thought of. But the point is, it does require that collaboration. Now, that being said, that’s as a one-off interaction, Pete. I think what you should do in this case, if that’s it, and what anybody should do is, if there’s a routine workflow, like, how often do you title a podcast?

Pete Mockaitis
At least, twice a week.

Jeremy Utley
Okay. So, to me, that’s kind of square in the crosshairs of a task that it’s kind of a creative challenge, probably takes some amount of time. There’s a potential, you know, so there’s, call it, there’s a two-by-two somewhere that you would hire BCG to spit out, right? But you got a two-by-two, and this probably falls in the top right corner in terms of, like, it’s in GPT’s wheel housing capabilities, and there’s enough regularity that it would meaningfully impact your life or productivity. Great. Okay, there’s your two-by-two. I think that that’s a prime candidate for making a GPT.

Pete Mockaitis
I’ll just make a full-blown GPT?

Jeremy Utley
Yeah, why would you not make a podcast-naming GPT? And then you would put in its knowledge documents, all of the titles and your rationale. And then, importantly, it’s not that you make a GPT and you’re done. You make a GPT, then you try it, and then you see where it’s deficient, and you work to get it right, and then you reprogram, you iterate the instructions to the GPT relative to the work that you had to do in addition.

And what’s the process for that? I would say probably you’re going to instruct the GPT, “I want you to analyze the transcript. I want you to find what are the key points of emphasis in the conversation. I define emphasis as we spent more than two minutes on it or whatever,” I don’t know, right? “I want you to find wherever there is more than five back and forth, that’s evidence that this was particularly engaging.”

Or, furthermore, you might develop a protocol where, after your calls, you have a two-minute Zoom call with yourself, where you say, “Hey, here are the four things I thought were interesting.” And you load that into the GPT as well. I don’t know, “Consult the transcript and the follow-up call transcript that I’ve provided for you. Look for these points, then distill these into these brand guidelines, perhaps, or whatever it is. Then do this, then do this.”

You’d kind of walk the GPT through, you would actually articulate and codify that workflow. And then you would test it, and then you’d iterate it, and you’d test it, and you’d iterate it. And you’d get to the point, I would say, probably, if you’re doing it twice a week, by the end of the month, you’ll probably get to the point where, if you really take it seriously to iterate the GPT’s instruction set, over the course of a month, you’ll have something that’s really great.

Now, the problem is most people aren’t really systems thinkers and they just want to do like a one-off kind of like band-aid solution, which is fine. I’m probably more that way myself, unfortunately. So, I’d rather just, it’s less painful on a one-off just to do the work again myself. Systematically, it’s much more painful to do it one-off every time by myself. And so, you kind of got to decide.

And to me, that becomes a function of “What is a task whose output you would refuse to settle for less than exceptional?” That’s a great task for a GPT because you’re not going to be okay with anything less than a really good GPT. And it summons the requisite activation energy required for you to continue to invest in iterating it.

Pete Mockaitis
Understood. Okay. So, it starts with a mindset of, “Okay, don’t talk to it like it’s an oracle. Expect we’re going to need some back and forth, some collaboration, some iteration, some refinement.” And then it’s your bullish take that, at the end of the day, it’s going to cut the mustard and deliver the goods.

Jeremy Utley
Unequivocally.

Pete Mockaitis
All right. Beautiful.

Jeremy Utley
That, to me, is it’s unfathomable that it can’t deliver on that use case.

Pete Mockaitis
All right. You heard it here first.

Jeremy Utley
I mean, really and truly, and I’d be happy to workshop with you if you’d like. But, to me, that is absolutely a use case that GPT can shine with.

Pete Mockaitis
Okay. Well, we talk about use cases. You’re real big on idea flow. It’s getting a whole lot of ideas, a whole lot of creative options generated. Tell me, how do you use AI in that endeavor well?

Jeremy Utley
Well, the easiest thing to do is, which you did well in your example, is request options. I think, for most people, they ask one question, they expect one answer. And with a probabilistic, non-deterministic model, which means LLMs are probabilistic in nature, every time you ask a question, you’re going to get a different answer.

And sometimes the answer is there’s a higher degree of overlap, sometimes they’re radically different, even within the same instruction sets. You could say it’s a bug. I actually think it’s a feature because I believe in variability of thinking is actually what drives creative outcomes. And so, when you realize that, then, “Wow, I could hit regenerate and it will reconsider the question again?” “Yeah.” “Well, why wouldn’t I hit regenerate five times?” Great question. Why wouldn’t you?

And most people go, “I’ve never hit regenerate.” I think it’s actually probably the most important button on the screen. Because you have a collaborator, you and I are going back and forth, and I say, “Hey, Pete, what do we do about this?” You go, “Well, here’s an idea.” And I go, “Okay. Well, what else?” And you’re like, “Okay, let me dig deeper,” and then you say something. I go, “Okay. Well, what, like five more ideas?” And after a while, you’d be like, “Dude, I gave you all my ideas.”

But ChatGPT is not like that. AI is not like that. And so, one of the simple tricks for idea flow with AI is recognizing you’re not going to tire itself out. In fact, you need to recognize your own cognitive bias. I mean, it’s one of my kind of nerd obsessions is what’s called the Einstellung effect, which is the tendency of a human being to settle on good enough as quickly as possible, demonstrated since the 1940s by Abraham and Edith Luchins, where they’ve kind of documented, very clearly how human beings kind of get in a cognitive rut, and they just want a good enough answer, and they don’t actually get the best answer. They just get a good enough answer.

And so, to me, the key to maximizing idea flow with an AI is recognizing that the creative problem in that collaboration is actually your human cognitive bias, not the AI’s bias.

Pete Mockaitis
Okay. Thank you. Oh, boy, Jeremy, I could talk about this forever. But before we hear about some of your favorite things, could you share any other top do’s and don’ts?

Jeremy Utley
One thing, I think, is a really simple thing that you can do, and it’s not unrelated to your idea of asking ChatGPT or whatever, for a number, kind of saying how confident it is. One thing that you can often do is ask it to evaluate its own work, “Scale of zero to 100, how great was the previous response? Be like a tough Russian ballet instructor, give me critical feedback.” And it’ll go, “Oh, it’s a 60 out of 100 for this reason.”

Well, then you could say, “Okay, based on that feedback, can you rewrite it as 100 out of 100? Rewrite it as 110 out of 100. Now, regenerate it. Now, regenerate it again. Now, grade that one. Is it really 100? Bring in another Russian judge. What does the second Russian judge think?” So, one thing that you should definitely do is get AI to evaluate its own work. It’s far better at being objective.

Like, as a simple example for me, and then I also want to mention chain of thought reasoning, so make sure I come back to that. But one thing I’ll do is I’ll do kind of parallel processing between ChatGPT and Claude, and I’m having both work on something. I take their output and I feed it to the other, and I ask, “Which one is better? Is Claude’s work better or ChatGPT’s work better?”

You would think that they both advocate for themselves. They don’t, but they almost always agree. It’s fascinating, actually. There are times where ChatGPT is like, “I actually prefer Claude’s response for this reason, this reason.” And if I go to Claude, it goes, “I think my response is stronger for this, this, this.” And half the time, it’s the other way.

But it’s actually exceedingly rare that they disagree. They often will say the other’s is better, but they almost always agree with the other’s assessment too, which is fascinating, which is to say you can have models evaluate one another’s work. The other thing, the other huge do, probably the single greatest empirically validated finding is that the best way to get better output from an LLM. is to prompt it with what’s known as chain of thought reasoning, which is to say, tell the language model to articulate its thought process before answering.

And so, humans have this tendency, so do AIs, of what we all know as ex post rationalizing. So, if I ask you, “What’s your favorite color?” You say, “It’s blue.” “Well, why did you say blue?” You go, “Oh, well, I like the sky, and I like the ocean, and da, da.” But if instead, I say, “Hey, tell me how you think about what your favorite color is,” and you go, “Well, I probably think about my favorite things.”

And then I go, “Well, what are your favorite things?” You go, “Well, my wife, obviously, and I think about her eye color, and they’re green. You know, green’s my favorite color.” “Well, is it blue or is it green?” Actually, and for me, even as I think through that thought exercise, green, emphatically. I take my wife’s eyes any day over the sunset. That’s a no-brainer, right?

Well, similarly, language models do the same thing. If you ask it for an answer, and it says blue, and then you go, “Why did you say blue, ChatGPT?” it will ex post rationalize. And blue is very subjective, but even with things that are objective, more objective, it will ex post rationalize its answer. If, however, you say, “Hey, before you answer the question, would you walk me through how you’re going to think about solving this problem?” It will articulate its answer and it arrives at, from a research perspective, empirically better, more valid, more cogent, etc. responses.

And the reason it does so is because of how language models work. They aren’t premeditating their answers. So, what it’s not doing, as Pete asks a question, and then it thinks of its answer and writes it out. That’s not what happens. What happens is Pete asks a question and it reads the question and says, “What’s the first word of the answer?” and it says it.

And then it reads your question, and the first word it thought of, and says, “What’s the second word?” And then it reads your question and its first and second word, and thinks, “What’s the third word?” So, it’s not premeditating responses. It’s, literally, only predicting the next token. And so, when you ask it for an answer, the only thing it’s predicting is its answer.

If, however, you ask for reasoning and then answer, it first next token predicts reasoning, and then it incorporates the reasoning that it has articulated in its response, which results in a much better response because it’s not only considered your question, but it’s also considered reasoning first. And as a user on the other side of the collaboration, what that enables you to do is not only, one, get better responses, but, two, you can interrogate its reasoning too.

And you can say, “Actually, it’s not that I have a problem with your answer. I have a problem with how you approach the question. I actually think you should do this.” And then you can guide its reasoning path because you’ve asked it to make its reasoning explicit. Those are the two probably biggest do’s, I would say, when you ask for do’s and don’ts.

Pete Mockaitis
That’s cool. And it sounds like the key is that you ask for it in advance as opposed to, “How did you come up with that?”

Jeremy Utley
Yeah, exactly. That’s ex post rationalizing. It will give you a great answer. It’s a sycophant. LLMs have been programmed to be helpful assistants. And when you realize what that means, it’s a euphemism for suck up. So, if you ask it what it thinks, it’s going to say, “I think that’s a really great idea, Peter.” But if you say, “I don’t want you to compliment me. I want you to be brutally honest. Don’t pull any punches,” like, you got to really ask an AI to level with you to get honest feedback.

When you’re aware of that, it influences how you collaborate with the model, which goes back to the question earlier about idea flow. It’s recognizing your own, I mean, there are limitations to the technology, but a lot of times the truth is we want a suck up. I don’t want to hear how my first draft sucks. I want to hear, “Actually, you don’t need to do any more work. You go have a coffee.” That’s what I want to hear.

And if I don’t realize that the model has been trained to be a suck up, I ask it, assuming I’m getting the truth, and then when it tells me I’ve done great work, I say, “Well, let’s take a break, boys. We’re all done here.” Whereas, if I realize, “You know what, unless I really push it to give me straight feedback, it’s probably going to tell me I’ve done a great job. And I know my human cognitive bias is to overweight the response that I did a great job, and to underweight…” So, you have to understand yourself. In a way, the key to good human-AI collaboration is to really understand our own humanity.

Pete Mockaitis
That’s powerful. Thank you. And now could you share a favorite quote, something you find inspiring?

Jeremy Utley
One is Thomas Schelling, Nobel Prize winner in Economics, who said, “No matter how heroic one’s imagination, a man can never think of that which would never occur to him.”

The second quote that I love is Amos Tversky, Danny Kahneman’s lifelong research partner, who died prior to receiving the Nobel Prize. But Amos Tversky was once asked how he and Kahneman devised such inventive experiments. And he said, “The secret to doing good research is to always be a little underemployed.  You waste years when you can’t afford to waste hours.”

Pete Mockaitis
Awesome. All right. And a favorite study or experiment or bit of research?

Jeremy Utley
I think there’s a great one that I always come back to called the creative cliff illusion, which is conducted by Nordgren and colleagues at Toronto, I want to say. You can look it up, creative cliff illusion. But the basic idea is when they ask participants what their expectations of their creativity over time were, there is an illusion that one’s creativity degrades to a point that reaches a cliff where it almost asthmatically falls off. And people’s, their expectation is, “I’m just going to run out of creative ideas.”

The paper is obviously called the Creative Cliff Illusion because then, when they test people, it’s not true. They don’t run out of creative ideas. They, actually, their creativity persists. And my favorite part of the study is the shape of the creativity, over time, the variable that it’s most highly correlated with, i.e. “Does creativity dip or does it increase?” because it does increase for some people. The variable that determines the shape of your creativity over time is actually your expectation.

So, if you expect that you will keep having creative ideas, you do. If you expect you will cease having creative ideas, you do. And so, that to me is just totally fascinating.

Pete Mockaitis
Totally. And a favorite book?

Jeremy Utley
I love Mark Randolph’s book about the founding of Netflix called That Will Never Work. It’s a fascinating story about entrepreneurship, about grit and perseverance, and about ideas. And there’s a lot of very practical takeaways about the importance of experimentation in finding product market fit and succeeding.

Pete Mockaitis
All right. And a favorite tool?

Jeremy Utley
I’ve got an electric chainsaw, and I love tromping around the woods, just chainsaw in hand, like, just in case I need it. It’s just so fun.

Pete Mockaitis
Awesome. And a favorite habit?

Jeremy Utley
NSDR, non-sleep deep rest protocol, Andrew Huberman. It’s, basically, laying down and becoming totally still, not for the purpose of sleep, necessarily. It’s okay if you do sleep, but it’s not in order to sleep, but to facilitate neurological replenishment, connections between neurons, and codification of memory. And I try, if I can, to NSDR once a day.

Pete Mockaitis
Okay. And is there a key nugget you share that seems to really connect and resonate with the folks; they quote back to you often?

Jeremy Utley
I talked earlier about the value of variation in one’s thinking. And the truth is ideas are naturally occurring phenomena, which is a nerdy way of saying they’re normally distributed. So, you got some really great ideas, very small, it’s a bell curve, right? You got a lot of ordinary ideas and you got some stupid ideas. Steve Jobs called them dopey ideas. He regularly shared dopey ideas with Sir Jony Ive.

Taylor Swift says, “It’s my hundreds or thousands of dumb ideas that have led me to my good ideas.” You got dopey or dumb on one side of the spectrum, you got delightful on the other side of the spectrum. The quote that I often say that people remember and resonates, and they take with them is, I tell people, “Dopey is the price of delight.”

The only way you get good ideas is by allowing yourself to have bad ideas. And the reason most people don’t have better ideas is because they won’t allow themselves to have worse ideas.

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you to point them?

Jeremy Utley
JeremyUtley.design And LinkedIn, I’m happy to chat with folks on LinkedIn. My website, JeremyUtley.design, I’ve got a newsletter folks can subscribe to. I’ve also got an introductory AI drill course where you get two weeks of daily drills for, you know, they say you need 10 hours of practice with AI to start to become fluent. This gives you daily practice to get your first 10 hours under your belt.

Pete Mockaitis
Okay. And a final challenge or call to action for folks who want to be awesome at their jobs? Sounds like we just got one.

Jeremy Utley
To me, it’s very simple. Do one thing you heard here.

Pete Mockaitis
Okay. Jeremy, this is fun. This is fascinating. Thank you. And keep up the awesome work.

Jeremy Utley
Thank you. My pleasure.

1112: How to Beat Digital Exhaustion and Reclaim Your Energy with Paul Leonardi

By | Podcasts | No Comments

Paul Leonardi reveals how notifications, multitasking, and endless tools quietly burn us out–and how you can reset your energy.

You’ll Learn

  1. The two hidden forces behind your digital exhaustion
  2. Simple ways to reduce attention-switching
  3. How to reclaim your energy from your devices

About Paul

Paul Leonardi, PhD, is the award-winning Duca Family Professor of Technology Management at the University of California, Santa Barbara. He is a frequent consultant and speaker to a wide range of tech and non-tech companies like Google, Microsoft, YouTube, GM, McKinsey, and Fidelity, helping them to take advantage of new technologies while defeating digital exhaustion. He is a contributor to the Harvard Business Review and coauthor of The Digital Mindset.

Resources Mentioned

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Paul Leonardi Transcript

Pete Mockaitis
Paul, welcome!

Paul Leonardi
Hi, thanks for having me, Pete. I appreciate it.

Pete Mockaitis

Well, I’m excited to be chatting. We’re talking Digital Exhaustion. But first I want to know, I understand you are the youngest blackbelt in U.S. Aikido history. Tell us about that.

Paul Leonardi
Well, I was, at least circa 1992, or somewhere around there.

Pete Mockaitis
I assume 12-year-old or someone just have to usurp you. The nerve.

Paul Leonardi
Yeah, well, they might have in the last couple of decades. Yeah, I started practicing Aikido when I was in second grade, and I didn’t like it when I started because I just wanted to be like Bruce Lee or the Karate Kid and punch and kick stuff. And my parents didn’t like that idea very much, and said, “We’ll put you in a defensive martial art,” and I didn’t really understand what that meant.

But Aikido is about using your opponent’s energy and reorienting it so that you can throw and pin and do things like that. And I think it’s actually turned out to be a pretty good metaphor in my life. Like, how do you take energy that’s moving in one direction and recast it so that you can move in other directions and do productive things?

And so, I’ve really enjoyed, you know, I don’t practice regularly anymore. But it’s certainly an important part of my identity. And what was kind of interesting is I did it with a bunch of kids, and several of those kids ended up going on to graduate school and getting PhDs. We didn’t come from like an affluent or highly educated area.

But I think there’s something about the discipline of doing a martial art, combined with, and Aikido is very much like this, where you have to do improvisations all the time on key techniques to deal with opponents that are doing different things. And that kind of focus of technique plus improvisation is something that lends itself really well to doing research and focusing on topics, you know, sort of ad nauseum for a really long period of time.

Pete Mockaitis
Well, I’m glad you mentioned directing energy because that’s exactly where I thought this might go. This is we’re talking about digital exhaustion. Well, first, can you define what do mean by this?

Paul Leonardi
It’s a hard thing to define in words, but let me try to define it in actions, behaviors. So, here’s the story I get from a lot of people. “I get midway through my day. I’m staring at my screen. I realize I’m just scrolling. I’m clicking on some random stuff. I know that there’s an email that I should respond to, but I just don’t want to do it. My eyes are sore, but I can’t look away from the screen. And I just feel this sense of bleh, even though I still like my job and I like the work I’m doing.”

I think that really characterizes the feeling of digital exhaustion. It’s that we are so enmeshed in this world of communication and tools and data coming at us. And we need it, and it’s useful, but it’s also just wearing us out.

Pete Mockaitis

Well, could you share with us, I think many of us can relate to that, like, “Oh, yeah, sure. Okay, mm-hmm, understood.” I’m wondering if you discover anything really shocking as you dug in your research here.

Paul Leonardi
One of the things that I expected to hear from people was, “I’m going to…like, I want to give up my tools. I want to go on a digital detox. I want to stop using…” name your social media platform. And rarely anybody said that to me. Most people said, “I want to be able to do all the things, but I need to figure out how do I do it better? How do I do it in a way that feels like I’m in control and isn’t sapping all of my energy?”

And I thought that was interesting because most of the discourse that we have today seems to be you have this sort of either/or choice. You’re on social media or you decide not to be on social media. You get a dumb phone or you get a smartphone. You stay away from your tools, right, whatever it might be. And we just don’t live in a world where you can choose to walk away from most of our technology. And most people don’t want to because our tools do great things.

If it weren’t for the internet and video conferencing and USB mics, we wouldn’t be having this conversation right now. So, we like our tools, we want to use them, but we need to reorient to them in ways that are making sure that they’re energizing us, allowing us to be productive, being engaged and not sapping us of all our enthusiasm and excitement.

Pete Mockaitis
Well, I wonder, are they? I mean, I think some of us feel it, like, “Yes, my phone is a problem.” And I wonder if others among us are not even aware of damage being done. Can you orient us to the lay of the land with the research here?

Paul Leonardi

I started questioning people about feelings of digital exhaustion in, roughly, 2001, 2002. And I did that because I had a few experiences when I was doing some research at this large atmospheric weather science organization.

And the scientists and the admin people there kept telling me about how they love doing research about atmospheric conditions, and they loved working with these fancy computer models. And they thought they were really making a difference by giving reports to the FAA to help with plane routings and things like that.

But that they just start were feeling like there was so much data coming at them and so many different tools that they had to learn, that they were kind of feeling overwhelmed. And almost everybody that I talked to said that. And when I asked them, “Okay, well, do you feel like you are exhausted by your tools?” roughly half of them said immediately, “Yes!”

And the other half said, “What do you mean exhausted by my tools? I mean, I kind of feel like worn out by them, you know, but exhausted? I don’t know. I just use them.” So, I’ve been asking that question ever since. And I’ve asked it thousands of times. And I’ve got over 12,000 people that I’ve interviewed and surveyed for the book.

And what’s happened over time is that, each year, it seems, that I asked that question, more and more people from that 50% that said, “No, I don’t feel exhausted,” have been moving into the exhaustion camp. I think we’re becoming more and more aware of the toll that our tools take on us.

And when you read a lot of the popular press and books and things, like Jonathan Hyde’s The Anxious Generation that talks about these big problems associated with social networking sites amongst adolescents, in particular, I think more and more of us are becoming reflective about the role that technology is playing in our everyday lives in ways that we hadn’t really considered before.

So, there’s this dark side that comes with all of the positives of using our technologies and that awareness has been growing.

Pete Mockaitis
So, boy, 2001, those feel like quaint, simple times as compared to today.

Paul Leonardi
Yeah, I know. It’s true.

Pete Mockaitis
So, what’s our percentage at nowadays with your surveys with regard to digital exhaustion?

Paul Leonardi
Yeah, so I survey people on a scale that goes 0 to 6, and it’s probably not super interesting to talk about why that scale is 0 to 6, but what in 2000 to 2001 timeframe, the average response was about a 2.5. So, you know, like, “Okay, I feel a little exhausted,” but sort of low. In 2022, which is the last time that I really conducted a large-scale survey of this, it was up above 5. So, it’s doubled in that 20-year period.

And what’s interesting is there’s been two major inflection points, so two points at which the graph just sort of trended up. The first one was right around 2010, and that’s a particularly important period because we had just seen the introduction of the iPhone two and a half years prior, and Facebook reached a hundred million monthly active users at that point. So, 2010 represents a period of time where social media, in particular, really has, you know, arrived en masse for most people.

And then the second inflection point was 2021, and that’s right after COVID. And, of course, we all know that even for those that worked really intensely on screens and in a very digitally mediated world before COVID, the move to mass working from home, interacting with everybody through digital platforms really seemed to create another spike in that graph.

And what surprised me is that I would have expected at both of those points, as I was watching those numbers increase in real time, some decline afterwards. But I’ve not seen a decline in either of those trends after 2010 and after 2021. The numbers just sort of remain flat. And so, I wonder if we just kind of keep adding a digital tax to our lives and have not been finding a way to reduce that burden.

Pete Mockaitis
And I also wonder, you asked about exhaustion associated with the use of the digital tools, are we pretty sure folks are attributing it accurately or correctly, there’s not some mystery third force bringing in exhaustion upon us and we just blame the tools?

Paul Leonardi
There absolutely might be. You know, there’s a whole confounding set of factors that are important to consider when we talk about exhaustion. One is stress. We get stressed by lots of different things. Not all stress is bad, right? Some stress is good. It creates an adrenaline and cortisol release that allows us to do good things. But we get stressed, and stress is different from exhaustion, I would say. Stress is kind of the more momentary feeling of, “Oh, you know, I just have to respond to these emails. It’s driving me nuts.”

And exhaustion is the cumulative effect of those stressors over time. Now, we get stressed by many things other than our technology, right? We get stressed by the demands people placed on us. We get stressed by, you know, the way people act or behave towards us. We get stressed by the volume of work we might have. So, there’s lots of other stressors that are kind of mingled in with the digital activities that we’re engaged in.

Also, stress and exhaustion are both kind of driving forces that can lead, ultimately, to burnout in our jobs. But burnout is a much bigger concept than exhaustion because burnout is about how we orient to our work more broadly. Are we getting opportunities for promotion? Are we feeling like we’re making a difference? If we don’t have those kinds of things, the research suggests that we tend to feel more burnout.

Exhaustion, though, is a critical component of burnout. Christina Maslach, who developed one of the best burnout inventories, talks about emotional exhaustion as being one of the key predictors of burnout. And it’s perhaps the one that is most prevalent when you are talking about burnout is like how emotionally worn are you. So digital exhaustion is certainly a part of that. Is it the only thing? No. But I do think it’s one important factor that we can control through some changes in our behavior.

Pete Mockaitis
Well, shout out to Christina Maslach, a guest of the show. Yes, understood. Well, then, I’m curious, theoretically, these digital devices “should” be making our lives easier, simpler, better, lower stress, right? Like, whereas, before we had to do all these old-fashioned things, like, you know, find an envelope and a stamp, to send an old-fashioned letter before email.

Or, you can just ramp it up, or we have to mosey on over to a computer to send a note as opposed to getting it on our phones, etc. So, in some ways, or at least that’s part of, I’d say, the promise or the marketing or the hype associated with tech tools, and we’re hearing it now with AI, “It’s going to make your life so much easier.”

Paul Leonardi
Oh, yeah. Oh, yeah.

Pete Mockaitis
How is it that it is a factual statement that I can spend fewer minutes of my life achieving a given outcome by utilizing these digital tools, and yet, I feel more exhausted instead of less exhausted with this empowerment?

Paul Leonardi
Yeah, it’s a great question and it feels like a paradox of sorts, doesn’t it? But let’s take a look at two major drivers of our digital exhaustion – attention and inference. And let me try to give you an example of why what you’re saying, you know, our tools help us to do these things that are supposed to make our life easier, but at the same time end up contributing to our exhaustion, like how both of those things can exist simultaneously.

Okay, so let’s start with attention. We, as humans, appear not to be very well made to move very quickly across lots of different tasks. Our brain takes a beat to disengage from what it’s doing and reengage in a new context. And there’s lots of good science that shows that the kind of disengagement that needs to happen makes it difficult for us to multitask.

But our devices are demanding more and more switches and attention from us all the time across different applications, across different areas of work, across different arenas of our life, from work to home and etc. And we’re just not made for those rapid switches in connection and disconnection that technologies create for us.

So, you’re right on the one hand that it’s wonderful that if an urgent work problem presents itself when I’m at a soccer game for my kid, I don’t now have to, like, you know, maybe 15 years ago, I got the phone call and I’m like, “Oh, no, I need to leave the soccer game and run into the office.” And that would have been really disruptive. Now I can deal with that problem on my smartphone pretty easily from the soccer field.

But what that has created is this fracturing of our attention between my home life and my work life. And I’m now, all of a sudden, situated physically on a soccer field doing work, disembodied, right, and I’m working through my screen in order to sort of be in the office. Not to mention that I’m on an application and, like, I’m working in Google Docs, and all of a sudden, I get an email notification, and I quickly switch to go see what that email notification is.

And then I go back to my Google Docs, and I don’t seamlessly pick up where I left off, because it takes a while for me to re-adjust and port my attention over from the thing I just left. And there’s lots of good research. Gloria Mark is one of my favorite scholars who does a lot of work on attention. And she gives an example that I love, which is that our attention is like a whiteboard.

We think that we’ve written all over the whiteboard and we just erase it and we can write something new. But if you look at most people’s whiteboards, you realize there’s still residue left over from what they wrote before. It’s really hard to erase everything.

Pete Mockaitis
Got to get the spray cleaner going.

Paul Leonardi
Oh, yeah, that little “pst, pst, pst” going. And that’s what our minds are like. And so, it takes time for us to reorient to different activities. And that reorientation, those switches in attention that those reorientations require, are really a great source of our exhaustion, even though the technologies that are allowing us this access in multiple ways are making our lives easier. So that’s one example right around attention.

The next one is what I call inference. And inference turns out to be a huge driver of our exhaustion. And let me kind of take it this way. We are inundated with many, many, many data points all the time. Pieces of emails that come at us, right? We see images that are posted on Instagram or little videos on TikTok. And we get a glimpse about, “Well, what is this person interested in? What is this report really saying? I got this little bit of data from our customers about how many emails they open or whatever it might be.”

And we are constantly forced to grapple with the fact that we see a little and we know we don’t see the whole picture. And so, we’re always trying to fill in the blanks or make assumptions about what’s going on behind the scenes. And that inference-making is like turbocharged now, because we’re constantly inundated with pieces and half-truths and little examples and almost never the full picture. And it takes a lot of cognitive and emotional work to be in a constant state of inference-making.

One example that I love is that I talked to, in interviews for the book, this guy by the name of Dean, and Dean was telling me how, when he was just after graduating college, his buddies wanted to go on a bicycle trip through Europe. And he decided at the last minute he couldn’t go because it just wasn’t a financially prudent move for him.

But he kept watching on Instagram, you know, all the great places they were cycling, the beautiful vistas that they saw, the great pubs that they went to along the way and the friends they were making, and he was making all of these inferences about how they were having the time of their lives, how he felt like a loser because he couldn’t go on the trip with them, so on and so forth, right?

And this might just sound like, “Okay, so what? You’re looking at a bunch of pictures of people’s posts on Instagram.” But having to contend with a world out there that’s giving you pieces of information and making sense about, “Where’s my role in that?” is a really exhausting experience. And we do that all the time. Sometimes it’s through images. A lot of times it’s through just pieces of data that are coming in.

And we’re always looking at ourselves in these platforms also, “How do I appear to other people?” And then making inferences about, “How must they think that I appear given what they see about me? And, oh, did I give the right impression? Did I not?” So, if that all sounds tiring as I’m explaining it, think about what it’s taking in our minds and in our hearts to do that.

Pete Mockaitis
Yeah, boy, you really put a nice point on that and in terms of inference being exhausting. And I’m thinking and talk about half-truths, I find it, I feel that when I watch the news, because I’m doing exactly that, I’m trying to make sense of what’s being communicated to me. And, particularly, I’m going to say politicians, or statements by leaders of technology or business, in terms of, “Is that true? Why do you suppose you said that? Am I being lied to right now? And is that partially true?”

When you said half-truths, I could imagine, in a way, that’s how I feel about most also marketing communications, particularly around AI products, I’d say in terms of, “Okay, what you’re saying seems to be technically not a lie. Like, this application does, in fact, do the thing you say it does. However, it does so unreliably and inconsistently with such need for correction, fixing, editing, redoing, babysitting, it’s like, I’m not quite sure it’s actually useful or value added at this stage of the game in late 2025.”

And, in fact, I saw a study associated with software engineering, for example, which says, “Hey, we actually did a randomized control trial associated with folks who are using AI versus not using AI, their experience, they know their code base and what they’re up to. And when you measure it on the clock, it was slower, fixing the AI errors.”

And yet it feels faster because sometimes it gets it right, and it’s like, “Whoa, that’s impressive.” And it’s just a good feeling and it is sort of, like, wowing. And so, I think you’re right, in a world where we’re getting lots of half-truths, it is exhausting. And I’m coming back to flashback. I had to check out, potentially getting a new roof.

We own a little multifamily home in Chicago, and it was over a hundred years old, the building. And so, it seemed like, “Oh, yeah, that roof may need some care.” And so, I was having a heck of a hard time getting anybody to come on over. So, I was like, “You know what, the heck with it. I’m just going to call 20 roofing companies.”

Paul Leonardi
See who shows up? Right.

Pete Mockaitis

“And we’ll see how many people show up.” And I got about five, which, I mean, is striking there.

Paul Leonardi
That’s about par for the course these days. Yeah.

Pete Mockaitis

You know, 15 out of 20, just don’t even want your money, but, okay. So, I got about five, and it was so tricky because some people say, “Oh, no, you got to tear off the whole thing and just start again.” And others were like, “Oh, no, we can just put another layer on the existing.” And it’s like, “Well, putting another layer is much cheaper, and so I would like to do that if I can, but can I?”

And I found it very mentally exhausting because, here I am, it was about three versus two, the opinions on just another layer versus just tear the whole thing off. And I think that this is just so common of so many situations. It’s like there’s ambiguity and we’re getting different messages from different people.

And you’re wondering, “Am I being straight up lied to by one of them? Is there a nuance I’m not understanding? Like, how can I deduce what is true?” And it’s exhausting. I see the same thing when I’m evaluating potential marketing initiatives. It’s just like, “Well, who knows what’s going to happen?”

Paul Leonardi
I like your roofing example. It rings true. Maybe we’re just unlucky and need to buy roofs, the two of us, but I think this sort of puts it into perspective. In 2000, or like early 2000, I also owned a rental property that needed a new roof. I’m not making this up. And I also got some conflicting bids.

And I remember thinking at the time, that I know nothing about roofing and I still don’t really know much about roofing today. And I had few ways of really knowing what was the best course of action. And, more importantly, I didn’t know, I didn’t think that I could find out. I really needed to figure out who was the best expert or who could I trust and I would lean in on their expertise.

Today in 2025, if I needed a new roof, and I got conflicting estimates that said, “You needed to do things,” the first thing I would think is, “I can figure out what really I need here.” We have this impression that the world’s information is at our fingertips, and if I only look in the right places and if I do the right kind of research, I’ll be able to determine what the right course of action is. The reality is, even though we might think that, it’s really hard to do.

But knowing that the possibility exists, and thinking I should be going and looking for it is exhausting. And for many people, it’s demotivating. And this is one thing I found over and over again as I was doing the studies for this book, that when you reach these kinds of critical decision points where you feel like, “The world’s information is at my fingertips and I should be able to make a great decision out of this, and I’m an idiot if I make the wrong decision,” people just don’t act a lot of times. It stalls them.

A kind of a funny related story, this was maybe 10 years ago. I was doing some work with a really large company, a software company that is, I won’t name, but is very into search. And I was with a group that sort of, that helped advise companies about ad buying.

And what was really funny to me in these meetings was, somebody would come, like a project manager would come, and they would say, “Okay, here’s the strategy that we think we’re going to use to advise this company on how to make their ad purchases,” how to increase click through rate, let’s say.

And someone on the team would say, “Oh, do we have data to test your hypothesis?” And then everybody would kind of giggle, and be like, “Yes, we have all the data.” And so, they would say, “Well, go test that hypothesis and then come back and then we’ll decide if we should advise the company to do this or not.”

So, they would come back, and then someone would say, “Hmm, what if this?” “Oh, do we have the data for that?” And then they’d all laugh and then they’d go back. And it was this whole, like, analysis, paralysis by analysis. It’s like they almost never made decisions about what to do because they realized, “We have all the data. We should just keep going back and looking at it.”

And this is the kind of thing that I see people doing all the time, is we just don’t act because we feel that we should do more. And the act of trying to do more is exhausting, and knowing that I’m never going to get the complete amount of information wears us out just thinking about that. So, it’s this matrix of data and technology and expectation and inference that we’re trapped in these days, I think, that creates these real deep feelings of like, “Aargh, why do I have to do more? Why can’t I just break free?”

Pete Mockaitis

Understood. Okay. Well, I think this is hugely valuable already, just surfacing what’s going on, “Oh, hey, you’re doing a lot of attention switching, you’re doing a lot of inferring, and you have too much to look at with regard to your switching of attention and your potential extra data points to go about your inferring.” So, Paul, lay it on us, if we want to find more energy, less exhaustion, what’s the most leveraged stuff we can do to achieve this?

Paul Leonardi
Yeah, so where I like to begin is to say, if you understand that these attention switches, this inference-making, these are the key contributors to our exhaustion, then what we need to do is figure out, “How do we reduce the amount that we are switching our attention and the inference making that we have to do?” So that’s the big picture. Those are the things we need to work on.

So, then we can start to talk about very specific strategies that help us to do that. One of them that I love that I call, it’s rule number three in my book, it’s called make a match. And the premise is simple. The execution, though, is harder. So, here’s the premise. We often are dealing with situations that are ambiguous. The answer is not straightforward. There’s going to be some amount of negotiation or conflict that I need.

These are regular occurrences in our work days and in our lives outside of work. We also deal with some situations that are pretty straightforward. You know, like, “Are you going to pick up the kid or am I going to pick up the kid?” “Do we send this email to the client tomorrow morning or this afternoon?” We don’t need to reduce a lot of ambiguity, have a lot of discussion around a lot of those issues. They’re pretty easy to resolve.

What I see happen often, though, is that we choose the wrong medium, the wrong tool for the job given the level of ambiguity, disagreement, discussion that needs to take place. So, think about an issue, I’ll just give an example of something that happened to me. We needed to do some re-budgeting in the department that I worked with, and I chair a department and I was working with one of our assistants.

I happened to be traveling. I was in Europe when this issue came up and we needed to sort of quickly talk about the budget and recategorize some things. And I just kept thinking, “This is like a straightforward issue. Let’s just do X, Y, and Z.” And my admin person that I was working with kept, like, responding in these kinds of weird ways. And it wasn’t clear that she was going to make the changes that I was suggesting.

And then, like I would get kind of more upset and my email became a little tenser, and I said, “Look, we just need to act on this.” And then there was a day of response, compounded by the fact that I was overseas, and I was eight hours’ time difference. And this became such an emotionally exhausting interaction for me because I began to think, “Oh, man, she’s trying to subvert me. Like, she’s not responding on purpose to this.”

And I was kind of spiraling, having these negative assumptions. And what I realized kind of in the process was, “You know, this is not a super simple issue. My first impression was this was simple, but if I really thought about it, this is much more complex. And I’m trying to resolve this complex issue through email asynchronously. And we have this time difference.”

“And the best thing that I could do to reduce this ambiguity and to stop me making so many assumptions and her making so many assumptions is just to hop on a Zoom call.” And we did, and we hammered out the whole issue in like 10 minutes. But it was two days, or almost three days, of me like wasting my life away, it felt like, being upset about this. I talked to my wife, I was like, “Oh, I’m so frustrated by this interaction that I’m having.”

But what didn’t I do? I didn’t stop to say, “What am I trying to accomplish here? And what’s the best mode of interaction to deal with this problem? It’s an ambiguous situation. It’s going to require some collaboration, some real time discussion.” And if I just had picked up the phone, just had done the Zoom, I would have resolved this so much faster.

But when we don’t do that, things escalate. We send more emails that are pulling us out of our attention that we’re paying to other things at the moment. We’re forced to make more inferences about, “Why didn’t this person respond faster? What did they mean?”

And the same goes in the opposite direction, that if we have a super simple issue and then we have a big meeting to discuss it, when really it was like, we pretty much could have just decided this via email, we waste a ton of time and attention and emotion talking to death about something that we could have resolved much more easily.

So, we can reduce our attention, we can reduce the amount of inference that we’re making, if we’re matching the complexity of the challenge with the capabilities of the tool. So, the shorthand here is, if you’ve got a more complex challenging issue, you want to use a tool that’s going to put you in real-time collaboration and discussion so you can resolve those issues interactively.

And if you have a pretty basic kind of thing that you’re trying to solve, then switching to a low-fidelity medium that just like allows you to say yes, no, agree and move on, probably is going to be the best bet. So, making a match between those information requirements and the capabilities of the technology is one key way to reduce that inference-making and attention switching.

Pete Mockaitis
That’s handy. And I’m also thinking about making a match associated with the time necessary for something. I think if you’ve got a mismatch on either side, it’s frustrating and annoying in terms of, “Why are we having a three-hour meeting about this? This is ridiculous,” versus, “Okay, we’re just going to figure out this tricky challenge that’s been vexing the business for eight years in our little 30-minute call.”

Paul Leonardi
Exactly.

Pete Mockaitis
Well, either way, you’re going to find frustration if you have a mismatch of the tool, the medium, or the time. And then I think that expectation piece as well is tricky in there because it almost seems like you “should” be able to resolve it in the time that you have scheduled for it when you may just have scheduled the wrong amount of time.

Paul Leonardi
Yeah, and then everybody feels frustrated and demotivated because, “Well, clearly, we didn’t do our job right. We should have figured this out in an hour. We must be a dysfunctional group or we must not have brought the right information to this meeting.” When, to your point, perhaps it was an inappropriate time allotted for this in the first place, “And we never could have done it. And now we just all feel worse for having tried.”

Pete Mockaitis
All right. So, make a match. What’s your other favorite approach?

Paul Leonardi
Yeah, another one that I really like is the first rule that I talk about, which is reduce half your tools. And this is one that a lot of people give me the side eye about when I say it, like, “What do you mean by just like stop using half of my tools? Am I really going to be able to do that?” The answer is, yes, you’re really going to be able to get most of the way there at least, you know, 50% is just a rough number anyway.

But if you think about these ideas of attention switching and inference, the fewer tools that we have in our toolset, the less likely we’re going to be to suffer the problems associated with those two drivers of exhaustion. So, one of the things that I really suggest that people focus on is to look at, and really make a list of, “What are all the different technologies that I’m using on a daily basis?”

I used to ask people to do this 10, 15 years ago, and they come up with about 10. And a lot of those were hardware. So, they would say, “I use my laptop, and I use my BlackBerry, and I use…” you know, whatever. Today, the number is more like 30. People come up with about 30 different tools that they use in a regular day, and most of those are applications. Many of them are at work, “I use SharePoint. I use Zoom. I use, whatever it might be, ChatGPT.”

And many of those are at home, “I use Instagram and I use Zillow and I use Game Changer app to keep track of my kids’ games.” And one of the things that I recommend is, when you make this list, that you first start going through and you say, “Okay, well, which ones of these do I have the actual power to cross off this list?” And, usually, we have more power at home than we do at work.

And then I say, “Well, which ones are functionally duplicates of each other? So, are we using two tools to do roughly the same job? So, do I have a Zoom meeting sometimes and then I have a Microsoft Teams meetings other times? Or do I use Canva and Photoshop, when, really, they’re doing the same thing and I don’t know why I use both of them anyway?” And so those are candidates for reducing from our list.

And then there’s other ones where, “I’m actually just sort of in charge and there aren’t network effects.” So, you know, it may be that I say, “I really would love to give up Slack in my organization, but I can’t just give up Slack because everybody uses Slack, and they depend on me.” However, I’ve talked to a lot of people that have two or three team chat applications. And when I ask them, “Well, why in the world does your team have two or three?” nobody can really recall.

And so, what I find is that many people have told me that they actually will raise this in their organizations, and say, “You know, like we’re chatting on Teams and on Slack and on this third application. Like, is it possible we could just reduce to one?” And usually the team is like, “Yeah, like why don’t we just stick with Slack or whatever?”

And so, we actually do have the power to reduce the number of tools in our toolset. I think, in more ways, we have more degrees of freedom than we typically think we do. And doing that just means that now we’re switching between fewer applications and we’re doing fewer things that are creating those attention-switching and opportunities for inference.

You know, just a super quick example in my own life, it used to be that in a given morning, I might be on Zoom, Microsoft Teams, and Cisco’s Webex, you know, I would be doing video conferences on all three. And that doesn’t sound like a big deal except that I’m very comfortable with Zoom, because that’s the one my organization uses most often.

And when I switch to a different one and I’m trying to share my screen or engage in the chat or create a breakout room, there’s those moments of, “Oh, where’s the button for that? And how do I create the breakout room because I’m not as familiar with the other platform?” And it’s those little moments of friction that add up to be exhausting.

And reducing those, as much as we possibly can, just give us a cleaner starting point and is going to reduce the odds that we’re going to feel exhaustion from our tools if we can reduce the toolset. And my advice to leaders in organizations is that, often it’s difficult to really make a noticeable difference in the volume of tools that we have unless you step in and you make some decision.

I had one senior leader tell me, “You know, I think of this like the Smokey the Bear slogan, ‘Only you can prevent forest fires.’ It’s like, I feel like I’ve really realized only I can prevent technology proliferation.” And that’s because you’ve got the model for many of these SaaS vendors who sell tools in your company, is to price it in just a way that anybody can buy that application with their credit card.

It sorts of sneaks in right below the spending limit of, “I need formal approval from IT.” So, you get all of these applications that kind of spring up everywhere. And unless you have someone looking and saying, “Look, we’re not paying for 20 different subscriptions to the same kind of tool,” or, “We don’t need three different kinds of computer rendering platforms,” it’s really easy to get stuck with too many tools and increase our overload.

Pete Mockaitis
Yeah, it’s interesting how I’ve experienced this and, it’s so funny, it doesn’t seem like it “should” be that big of a deal. But if I have to hop into six different tools to accomplish a task, even if it’s only like a 10-minute task, it really does take a toll, more so than if I were just cruising through email, say, for 10 minutes. And it’s just so funny that that’s just kind of the human condition.

Paul Leonardi
It’s true. And we don’t notice it. I think I liken it to running sprints, okay? So, if you run all out on a sprint, let’s say for 10 seconds, and you cover a hundred meters, you feel pretty good. And the next sprint that you run, if you’re not resting adequately, you might cover a hundred meters in 12 seconds. And then the third one, you cover a hundred meters in 14 seconds.

You feel energetic, right? You feel like, “I can do it,” but it’s the accumulation of that fatigue over time that eventually hits you, and someone says, “Okay, run one more hundred-meter sprint,” and you’re like, “No, I can’t do it. I’m too exhausted.” And it’s those little micro moments that add up to big exhaustion feelings at the end of the day, just like you described.

Pete Mockaitis
All right. Well, Paul, tell me, anything else you want to make sure to mention before we hear about some of your favorite things?

Paul Leonardi
I just want to say, okay, AI, this is where I think AI, if we do it right, because we’re still in the early stages, could be really useful. If we can figure out how to put AI in a role that helps us to stay engaged in a task, keep our focus without having to switch across so many different applications, without having to go look for so many different pieces of information, that’s where these tools could be most useful in helping to reduce our exhaustion.

So, I’m optimistic. I wouldn’t say that I think that that’s where everything is going, but I’m optimistic that these tools might be helpful as they keep us in our workflows, keep our focus and engagement in areas that we want by reducing the number of tools we need to switch across and reducing the amount of attention changes that we constantly have to make.

Pete Mockaitis
All right. Well, now could you share with us a favorite quote, something you find inspiring?

Paul Leonardi
It’s attributed to the philosopher Voltaire. I’m not sure if there’s any real record that he said it, but the older I get, the more I appreciate this quote. And it’s, “Cherish those who seek the truth. Beware of those who find it.”

Pete Mockaitis
Okay. And a favorite study or experiment or bit of research?

Paul Leonardi
Yeah, one of my all-time favorites is The Jam Study that was done by researchers at Stanford, Iyengar and Lepper. And what they looked at was people buying jams. And it was a really neat little experimental condition where they showed people, I forget the exact number, but like three or four jams, and then said, “How many did people buy jam?”

And then they gave them a display that had like lots of jams, like 20 jams on them. And then they said, “How many people bought jams?” And you’re way more likely to buy a jam if you saw three or four jams than if you saw 20 jams. And their conclusion was too much choice is demotivating. And I love that. It’s a simple study, a powerful finding. And every time I go to a restaurant and get one of those menus that seems to span 30 pages and can’t decide what I want to eat, I remember that study.

Pete Mockaitis
Yeah. And a favorite book?

Paul Leonardi
One of my favorites is At Home by Bill Bryson. I just really love the way Bill Bryson writes. He does a couple of things. One, he just takes these, what you would think are mundane topics, like At Home, he has a 17th century English farmhouse that he lives in, and he uses that, he walks through every room in the house, and uses that to talk about, “Well, what was life like four centuries ago?” And that’s cool.

Pete Mockaitis
All right. And a favorite habit?

Paul Leonardi

This is one that I’ve been cultivating much more since writing the book, and it’s about being intentional. So, when I pick up one of my devices, or I’m going to get on my computer, I really take a beat and think, “What am I trying to accomplish? And how will I know that I got there?” And what that does for me is it allows me to bookend my experience.

It tells me, “You did it. Time to close your browser,” or, “Okay, you finished doing this. Time to put your phone down.” And if I don’t start with that intention, it’s easy to spiral into just continuing to scroll and doing all the things that make me exhausted. So that’s my new favorite habit, be intentional every time I sit down in front of a device or pick one up.

Pete Mockaitis

Okay. And is there a key nugget you share that really connects and resonates, and people quote back to you often?

Paul Leonardi

Yeah, they say about this, the idea of, “I don’t want to give up all of the technologies that do great things for me. And I haven’t been able to figure out what I’m supposed to do then to find the right balance.” And the fact that you give some rules and say, “Technology is not the problem. It’s how we use it, how we orient to it, that it really is,” they tell me that’s been empowering.

Pete Mockaitis

All right. And if folks want to learn more or get in touch, where would you point them?

Paul Leonardi

Yeah, I say go to PaulLeonardi.com, or you can find me on LinkedIn. I think P. Leonardi is my handle there. Those are great places to find me, or at UCSB’s Technology Management Department.

Pete Mockaitis

All right. And do you have a final challenge or call to action for folks looking to be awesome with their jobs?

Paul Leonardi
Yeah, I would say really practice being there, wherever you are. We live in a world that makes it very easy for us to be everywhere else but here, which we can teleport in our minds to places, we can be on our devices and be halfway across the world. But there’s a real power in just being where you are, be in the meeting, be in the conversation, be with your kid. Try that and I think you’ll see there’s a big difference.

Pete Mockaitis
All right. Paul, thank you.

Paul Leonardi
Thanks so much for having me.

1111: How to Get Better Results from AI to Amplify Your Productivity with Gianluca Mauro

By | Podcasts | No Comments

Gianluca Mauro discusses the mindset and habits for getting the most out of AI tools.

You’ll Learn

  1. How to avoid the trap of AI “workslop”
  2. What you can and can’t expect AI to do
  3. The CIDI framework for better prompting

About Gianluca

Gianluca is the Founder and CEO of AI Academy, an AI education company founded in 2017. AI Academy has trained more than 12000 individuals and teams to harness the power of artificial intelligence for more productivity and better results.

Gianluca has over 10 years of experience consulting and building AI for organizations and currently teaches at Harvard’s Executive Education programs. He’s also the author of the book Zero to AI and the investigation on AI gender bias “There is no standard’: investigation finds AI algorithms objectify women’s bodies”, published in The Guardian.

Resources Mentioned

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Gianluca Mauro Transcript

Pete Mockaitis
Gianluca, welcome!

Gianluca Mauro
Hey, thank you for having me.

Pete Mockaitis
Well, I’m excited to be chatting with you about AI. You are a genuine expert. You’ve been researching and studying this stuff way before even normal folks had heard of this ChatGPT business. So great to have you. And tell us, any super surprising discoveries you’ve made along the way as you’re researching and teaching this stuff?

Gianluca Mauro
Well, first of all, I think something that is interesting to think about is when ChatGPT came out three years ago, it was the “Oh, my God” moment for most people, right? But AI has been out there for quite some time in different shapes and forms and with different levels of usefulness, let’s say. And I think the first “Oh, my God” moment for me was when I realized that, basically, every industry and every professional could find a use for AI.

And I’ll tell you probably what was the most interesting, or strangest maybe, project I worked on. I worked on an AI project to control the quality of diapers in a factory. So, yes, you can use AI for pretty much everything.

Pete Mockaitis
Well, now I just can’t let that go. How does AI help do quality control for diapers?

Gianluca Mauro
Well, so are you ready to go on a journey on how a diaper factory production unit works?

Pete Mockaitis
I imagine AI might be able to analyze rapid photographic imagery of diapers as they come off of the line to assess quickly potential for defects and fix the issue more quickly upstream prior to them being packaged and having to be thrown away. But I’m totally making that up.

Gianluca Mauro
You got it.

Pete Mockaitis
Oh, I feel like a genius. Yes!

Gianluca Mauro
Oh, my God, you are. This is extremely accurate. Extremely accurate. We had this issue that, you know, they basically have, a diaper is basically two layers of elastic material with something that is absorbing in the middle. And then if you pull this elastic material too much, it breaks, especially when you’re cutting it into shape.

Pete Mockaitis
Been there.

Gianluca Mauro
Yeah, exactly. So, if you had kids, you know that that’s not fun. So, we were looking at all these pictures in the factory as they were cut into shape to try to understand, well, what was the ideal size of those big elastic rolls and try to basically optimize productivity. So, that was quite a crazy moment because, think about this.

I did this project maybe seven or eight years ago, so three or four years before ChatGPT came out. It was not obvious for anybody or for any company that they might have a use case for AI.

So, imagine me when I went and pitched a diaper production company, “Hey, maybe you should look into AI to minimize the mistakes, the defects that come out of your factory.” It was not obvious at all. It was quite interesting to find actually amazing use cases in that context as well.

Pete Mockaitis
Well, that’s very, very intriguing. Well, so we’re talking about everyday professionals utilizing ChatGPT or other AI tools to be more productive. You’ve got a LinkedIn Learning Course on exactly that. So that’s pretty handy. Could you maybe start us off by sharing what’s perhaps a fundamental misconception or mindset shift that helps make all of this stuff make sense?

Because I imagine we could spend all day talking about, “Oh, here’s a really cool prompt,” or, “Oh, here’s a fun little tactic,” “Here’s a nifty little thing you might try.” But could you maybe set the stage for us on a more principled foundational level to help us scaffold the rest?

Gianluca Mauro
Absolutely. And I think the most important thing for everybody listening, you need to understand that, in order to really get value from AI, the number one thing you should focus on is your mindset and changing your habits. This is not anymore about necessarily getting the right tools. Most tools are pretty good today, not perfect, but, you know, they’re pretty solid, especially compared to three years ago. And it’s not even about having the most amazing prompting skills.

The biggest bottleneck is your habits. How much have you embedded AI tools and new different workflows and ways of working in your day-to-day work?

I’ll give you an example, I love making this metaphor. It’s like going to the gym. So, let’s say that you have the best equipment. That’s the equivalent of having the best tools. And let’s say you also have amazing skills. You have a squat with perfect technique and you know exactly how to do a really good bench press. And that’s the equivalent to having really good prompting skills.

But then let’s say you never go to the gym. Guess what? Your muscles ain’t going to grow. You’re not going to lose the weight that you want to lose. That’s not going to happen. I would rather see somebody with okay tool selection and with okay prompting skills, but, really, somebody who’s invested a lot in rethinking the way that you work and is curious and is constantly trying new things out than having somebody who has read all those scientific publications about best prompting techniques and has bought all the AI tools, but then has not adapted the way that you work to work with these tools.

That’s the most important thing today in this context. I wouldn’t have said that three years ago, but that’s where we are today. You need to really change the way that you work and embed them in your workflow. And that requires a little bit of effort.

Pete Mockaitis
I hear you. It does require a little bit of effort. And I would also say some discernment, because I think that my impression is, and you can tell me if this is accurate or not from your research-based perspective, it almost feels like a lot of companies, CEOs, products, just kind of want to shove AI into something because investors want it, the stock market seems to like it, and maybe some people are impressed.

But I’m almost at the point now, when I see a tool say, “Oh, now we have AI,” I’m like, “Oh, geez. Is it any good or is it just going to disappoint me again like all the rest, you know?” And so, that’s my take is that, yes, we should take a look at our habits and get into the groove of using AI tools where they’re genuinely helpful and useful and handy. And that requires a little bit of change management on our own parts.

But my hunch is there are also times where you say, “No, AI has actually no place in this little piece whatsoever, and so we’re going to deliberately choose to not stick it here but instead put it over there.”

Gianluca Mauro
You’re spot on. And there was actually research about this that I found really interesting. It was done by Stanford with a couple of other people, and then the Harvard Business Review wrote an article about this that went quite viral. The title of the article is “AI-Generated ‘Workslop’ Is Destroying Productivity.”

Pete Mockaitis
That’ll get some clicks.

Gianluca Mauro
That’s going to get some clicks. Exactly. And so, the main outcome of this research was that if you ask people, “Hey, what do you think about your colleagues who use AI?” You’re going to find that colleagues who use AI are often perceived as less creative, less capable, less reliable, less trustworthy and less intelligent. And that is not great.

Pete Mockaitis
Yeah, fair.

Gianluca Mauro
You do not want to be perceived as less intelligent, trustworthy, reliable, capable and creative. So, the interesting thing in this case was I honestly don’t think, and that’s also what the researchers found, that that’s a problem of AI per se. The problem is that a lot of people are using AI just in the wrong way. What does that mean in practice? Well, AI workslop is basically when you are trying to use AI as an amplifier of your laziness, basically.

Pete Mockaitis
Ooh, tweet that!

Gianluca Mauro
Yeah, and I want to give a practical example, okay? Let’s say that you ask me, “Hey, Gianluca, I want to know how I might use AI in my podcast,” okay? And let’s say that I am just so lazy, I don’t want to think about what are your challenges. I don’t want to think about what are your objectives. I don’t want to think about your audience. I just go on ChatGPT and I ask, “Hey, how might a podcast producer or host use AI?” I get a research. I copy it. I send it to you. What happened?

I got a generic piece of, like a bunch of text basically, on a PDF. I gave it to you and it took me no time to produce that. It took me, like, 30 seconds to get like a bunch of text that sort of makes sense. But I’m going to waste your time reading something that is so generic that you could have found on one Google Search. So that is something that damages you because you just wasted your time reading the report that is generic and has wasted my time as well, because now you’re going to ask me questions I need to go and fix it and you’re going to think less of me, etc.

Now let’s see what I should have done if I wanted to use AI to make it way, way better, way more interesting. I would have started asking you questions, “Hey, Pete, what are the top challenges that you have? What are your objectives for next year? What do you think could be the thing that helps you the most? Do you want to be more productive? Do you want to repurpose your content more effectively? Do you want to be able to research your guests better? Like, just tell me, tell me what’s going on.”

You provide me some context. Context is a keyword that is super important in today’s AI era. You give me some context. Then with this context, I go on ChatGPT, and I say, “Hey, I interviewed Pete. These are his top challenges. What do you think might be a relevant use of AI?” Now start getting something interesting. I start getting something that is more relevant.

And then I might say, “Okay, cool, ChatGPT. Now go and find top case studies of similar podcasts to How to be Awesome at Your Job that have done something similar. Now find some tools. Now tell me what could be potential risks.” The output, then, that I send you is going to be much higher quality and it’s going to actually give you value.

But notice how the difference is not the tools. It’s not that I used a different tool that is not ChatGPT, or is that I had some special prompting skills. It’s just that I’ve been mindful. I’ve been mindful of what might be interesting, what might be relevant for Pete, and how might I use ChatGPT to basically boost my productivity and make my suggestions for Pete even more and more relevant and useful.

You see the difference. It’s not about the tool. It’s not about how good am I in prompting. I didn’t talk about doing anything particularly fancy here, okay? It’s not fancy prompting technique, there’s no coding involved, it’s just a different mindset. I tried to use AI to amplify what I would have done if I didn’t have AI. And that really works.

Pete Mockaitis
Yes, it really does. And what you’re reminding me, and you’re talking about amplifying your laziness. I’m thinking about there was a fabulous interview on The Copywriter Club Podcast, which I listen to, even though I’m not a professional copywriter, but we’re doing copywriting all the time. And there was a famed copywriter on there. We’ll look him up and put him in the show notes.

And he said, “When I’m using AI to assist me with copywriting, I don’t say, ‘Write me a sales letter.’” It’s like, “What I do is…” well, first of all, he’s using the custom APIs of an AI tool as opposed to any off-the-shelf chatbot. And then he’s saying, “Okay, I’m going to write this part of a sales letter, given all of these instructions that I have previously written for what I’m into, as well as several examples, as well as what the product is and how it’s helpful to a certain user base on these needs and want and preferences and desires and pain points. And then, so voila.”

And so, there are numerous multi hundred-word prompts associated with doing a thing. And then he was like, “Okay, this is a pretty good draft. And from that I can tweak.” And so, we’re not amplifying laziness. In fact, a tremendous amount of thought has gone into what we’re doing here. And then, because he’s done it many, many times, and he also said AI does not account for taste.

Gianluca Mauro
Yeah, exactly.

Pete Mockaitis
And then from there, you can get it. And that was a real lightbulb for me, which I’m connecting now with your amplifying laziness comment. It’s like, yeah, if you just say, “Hey, do this thing,” you’re going to be disappointed. But if you put a ton of thought into it, it can kind of get you to a draft substantially faster.

Gianluca Mauro
Absolutely. And I’ll tell you what, you can amplify laziness, but you can also amplify your expertise. You can also amplify your perfectionism, if you’re a perfectionist like me. And I will give everybody a very simple thing that they can try right now. So, I’ll give you a simple prompt structure that you can use. And it’s very simple, okay? Just four lines.

So, start with some context. Context is basically the who, the why, and the what. So, you might say, “Hey, I am a podcast host. I need to…” whatever, “…prepare for a new interview with this person. My objective is to make sure that I ask the most interesting questions about this person.” Okay, that’s context. What are we talking about? I’m assuming I’m putting myself in your shoes, by the way.

Okay, so that’s the context. Then you say, you ask AI, “I will give you, for instance, a list of questions I prepared.” Something you’ve done, okay? Something that, you know, maybe 50% effort, something that is almost there. And then it will say, “You will tell me…” that’s what you’re telling the AI, “You will tell me three things I’ve done well and three things I could improve.”

“For each improvement opportunity, provide suggestions on how I could implement them. Make your feedback concise and reference specific parts of the text I gave you.” And then you just paste in your work at the end. I use this all the time.

And it’s such a simple way of using it, right? It just takes something you’ve done, and you just say, “Hey, this is my context.” Again, context is super important. It’s super important, because if you don’t put your who, why and what, then you’re get generic advice that might actually lead you in the wrong direction, right?

So, if you put the right context and if you ask this, so much value and, honestly, you can get to some pretty amazing return investment in like two minutes. Every skeptic I have, every skeptic I speak with, and, you know, I still meet quite a lot, I ask them to do this, and they always come out quite interested in the tool after that.

An example I can give you is I worked with lawyers. Gosh, lawyers are an interesting crowd, because obviously, they’re very critical for really valid reasons.

And I always tell them, “Look, take a case that you have that you can share publicly, take a response that you have written or something that you’ve produced, and just ask for three things that you’ve done well and three things that you could potentially improve and how.” And, usually, they get one thought, and they’re like, “Huh, I haven’t thought about it. Interesting.”

Then they might decide not to use it. That’s up to them. But having a really expert second opinion with a one-minute effort and for free, honestly, “Where do I sign?” It’s amazing, isn’t it?

Pete Mockaitis
Yes. And I’m thinking about, when you said expert opinion, it’s funny, when I heard that, I reacted a little bit because I’m thinking about Sam Altman talking about, you know, doing his very Sam Altman storytelling thing that he’s good at. Talking about the release of GPT-5, it’s like, “You know, before it was like you’re talking to a high schooler. And now it’s like you’re talking to a PhD in any area.”

And so, I was like, “Hmm, this is really not my experience at all, good sir.” But I think it’s expert in the sense that it’s been around the block. It’s like, “Yo, I’ve read the whole internet, okay? So, in that sense, I’m expert.” And I’m thinking about, there’s this book called Obvious Adams. It’s all about thinking, “Well, what would be the most obvious thing?” Or, Tim Ferriss says a question, “What would this look like if it were simple?”

That’s often my experience is it says the thing that’s not crazy, innovative, and brilliantly never before seen, but it’s like, “Huh, I probably should have thought of that, but I didn’t, and you did. And because you’ve surfaced that, we’re moving this forward, and that’s helpful. Thank you.”

Gianluca Mauro
Yeah, absolutely. So, I think one thing that is really not intuitive is that AI sometimes feels extremely smart and sometimes feels extremely dumb. And it’s really hard to predict, whether for my specific task is going to be, you know, the former or the latter, like, “Is this a 10 out of 10 question or is it going to be a one out of 10 question?”

There was this famous viral thing, viral experiment that came out, which is if you asked AI to count how many Rs are in the word strawberry, it would just say two, and there are three, right? I think a five-year-old can do that, probably, you know, but AI can’t do that. But, hey, it can write a pretty good legal letter for, you know. It’s just like so weird. It’s like it can do math, it can write code, but then it can’t count Rs in the word strawberry. Like, what is this?

And I think we just need to understand that it’s called artificial intelligence, but it’s not intelligent in the same way that humans are. It’s a different kind of intelligence. It processes data in a different way. It’s really hard to just give people a sort of like cookie cutter, very simple rule of thumb to understand when you’re in a good space to ask questions to AI and when not.

You just need to develop a little bit of sort of a gut feeling for, “Hey, this is something where I might get something good, and this is something where I might not get something good,” but there are guidelines. And the guidelines are, there was this research done by Harvard Business School, and they basically came up with a very simple classification of skills that AI has, so to say, AI capabilities. They call them within the frontier skills.

And these are four, very simple. Copywriting. AI is amazing at taking text and just turn that into other text. Now, a professional copywriter might argue whether that’s good copywriting or not. That’s a different conversation, but it’s amazing at just manipulating text, writing poetry or, think about this. It can write poetry and a legal document. I can’t do either, okay? So, it can do all these things. So that’s the first one, copywriting.

Second one is persuasiveness. So, it can write pretty good arguments if you ask it to, which is interesting. The third one is they call it analytical thinking. And it’s quite interesting if you give it a complex problem, and if you ask it to analyze it, it can give you recommendations or different ways to look at it.

And that’s the example that I gave you before, right? If you give it something that you have produced, legal letter, interview questions, whatever, and you say, “Tell me three things I have done well, three things I could improve based on the context,” it does it really well. So, this sort of like analysis, analytical capabilities.

And the fourth one is creativity. Now, people argue whether that’s real creativity or not. I don’t want to get into that philosophical conversation, but from a pragmatic point of view, it is quite creative, honestly. I had this thing a few days ago where I had a framework that I came up with to support companies in finding use cases for AI. And I was like, “How do I call this thing?

And I just gave it to GPT-5 Thinking, and I said, “Just please come up with an acronym.” And I would have never come up with any of them. It was super interesting and creative and it worked quite well. So, these are four things where you can feel quite confident. So analytical thinking, copywriting, persuasiveness, and creativity.

Now they also found where AI does not perform well at all. And that’s when you’re asking it to give you a recommendation, analyzing a bunch of different conflicting pieces of evidence. Let me give you an example. What they did is they took a few researchers, sorry, a few consultants from Boswell Consulting Group.

They took these consultants and they asked them to analyze a bunch of evidence of different strategies that a business might decide to go for to launch a new product, okay? Three different strategies. There’s a PDF with a bunch of interviews. There’s an Excel sheet with a bunch of numbers. All of these things, you need to look at this evidence and ask AI to help you in identifying the right strategy.

What they found is consultants perform better if they did not use AI to come up with the right strategy. Why did that happen? Well, because when you have conflicting evidence, conflicting pieces of information, in this case, imagine data said, I’m just coming up with stuff now, data said that sales were going up. But in an interview, somebody’s sales are going down. There was this conflicting piece of evidence.

AI was basically just like going with one. It was really hard for the AI to understand what was true and what was not. Whereas, for humans, it just made more sense to, for instance, look at Excel sheet, but ignore the interview because they thought maybe this person doesn’t know, doesn’t have the most updated data, for instance, that’s an example. So, AI was just like misled by the data that you provided.

Unfortunately, that’s how a lot of people use AI. A lot of people use AI today this way. Get a bunch of PDFs, a bunch of data, a bunch of emails, a bunch of stuff, throw it in, and they just ask for a quick answer to the problems. AI doesn’t work that well when you provide an insane amount of information and just ask, “Hey, tell me what I should do.” You should go step by step. You should use it to, again, amplify your thinking.

So, a better way would be, put this data in and say, “Hey, can you summarize the key takeaways from each one of these documents?” You take them and then you say, “Okay, what might be a good strategy? What might be good arguments for strategy one? And what might be good arguments for strategy two and strategy three?”

You see how you’re using it as a co-pilot. And that’s a really good branding from Microsoft, by the way. You’re using it as something that assists you in thinking rather than a, “Hey, I’m going to throw all my data. Just go ahead and do my thing. I’m lazy. I’m just going to copy your output and give it to my boss, you know.”

Pete Mockaitis
Yeah, I like that a lot. And, in a way, it really makes sense that it is that way because it just says, “Hey, I just know what words mean and what words tend to come after and next to other words. I don’t actually know that some dude’s opinion is of less importance and should be given less weight, gravitas, than a summary sales data reflective of millions of transactions.

Gianluca Mauro
Yeah, and it’s sycophantic as well, so it’s trying to please you. Imagine like, you know, you go to a doctor and say, “Hey, I have some headache,” and the doctor tells you, ‘Get this. Get this pill and just go.” Well, that’s not a good doctor. You should ask a little bit more questions and trying to understand.

What AI, and this is improving by the way, but historically, has been trained and, you know, it’s used to just get an answer. And so, if you provide maybe conflicting piece of information, as we said in the case study before, it’s just going to try to give you an answer rather than pushing back. And I go back to what I was saying before. This means that the tool is powerful, but it all comes down to the mindset that you have when you use it.

Do you want to have quick answers and you just want to get as fast as possible to a bunch of texts you can send to your boss or you can publish on LinkedIn? It’s probably going to just boost your laziness and just not get anything high quality. But if instead you use it as an amplifier for your curiosity, for your expertise, for your capabilities, well, now we’re talking. Now you can really get to some amazing outputs.

Pete Mockaitis
Yes, I like that a lot, the amplifier. And it’s interesting, is sometimes, I think when you look at the prompt that you’re sharing, it really does kind of garbage in, garbage out, and it’s the opposite, you know, magnificence in, magnificence out. So, I could say, “Hey, give me some information about sleep apnea.” And so, it can say, “Oh, well, this is a common affliction, blah, blah, blah.”

But then what I’ve said is, “Show me the results of several human randomized control trials that utilize novel interventions for the treatment of sleep apnea, i.e., not a CPAP machine. And give me a summary of the quantified impacts associated with the apnea hypopnea index reduction associated with each.” Now that, and sure enough, that has led me to some interesting places. And I found this thing called inspiratory muscular training. You breathe against resistance. And what do you know, that really helps.

Gianluca Mauro
Interesting.

Pete Mockaitis
And I’m not using a CPAP machine. So, thank you AI for putting me in some good directions. But I think it shows that, “Are we amplifying laziness or are we amplifying a targeted, ferocious curiosity?” Like, “No, find me precisely this, and then we can play ball.”

Gianluca Mauro
Absolutely. You’re spot on. It’s perfect. But, to me, the interesting thing about this whole concept is that there’s quite a lot of responsibility on the user.

It’s basically telling people, “Hey, if you don’t get the right output, it might not be because of the tool. It might be because of the way that you are using the tool,” which from one point of view, I think is empowering because it’s basically telling me, “Hey, amazing, I have some agency over the output that I get.”

But from the other point of view, I think some people might find it a little bit stressful, “Now I need to learn about A, B, C, D, all these different things so that I can actually use this machine well.” Well, yes, but at the same time, honestly, as I was saying before, it’s about changing habits. It’s not that hard. You don’t need to get a PhD in Math to understand how to use one of these tools.

And so, what I recommend to people who might feel a little bit maybe overwhelmed, or maybe afraid that you’re using it wrong, I always tell people, “Hey, find your little safe space to experiment. Take a hobby that you have. Maybe you’re interested in, I don’t know, Formula One.”

That’s one of the latest things that I’ve been nerding about. And just go and try to do your researches and prompts and test things about Formula One that’s maybe not related to your job so you feel safe. There’s no fear of putting sensitive information into these tools, and just try to get a sense of how the tool might be helpful and useful for you in a setting where you’re free to experiment. And then you can take all these learnings and apply them to your job.

Pete Mockaitis
Okay. Well, so you are somewhat famous for your CIDI framework – context, instructions, detail, and input. And it sounded like you were giving us exactly that in the context of, “Hey, give me some feedback on a thing.” And so, can you give us a little bit of detail for how we might think about applying this in all kinds of different ways?

Gianluca Mauro
Absolutely. So, the CIDI framework is a framework that I came up with, I think, a couple of years ago, maybe. And my objective was to find a simple recipe to get people to think about their prompts in the same way that I think about my prompts.

And so, it’s quite simple. It starts with C stands for context. Tell me who you are. Why are you doing this task and what do you need to do? Just try to make AI get into the zone of, “What are we talking about?” Think about this, AI might act like a lawyer, might act like a doctor, might act like anything, right? So, you need to zone in.

The second part is instructions. When I say instructions, it’s important that you’re very clear, and you’re talking to a thing, not to a human so you can be very direct. And I typically give my instructions this way, “I will tell you this, you will do that.” “I will give you an email I wrote, you will give me feedback on it.” That’s the instructions part.

The third part is details. Details are, basically, I look at it this way, it’s very simple, “Explain what good means for you. What does a good output look like for you?” And that’s an interesting question. I feel like it’s almost meditative. It’s almost like therapy. You need to ask yourself, “What do I want? What do I really want? How does a good podcast script look like? How does a good LinkedIn post look like?” And just describe it in plain words.

Pete Mockaitis
Or, I guess this could also be examples, like, “And here are three instances that I consider good.”

Gianluca Mauro
You got it. That’s the part of the prompt where you might want to put, for instance, something you’ve done in the past, and say, “Hey, look, this is something that I consider to be really good,” or, “This is something that represents my tone of voice, and I want you to try to replicate that.” That’s the details part.

And the last part, the input, is when you put actually what you need to produce. So, for instance, if you need to have feedback on a legal document, you put it all the way at the end. The reason why I structure it this way – context, instructions, details, and input – is that it’s very easy to reuse.

So, if I write a really good prompt that explains exactly who I am in the context and what I need to do, exactly what I want out of it in the instructions, in the details, and then the input is, let’s say, this legal case that I need to analyze, the next time I have a new legal case to analyze, I just need to replace the last part of my prompt. The first part of the prompt, the context, instructions, and details are the same.

So, it makes you, number one, think about all the important things in a prompt and leaves really little room for error, because you need to think about all of them – context, instructions, details, and input. But it also makes your work scale a little bit. Because some people, and I get it, get stressed, “I need to write a good prompt. How long is it going to take me to explain who I am, what I need to do, yadda yadda, yadda. What does good look like?” I understand it can be a little bit of a pain if you want to write a really long and cohesive and complex prompt.

But if you write it this way, then it’s very simple to reuse. And that’s your copywriting podcast guy. That’s a perfect example. I think he was prompting, using, maybe without knowing, but he was using that sort of structure, it sounds like, because he had some things that you could probably copy and paste again.

Pete Mockaitis
Certainly. I think it is John Morrow is his name, and we’re going to include that in the show notes. Indeed, the context is, “Hey, we’re a sales letter for this product for, you know, which serves this user with these needs, wants, concerns, who use language like this.” And then the instructions are, “Write the headline of a sales letter.”

The details are, “Here are some other headlines that we think are fantastic, as well as the general guidelines of copywriting that we find to be effective in this industry.” And that might be hundreds or thousands of words, and that’s acceptable, right?

Gianluca Mauro
Yeah, I mean, always try not to go too crazy because then it becomes too much context, right? I think AI could maybe process it, but I always say, you know, if you try to put too much stuff and you’re not fully sure about what you actually put in, then you might have added something that is actually misleading. So, try to keep it in check. Don’t put too much if you don’t know what you’re putting in. But, yes, conceptually makes sense.

Pete Mockaitis
And to that point with the context, I mean, I believe, you know, we’re like a hundred thousand plus tokens. So, is it your professional opinion that, okay, you might have a hundred thousand tokens, but don’t use 50,000 words? Or, what’s your take?

Gianluca Mauro
Yeah, so, I mean, for people who don’t know what tokens are, tokens are basically AI breaks down your messages into parts, parts or tokens. So, if I say, for instance, “Hello!” it might be two tokens, “Hello” and the exclamation mark. And there’s something the AI models have called a context window, which is basically how many tokens they can take a look at, at once. And I think GPT-5, the latest model from OpenAI, is at 400,000 tokens. Some models are up to one million tokens.

So, while you can add a million PDFs and resources into a prompt, then you risk getting into a situation in which you’re adding, if you’re adding not high-quality context, you’re just misleading your model. An example that I always make is the following. You go to a doctor and you say, “Hey, as I said before, I have a headache. What do I do?” That’s way too little context.

But if you say, “Hey, I have a headache. Let me tell you my medical history. When I was two years old, I once fell and hit the knee on the floor, and it was really painful. Then when I was three years old, I once ate spoiled milk. When I was four years…” that’s too much. You’re just confusing your doctor, right? So, you want to try to select some context that might be relevant.

Because, again, you never know if you’re just putting something that is just misleading or it’s just not very relevant to your question. Don’t stress too much about not putting enough but also don’t go crazy.

Pete Mockaitis
Well, I guess what I’m saying is, what I want your professional judgment on is, if I throw in the full transcript of a meeting, or a book, you know, is that likely to help or hurt me or under what context?

Gianluca Mauro

Oh, I do this all the time, by the way. Like, if I take the whole transcript of a meeting, and I need to write a sales proposal, transcript of the meeting, the whole thing, because it’s all relevant. It’s my meeting with a customer, it’s all relevant. And I take that, I take an old proposal that I wrote, and say, “Adapt this proposal to the context of this meeting.” That’s perfect. But think about what I added in. I added only relevant material for my task.

Pete Mockaitis
Well, that’s helpful. You mentioned it’s bad at analyzing conflicting information. And I’m thinking, sometimes it also seems bad at giving me precise pinpoint pieces. For example, if I say, “Give me verbatim quotations of something,” it seems to really struggle.

And maybe it’s just trying to not violate a copyright or something, but I feel like the more I want it to be super precise, specific, narrow, exact, data point or quotation, it seems to struggle.

Gianluca Mauro
Yes, and you will be correct in saying that. And, I mean, there’s a technical reason why this is happening. It’s just in the way that these tokens are processed. It’s basically making a big average of everything that it has read up to that point. But conceptually, you can look at it this way. This is not a truth machine, okay? This is not like a search engine.

A search engine takes a bunch of data, the entire internet, and it just points you to the right point. It tells you, “Hey, this is the link that it’s the most relevant to your query.” This is not that. A good way that I look at AI is it’s a compressor of knowledge. It took all the knowledge of the internet, compressed it into a thing. And then when you ask questions, it can decompress it and give it back to you.

So, what this means is that sometimes you lose some information in that, say, decompression. And I mean, I think this is a metaphor that is, really, maybe it makes sense just to people who are into audio and this sort of stuff because you have this thing. You’re losing quality as you compress it. It’s the entire internet, but you can just like quit it like this in a second. So, you lose a little bit of quality. And so sometimes you have these errors. But I have to say it’s improving really fast.

Pete Mockaitis
Okay. Well, is there anything else that it’s bad at?

Gianluca Mauro
I think a good way to look at this is thinking that it’s an amplifier, okay? So, it’s bad at telling you, “Hey, what you’re doing, it’s not ideal.”

Pete Mockaitis
Yeah, “You’re asking the wrong question,” you know?

Gianluca Mauro
Exactly. It’s not going to do that, which is like, I think, the most important skill today is not being able to find answers. I think it’s being able to ask the right questions and being able to look at answers and be like, “Oh, this isn’t, actually, this doesn’t make any sense.” I’ll give you an example. I think this is quite funny.

I asked AI to give me feedback, as all of you know that I do that quite often, on a PowerPoint presentation that I created. But instead of, like, uploading the slides, I just took all the texts and I put that in. And in the feedback, it told me, “Hey, you’re not using enough visuals.” And I was like, “Of course, you’re telling me this. I didn’t give you the visuals. I just gave you the text.” It makes no sense, right?

But looking, you know, critical thinking, and this is a very simple example, but I had to take that piece of feedback. And even though the best top AI model in the world told me that I need to add more visuals, I discarded that feedback because I was like, “I know that you’re just lying to me. You’re just coming up with random stuff.” So that’s one important thing.

And, by the way, I think something that really scares me is a lot of people are using AI for almost as a therapist to get support in relationships with their loved ones. And, again, remember AI is sycophantic and it’s going to try to please you, so you’re always right. It’s really rarely going to tell you, “Hey, Gianluca, you know, your…”

Pete Mockaitis
“Your behavior is toxic and causing problems. Look in the mirror and fix it.”

Gianluca Mauro
Exactly. It’s always the other person’s fault. Yeah, I had this friend of mine who came to me, and was like, “Hey, I have an issue. Every time now I have an argument with my partner, she goes in a room and then comes back and has a perfect, like, perfectly phrased argument to explain to me why I’m wrong. And I know that’s coming from ChatGPT.”

So, she’s just getting in a room, and saying, “My boyfriend did X, Y, Z, you know. How can I just try to win this argument?” which, again, I think there is some value in that if you use it correctly. Again, I feel like I said it a few times, but I really want to make sure the audience comes back with this. Think about if you instead use it this way.

Go back to your room and say, “Hey, I had this argument. What might be the other person feeling that I’m not thinking about? What might be some blind spots that I might be having? What are things that I’m not considering when I’m accusing, I don’t know, whatever my partner of, X, and Z?” Now you’re actually going to use it as an empathy machine rather than as a, I don’t know, ego booster kind of thing, right?

Pete Mockaitis
Yeah, well said. Are we amplifying the, “I’m right, they’re wrong,” make the case, or are we amplifying, “I’m trying to be understanding and compassionate”? And it will seek to please you. And so, yes, if we amplify the wrong thing, we’re just getting farther down a bad path.

Gianluca Mauro
Correct. And isn’t this cool? Like, the idea that I have so much agency and power over the outcomes of my use of AI, depending on how I use it, depending on the questions I ask and what hat I decide to wear on this day. “I want to wear the hats of the empathetic person who tries to understand what this person might be feeling.” I can have vastly different outcomes. I found this really empowering.

I understand it might be a bit scary, because it’s like, “It’s all of me?” Yes, I get it. But, again, if you have that approach of being curious and just trying different things out, I find that super empowering, honestly.

Pete Mockaitis

Cool. Thank you. Well, now I’d love to get your take in terms of, boy, there’s a lot of different chat bots and AI tools, if you want to do ChatGPT or Gemini or Claude or Grok. Is there a way, and this is going to change every few months but, you know, for now, is there a way you think about for certain use cases, “I prefer this tool over the others”?

Gianluca Mauro
Yes, but in a way that might be unusual for the audience to think about. So, I think about it this way. I think in my AI, I call it my AI tool stack, like all the tools that I use, I think about three main categories. The first one is generic AI tools. These are ChatGPT, Gemini, Copilot, Claude, Grok, basically these five. And, for me, it doesn’t matter too much which one you’re using. All have each respective strengths and weaknesses, but they’re all quite similar at the end of the day.

I personally use ChatGPT. That’s the tool that I started on. That’s just the tool that works the best for my use cases. But, again, I don’t have a strong argument for people to say, “You must use ChatGPT.” Use whatever you want. But the interesting thing is when I look outside of these generic AI tools and I start looking at specialized AI tools, and these are tools that are specifically built for one use case.

An example, I use a note taking tool called Granola, which I really love. I have a lot of meetings in my life, and Granola is specialized in note taking during meetings. Absolutely beautiful. And I’m not affiliated with Granola at all, so I can tell you there are other tools that do that as well. Otter is one. It’s pretty good. There are a few ones.

But, again, for me, who, I take probably too many meetings. Having a specialized tool for note taking during meetings is super valuable. But there are specialized AI tools for lawyers. There’s a tool called Harvey. There’s a tool in Europe called Legora that’s amazing. And these are specialized for lawyers. They give you a bit more features that you might be interested in. They’re a bit more accurate. They have maybe all the laws of a country already loaded in. You know, they’re more helpful.

I have a startup called Epiphany and I built a specialized tool for instructional design. It helps people who create training, create better training faster. And it’s really interesting when you start looking at those specialized AI tools, because, again, you might find something that, for you, specifically for you, can have a lot of value.

I know, for instance, there are tools for podcasters. Like Riverside has some pretty interesting tools to, like, repurpose content. You might find a lot. Curious to know if there’s anything that has really changed the way that you work in that space.

Pete Mockaitis

You know, it’s funny, we do a little bit here and there, but we’re actually still transcribed by humans, which could shock some people. So, we use it in specific, narrow targeted places, but, still, each episode is getting many, many human hours to put out the door.

Gianluca Mauro
And that’s perfect. Again, for me, what I advocate for is thoughtful AI use, not just like take it and put it everywhere. That doesn’t work for me. So, it makes total sense. But that’s the second sort of area that you might want to look at. So, pick one generic tool. That’s like saying Excel. You can use Excel if you do marketing, if you want to track your campaigns. You can use Excel if you’re in finance. You should use Excel if you’re in finance, but you understand where I’m going.

Same thing, ChatGPT or Gemini or Claude can be used by people in every single industry. But then look at those specialized AI tools that might help you even more.

And then the third area is those custom-built automations that you might want to build for yourself. That’s when we’re getting really nerdy, okay? But I love that. And the interesting thing is that the barrier for building your own custom automations has gone down so much. It’s crazy. There are all these AI no-code tools that allow you to plug different tools together so you can build an automation like, look, I’ll tell you one that we have in my company, in AI Academy.

Whenever somebody writes on our website, “Hey, I’m interested in a custom enterprise training.” There’s this custom automation that researches the company and just gives to our salespeople on Slack a message, and says, “Hey, this person has reached out. This is who this person is. This is what the company does. This is what they want.” Research is done already. It’s like a sales assistant, basically.

We built it ourselves. It took us, I don’t know, we know how to do it so it took us a couple of hours maybe, maybe three, I don’t know, something like that, okay? Hours, not days. All right? But we have seen people starting from very limited technical skills, being able to build those custom automations for their business or for their freelance profession in just a few weeks.

Pete Mockaitis
That’s cool. That’s good. Well, talk about dorky, even though I am not at all a coder or a developer, my favorite YouTube channel is Fireship, which has all these jokes and stuff. And so, I’ve heard, I know a couple of the buzzwords associated with AI automation, like the MCP, the model context protocol, as well as the N8n.

Gianluca Mauro

Amazing.

Pete Mockaitis
And so, I know those are key words I might Google and research. But you tell us, if we are just starting to tiptoe down the, “Hey, I got a thing in my life I need automated. I think AI could probably do something about it,” what are the first steps to explore pulling that off?

Gianluca Mauro
Yeah, so I’ll just tell you basically how we help people go from, “I might want to automate something” to “I’ve built an automation.” And that’s just because we know that that’s a process that works. The first thing you have to do is understand what to automate, what not to automate. And it sounds very basic, but I guarantee you that’s where you decide if you’re going to be successful or not.

Most people want to automate too much. And then they start building spaceships that are never going to work, never going to give them the result they want. They’re going to get tired after some time when they try to build it and it doesn’t work, and then give up.

Instead I always tell people one day I’m make a T-shirt with this sentence, “Find the smallest possible thing that could possibly work.” The smallest possible automation that could give you some value. Start with that and then you can expand, all right?

The second part is don’t stress too much about the tools, you know, the N8n or Make.com or Crew AI, all these tools that are coming up, but try to write a pretty good prompt that should power your automation, okay? So, focus on the AI component, and find a way to test it well.

What do I mean by this? I’ll give you an example that I had. There was this one of our students, he was a doctor and he wanted to not just build an automation. He wanted to build a product to give to his colleagues so that they could easily write referral letters, okay? And so, he had to make sure that this thing worked really well because, again, doctors, you know, it’s a lot of responsibility.

So, what did he do? He just found a bunch of referral letters, or he wrote a few with ChatGPT, and he corrected them by hand. And that was his set of examples to test whether his prompts were actually producing something that was good enough.

Pete Mockaitis
Yeah, like, “Can the AI actually achieve the thing I’m hoping it to do? Let’s test that before I build out a whole thing and go oopsies.” Love it.

Gianluca Mauro
Correct. Another one of our students, I saw this last week, so I remember really well, did something to create LinkedIn posts. This guy works in marketing and risk is very low in that case. What’s going to happen if you publish a really bad LinkedIn post? I might get annoyed, but no one is going to die, right? But still what he did is he used his prompt to create a bunch of LinkedIn posts and then he wrote some and then he gave them to some of his friends and said, “Hey, which one do you like the most?”

And he tried that with a few different prompts, with a few different models. He tried with GPT-5, he tried with Claude, he tried with Gemini, and then he just found the best. And then he knew, he had the confidence that this automation was going to work because he had done the work of testing it and collecting the data.

After you’ve done this, step three is now, build your automation. And, you know, there are different tools that are pretty good at this.

Make.com is one that I really like. I use it a lot. Zapier is probably the easiest one to use. If you want to get started and don’t want to waste too much time learning how to use slightly more sophisticated tools, Zapier is a great place to start. N8N is probably the one that gives you the most flexibility on things that are the most capable. And I like that a lot as well.

But again, does it matter? Not really. At the end of the day, if you had a good idea about what to automate and there’s real value, then you can just swap tools and you’re going to be good. So, I suggest that that’s the last thing that you start thinking about.

Pete Mockaitis
That’s good. Well, shoutout to Zapier. We had Wade Foster. Or is it Zapier? I don’t know. Zapier or Zapier, we had Wade Foster on episode 466 back in 2019, and they are still going strong.

Gianluca Mauro
Amazing. Super strong.

Pete Mockaitis
Good, handy stuff there. All right. Well, Gianluca, tell me, anything else you want to make sure to mention before we hear about a couple of your favorite things?

Gianluca Mauro
No, I think we’re good.

Pete Mockaitis
All right. Well, now can you share a favorite quote, something you find inspiring?

Gianluca Mauro
I wish I could say who it comes from, but it unfortunately comes from a random guy on the internet. And the quote is, “The hardest part of getting what you want is figuring out what that is.”

Pete Mockaitis
I dig it. And can you share a favorite study or experimental or piece of research?

Gianluca Mauro
I will share the research that I was talking about before, the one from Harvard, where they looked at all the different capabilities of AI. And the name of the research is “Navigating the Jagged Technological Frontier: Field Experimental Evidence of the Effects of AI on Knowledge Worker Productivity and Quality.” It’s really cool, still very relevant from a couple of years ago, but, honestly, I still quote that, basically, in every workshop that I do because it’s really valuable.

Pete Mockaitis
And a favorite book?

Gianluca Mauro
Ruined by Design.

Pete Mockaitis
All right. And a favorite tool, something you use to be awesome at your job?

Gianluca Mauro
Another tool that I started to use recently is a tool called Wispr Flow. It’s quite interesting. It basically allows you to dictate and it just puts whatever you said into a box. But again, it uses AI to just change that a little bit so that it’s, first, it’s formatted already.

So, when you’re writing emails, you might want to just record and say what you want to say, and say, “Here, I want some bullet points,” and you’re going to see the bullet points. I’ve been using it for a couple of weeks and I might see that becoming a key part of my tool stack.

Pete Mockaitis
Okay. And if folks want to learn more or get in touch, where would you point them?

Gianluca Mauro
You can go on GialucaMauro.com. That’s G-I-A-N-L-U-C-A-M-A-U-R-O.com or on AI-Academy.com where you can see all of our trainings so you can get better at AI.

Pete Mockaitis
Okay. Well, this has been so fun. Thank you and good luck.

Gianluca Mauro
Thank you. Thank you for having me.

1099: How to Buy Back Your Time with the Right Assistant with Jess Lindgren

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Music by Breakmaster Cylinder | Sound Design by Cashflow Podcasting

 

Jess Lindgren shares what it takes to build a working relationship that helps give you back your time and focus.

You’ll Learn

  1. The must-have traits of any great assistant
  2. The key to hiring an assistant
  3. Where to find great assistants hiding in your own network

About Jess

Jess Lindgren has worked in the C-Suite of small companies for 20+ years, and developed a diverse skill set by wearing many hats on any given day. She focuses on supporting her current CEO in his many endeavors, works to improve the effectiveness and efficiency of EAs around the world, and has very low tolerance for any meeting that could have been an email. Jess hosts the wildly popular* business podcast, Ask An Assistant.  (*in her Grandpa’s woodshop)

She loves living in Syracuse with her husband and three cats in their century home. An avid fan of putting pen to paper, Jess personally replies to every handwritten letter she receives.

Resources Mentioned

Thank you, Sponsors!

Jess Lindgren Transcript

Pete Mockaitis
Jess, welcome!

Jess Lindgren
Pete, thank you so much for having me.

Pete Mockaitis
Well, I’m so excited to get into your wisdom. We are talking about assistance, assisting. Whether you are the assistant or the assisted, I think we’ll have a lot of valuable wisdom to unfold here. And I want to, first, hear, in the assisting game, what is something that has been a surprising learning you’ve picked up that is just transformational, that makes for assistance working great versus not so great?

Jess Lindgren
I think the biggest thing is that people don’t think about this. People don’t think about this more now than they did. I have been an administrative professional, an executive assistant, for over 20 years now, and, things have definitely changed in that time. And people used to be way more focused. And this is general, because people still are focused a lot on hard skills over soft skills.

But people used to get really hung up on, “Oh, well, if you can’t type 90 words per minute,” “If you can’t pass this super nuanced clunky test on Outlook from 1998,” and a lot of those tests are very, like, you can’t do anything with shortcuts. You have to know exactly where to find stuff or you get knocked down on it. Nobody used to care if you were a good fit with your executive.

Like, people would look for executive assistants who were exactly like them, which is kind of the opposite of what you want. Like, you really want somebody that, if this is you, you want an executive assistant who’s going to come in and fill all those gaps for you, right? So, people really never used to focus on soft skills, emotional intelligence, that kind of thing.

And it’s always been something that’s bothered me in my earlier roles that we weren’t a good fit. We didn’t mesh well together. We were a little too similar and kind of butt heads quite a bit. So, that’s really something that I felt from an early time in my career, and have been very fortunate for the last 12 years to be working with somebody who appreciates a good working relationship in terms of emotional intelligence, in terms of soft skills, in terms of fitting better together.

And I do feel like industries as a whole, especially in the entrepreneurial sphere where we find ourselves, people are finding that that’s a much more valuable thing when they look for someone to hire to be their righthand gal or righthand guy.

Pete Mockaitis
Yeah, that makes total sense to me. And to that point about opposites, or filling in gaps, I think that’s fantastic because we humans have this natural affinity for folks who are similar to us and see the world in similar ways to us, and it feels so good. For example, I’m big on ideas, creativity, ideation. That’s really fun for me. And so, if I talk to someone else who’s the same way, it’s very exciting.

Jess Lindgren
Oh, for sure.

Pete Mockaitis
And we’re just like firing out ideas all over the place. And yet, if we wanted to accomplish something, we’re not a great duo.

Jess Lindgren
You need somebody behind the scenes, like kind of pulling you back down to the earth. Like, you’re up there, you’re just floating away with all of these ideas and stuff. And that’s not to say that I don’t have creativity and ideas of my own. They’re just different. So that’s something that’s really, really nice, is to have those, you know, respect for what the person does that I work with for sure.

So, yeah, that creative conversation, like it’s very fun and very important, but it is also good to have somebody, you know, like I said, like you said, filling in those gaps, pulling you back down to the earth and being able to get you on task, like, “Okay, it’s great that we’ve got these ideas, but has anybody written anything down? Have we put anything into the project pipeline? Are we making progress forward?”

And just someone to kind of, “Okay, there’s 20 minutes left of this hour meeting. We need to actually make some progress here.” So, it’s really great to have that give and take, and have somebody who really just kind of fills in your other half. You need that right brain to the left brain, the type A to the type B.

Pete Mockaitis

Okay. Well, could you, perhaps, give us a story, illustration, demonstration, example to make it really clear for what does outstanding assistance look like versus what okay assistance looks like?

Jess Lindgren
Okay. Yeah, something that really comes to mind for me is that there are a handful of careers in this world that people think just anyone can plop in and do it. People think that they can do real estate. People think that they can do retail. People think that they can do administrative work. And that’s just not true.

Like, I personally, I cannot go. I worked one. I didn’t even complete the four-hour shift at Victoria’s Secret in college because it didn’t work for me. Like, everything that they were training me to do, I was like, “Nope, this is not for me.” Real estate, you have to have, like, the back of your hand, you have to know, you have to have relationships all over town. I couldn’t do that. I don’t have that breadth and depth of knowledge and relationship the way that really successful real estate agents do.

When it comes to administrative work, it’s a lot of creative thinking. It’s a lot of connecting the dots. It’s a lot of thinking ahead. It’s just skills that not everyone has. So, the okay assistance is the person who says, “Oh, yeah. Well, you know, I’ve been working in sales for like 20 years, and I think I want to pivot and just do administrative work. Like, anybody can do that, right?” Like, people who are just sitting there, trying to bridge a gap.

And, like, I’ve been there. I’ve tried to, I’ve had times in my life where I need to bridge a gap from job to job where you just take whatever is available. But people think that it’s just a job that anybody can do, and that’s just not true. I think you do have to have interest in it. I think that you have to have really sharp critical thinking skills. And I think that you have to really be a helper. Like, you really have to be someone who wants to help, not just someone who wants to come in, cash a paycheck, kind of half-ass it?

Pete Mockaitis

Yeah, understood.

Jess Lindgren
Yeah, like you really have to have some grit behind you. You have to really be into it, especially to be a career administrative professional.

Pete Mockaitis
That’s good. So, let’s hear the rundown there. Grit, creativity, interest. What are the other critical components, both in terms of if you’re thinking about a career in assisting, or if you’re thinking, “I need to hire somebody,” what are the top things to be looking out for?

Jess Lindgren
Like I touched on earlier, you’re looking for emotional intelligence, really, because a lot of it is, especially in an executive and/or personal assistant with your executive relationship, there’s a lot of access. You’re in a lot of rooms where a lot of other people aren’t, you know? My last in-office job, I would sit in on weekly board meetings.

I would sit in on meetings with the executives’ direct reports, like they’re director-level people, they’re manager-level people. And you have a lot of access to a lot of information. So, like, you’re looking for confidentiality, discretion. You’re looking for people who just care. You’re looking for people who care. That’s really important.

Pete Mockaitis
Yeah, I’ve heard that’s probably the top theme when people ask me, “So, Pete, how do I be awesome at my job, Pete?”

Jess Lindgren
You care.

Pete Mockaitis
“You’ve done a thousand interviews.” Like, that’s kind of the thing is to care, fundamentally, about the work, about your customers, clients, your colleagues, the product or service you’re delivering. Like, to the extent to which you give a hoot, to the extent to which you get cool creative ideas, to the extent to which you go the extra mile, you try something different, you’re proactive, you’re into it, you’re engaged, versus kind of just chugging along isn’t great for anybody.

Jess Lindgren
Right. And there’s finitely, I’ve had days like that. I’ve had weeks like that. I’ve had months like that, where you are just kind of not engaged or you’re feeling burnt out or whatever. But, like, in the long run, you really do need that interest, that drive, that passion.

And when you are in an entrepreneurial sphere, you need to surround yourself with people who, I mean, A, you need to know what your mission is. Like, you need to know who it is that you’re serving. You need to know why you’re serving them. And you need to be able to articulate that to people when you hire them to work with you, and have it be a very intriguing mission that it is that you’re trying to fulfill.

Pete Mockaitis
And when you say be a helper, tell us about that, because in some ways, every job is being a helper, but I think you mean something specific.

Jess Lindgren
Yeah, I mean, even using a salesperson as an example. They’re trying to sell software to a company, or whatever the product might be. So, we’ll just say that this is a software company. They’re trying to help a company make a decision between five different software that are out there that all kind of do the same thing.

But that is still, at the end of the day, kind of a self-serving help. They’re trying to make a commission. They’re trying to make a sale. They’re trying to be number one on the leaderboard. They’re trying to get a bonus at the end of the year, whatever it is. But when it comes to being an executive assistant, being a helper is just so important because, a lot of times, you are the person who is picking up a lot of pieces.

You’re filling in a lot of cracks, and you also have very high standards when it comes to your work. You care about yourself doing a great job. You care about the company succeeding. You care about the executive that you’re supporting being successful. And, yeah, just every successful executive or administrative assistant that I’ve ever met just, like, really cares a lot.

You care about the office looking nice. You care about putting a good presentation, a representation of your company. You care about putting yourself out into the world. You care about, honestly, really great administrative professionals care about doing impactful work. They really do.

Pete Mockaitis
Yes, I hear you. And the salesperson, not that those motivations are evil, and, in fact, they’re sometimes extremely helpful. It’s like, “Ooh, this guy is on fire to make it rain. And thank goodness they do.”

Jess Lindgren
Yes. That’s great. Good for them.

Pete Mockaitis

Everyone is able to have paychecks from that revenue generated.

Jess Lindgren

Exactly.

Pete Mockaitis
And that variety of motivation and hustle works there, but it’s a very different flavor of motivation and drive than that which is a great fuel for a successful assistant.

Jess Lindgren
Yes.

Pete Mockaitis
Okay, I’m grooving with it. So, then I’m curious, if one is doing a recruiting process, maybe engaging in some interviews to assess some potential candidates, what are some top approaches for interviews or selection or recruiting that could help us find, indeed, these helpers who really care?

Jess Lindgren

Yes. Okay. So, I have really strong opinions about this, and I’m really glad that you asked. Right now, for anyone who’s out there paying attention, hiring processes are completely out of control. The number of people that I have spoken with who just, “I went through three, four, five, six interviews,” you know, they’re like, “Okay, you’re our top two candidate.”

And then they get ghosted, or then they get like, you know, “Oh, well, we almost picked you,” or, like, someone will come back, you know, three months later, “Well, we picked the other person and they didn’t work out. Are you still interested?” You need to slim down your hiring process. This is not respectful of the candidate’s time. This is not respectful of your time.

What are you doing if you are putting someone else through six rounds of interviews? Like, what is everyone else on your team doing? Your salesperson is not out in the field making sales because they’re sitting there interviewing a candidate. They’re part of the fifth round of the interview and you’ve got 30 candidates, and you’re going to make that salesperson.

Like, the number of people that I’ve spoken with, who are executive assistants, who are looking for work, and they’re just like, “Yeah, I had to meet with the recruiter first, and then I met with the outgoing assistant, and then I met with the sales team, then I met with the marketing team. Like, these are people I’m not even going to work with. Like, why are they putting the whole company through this?”

And if you’re doing this with dozens of candidates every time, that is such a poor use of everyone’s time. And every person right now, they have to take work off. They have to stay late at work because they took a long lunch break to come to your sixth interview, the seventh or eighth or ninth or 10th interview. Like, you need to slim it down. Honestly, every time that I’ve hired someone, I can tell from the time I shake their hand if I like them and feel like it would be a good working relationship or not.

Like, slim it down, make it shorter. You don’t have to purely go on vibes, but, like, hire, what is it that I like to say? Hire slowly, fire quickly.

Pete Mockaitis
It makes sense to me in terms of like, let’s be very thoughtful about who we take on. And if it’s not working out, don’t drag it out for three years.

Jess Lindgren
Exactly. Don’t drag it out. Don’t drag it out for three years. But also, like on the flip side of that so like, what I mean by hire slowly is, like, get somebody in the door, but there is going to be like a ramp-up process, especially when you’re dealing with executive assistants. Like I touched on earlier, you have a lot of access as an executive assistant.

In terms of the hire slowly, fire quickly, I like to say to people, “Give your new assistant the garage code. Don’t necessarily give them the keys to the whole castle.” Like, you can give them some information. You can make the training process, make the onboarding process kind of slow, methodical, thought out.

But make the hiring process itself, like have a clear job description, but know that there’s a lot of room for nuance, that things are always going to shift, especially with an executive administrative or personal assistant. There’s always going to be things that you didn’t think of, that you didn’t know you needed help with, that you didn’t know they could do, that you could hand off to them.

Like, just know that it’s a living document, that it’s something that you’re going to need to update as time goes on. But really, strip that hiring process down. It’s not a good use of anybody’s time. Make a decision, roll with it. But that’s what probationary periods are for. That’s what that onboarding time is for, is to get to know them, see if it’s a good fit.

I’ve certainly had people who came very highly recommended, who interviewed very well, and then performed very poorly. And that’s where the hire slowly, fire quickly comes in. Like, I hadn’t bought them a new computer. I hadn’t bought them a ton of software. I hadn’t given them access to everything, but, like, I did make a decision, hire them, bring them on. And then I’m just like, “Well, this isn’t working out. Sorry.”

Pete Mockaitis
Understood. Okay. So, you’re saying, let’s not do nine interviews, but rather, let’s give someone a shot, do the probationary period, and then that goes well, we really say, “Okay, here’s more access, here’s more things.”

Jess Lindgren
Yes.

Pete Mockaitis
What are some key things that might show up as indicators that, “Ooh, this person seems special out of the pack, and, thus, it likely warrants to advance to the probationary period”?

Jess Lindgren
Yes. I mean, I think a lot of it is just looking for that caring, looking for them filling in gaps, looking for them noticing things when they say, “Hey, Pete, we’ve been working together for a couple of weeks here. I’ve noticed that you have X, Y, Z thing. Have you ever thought about doing it this other way?”

So, looking for people who really care about not necessarily that everything needs to get totally optimized and automated, but, like, sometimes things are too close. Like, you’re too close to things to even notice that there’s an issue, and you just do things that way because that’s how they’ve always been done.

And then when someone brings their specific experience, their specific expertise to the table, listen when they have ideas, implement what makes sense, but really look for them caring. They want you to have more time.

If you’re the salesperson of the company, they want you to have two extra hours in your day to be focusing on your job because you’re doing something inefficiently, or maybe doing something that’s not impactful, something that doesn’t even really need to be done anymore, something that’s outdated. Look for them making suggestions that make everyone do a better job. Like, that’s really important.

Pete Mockaitis
And so then, back into the interview, of which there might just be one or two and not nine, there might be some questions along those lines, like, “Tell me about a time that you noticed an opportunity for improvement, and what you noticed, and how you communicated it, and what happened.” And so, it was like, “Oh, shucks, that’s never happened before.” It’s like, “Oh, well, maybe we should go with someone else.”

Jess Lindgren
Maybe it’s a different, yes, maybe you go with a different candidate if that’s never happened. Process evaluation and improvement is, honestly, my favorite thing to do. I’m constantly just like, “Okay, we did it this way. It turned out okay. Is there anything we could have done better?”

Pete Mockaitis

I like that. And then, so I think, as we talked about recruiting, hiring, we were thinking about it perhaps from a vantage point of a dedicated, full-time, or many hours of time person. I guess in the universe of acquiring assistance, I suppose there’s a whole spectrum from a full-time, 40 hours plus a week person, like on site, to remote, to asking a bot to do a thing, or asking a service. How would you lay out the spectrum or continuum of assistance? And what answer is probably right for what needs?

Jess Lindgren
Yeah, that is a wide spectrum. So, there are lots and lots of options out there. I will say that a bot, or your average ChatGPT or AI, I am not a fan. I really think work like this is nuanced. Like, people in the executive assistant sphere are, “Oh, my God, AI is going to take our job.” No, it’s not. It’s fine. Like, there’s way too much nuance in a lot of work.

And if the things that you need help with are things that can be automated by a bot, or an AI, you don’t need an assistant. But I do think that most organizations and most individuals, especially individuals running companies, really could benefit from having one, whether it’s five hours a week to 40 plus. When you get into that 40 plus timeframe, hire a second person. It is absolutely unfair to have, like, I’ve worked 60-hour weeks. It’s not fun or cute for anybody.

Your productivity, your effectiveness, your efficiency, totally starts to drain once you’re past like 35 to 40 hours a week. It just, it’s not sustainable, you know? But, yeah, there’s definitely opportunities. There’s virtual assistants based out of the Philippines. Like, that’s a very strong industry at this point. It was definitely something, when I started my company back in 2014, it was, “How do I differentiate myself?”

Like, VAs out of the Philippines were newer. But like, “How do I differentiate myself as the in-person personal and executive assistant here in the United States who is not charging $5 an hour? Like, how do I?” Because it is different. It’s a very different service. It’s a very different product that I have to offer.

And, yeah, you still can, like it’s a much more developed and stronger industry. People based in other countries outside of the US have seized the opportunity. I don’t want to say taken advantage of the opportunity because that’s not the right wording, but like seized the opportunity. There’s a demand, and people are meeting it. And I’ve heard nothing but wonderful experiences that people have had with virtual assistants based out of other countries.

And you can get five hours a week. You can get 20 hours because you had a busy month or maybe you had a launch coming up. You can hire someone for 40 plus, like that’s, honestly, how I started working with my current executive, is he hired me for a one-off project. And after that one-off project was done, he was like, “Well, do you want to help me maintain it?” because I was hired to tame his inbox.

Like, we went from 9,000 unread emails to inbox zero. And he was just like, “Well, you cleaned it up. Like, I can’t maintain this. Like, can I hire you to stick around? Can you do 10 hours a week for me ongoing?” And I was like, “Absolutely.” And then 10 turned to 15, 15 turned to 20, 20 turned to 60. I hired that second person, and then you adjust from there.

Pete Mockaitis
Well, that’s beautiful. And kudos to jobs well done. I mean, that’s often the reward for great work, is more work.

Jess Lindgren
It is more work. But, you know, when it’s work that you love, it is a reward.

Pete Mockaitis
All right. So then, we talked about there’s full-time, there’s half-time, there’s other countries like the Philippines, there’s the bots can do what the bots can do, but they are limited, all right.

Jess Lindgren
Very limited.

Pete Mockaitis
And so then, I’ve heard there are a number of services. I’ve tried Fancy Hands, and it’s quite limited.

Jess Lindgren
Okay, that’s a new one to me.

Pete Mockaitis
Well, the nature of the tasks were limited, in that they’re like 15-minute requests. So often, like it’s really crap shoot. It’s kind of like an Uber situation. It was like, you’ll get who you get and, hopefully, they’re with it. But it’s hard to say, “Oh, you’re great. Let’s keep doing the thing.” It’s like, “Well, no, you might get me next time. You might not.”

Jess Lindgren
Oh, you might never get them again. Interesting. So, it’s not something where you can say, “Okay, Jess did a great job. Five stars. I want her again.” Interesting. Fancy Hands. I’ll have to look into that.

Pete Mockaitis
Yes, so it’s very limited, such that I’ve actually had a hard time using my requests, and I’ll probably be canceling them shortly. So, are there any other services or resources or directories or agencies or spots folks can go, and say, “Oh, they usually have some great folks”?

Jess Lindgren
You know, there are agencies out there, the ones that I have personal experience with, and the ones that I’m familiar with are, unfortunately, out of business.

Pete Mockaitis
Oh, bummer.

Jess Lindgren
Yeah, so I don’t have specific agencies, necessarily, to recommend at this point, but I can say that there are more people who would be great at being an assistant in your network than you probably could ever imagine.

Like, the number of people who have a kid in college, who has 10 hours a week to give you, or the stay-at-home mom who’s been out of the workforce for a number of years, and, thankfully, kind of like the emotional intelligence piece, like people place more importance on the emotional intelligence piece. People are less, like there used to be a big stigma if you had a huge gap on your resume like that.

But people are really coming around to, “Okay, a stay-at-home parent is, like, the perfect person to hire for a role like this because they are managing a household, they’re managing children’s schedules, they’re managing all, they’re feeding however many people, however many meals every single day, they’re staying on top of laundry.”

Like, being a stay-at-home parent is a whole huge job and a really untapped market. Like, you just never know who has, like a friend of mine, their youngest just went to kindergarten this year, so all three kids are, like, eighth grade, fourth grade, kindergarten. All of a sudden, the stay-at-home parent has two, three hours a day where they could pick up some work, if someone had it available for them.

So, really, I like to recommend that people just put out, especially when you’re in a position where you have a podcast, you have a newsletter, you have social media, “Hey, friends, hi, I’m Taylor Swift, and I’m asking the Swifties. I’m looking for, hey, Swifties, I’m looking for an assistant for 10 hours a week. Who can help?” Taylor Swift is going to get a slightly different response than you or I would, you know?

Pete Mockaitis
“Ahh!!”

Jess Lindgren
And, Taylor, if you’re hiring, hello. But just, like, ask, and you just never know. Like, that’s how I ended up in the role that I have, is I wrote an email, I quit my job, I threw a party and just told everybody I knew about it and I was like, “Hey, you should come to this party, and here’s what I’m doing. I’m, basically, what people now might call a fractional executive assistant.”

So, I was like, “Fractional executive assistant work. And I guarantee, if I can’t do what you need, I know somebody who does.” And 15 minutes after I sent that email, someone reached out to me, and said, “We have a job for you.” And 12 years later, I’m still doing that job.

Like, the power of networking is so real and you will see people all the time say, “It’s not what you know, it’s who you know.” That’s unfortunate because not everybody knows everybody. But when you do know some people, it can be very nice and very cool.

Pete Mockaitis
Yeah, I’m thinking about my buddy, Scott, mentioned, I think, one of his kids’ friend’s moms, they just had a number of very pleasant exchanges with her, and she indicated that she was looking for some stuff to do, I think, with kids in school situation. And they said, “Well, hey, maybe you could help us with this and this and this.”

And now, there’s like just a growing list of, she does all these things that make their life work in terms of, “Well, hey, could you help coordinate some things with our Airbnb property? And could you coordinate these Amazon returns?” And so, there’s like a dozen bullet points or more by now. And so, it just seems like, “Are you a billionaire, Scott?”

He’s like, “No, no, he’s not. But he’s found someone delightful who does have that helper’s heart, who just enjoys doing this, and they appreciate just the heck out of her,” because, like, “Oh, my gosh, our lives are so much less stressful and more wonderful because you’re in it. Thank you.” And she’s happy to help, and, it’s win, win, win, win.

Jess Lindgren
Yes, that’s the phrase I tell to everybody. Like, anybody reaches out, and I’m like, “Happy to help. I’m going to write a book someday. Put a pin in that.” But truly, like, everybody brings different skills and different tools to the table. Money is a tool. Stop hoarding it. Start using it to make your life better.

And the stay-at-home parent who was looking for a few things to do, as their responsibilities at home start to change, as the kids get older and maybe graduate, go off to college, all of a sudden that person has more time, effort, and energy to put into their work. You can take more things off of the person that you’re working with. You can take more things off their plate. And it’s a very reciprocal symbiotic relationship. And, yeah, it can be really great for everybody.

Pete Mockaitis
Well, let’s talk about the assistance and the assisted relationship, and that doesn’t necessarily need to be an executive, per se. I think there was even a piece recently in the Wall Street Journal or New York Times about how, “Hey, normal professionals are hiring assistants now, and it’s just so great.” So that’s cool.

The term executive assistant is, I don’t even know, if it’s the one to use. You may or not be an executive and assistance is great for you, regardless. So, tell us, within the relationship, what are some top dos or don’ts? What are things that drive you and other assistants just nuts, like, “Don’t ever do this. This is so, I don’t know, demeaning or frustrating or annoying.”

Jess Lindgren
Ooh, those are good questions. So, really, I just touched on this. Money is a tool, don’t be stingy. Pay your assistant well, pay them better than you think. You’re going to get what you pay for. If your budget is $5 an hour, you’re going to get very different service than if your budget is $150 an hour. And, like, that’s what I charge and that’s what I get paid, and that’s what I do. I mean, depending on the project.

But, you know, like your budget is very different and you’re going to get people who can prioritize things differently for you. So, like, really, if you, as an executive, I mean, even if you’re not like an executive-executive. You are the executive of your home. You can call them personal assistant, if executive assistant feels wrong. You can just say assistant. Like, we don’t really get super hung up on titles, but, like, pay them well.

If you’re some Fortune 500 executive-level, director-level, manager-level person who’s pulling in $500,000 a year, you have a budget to pay for someone good, and you’re going to get what you want the better that you pay. So don’t be stingy. You also need to not be a micromanager. You need to understand that people who are assistants are professionals. We’re good at what we do, especially when you’re talking with somebody like me who has been doing this for 20 years.

I am fantastic at what I do. You can give me very vague instructions. You can throw me into the deep end. I’m going to swim. It’s fine. You don’t need to hire me slowly. You can just bring me on and say, “Okay, here’s this whole backlog of tasks. Start wading through things.” Like, I love fixing problems. I love untangling messes. I love doing those things that feel so impossible to you, that feel your to-do list is just, it’s a list of things for me to just check boxes off of.

It doesn’t have the same emotional weight or stress associated with it for me. So don’t be stingy. Don’t be a micromanager. Like, tell me what you need done and then trust that it’ll get done. If it doesn’t get done, you’re going to know about it and then you can step in and micromanage, or whatever. But, like, back off.

Like, tell us what you need us to do and then let us do it. Give us some breathing room because we’re professionals and we’re good at it.

Pete Mockaitis

Well, I guess I’m thinking about the universe of expectations. And, for example, and I don’t know if this is a dated reference. But, I think, I’ve heard instances of, “Oh, if someone is getting coffee and getting dry cleaning, like that’s demeaning and beneath them.”

But, in other ways, another way of viewing it, it’s like, “Oh, that’s exactly what is needed and is helpful for that person at that time.” And so, I guess I’m guessing, you tell me, that whether that is or is not appropriate or, you know, “Pick my kids up from daycare,” or school, or karate lessons, really just depends on communicating those expectations upfront, and seeing if that’s a fit.

Like, you know, “Actually, driving kids around is something I can’t stand doing for whatever reason. They’re noisy and they are sticky.” Or, like, “Oh, how delightful. I get to spend some time with these precious cherubs.” So, I’m guessing that’s a do is to be clear about expectations and get aligned, and you can be able to share either way, like, “Actually, that’s kind of outside of our scope and not really in my zone of skills,” and just doing that dance.

Jess Lindgren
Yeah. So, that really is communicating what the job description is, because when you say executive assistant, that has the connotation of being, at least in the United States, you know, other countries like the UK, if you have seen any references to this at all, whether in the business world or the entertainment sphere, you’ll see people talking about their PA, their personal assistant.

So, in other countries, the title does mean something different. But here in the United States, executive assistant has the connotation of being a person who helps you with your professional life. Whereas, a personal assistant is the person who helps you with your personal life, or your assistant, again, whatever title it is that you’re going to give it.

I talk a lot about your time split, like how your job is split between professional and personal responsibilities. In my present role, it’s like a 95-5 professional to personal split. So, like 95% of the time, I’m doing professional stuff, and there’s a pretty, not a hard line, but like I don’t do any of the personal stuff, and that’s fine.

And I’ve also had roles where it’s like 95-5 the other direction. I’m just doing personal stuff. I’m helping you with, like one of my favorite things I ever did. I got hired to help someone hire and manage a plumber. They had a leak under their sink. So, like, I had to vet the different people who were available. Thankfully, I had a plumber that I loved.

So, I just hired them, came over, had to buy them, you know, they’re like, “I need a new vacuum. I need a new cat tree. I need a new…” whatever. So, like, got to knock everything out, like had everything delivered to the house the day that I was coming to manage the plumber. Got to just sit at the house and manage this service person, while they were there. And then I got to take their Instagram celebrity cat to the vet.

And so, you know, like sometimes it can be, I think that stuff is really fun and really cool. There are people who do not want the responsibility of being in charge of someone’s pet, being in charge of someone’s children. So, like, just making sure that the job description is clear from the get-go of what it is that you, the person needs help with, and what you are expecting the assistant to do, because you can also hire five-hour a week professional support and 10-hour a week personal support.

I like what you said, though, about things that are considered dehumanizing. I don’t find it dehumanizing when somebody, when my executive, like in my current role, when we work together in person, a lot of it is making sure that he is fed and hydrated and caffeinated. And that’s not offensive to me. I love doing that stuff. By feeding him and giving him coffee, he’s able to do his job. Like, that is not offensive.

Pete Mockaitis
Well, that’s, “How Pat going to be ‘super stoked’ if one of these fundamental needs are missing?”

Jess Lindgren
Right? Like, this is just basic needs. Like, his shelter is taken care of because I got him a hotel room. His food needs are taken care of because I, literally, scheduled into his day, “Okay, here’s where you have a break. Here’s where you’re going to eat a Caesar chicken salad.” And I have protein bars in my bag. Like, that’s not offensive to me.

But some people, that would be very offensive. What is very offensive across the board is people not having their tempers in check, “I’m not your mother. I’m not your wife. I’m not your teacher. I’m not your daycare provider. Like, grow up.” That is absolutely unacceptable. I don’t care what it is that’s frustrating you. You need to have your temper in check.

And if that’s not something, that not a skill that you currently have, you need to work on that. And you need to hire somebody else who is fine getting yelled at. Like, treat people with basic respect. I have been yelled at. I have had things thrown at me.

Pete Mockaitis
Oh, jeez.

Jess Lindgren
Like, seriously, I have had people, you know, throw a sheaf of papers, like, right into my face. And I’m like, “That is unacceptable.” So, like, have your temper in check, have your behavior in check. This is either a professional office or it might be inside of your personal home. But when you are bringing someone in as a hired professional, whatever that profession is, get it together.

That’s the dehumanizing stuff. That’s the unacceptable stuff. The number of times I’ve heard from assistants that, “I got yelled at yesterday, and it was worse than last week.” And I’m just like, “This is escalation. This is abusive. This is not okay. And, like, don’t tolerate that in the workplace.” But, like, also, if you’re the person who’s hiring the assistant, don’t act like that.

Pete Mockaitis
Yeah, absolutely.

Jess Lindgren
Yeah, that’s the unacceptable stuff. Like, anything else, like job duty-wise can definitely be negotiated. And if you don’t, as the assistant, want to be the person who gets the coffee or the dry cleaning, it’s 2025. Like, Uber Eats is a thing. There’s plenty of services that will deliver your dry cleaning.

Pete Mockaitis
That’s right, “I will coordinate the delivery services associated with these tasks and forward you the bill.”

Jess Lindgren
Yes, you can be the person who does the project management of it, right? But you don’t have to be the person physically going to the coffee shop. You don’t have to be the person carrying the dry cleaning down the street. Yeah.

Pete Mockaitis
And when you brought up those examples of the plumber and the cat, and you mentioned that, “It’s your to-do list. I don’t have any emotional pulls associated with it,” I think that’s a really great concept to highlight here, is that there are many things that I think we’re capable of doing, but we have some sort of emotional resistance.

And so, like, I’m thinking about, “Oh, I should probably upgrade my video backdrop, but that feels like such a project. And I’m going to have to talk to a dozen different salespeople who are going to ask about my needs and my desires and my measurements.” And because I just have emotional resistance, like I’ve been dragging my feet, I haven’t really done it.

Jess Lindgren
Yeah, for sure.

Pete Mockaitis
And yet, if someone else who’s just like, “Okay, I feel totally neutral about that. I would be happy to pull together all of those options and go through that legwork of talking to those people and relaying those measurements and your preferences a dozen times so as to find a winning option for you.”

Jess Lindgren
Yeah. And the other thing that a great assistant will do is say, “You know what, Pete, you don’t have to take a dozen meetings for that. You need to take three to five meetings. You need to pick the person who…you know, I’m already lowering your ceiling of 12. I’ve lowered your ceiling to five. I’m not going to talk to more than five people.”

And if I already have a service provider or, “Oh, hey, I had a video backdrop created. Just last year I have a great service in mind.” Now you’re talking to zero people. You’re just giving me a credit card so I can order it for you.

Pete Mockaitis
That’s good. Beautiful. Well, tell me, Jess, are there any other key things to keep in mind before we hear about some of your favorite things?

Jess Lindgren
Key things to keep in mind is just, I really love to recommend to people that, when they’re getting ready to hire an assistant, it means that they have been ready for six months to a year. So, like, it’s time if you’re really thinking about it, that means that you have been ready for a while. I want you to talk with the people that you work with.

So, if you are the manager of a department, talk to all the people that you interact with for a week, just say, “Hey, if I was going to hire an assistant, what do you think I need help with? What do you think I could offload from my plate?” And you just never know what things that you, I don’t want to say complain about, but like what things do you say like, “Ugh, it’s time to do the TPS reports.”

Like, maybe you need somebody that you can hire that can help you do the TPS reports. And, again, you’re too close to it. You’re too in it. You are just in it. You’re bogged down by the emotional weight of everything that you have outstanding to do, and it’s hard to even know what you might need help with. So, ask the people around you that you work with.

Ask the people around you at home, because you definitely don’t know, what are you letting off steam about to your spouse, to your children, to your friends, to your family? What did they hear when they say, “How’s work going, Pete?” And all they hear about is the quarterly inventory night or whatever.

Like, your assistant could come in and totally revamp the process to the point where you get excited about doing quarterly inventory, because now that it’s been evaluated and optimized, it’s, all of a sudden, really exciting and everybody orders pizza and it only takes three hours when it used to take eight. And now it’s like a big company party because you hired this person to come in and help you.

Pete Mockaitis
Yes, I like that a lot. And I think that this notion of the emotional weight of things is powerful in terms of it’s not just a one to one, you know, hour-dollar exchange situation. Because if you have a lot of emotional angst associated with, “Oh, I’m dreading this, leading up to it. And then, afterwards, I’m so drained from having done it. And then I’m complaining about it.”

It’s like, you may have paid for one hour of services that goes away from your plate onto the assistant’s plate. And yet, that has freed up more than an hour of product goodness in your world.

Jess Lindgren
Yes. Yes, absolutely. And, like, the other thing I really like to tell people is make a list, no matter how big or how small, because you touched on this, too, that there’s a lot of people who feel like, “Oh, well, I should,” or, “I already know how to do this. Why can’t I fit this in?” Everybody needs rest and recovery time. And so, you are buying time, you’re buying services, you’re buying expertise from someone who can help you.

And again, it’s 2025, almost 2026, some crazy how. There is no shortage, depending on where you live, of things that you can hire out. There’s a really great site called Care.com. It definitely is geared more toward housekeepers, nannies, that kind of role. You don’t know what retired grandma, that lives right around the corner from you, wants 15 hours a week, of picking the kids up from their activities, folding your laundry, and making dinner for everybody.

You just don’t know until you pay Care.com for a subscription, you invest the money, because Care.com is going to give you, like they do the vetting, they do the, you know, they’re saying, “Okay, here’s the five candidates that we think, based on what you’re looking for help with, that you might like.” You, ultimately, have to interview them, make the decision.

But, like, Care.com, they’re the hub for you, where the people come that are looking for work. When you ask your network, when you say, “You know, these are the things that’s kind of a weird mishmash of personal and professional stuff that I need help with,” you don’t know who has five or 10 or 15 hours, and who has what expertise and interests to bring to the table for you. Ask.

Pete Mockaitis
Perfect. Thank you. Now could you share a favorite quote, something you find inspiring?

Jess Lindgren
Yeah, absolutely. My favorite quote is from Leslie Knope, the character from Parks and Rec, “One person’s annoying is another person’s inspiring and heroic.”

Pete Mockaitis
Thank you. And a favorite study or experiment or bit of research?

Jess Lindgren
A favorite study. So, I really love the Pareto principle, the 80-20 rule. Just 80% of your client, like, especially as an administrative professional, 80% of the emails I receive, one minute less don’t even need to be answered. Twenty percent of those emails are going to take up 80% of my time. It’s just all day, every day.

Pete Mockaitis
Yeah. And a favorite book?

Jess Lindgren
I really read a lot of fiction. I am a huge The Hitchhiker’s Guide to the Galaxy gal.

Pete Mockaitis
Yeah. And a favorite habit?

Jess Lindgren
Favorite habit. I love to get enough sleep and drink enough water and get enough exercise.

Pete Mockaitis

Agree. And is there a key nugget you share that is frequently quoted back to you, a Jess original that people find so delightful?

Jess Lindgren
I would say the biggest thing that I put out into the world is the five W’s, the who, what, when, where, why of it all. Like, really, just any problem, any situation, can be solved or enjoyed or put together with the who, what, when, where, why of it all.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Jess Lindgren
I would love it if you checked out my website JessLindgren.com, J-E-S-S L-I-N-D-G-R-E-N.com.

Pete Mockaitis
All right. And a final challenge or call to action for folks looking to be awesome at their jobs?

Jess Lindgren
People looking to be awesome at their jobs, stay hungry and stay foolish.

1073: How to Cut Clutter and Distraction from Your Life with Shira Gill

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Shira Gill shares minimalist strategies for reducing both physical and mental clutter.

You’ll Learn

  1. The hidden costs of clutter
  2. Why organizing tools won’t help you—and what will
  3. The easiest way to make your space feel less overwhelming

About Shira

Shira Gill is a world-renowned organizing expert and the bestselling author of three books: Minimalista, Organized Living, and LifeStyled. She’s a sought-after expert for media outlets and has been featured by Good Morning America, The Wall Street Journal, TIME, People, Forbes, goop, Architectural Digest, Oprah Daily, Vogue, and The New York Times. Her popular newsletter The Life Edit inspires readers from all 50 states and 150 countries.

Resources Mentioned

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Shira Gill Transcript

Pete Mockaitis
Shira, welcome!

Shira Gill
Thank you. I’m happy to be here.

Pete Mockaitis
Well, I’m excited to hear about your wisdom because, well, I think home organization is generally fun, and when I go to The Container Store, it is genuinely exciting. However, we’re talking about being awesome at your job, so I’d love it if you could make the connection for us here. In the universe of organization and minimalism, how does that have impact on our professional experiences and ability to be awesome?

Shira Gill
So, I use principles of minimalism and my expertise as a pro-organizer to help people gain clarity, clear clutter, and streamline and simplify everything. So, that’s from home and wardrobe to life and business.

And as an entrepreneur myself, I’ve run a business for 15 years. So, I have found how to leverage minimalism in organization to really dial down on what are the things that are most essential and what can I let go of. And it’s the number one tool that I use to work more efficiently and even joyfully.

Pete Mockaitis
Whew. Let’s talk about joy first. How does that increase our joy?

Shira Gill
So, I think we have so much coming at us all the time. Everyone I know is feeling that their lives are overstuffed, over-scheduled, they’re oversaturated. And it’s hard to feel joyful when you feel bombarded by clutter. And that can be digital clutter, physical clutter, mental and emotional clutter. My work helps people deal with every type of clutter. And I think when we feel like we’re drowning, we can’t be the best versions of ourselves.

And so, I think there’s this myth that, in order to feel better, look better, be better, we have to have more, we have to do more. And what I have found in my now 15 years as a professional organizer, a minimalist, as an author who writes about simplicity, is that the converse is actually true, is that the less we own, the more liberated we can feel, the more time and spaciousness we have for the things that matter most, for the things we care about deeply.

And so, most of my work, really, is about helping people cut the clutter and clear the distraction to enable them to do the things they actually care about and enjoy.

Pete Mockaitis
Now, you said minimalism is the number one tool. I think of minimalism as a philosophy or perspective or value, but you’ve used the word tool, which I find intriguing. Can you expand on that?

Shira Gill
Absolutely, yeah. So, for me, minimalism is, I define it as being radically intentional. So, when I say that it’s a tool, it’s like the intentionality tool, right? So, not just with the things you own, but with how you spend your time, your resources, your energy. It’s really a tool to help you clarify what’s important so you can cut the clutter and distraction that stands in the way.

So, I think about everything in my life through this lens of minimalism and intentionality, and it helps streamline and simplify decision-making. It helps me decide where to allocate my resources. It helps me decide which projects I want to dig into and which I want to say no to. So, it’s really, it is a tool that people, I think, don’t realize is at their disposal anytime they want.

Pete Mockaitis

Okay. Well, could you perhaps tell us a tale of a person who applied this tool and saw some really cool results that showed up in their professional world as well?

Shira Gill
Absolutely. Yeah. So, I had a client, Elizabeth, and she had always wanted to be an executive coach. She wanted to work out of her home. She had three young kids. And her home, in her words, looked like a preschool had exploded. And so, she didn’t have the confidence or the focus or the clarity to get cracking on this business.

And so, what we did together is we said, “What would an executive coach’s workspace look like and feel like? How would you be able to show up, that you can’t show up in the way that you want now?” And so, what we did is we took what was her kind of guest room that had turned into a dumping ground of playthings and toy mats and diapers, and we cleared it all out. We probably donated half of it.

And then we kind of reallocated and relocated things to other parts of her home, like her kids’ room and her playroom. And we set up a really streamlined simple office space for her. So, she had a desk, she had a monitor, she had a speaker and headphones, and the kind of bare bones minimum thing so that she could go on podcasts, she could have client meetings.

And what happened was, as soon as her space changed, her motivation changed and her sense of empowerment to do this job that she had always wanted to do shifted. And so, she started putting herself out there. She started going on podcasts. And it really was about affecting change from the outside in, like she felt completely paralyzed and, like, she couldn’t work. She didn’t have the confidence.

And just by carving out a slice of real estate in her home that felt clutter-free and organized and professional, she was able to leverage that to start her dream business, and she now does that full time from her home.

Pete Mockaitis
Well, I love so much what you said there about change from the outside in. It can happen. And we had Dr. Srini Pillay on the show talk about a term he used, psychological Halloween-ism, in which that can show up with what you wear. You put on a blazer jacket, like, “Ooh, I feel professional.” You put on your dance pants, you’re ready to go out to the club or whatever, and you’re in maybe more of a playful and adventurous kind of a mood. So, that could happen with our dress.

And you’re saying that could happen with our space. And it’s really intriguing, I’d love to dive into some of the distinctions here because if…I’m thinking about exercise equipment. Like, that’s an example of where that tends to often not work. It’s like, “Hey, I bought a treadmill, I bought a weight bench and some adjustable dumbbells, and now, because my space is all set up to exercise, I’m going to be exercising all the time.”

And yet, in practice, often these devices end up holding clothing instead of holding our bodies as we get fitter. Is there a difference or a distinction that we can dig into and unpack? Like, what makes one more effective than the other and why?

Shira Gill
Yeah, it’s super interesting because I have found that if I like my workout wear, I do want to work out more. So, I guess that’s not about buying, like investing in a new gadget or a new trend, right? Like, those efforts typically do seem to fail.

But I have found that if I, instead of wearing like the schlubby pajamas or the loungewear from college, that if I put on like a really sharp workout outfit, like I’ve got my spandex on, I’ve got my like really supportive sneakers, suddenly, I actually feel like being more active. So, that has been effective for me.

I think what is not effective that I see a lot in my work is people trying to become organized by buying organizational gear or gadgets. And you had mentioned The Container Store earlier. I think one of the biggest mistakes I actually see in my work is people saying, “I’m going to go get organized,” and they run out to The Container Store and they buy a million organizing products.

So, they buy, like, bins and baskets and hangers and drawer dividers, and they get home and they wonder why they’re not organized. And the reason is that organization is a skill which is as simple as grouping similar things together and making sure that every category has a home. And so, if we bring more things into our home, now we have more to organize.

And one of the biggest things I see, ironically, is organizing products covered in dust that never got used because they were bought kind of in a vacuum without a purpose. So, what I caution people is to always start by editing and decluttering. There’s a saying in my field, “Organized clutter is still clutter.” So, you don’t want to organize things in your workspace or in your home before you’ve really thoughtfully gone through and decluttered and edited and made careful decisions about, “What are the things I need to do my job effectively? What are the things that are just taking up space or collecting dust?”

And a really concrete example of this is, I used to have a home office, I have two, now, teenage daughters, and they rallied together and wrote me a letter saying, “We would like to each have our own rooms, and we don’t think you need an office anymore.” And so, I really thought about this.

Pete Mockaitis
My kids are young. I’m thinking, “Oh, wow, is this my future?”

Shira Gill
Oh, yeah, it is.

Pete Mockaitis

They will gang up on me and craft correspondence to get their room.

Shira Gill
That’s right. Yes, there will be convincing articles written and cases laid out. So, my kids are very convincing, and they convinced me that if they had their own spaces, they would be more independent, they could have privacy, all of these things, right? And so, what it caused me to do is to look around. I had a proper office. Like, I had a workspace with a desk and a file cabinet and office supplies.

And what I realized, when I decided to take them up on this and give them their own rooms and downsize all of my stuff, so now I work at the dining room table or, you know, a shared workspace elsewhere, is that all that I needed to be able to do my job was a laptop, a microphone, and a notebook.

And so, I ended up selling and downsizing and donating pretty much like 95% of the things that I had in my home office, and now my entire office can fit in a tote bag. And what it did is it actually, ironically, gave me this huge sense of freedom to know I can work anywhere in the world. I can pack up my laptop and I can go work out of a hotel. I can work out of a cafe.

And so, I think when we think about organizing, we think about it wrong. I didn’t need to organize more. I needed to edit and declutter and be really thoughtful about assessing, “What are my tools so that I can do my job?”

Pete Mockaitis
Okay, that’s really interesting.

Shira Gill
Are you looking around your workspace?

Pete Mockaitis
I think that just the timing is hilarious because I just recently had four strong men haul a massive sound-blocking door to outfit a better recording studio space for me to move into, kind of the opposite.

Shira Gill

That’s fair. Maybe you needed that.

Pete Mockaitis

Well, I guess need is so subjective, just like, “The audio quality will be superior and it has benefits,” but I think you’re highlighting, well, it also is, there are other benefits associated with moving in the exact opposite direction. And so, it’s thought-provoking.

Shira Gill
Yeah, I mean, what I find, having been in people’s homes for the past 15 years, is most of us have so many things that we don’t need or use that add zero value to our lives and our careers.

So, like, a prime example is most people that I have met with have an entire collection, like an Office Depot-size collection of things that have kind of been rendered obsolete, like highlighters and Sharpies and Post-its and staplers and binder clips, when most of us are working in this digital world.

And so, I just find it really interesting to question, like, “If I had to go do my job tomorrow, what are the things that I need in front of me to get that job done? And what are the things that, really, are just collecting dust that could better serve, I don’t know, maybe a school or a nonprofit or a theater or a community center who may use those things?” For me, I was, frankly, shocked to learn that I didn’t need 95% of the things that I owned.

Pete Mockaitis
Yeah. Well, so let’s zoom way in on the stapler, because I love office supply stores, too. So, if we use a stapler three times a year, are we better off not having a stapler?

Shira Gill
Yeah, I love that question. It’s very personal for each person, right? So, for me, probably not. I live in a small house, so I should clarify. I live in a house that’s 120 years old. It’s about a thousand square feet. I share it with three other people – my husband, two teenagers, and a dog. And it has almost no storage space. It’s a very charming craftsman bungalow, but it was built in a different time, right?

So, for me, my goal is kind of, like, “How much can I get away with not owning?” I’m really on one end of the spectrum. For someone else, it may seem too inconvenient to borrow a stapler or have to figure out a stapler those three times a year. And if they have plenty of space in their workspace, that stapler is not hurting or harming anyone.

So, one of the questions I always have people ask is, like, “Would you rather have the stuff or the space?” And I think that can be really clarifying. For me, I really value space and spaciousness in my home and in my life.

And so, nine times out of 10, if I’m questioning something, I’ll decide to live without it. And if I need it, I’ll get scrappy and resourceful and borrow it from a neighbor or from my husband’s workplace, something like that. That’s worth it to me.

For someone else, they might value convenience more than they value having a little extra space. So, it is a very customizable framework.

Pete Mockaitis

Okay, yes, the stuff or the space. And it’s interesting, I’d love if you could speak to our human psyches or the research on this. It’s, like, I feel better in a space that is less cluttered. And think that’s, generally, a nearly universal human sentiment.

And, personally, I feel really awesome. I think about speaking. When I am invited to a keynote speech and I am there early in the auditorium and it’s just vast emptiness, there’s like nothing but space – empty stage, empty chairs. And it’s like, “The room is all mine.”

And I don’t know if it’s just the impact of being in a non-cluttered space multiplied by 10. Or, what’s going on here? But since, Shira, you study this stuff and teach it, what is going on here?

And, as we make that choice, “Do I want the stuff or the space?” how do I properly value the benefit of space, even though it’ll vary person by person?

Shira Gill

So, what we know about clutter is that over 80% of people experience stress and anxiety directly linked to physical clutter. So, part of why this is, if we just break it down, is that if you think about being in a cluttered room, every single item in that room is something that our brain has to process.

So, even if we don’t think, “I’m thinking about all these things or these piles,” on a subconscious level, our brain is having to work overtime, processing it as information, right? So, when you walk into that empty room, there’s almost nothing for your brain to process, which means your brain actually gets a break, which feels like relief and ease. And who doesn’t want more of that?

And so, I think what I realized, as a busy working mom, is there’s always stuff coming at me. There’s a long to-do lists, there’s errands, there’s driving carpool, there’s all of the things, all of the input that’s coming at me all the time, and most of which I don’t have control over. But what I do have control over is my physical environment and how I curate it and what I put in it and what I say, “I’m not going to bring this through the front door.”

And what I’ve realized is that the less that I own, the less that I have in front of me, the more relaxed I feel, the more clarity I feel, and the more efficient I can be. And so, I think that’s the thing, is clutter has a big cost, and I’ve seen it in my work, not just this kind of emotional toll of feeling stressed out or overwhelmed, but I’ve seen a huge relationship cost to clutter.

It’s one of the hottest topics in a family of having different clutter thresholds and different ideas of what being organized looks like. It can lead to huge fights and friction between partners, spouses, kids and their parents. And so, by eliminating some of that clutter, you are eliminating this incredible toll and cost that most of us feel every day.

Pete Mockaitis
Okay. And so, then it sounds like, according to this, every bit helps.

Shira Gill
Every bit helps, yeah, absolutely.

Pete Mockaitis
In terms of it might be hard to go from clutter to Marie Kondo-nirvana in a day or even a week or month. But every morsel will be appreciable to our brains.

Shira Gill
Absolutely. And I think I’m clearly on one far end of the spectrum. Like, my children and my husband think I’m crazy, right?

Pete Mockaitis
Well, they got their own room out of it. I mean, I think a lot of parents are like, “Nope, this office is what puts this roof over your head, girl. So, get some bunk beds or figure something out, you know?”

Shira Gill
That’s exactly right. Yes, they should show me a lot of gratitude for that. But I think, like, I can recognize, look, I am a minimalist in a world that values maximalism, in a world that tells you to consume more and buy more and do more. I’m going the opposite route intentionally. But what I’ve seen, working with all of these different types of individuals and families, is that I have yet to meet someone who says, “I have the perfect amount of stuff for me.”

And I think that’s the goal that we want to strive towards, is not “Having the perfect amount for me, Shira,” but having the perfect amount for you in your life circumstance, in your specific career. And so, it’s starting with these questions, like, “What’s being neglected that you care about? What is a new result that you want to create in your life or in your work or business?”

And my favorite is just asking, “What do you want more of on the day-to-day? And what do you want less of?” And I think we don’t slow down enough to really ask ourselves those questions because, frankly, we’re so busy and we’re so oversaturated.

Pete Mockaitis
That’s good. Thank you. I love those questions. Now in your book, Lifestyled, you mentioned three tools. Could we hear about adjusting volume, creating systems, implementing habits, and maybe your top tip, your top do and don’t within each?

Shira Gill
Absolutely, yeah. So, I have these three universal organizing tools, and they came from over a decade of organizing people’s homes. And then in my second book, I actually traveled the world to interview the 25 most organized people I could find. And in interviewing the most organized people in the world, and this is like from Canada to Mexico City, to Paris, to Lisbon, to Stockholm, I found that all of these people were practicing these three universal tools.

And so, here’s what they are. So, number one is adjusting volume. I think this is the most critical tool. And the way I define it is, volume is the quantity or the capacity of something. And so, if you think about, like, a radio dial, like we get to turn it up or turn it down. In most cases, we need to turn down the volume of our lives. We have too much going on. We have too many things to deal with and to go through.

So, an example here would be looking at just like one small thing where you can adjust volume. So, maybe it’s like the subscriptions. Like, I just found out I had been paying for an app for three years that I didn’t even know what this app was. I mean, how embarrassing is that?

And, like, if you add up the amount of money that most of us are paying for, like, memberships or subscriptions or apps, that we don’t even realize we have or we’re certainly not using enough, that’s like a teeny micro example of how you can turn the volume down on something, and you can save money instantly.

I also think about volume in terms of, like, what we’re consuming from social media to the news. Like, how can you streamline your sources and be more intentional about curation? And another example with volume, I could go on and on about volume, so I’ll move on to the second. But it’s thinking about your wardrobe, right? So, there’s a statistic that most of us wear 20% of our wardrobes 80% of the time.

And if I think about it, even as a minimalist, I’m probably reaching for the same, like, five things again and again and again. So, thinking about, “How do I have less but better in my wardrobe?” We all know about, like, Obama and Steve Jobs and these powerful leaders who have, like, one uniform that they wear every day so that they can optimize having more time for other decisions.

So, it’s really just thinking about in all areas of your life, even things like friendship or relationships, how can you turn the volume down so that you’re investing in the things that matter the most that you value?

Okay, so tool two is creating systems. So, I think of a system as an organized framework. It’s like a strategy that solves a problem. So, an example would be my husband went out and he bought a camera. And this camera came with a lot of accoutrements. So, it was like all of these charging cords and batteries and the manual, and he was leaving these things all over our very small home which, of course, drove me crazy.

And what I realized is we brought this new thing into our home, but there’s no system to contain it. And so, I said to my husband, “If I got you, like, a basket or a bin, would you put all of your camera-related things into it so that it’s not all over our house?” He said, “Sure.” And that’s how simple a system can be. So, it’s looking at like, “What’s something that’s not working in my home or my workspace that feels scattered or disorganized? How can I systematize it in the most easy way imaginable?”

And then the final tool is implementing habits. And this one cannot be overlooked. I think, as an organizer, I’m mainly helping people reduce volume and then set up systems and then I leave. But then it’s up to my clients, right, to implement the routines and the practices that ensure that those systems are not rendered useless.

And what I realized in interviewing all of these organizers from all over the world is they all had the same complaint, they said, “Well, I’ll help people get rid of their clutter, and we’ll do these beautiful systems, and we’ll label them, and we’ll set everything up. And then I come back a month later and it is chaos. And, like, what’s not working?”

And so, the lightbulb that I had was you can have the most pristine, perfect system, but if you don’t follow a habit to maintain it, it’s rendered useless. And so, I write about a lot in the book, “How do we make habits easier?” because most of us know what we want to do, but there’s just so much friction in the way. So, it’s like, even for me, like I have a really hard time exercising.

So, I use that very simple hack that most people probably know about, which is the night before, I fill my water bottle, I put it by the front door with my shoes and everything I need, so I wake up and there’s a visual cue, like I’ve already taken care of business. Now I just have to go walk out the front door. So, those are the three tools in a nutshell: adjusting volume, creating systems, and implementing habits.

Pete Mockaitis
Okay. So, that seems sensible. I’m intrigued, with adjusting the volume, most of us need less. What are the indications that we need more or less?

Shira Gill
So, I think that it’s asking yourself, “Do I feel like I have too many options? Do I feel overwhelmed?” Those are very clear cues. I would say the biggest word that I hear on repeat in my work is overwhelm. Almost everybody who works with me starts off by saying, “I just feel overwhelmed.” So, typically, that’s a sign that you have more volume than you can manage.

When we need to turn up the volume, it’s things like, “I feel lonely,” or, “I feel disconnected.” Like, there have been times in my life where I feel like I have more people and things and outings than I can manage.

And there have been other times in my life where I feel lonely or cut off or like, “Gosh, I’m not seeing the people that I love regularly.” Or, maybe I’ve moved to a new city, and I haven’t yet made new friends or connections, then it’s a matter of, “I need to turn the volume up on my effort towards connecting with people, reaching out, inviting people over.”

So, I think that’s a very real thing. Or, like, in your career, do you have more than you can successfully manage? Or, are you in a dry spell, where you feel like, “God, I don’t have as many clients as I want or as many projects as I want. Maybe I need to do more networking or connect with colleagues more”? So, I think those are some easy ways.

It’s like asking yourself those questions, “Do I have more than I can manage?” or, “Am I feeling some sort of a gap in my work or my relationships or even my home?” Sometimes a home, very rarely, but can get too minimal.

Pete Mockaitis
And I’d love to hear, when it comes to implementing the habits for non-cluttering of spaces or life, do you have a top habit or two that is truly transformational? And how do you recommend we get it started up?

Shira Gill
Yeah, so one of the biggest things that I see is paper clutter. And paper clutter is probably the most overwhelming and time-consuming thing to process because you can have like a small pile of papers, but that small pile represents maybe a hundred individual decisions to make. And so, what I find in most people’s homes and workspaces is their paper is strewn about in little micro piles everywhere, right?

So, typically, on the dining room table, on the kitchen counter, maybe in the entry, maybe on your nightstands in your bedroom. So, one of my easiest hacks that you can implement today is you can gather up all of the unprocessed paper piles that are in your environment, wherever they may be, and centralize them into one vessel. And the vessel is simply your action item basket.

So my rule is if anybody needs me to deal with any anything, look at anything, process anything, pay anything, it has to go in my action basket. So, now instead of having papers all over our home, I have one basket. I review it once a week. And so, it doesn’t feel like endless or daunting.

And, in the first place, like when you do this, it might feel like more of a mountain than a molehill. But what I can tell you, from years of feedback, is that just having all of those kind of nagging to do’s and open loops, open tabs in your brain in one place is really relieving for your brain. And then you can think of it as like, “This is one big project instead of a million overwhelming projects.”

Pete Mockaitis
Yeah, that’s an interesting organizational concept, in general, like the consolidation, one thing versus many things. And I’ve just been astounded, even in like a hotel. Like, I’ve got my bathroom stuff in a variety of places. There’s a little moisturizer, there’s a razor, there’s a toothbrush, there’s toothpaste. Okay, so those are kind of like all over, like, the sink area.

And then, when the housekeeper comes and does the tidying up, perhaps they place a washcloth next to the sink, and they place the items on the washcloth. And, somehow, to my eyes and brain and psyche, it’s like, “Ah, that’s much better.”

And nothing substantially has changed at all except, somehow, it seems, I am processing all of these toiletry items as one because they’ve been placed on a washcloth and it blows my mind that it’s like I’ve been tricked. It’s, like, “I fell for that. Like, this is making a huge difference to me.” What’s going on?

Shira Gill

I love it so much. Yeah, it’s the art of containment, right? So, instead of having all these random disparate things, we now have one thing, a pile of toiletries on a towel, contained and organized for your brain. So, it’s, again, like less for your brain to process.

And I think a big organizing hack that all of my colleague love, is just, like, make anything a system by batching it, containing it. Like, we love a tray, we love a basket. Like, it’s so, so simple, but even, like, thinking about for the people who make a smoothie every morning.

If you have a smoothie station that’s all corralled in a neat little pile on a tray, on your kitchen counter, suddenly, it feels organized and soothing to the brain, instead of having all of these different random things all over your kitchen.

And, I mean, I think, you’ve mentioned the hotel a couple of times, and I have to say people are always saying to me, like, “God, I just want my space to feel like how I feel at a hotel.” And I think the thing is, when we go to a hotel, there’s everything we need, but nothing more. They’ve cleared away all the excess.

And I think what people forget is that we have the ability to do that for ourselves in our own homes to clear away the excess, and to think about, you know, like my example in the home office, “What do I really need to do my job effectively? And what’s just collecting dust and creating mental clutter for me?”

Pete Mockaitis

Okay. Well, now let’s hear about a favorite quote, something you find inspiring.

Shira Gill
Joshua Becker, who is a fellow minimalist and life simplifier, says, “The first step in crafting the life you want is to get rid of everything you don’t.”

Pete Mockaitis
So good, yes, Joshua was on the show.

Shira Gill
Oh, love that.

Pete Mockaitis
And a favorite book?

Shira Gill
Okay, so my new favorite book is called No New Things, not surprisingly. So, this is written by a colleague of mine, Ashlee Piper. She doesn’t think of herself as a minimalist, but she is a sustainability expert. And she has a 30-day “No New Things” challenge, where you just start thinking about, “What are the things that I want to bring into my life?” And she offers a bevy of tools to radically shift your relationship with consumption.

Pete Mockaitis
Okay. And a favorite habit?

Shira Gill

Oh, mine is really simple. It’s just a five-minute tidy before bed. I think setting yourself up for success in the morning should not be underestimated. So, for me, that’s, like, the quickest tidy with my family, wiping down the surfaces, making sure the dishes are done. If I have time, even laying out my outfit for the next day. It’s kind of like a gift to my future self.

Pete Mockaitis

And is there a Shira-original sound bite that really resonates with folks?

Shira Gill
I mean, I always say “Owning less is easier than organizing more.” And I think it’s, really, it’s a simple way of saying, like, “If you have less to organize, you can spend less time organizing.” It’s just kind of simple math.

Pete Mockaitis

Yeah. And if folks want to learn more or get in touch, where would you point them?

Shira Gill
So, you can check out my website, which is just my name, ShiraGill.com. I have a free newsletter called “The Life Edit” on Substack. And you can find my three books anywhere books are sold, so Minimalista, Organized Living, and my new book is called Lifestyled.

Pete Mockaitis
All right. And do you have a final challenge or call to action for someone looking to be awesome at their job?

Shira Gill
Swap something you want to do less of with something you want to do more of. A simple example is most people tell me they want to spend less time scrolling social media and more time reading and absorbing new information that feels good. So, thinking about something you want to do less of and swapping it with something you want to do more of.

Pete Mockaitis
All right. Shira, thank you.

Shira Gill
Thank you so much for having me.