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

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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.

1108: How to Think, Act, and Achieve Like an “A-Player” with Rob Monson

By | Podcasts | No Comments

Rob Monson reveals how professionals can become A-players—and what leaders can do to retain them.

You’ll Learn

  1. The hard truth many leaders don’t want to accept
  2. What A-players do differently from the rest
  3. The simple trick to get a day back every week

About Rob

Rob Monson, founder of Tenfold Advisors, is Utah’s leading business growth coach. A Scaling Up and Metronomics coach, he helps mid-market CEOs install disciplined systems that transform people, strategy, execution, and cash. His clients have driven Utah’s most founder exits at a 7X EBITDA multiple, 10X profit gains, Inc. 5000 honors, and award-winning cultures. Formerly with Golf Channel and 1-800 Contacts, Rob now shares practical scaling insights as Tenfold Biz Coach on TikTok.

Resources Mentioned

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Rob Monson Transcript

Pete Mockaitis
Rob, welcome!

Rob Monson
Hi! Thank you, Pete. Thank you for having me.

Pete Mockaitis
Well, I am so excited to hear your wisdom. You are privy to a lot of deep, high-stakes, personal conversations, coaching executives and business owners. Can you give us a little bit of context for those conversations?

Rob Monson
Yes, so I’ve been a business coach for eight years this month, as a matter of fact, and what I do in my role is I coach CEOs and their leadership teams to help grow and scale their companies. And I do that through helping them install systems and routines and behaviors that help them eliminate drama and focus on the right things.

Pete Mockaitis

Well, that sounds fantastic. Eliminating drama and focusing on right things are themes and powerful levers, it seems, in terms of accelerating careers and results.

Rob Monson
Yes, absolutely. And one of the big things we focus on is, “Initially, do you have 100% A-player leadership team? And how do you get to what we call an A-player leadership team? And how do you make sure and can identify whether you have non-A-players in your team? And what does that look like?”

Pete Mockaitis
Well, I was watching your TikTok and it’s amazing. You have a tremendous number of views for coaching insights on TikTok. Didn’t even know you could find that there, but now I do. And you got them, Rob. I was watching one of your videos, and you talked about, very quickly, eliminating C-players, and that sounds a little bit spooky.

So maybe let’s define what makes an A-player, B-player and C-player, and knowing maybe first of all that some folks feel a little bit perhaps even bristle-y about the language. What about a growth mindset, Rob? Can’t we all flourish and become A-players?

Rob Monson
They do. And this is the difficult part, is in the modern era, we try to avoid labels. However, if we cannot label the behavior and the performance, we will not grapple with it and we will not grow. And so, when we talk about an-A player, it’s someone that lives the core values 90-plus percent of the time, the organization’s core values 90-plus percent of the time, and hits KPI-driven goal 90-plus percent of the time.

So, we have a subject of measurement that’s normed over time by leaders in an organization. We share our scores with each other and we grade out our teams, which we do quarterly. And then we have an objective measurement, which is how often they hit goal. In between those two things, you find whether they have an A-player or not.

And your B-players tend to be people that live the core values consistently, but they aren’t as productive as we need them yet to be. Maybe do not have the habits, routines, behaviors. Sometimes, it’s skillset, but usually it’s embedded in the other area of habit, routine, that really makes them successful. And finally, we have C-players who do not live the core values and are not productive.

And here’s a fascinating statistic. C-players drag down each team by at least 30% productivity every single time.

Pete Mockaitis
Wow! So, a single C-player can drag down a whole team by everyone by 30%.

Rob Monson
A single C-player can drag down an entire…yep, A single C-player will drag down a team’s results. It doesn’t matter what the KPI is or growth measurement, by at least 30% every time. And it’s remarkable how often that’s held up over the last eight years.

Pete Mockaitis
Well, that’s intriguing. And so, you’re measuring that based upon the attainment of these KPIs?

Rob Monson
Yes, well, attainment of the KPIs, and also, you see some behavioral practices as well that tend to fall off in terms of how they live the core values because they’re making up for this person’s lack of behavior and productivity. So that’s why, when we identify if we have a C-player in our presence, my usual question is, “What time are they leaving today?” And I don’t mean that to be…

Pete Mockaitis
Okay, ooh, Rob, spicy. Right to the quick.

Rob Monson
I learned that from an amazing coach named Dave Baney out of Las Vegas. And Dave had it spot on, which is you’re on the clock. It’s like the NBA shot clock. You are on the clock before your A-players leave. And what you want to do above all, that’s the number one reason you’re a-players will leave is tolerance for C-players.

Number one thing you want to do in an organization is preserve your A-player team and be able to remove the C-players that drag them down. And what happens again, that’s the weight that drags us down. So, most organizations, if you follow the rules that were established about 30 years ago, or the research that was established years ago by a person named Bradford Smart, who wrote a book called Topgrading. By the way, don’t ever read that book. It’s a really rough book, but the concept is great. And in “Topgrading,” the logic and philosophy is that about 25% of your organization will be C-players.

Pete Mockaitis
You say Geoff Smart?

Rob Monson
Brad Smart, his dad. Read Geoff Smart in Who. That’s a great book.

Pete Mockaitis
Oh, well, I was going to say we had on the show, way back in the day, episode 30 in 2016, Randy Street from ghSmart, because this language of A-player is bringing me back. And he said something kind, I think, if folks are bristling out the labels, and I think it’s true. Everybody is an A-player at something. In the right organization, in the right role, they can flourish as opposed to, “Oh, you’re just dumb and worthless. So, I guess you’re out of luck everywhere.”

Rob Monson
Absolutely. And, you know, in the modern era, because there are just so many ways now for us to make money and so many outlets, today’s C-player usually is an A-player on their own. And one of the one of the big key pieces of advice I give to people who are not flourishing and have a sort of a track record of not flourishing when you dig into their history, it’s, “Hey, you have a great skillset in this particular area and you have great behaviors in this particular area, but you just don’t flourish under someone else’s values. Go start your own thing.”

Today’s entrepreneurs were yesterday’s C-players, and A-player entrepreneurs, too. So, there’s a way to get into a great role and a great fit, even if it’s not with someone else’s organization.

Pete Mockaitis
Okay. Well, let’s define some of these behaviors. It sounds like there is some variability in terms of the organizations and the cultures and the values. But, perhaps, could you zero in on a few universal or near-universal behaviors or things that comprise an A-player?

Rob Monson
Yeah, absolutely. So, we talked about living the core values and hitting KPI-driven goal, and the question is, “How do they do that?” And what we find is they are better at developing habit and routine, meaning that those who set their day in a predictable way, who go out of their way to figure out, to realign themselves to a set of key priorities they’ve established, hopefully for the quarter, “What am I doing relative to those priorities that I’m going to accomplish today?”

“Where am I stuck?” Understanding, “Where am I stuck and need help from others to be able to accomplish those priorities?” And then number three, “If I’m pacing behind on one of my key KPIs, what am I doing to catch up?”

And those are sort of the behavioral traits that the A-player tends to have in addition to some of the things that you talk about with on your podcast on prioritization and time management, those tend to be the hallmark of the A-player is they can prioritize, they can time-manage they can look at that set of priorities and say, “This is important. This is not important.”

What we see, really, really important, in this in this scenario is, one, successful people time-block two weeks out consistently. They block their time. They have their calendar blocked out with time, specifically spent to work on their handful of one, two, or three key priorities they have to accomplish for the quarter.

Number two, their heads are out of email or Slack or Teams. And I remember, like, the Slack tagline 10 years ago was something like, “Be more productive,” and those tools kill our productivity because they encourage us to respond to urgent instead of important. I’m not saying there isn’t any use for those tools, but you have to get into the same habit of Slack or Teams as you do with email, which is if you’re highly productive, you get into a mechanism where you’re responding three times a day.

I do it at 8:00 a.m., 12:00, 4:00, and spend a half hour doing it and economize my responses with AI or other tools, or I get into the trap of being stuck in email. And one of the most painful things we have to do as coaches, is remove leaders who cannot get their heads out of email because that’s not where we need them focused.

Pete Mockaitis
Okay. Well, these are some very specific perspectives. And, it’s funny, I’m imagining, this brings me back to a conversation I’ve had with a couple folks who are in the mortgage game and doing very well. And so, I say, “What’s the trick? How are you able to just really generate so many more loans, deals than the other folks?” And it’s like, “You know what? The thing is, when I’m at work, I’m doing my work.”

And it sounds like, “Well, duh.” But especially, when there are some activities, we feel some reluctance towards like, “Okay, I’ve got to go do prospecting in the sales universe. Like, oh, that’s kind of uncomfortable. That’s kind of unpleasant. I’m going to get some folks who are not pleased to be hearing from me.”

And yet it seems that, from my limited sampling, those who go do that, as opposed to find any other thing they could be doing on email or anything else, tend to flourish in a sales role, for example.

Rob Monson
Yeah, yeah, absolutely. And there might be some people that are very task-oriented and very relationship-oriented, right? And sometimes we have to make sure we can put them in the right role. They are good at some things. Sometimes you have to have the self-awareness to be able to realize whether you are task- or relationship-oriented.

Like, that’s why I have to minimize task for salespeople, meaning the systems do the tasks for them, whether it’s follow-up or tools they’re using. They have a minimal amount of data entry because they tend to be good at relationship and not tasks. Things that are high relationship and high tasks don’t tend to have a good middle ground unless you have extremely high-level people.

Pete Mockaitis
Okay, understood. Well, could you maybe walk us through a couple examples of folks you’ve seen see some transformational cool things in their career by following this kind of three-step process?

Rob Monson
Yeah, so what I’ve seen really consistently is, to your point, not everyone’s going to elevate, right? They just don’t have the ability to be able to grasp onto new habit and new routine. And it’s something sort of deep within them. It can be caused by a lot of things. It can be caused by habits growing up, childhood trauma, there are things. ADHD is a big component.

If you know the amount of people in society who suffer from ADHD, it’s about 6%. And then the number of people that suffer from slowish cognitive tempo is about 15%. That lines up perfectly with what I see among executives, which is about one out of five suffers from something that looks like ADHD, making it harder to form habits and routines.

Pete Mockaitis
Fifteen percent slow cognitive tempo.

Rob Monson
Sluggish cognitive tempo, yeah. Dr. Russell Barkley, I believe, has talked about that. That’s someone that’s a very interesting ADHD expert. I’m someone who suffered from ADHD myself. I have very good medication at this point, and that’s helped me develop habit and routine successfully, whereas without the medication, I could not do it.

Pete Mockaitis
Let’s define a sluggish cognitive tempo. Does that just mean I’m thinking slow?

Rob Monson
It usually just means that, you know, between the ADHD receptors, right, we’re not getting quite as much of a chemical reaction that we need to. I think it’s dopamine and norepinephrine, right, or something in those neighborhoods, the same neighborhood. You’re not getting enough that you need out of those two to be able to be as effective as you need to.

So, it becomes an executive function issue, meaning we’re not able to consistently make decisions and listen appropriately in such a way where it translates into us being able to either absorb new habit or routine, or be able to prioritize and manage our work effectively so we get through things, we accomplish things we need to, and we excel, learn new patterns as we go.

Pete Mockaitis
Okay, understood. And so then, it sounds like, sometimes you find yourself in that boat, it may just be a biological matter, something in the realm of medication, in the realm of nutrition, exercise, or kind of outside of what happens inside the office.

Rob Monson
Yes. So, to your point, those situations are very difficult to deal with. Those who are successful can, basically, with a little bit of coaching, even though they might not have had in the past, to say, “Hey, let’s really focus on blocking your time out now more effectively so you have time to be able to spend focused on your priorities. Let’s make sure that you are spending way less time in email on a daily basis, that you’re only checking it three times a day, over Slack,” for instance, right?

“Let’s take those distractions that maybe you’d walk down the hall to be able to go talk to someone and let’s get those knocked out of the way in a daily huddle.” We haven’t talked about that yet, but in a daily huddle, we usually put our executives and all of our teams in a daily huddle where they can knock out things that don’t distract them later in the day.

And if you can do those things successfully, what we find is, and about 30% of leaders will be able to do that, so probably low for a lot of people, but that’s the reality is you can get about 30% will be able to develop new habits and routines, they will be able to be successful in their role.

Pete Mockaitis

Okay. Well, let’s talk about a few of the particular habits with regard to time blocking, and the process by which you identify, “Hey, what is the high-value thing? And how do I think about where the best place is to block that time?” Maybe just walk us through a couple examples of folks putting this into action specifically in their roles.

Rob Monson
Sure. So, the most successful way that it starts, by the way, is at a higher level than maybe all of us start with as even leaders or even doers in an organization. It starts with the leadership team coming up with a set of priorities. And once those set of company priorities are known, then we can actually tie our priorities back to the company priorities.

And can they always tie back? No. But in most cases, everyone can usually tie their priorities back to something that’s a key priority for the organization. That’s step number one, “Is what I’m working on tied into the most important things the organization has deemed worthy or important to work on?” That’s number one, “And do I have a handful of things tied to that?”

Then, usually, the KPIs or the measurements that I own are also tied to those priorities as well. Not always, but most of the time. So, it’s, “Am I devoting a portion of my week to making sure that I accomplish those priorities and the tasks related to them, rather than getting distracted by something that comes up like an emergency?”

Because the job isn’t to do the job, by the way. The job is to do the job better. And that’s where most people fall off into non-A-player land.

Pete Mockaitis
Expand on this notion the job is not to do the job?

Rob Monson
In a scaling company, we want A-players. And what I mean by that is we want to grow the A-player percentage inside the organization. And the percent of A-players is something that each leader is measured on. And again, that’s the person that lives core values, that’s KPI-driven goal. And what we want, and we pay for this as well, we’d rather have one great person than three average people. We’ll pay that one great person two times their average salary and still win.

And when we do that, what we expect out of that role is they will not just come in and sit in the seat and do the job. It’s they will actually excel with the job. They will be better than the role. They will wipe out portions of the role that are inefficient and ineffective. And these are things that are very clearly set as expectations up in the hiring process.

Pete Mockaitis
Okay, well, could you walk us through a story of an individual who wasn’t doing the things, then turned around and started doing exactly that?

Rob Monson
Yes, so I had a member of a leadership team, and this is someone who, you know, had struggled previously before I became the coach of the organization, had struggled by getting distracted by the wrong things. With her, it was, “Hey, we’re going to be focused on things that are emergencies or things that are popping up throughout the day.” And this person was not doing what they needed to do to actually systematically work through, “How do I make sure this emergency never happens again?”

And what that meant was they, and because they weren’t accomplishing their priorities, which were directly tied to being able to eliminate those emergencies that popped up consistently, they just kept running into the same issue again and again. Once this person adopted a time-blocking routine, and by the way, was she immediately better at all aspects of time blocking? No, she gradually worked up to it. She blocked out a day, a week, you know, a week and a half and up to two weeks as she did that.

And as she got, she was coached by myself and by the CEO to be able to let go of things that were not the most critical priorities and be able to stay focused on certain times of day to respond to her email, she became one of the most productive members of leadership team and is still in her role to this day excelling.

And she’s learning not only is she able to excel and sort of think past the role, which is where we need our A-players to be, she is becoming an expert at recognizing patterns. And that skill of pattern-recognition is something that is built up over time by focusing on the most critical things.

Pete Mockaitis
Understood. Well, so let’s get into some detail associated with the priority and the time-blocking, how it is done better. So, we already talked about getting the alignment associated with the organization’s priorities and getting your priorities and the key performance indicators that we’re responsible for and what are the activities that will move those forward. Are there any magical questions that you find are super handy to cut through the lesser important things and really highlight the magical things?

Rob Monson

So, what we see is that most people who are successful with prioritization, they learn to do something that we teach them, which is a priority, usually, it’s a longer-term project. It takes several weeks to accomplish.

We teach them a practice of breaking down that priority by week and putting in place one major milestone they have to accomplish related to that priority in a given week, by the Friday of every week, to be able to successfully complete a priority in the time that they’ve allotted themselves.

Now again, they’ve gone through a process of sort of aligning, “Hey, is this something that’s critical and tied into one of the company priorities? Is it tied into the department priorities that I’m a part of?” And then we go through a process again of laying it out and being able to say, “Hey, how do I get into measurable steps that I can go through and be able to be more effective at hitting on a consistent basis?”

Pete Mockaitis
I dig that. And it’s funny, I imagine, as you do that, then the emergencies become even more irksome to you, such that you’re like, “No, the mission of this week is this, and instead I’m dealing with that.” And that question you asked, “How could I make this never appear again?” feels all the more weight-y, substantial, and critical that, “No, no, I’ve entertained this little interruption, annoyance, urgent thing, dozens of times. And before, whatever, I was cool, I was patient, and friendly, and no more. No more. That comes to an end now.”

Rob Monson
Yes, they get out of what we call firefighter mode, which is, and we love real firefighters that respond to real fires, but the rest of us in our work cannot be firefighters. Those jobs are all going away. So, if you believe your job is to show up and put out the fire, or to respond to the same problem again and again and again, that job will one day be erased.

What I want to get into is a role of being able to say, “How do I make the job better? How do I get rid of things that are constant pains to me and the organization? How do I do that with my priorities? How do I make sure that I’m changing the outcome in my role?”

Pete Mockaitis
And can we hear some cool examples in practice how a particular recurring emergency fire kept showing up and how a person figured out how to prevent that from ever emerging again?

Rob Monson
So, a good example of someone being able to systematically sort of see past daily emergencies and be able to sort of put out the fire is someone who works at a manufacturing organization that I coached. And we hired, we do not have a history of hiring A-players in this organization. We did manage to hire A-players in the roles in our back shop, and we had a pretty high defect rate. The defect rate was something like 6%.

And what, literally, within the first couple of months, a couple of key A-players said, “Wait a minute, why are we making the same mistake again and again and again with how we are pulling product off the line? Why don’t we, in fact, change the process of how we’re doing that so that…” in this particular case, it’s a facade that we manufacture for buildings, “…so that it occurs in a different spot than it did previously?”

And this is something that no one had ever thought of. They just kept doing what they were doing, meaning they just sort of kept wallowing in it, “Hey, it was really painful. We have a defect rate,” and rework costs companies so much money we don’t even realize it. And this was creating a very unprofitable entity, by the way.

And once they realized that, and we had all the other A-players in that role, number one, those people were thrilled and happy because they didn’t feel like they were failing every day. Number two, that organization’s profit went up by 8,000% the following year.

Pete Mockaitis
Oh, 8,000. Okay, there you go.

Rob Monson
It literally went up 8,000%. That’s the craziest thing. Yep, that might be one of the crazier stories of all time, but you get your defect rate low enough, and it can just be, that’s the stuff that’s shooting ourselves in the foot. Everyone thinks they’re going to grow because of demand or competition. It’s all just stopping you from shooting yourself in the foot.

Pete Mockaitis
Well, this is bringing me back memories. I had a consulting project at one of the world’s largest cookie-manufacturing plants, and it’s wild, yes. Especially in a manufacturing world in which, if margins are slim and competition is fierce, and it often is, then, yes, a meaningful change of the defect rate is huge.

And it’s funny, now I’m thinking about there’s so many things that we just kind of accept or put up with as normal, how it is, and it takes sort of an extra level of acuity, awareness to say, “No, no, time out. That’s not acceptable.”

And so how do you develop a little bit of that wise sensibility to recognize, “Hmm, this is a reality of which, you know, humanity must deal with,” as opposed to, “No, that’s jacked up and we got to fix that pronto”?

Rob Monson
Right. So, you touched on something that’s very, very critical. By the way, there’s a great website called The Systems Thinker, which is very useful, and it talks about people that are more predisposed to linear thinking versus systems thinking. And systems-thinking people tend to be able to see patterns in things.

So, one of the key things that I will ask, when I start coaching an organization is, “What are some basic things that you’ve seen over the last several weeks or months that aren’t good that you would like to change?” It sounds really, really basic, but sometimes no one, and again, a lot of organizations are poorly managed, most are, and nobody asks sometimes.

Pete Mockaitis
“Well, last time, nothing happened. I was ignored. They bit my head off. I’m just going to keep quiet here.”

Rob Monson
Yeah, the number one thing we deal with are dysfunctional leadership teams, right? And that creates that lack of psychological safety. Or, you know, you might have a manager that’s below leadership team who still creates that lack of psychological safety, and people don’t feel comfortable doing that.

But, “Hey, it’s just, what would you change? If you could, what would you get rid of that wastes your time, right, that would actually help you have a more high-level job to be able to get you promoted in the future if you could spend more time on this?” Those are the basic things that help people realize annoying tasks that waste their time.

I ask every one of my leadership teams to say, “Tell me the top five things that waste your time.” And they write them down. And then I say, “Okay, how much of that could you automate, eliminate, delegate, or simplify?” Most will come back with half a day to a full day of time savings that they can re-deploy.

Pete Mockaitis
Per week? Per month?

Rob Monson
Per week.

Pete Mockaitis
Okay.

Rob Monson
It is a per week savings in time when they go through that process. Because again, we just don’t proactively, in a lot of cases, or the organization hasn’t created psychological safety enough, to make it a practice to routinely think about, “How do you economize time spent on low level tasks?”

Pete Mockaitis
I love that. Could you give us a couple examples of, “Here’s a time waster we identified and how we busted it”?

Rob Monson
A couple of critical things. So, I have an example of a COO, for instance, who was struggling with time management, and I asked him to write down “What are the top five things that waste your time?” He did. And one of the most compelling things that came out of it was that none of the lists were very compelling at all. And I said, “How many of those could be delegated?” And guess what his response was?

Pete Mockaitis
All of them.

Rob Monson
All of them. Yep, every single one of them. And that’s usually kind of what you find out of that process is, you know, there are a lot of low-level tasks. It can be the time you spend polling reports where you can’t get to transactional data fast enough. It can be the time spent chasing the problems caused by your B & C players that are creating in the business, right?

People, because they have a fear of letting go, are holding onto the very low-level tasks, sometimes in very high leadership positions. So those are the kind of things that tend to hold people back in how do they use their time more effectively.

What I find in organizations, I’ll come in, and most people, I’ll tell you right off the bat, most people are at about 30% of what their true capacity is. And people say, “How is that possible? How is that humanly possible given how much I’m working?” One, we’re not focused on the right things. Two, we’re not focused on the process of automate, eliminate, delegate, simplify in how we look at work.

And, three, we’re not doing the time management things I was talking about earlier. So, when you get all those things going in an organization, you see that people have a completely different level of output and behavior, not just with themselves, but with each other if they’re an A-player.

Pete Mockaitis
Understood. Well, Rob, I’m curious, can you tell us any other key tips, tricks, do’s, don’ts that we haven’t covered yet?

Rob Monson
So, there are a couple of things that when we talk about habit and routine, and what we find is that, consistently, if people are not doing something daily or, at the minimum, weekly, it will not form into a consistent habit.

And so, what we want to do is, with one-on-one coaching, we try to get that into a weekly behavior, meaning you are in a one-on-one coaching session with your supervisor all the time, as much as possible. By the way, some of the worst times I’ve had in my career is when I did not have a consistent one-on-one with my supervisor.

And there’s a huge difference between organizations that will do consistent one-on-one coaching and those that will not. So, one of the things I encourage people to do is, if you’re not having a one-on-one with your supervisor weekly, I would ask for it, first and foremost. And I would get feedback on what I’m working on for two reasons. One, stay focused on the most critical things. Get aligned around that.

Two, “Behaviorally, are we both seeing the same thing? How are you growing? Where do you need help and support?” There’s a massive difference when people get both quality and quantity in coaching. And the organizations that do not do consistent one-on-one coaching, they’re always in my bottom three in terms of year-over-year results if they do not one-on-one coach on a weekly basis.

So, it’s like, “Hey, if you’re an organization that won’t coach you, that your boss keeps giving it up, you’ve probably got the wrong boss,” they’re saying, “Hey, I can’t get to your one-on-one this week because something else is distracting me,” I’d find another job.

Pete Mockaitis
Okay. Understood. Well, that has been my experience, that I have experienced way more learning growth development when I did have that regular recurring thing in conversation happening. And I like what you had to say about a habit. I’m reminded of, I’ve got fond memories in consulting with a teammate named Blair.

And whenever we were returning from the client trip, it was understood that he and I would be taking a cab together from the Chicago airport, Midway or O’Hare, back to the office. And folks would be like, “Oh, well, we can all get on the same cab.” And Blair would say, “No, Pete and I,” he’s from New Zealand, “Pete and I will be on this cab. We’re going to be chatting.” And so, I loved it because I felt like I was a priority for him, so I felt tremendous loyalty.

As well as it was a nice, we talk about habitual, it was a nice groove. It’s like, “Okay, this is a sensible time. We did a bunch of work at the client site. We’re now about to have more of a chill Friday with, whatever, filing expenses or whatever. And so now, while it’s fresh, we’ll talk about what we observed during the course of working at the client site week after week after week,” and it was gold.

Rob Monson
Yeah, absolutely. And what you find is that most people will say, “Well, I have no time,” or, “I have no time to coach.” And the real answer is you have no time because you will not coach. So, what we try to do is get people’s mindset around that.

And if anyone listening to this, if they’re in a coaching position, and if you’re in a manager role, that’s the job, unfortunately to some people. I mean, fortunately, for people that want to do it, that’s the job. But a lot of people will go, “Well, I don’t have time to manage my team.” Well, that’s the job.

Now you do get into these really unfortunate things like ratios when they’re managing more than, I mean, eight people is kind the maximum anyone can really coach effectively. Like, eight is a burn line. People get to 10. Weird things like insomnia and anxiety go through the roof in the leader. So those are the things you have to look out for.

You can appoint team leads or do other things to solve for that situation without, by the way, having to pay more in a lot of situations. It’s just, hey, give someone a coaching assignment. Remove the 10% of their week that was focused on those tasks that could be automated, eliminated, delegated, and simplified, and give somebody an assignment to coach their team member. That’s a great way for people to build their skills and capabilities over time.

Pete Mockaitis
Beautiful. Well, so that’s one critical key, weekly, behavioral, habit thing is these recurring one-on-one coaching bits. Any others that you would elevate to similar criticality?

Rob Monson
So, you heard me talk about a daily huddle. And this is something so you might have heard of Vern Harnish who wrote the book Mastering the Rockefeller Habits and Scaling Up. I was part of an organization that had a daily huddle several years ago, and we grew and scale like wildfire. And a couple of things I never heard because of that daily huddle were, “Hey, no one’s ever told me about that,” or, “Hey, we don’t know where someone is on this particular project or priority.” We were always on top of those critical things.

So, we get everyone into a daily huddle where they’re there for five minutes a day with their team members. There’s usually a minute per person on the team. It might go a little bit longer than five minutes if it’s a bigger team, right, 10-people team, 10 minutes. But, “Hey, what are we focused on the next 24 hours? Where are we stuck? Where am I with my KPIs? And what do I need to do to get them back to green if they’re not?” And that’s basically it.

Pete Mockaitis
And one thing I love about that is just the basic accountability. There’s no hiding out when that is occurring. It’s like, “Oh, Rob, it seems like you’re not doing much. Well, lucky us, we have some resource available to give you some stuff.”

Rob Monson
Yeah, and you get the non-A player responses at first in organizations which are, “Well, that might be like micromanagement.” No, we’re just going to manage the company. Most people don’t even run their companies effectively. We’re just going to have basic alignment every day. It’s going to take a couple minutes. It’s going to free you up throughout the rest of your day.

And the one thing that really changes you, and this is what’s really silly when people fight putting in place a daily huddle. At the end of the day, the five minutes of prep that you take for that particular meeting is what changes you. And again, it’s part of that habit routine we talked about earlier. It’s, “I know what I’m supposed to focus on today. I know where I’m ahead and where I’m behind. I know where I need help.”

That little thing, fundamentally, allows us to put all the other systems and tools we put in place to grow organizations. And people will fight it.

Pete Mockaitis
Yeah, certainly. Yeah, you’ve got that perspective. It’s like, “Oh, I said yesterday I was working on this thing, but I’m about to end my work day with very little progress on that thing. And so, I’m going to have to fess up to that tomorrow. That sounds very unpleasant. Maybe I’m going to kick it into gear here.”

Rob Monson
It’s a little bit uncomfortable. And I remember back in the day, I worked at a company called Compass in Florida, and we help big universities take degree programs online, and Dan Devine was our CEO, and it was a little bit uncomfortable. And Dan was a super nice human being, by the way. But it was professional. You walked into the meeting and you were ready to go. And, by the way, being ready to go and being professional are not bad traits to be able to grow your behaviors, capabilities, how you treat other people on a daily basis.

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

Rob Monson
One of the things I’d like to say about pattern recognition, just very, very quickly, is that that is a skill that not everyone has.

Our A-players tend to have it, meaning 25% of the population will tend to have it. It can be developed over time and you have to be able to ask yourself some really key questions, which are, “Hey, what are the effects on the ecosystem around me? Have I seen this before? Have I seen anything remotely like it in my past that I can compare what I’m looking at right now to?”

Those are things that we don’t do that often in business, but those are kind of some of the key questions we have to ask ourselves to try to get more into systems thinking or pattern-recognition mode over time. And so, people can get better at those areas, but it can be a struggle if we’re more of, “Hey, this straight line gets me from point A to point B and it’s hard to think outside of that.”

There can be some great linear A-players though, to be very, very clear. I’ve worked with people like that in the past and they were amazing at keeping someone like me in the right spot when I needed it. And so, you can get some very, very highly effective A-players that are linear thinkers. They might not be as abstract as everybody else and they’re not dumb. They just think differently than the rest of us. They’re very precise in how they think about their day, their week, their month. And they don’t deviate from that too much. That’s fine.

Pete Mockaitis
Okay. Well, now, could you share a favorite quote, something you find inspiring?

Rob Monson

“Plan your work and work your plan.” And I believe my boss, Suzanne, back in the day at Compass, heard that from Johnson & Johnson. That’s one of my favorite quotes of all time because, really, that’s the essence of how to do successful work is, “I plan what I’m going to do and I fight toward it, and I get better at prediction.”

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

Rob Monson
So one of my favorite studies is the research that Bradford Smart did, Brad Smart did, back when he created the hiring process for GE, back when GE was GE, and that’s what we refer to as “Topgrading.” There’s probably a better name for that in the modern era, but that’s the same process that Geoff Smart, basically, shows us in the book Who.

But the research behind that was very accurate. And what it says is that 25% of the organization will be A-players, meaning, again, those people that live the core values, hit KPI-driven goal, 50% will be Bs and 25% will be Cs. And the crazy thing about that, when you actually tie in everything else that we talked about today, is that you could have 25% of your organization walk out the door tomorrow that were C-players and your happiness and productivity would actually go up.

I have a client that I’ve worked with recently, actually started them several months ago, and they’ve done a great job. This is going to be a very well-known nationwide brand in the very near future. And they realized very quickly, the CEO realized they had people that were not living the core values and were not productive in their midst, and they quickly changed that outcome. They did try to coach up, that didn’t work, so they quickly removed those who would not elevate.

And guess what? Everyone’s happiness has gone up dramatically, the organization is now going towards its goal tiers. Here’s the number one thing. The A-players have not left. And that’s what we want more of.

Pete Mockaitis
Okay. And a favorite book?

Rob Monson

The Five Dysfunctions of a Team by Pat Lencioni. And I have every leadership team member read that, and I wish I would have read it even sooner than I did. I read it several years ago, but wish I’d read it even earlier than that. It would have really helped me understand what my role is on a leadership team.

And that is you are on the leadership team first. You’re not the head of marketing. You’re not the head of sales. You’re not the head of operations first. That’s where we get into the most trouble as leaders is you think you’re the head of the other team first and you come to the table as their advocate and not coach them through obstacles. That’s where you get into the biggest challenges.

Pete Mockaitis
Pat was on the show. He was awesome. And a favorite tool, something you use to be awesome at your job?

Rob Monson
There’s a great toolset that I’ve used consistently lately, which is an assessment of ironclad emotional control in leaders. And one of the key behavioral characteristics we find in Sam Walker’s book, The Captain’s Class, is that leaders on sort of dynasty, very successful sports teams had some very similar characteristics. And one of them was ironclad emotional control.

And what we do is I give them a really quick 12-question assessment to see where they are with their own Iron cloud emotional control. And that’s created, not only in myself, but in my team, some of the greatest improvements in self-awareness that you’ll see as leaders. So, that’s definitely been a favorite. Multipliers assessment is also a favorite tool, by the way, if we’re talking about team members. And if anyone’s talked about it in the past, Liz Wiseman Multipliers is a great tool.

Pete Mockaitis
Yeah, she was on the show.

Rob Monson
Liz Wiseman, the multiplier assessment, there are some quirks with it. There are some questions that I would word completely differently, but it is the fastest dose of self-awareness that you’ll put a leader through. And it’s pretty cool when they realize that, “How much did a previous leader multiply out of me? And how much did one that was diminishing get out of me?”

And if they realize they want to be like the one that multiplied more out of them, it’s a pretty fast change for those that are willing to do it

Pete Mockaitis
All right. And a favorite habit?

Rob Monson
My favorite habit is I get up. I look at everything I have to do that day and I say, “What is the one thing I’m doing tied into my top three priorities for this quarter?” And make sure that I have time, energy and effort focused on those things.

Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks, they’re retweeting and commenting up a storm on TikTok, etc.?

Rob Monson
Yeah. So, yes, there are. Yes, there are some things that resonate. And sometimes, again, it’s that things resonate because they defy conventional wisdom. And one of the things that defies conventional wisdom is to be able to remove your C-players immediately. So, for eight years, in dealing with 35-plus, almost 40 CEOs, I have not, in eight years, ever heard the phrase, “I should have held onto that C-player longer.”

And what that means is, we usually, so mid-market CEO problem is way different, by the way. I mostly deal with mid-market CEOs, way different than the big bad CEO problem that a lot of us, we might have our impression of in our mind. We have a lot of really, really, well-intended mid-market CEOs that are members of EO, YPO.

By the way, great tip for your audience, if you want to find organizations that want to find A-players, look for organizations that are in your local EO or YPO chapter, the CEOs are in that. Those who are in peer learning groups are usually way more self-aware and open to A-player hiring, paying more for the right person in the right role than others that will not.

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

Rob Monson
One, they can follow me on TikTok, @robmonson12. Two, they can find me on TenfoldAdvisors.com. That’s my website as well. So, if they’re interested in learning anything more about what I do, that’s where they would go.

Pete Mockaitis
Okay. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Rob Monson
The one challenge I would leave everybody with is the email challenge, which is find a way to get yourself out of email or Slack. Really try to set a habit and routine. That’s the fastest and easiest one. It’s, “Hey, you know what? I’m going to respond. I’m going to get in here three times a day rather than have the dopamine hit of doing it all day long,” so that you can spend more time focusing on more critical things.

Pete Mockaitis
All right. Rob, thank you.

Rob Monson
Thank you. I appreciate the time and getting to know you, and hope that was helpful.

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.

1095: Keeping Your Productive Groove through Movement, Thought, and Rest with Dr. Natalie Nixon

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Dr. Natalie Nixon discusses how to develop strategic thinking, prevent burnout, and enhance creativity through her move, rest, and think framework.

You’ll Learn

  1. The inner skills that make us more strategic and effective
  2. The neglected skill that makes us more strategic
  3. How to prime your best ideas in 90 seconds

About Natalie

Dr. Natalie Nixon, creativity strategist and CEO of Figure 8 Thinking, is known as the ‘creativity whisperer to the C-Suite’ and is the world’s leading authority on the WonderRigor™ Theory. She excels at helping leaders catalyze creativity’s ROI for inspired business results. She is the author of the award-winning The Creativity Leap and the forthcoming Move.Think.Rest. 

With a background in cultural anthropology, her career spans global apparel sourcing with The Limited Brands and a 16-year career in academia, where she was the founding director of the Strategic Design MBA at Thomas Jefferson University. She received her BA from Vassar College and her PhD from the University of Westminster in London. She’s a lifelong dancer and a new aficionado of open water swimming.

Resources Mentioned

Thank you, Sponsors!

Dr. Natalie Nixon Transcript

Pete Mockaitis
Natalie, welcome!

Natalie Nixon
Thank you. It’s good to be here.

Pete Mockaitis
Yes. Well, I’m excited to hear some of your wisdom from your book, Move, Think, Rest. Can you share with us one of the most surprising, or counterintuitive, or wildly fascinating discoveries you’ve made in investigating this stuff and putting together the book?

Natalie Nixon
I think one of the most interesting learnings I got was to really leaning into this idea of emotional recovery. I think that we spent a lot of time thinking about physical fitness and endurance so that our cognition is nice and sharp.

And we think, obviously, about mental agility and sharpness. It’s really the emotional dimension of ourselves that kept coming up over and over as I was building out this “Move, Think, Rest” framework. And I think that really matters in a time of ubiquitous technology. It’s really interesting to me.

Pete Mockaitis
Emotional recovery, that’s a nice turn of a phrase. Can you share with us, well, one, a definition and, two, maybe just paint a picture of what the opposite of emotional recovery looks like, and then what emotional recovery things one does to emotionally recover?

Natalie Nixon
Emotional recovery is our capacity to feel the feels internally, to be self-aware in terms of where our barometer is emotionally, as well as that emotional intelligence, that outward external ability to identify where people with whom we’re having conversations, people who are leading or managing, where they are emotionally, but we actually are not good at the external identification of that unless we are whole emotionally.

And I learned this turn of phrase through someone named Scott Pelton. I interviewed Scott Pelton, who’s the co-founder of an executive leadership coaching practice called Tignum. And in a time with a lot of economic instability, a lot of uncertainty in the markets, where we’re hearing of downsizing, where managers are having to do layoffs, where people are observing their friends, their colleagues, family members going through these sorts of things, to expect a manager or a leader to show up at work, like, “Nothing to see here. Everything’s great, and I’m feeling great.” That’s not true.

And so, the ability to recover emotionally after one has had to deliver really harsh news, bad news, to a team, to colleagues, is essential actually for your clearer thinking and for your ability to rebound and maintain momentum. And one of the things I’ve been saying for quite a while is that, in the future of work, work will increasingly become inside-out work.

And what I meant by that, and it’s now even more grounded in my learning about emotional recovery, is that the companies that will be able to attract and retain the best talent will be those that are curious about who you are as a person and want to integrate those assets, those capabilities, those abilities into the ways that you are doing your work and your job, instead of shying away from that.

And I’m not, I’m not saying that leaders should have a good cry with their team. That’s not what I’m talking about because there is still this need to feel that the person who is leading has it together. But there’s also this need to trust that leaders get where we are. And we trust that when leaders reveal, in a more vulnerable way, their own uncertainty, when they’re self-reflexive in the types of questions that they’re raising about a strategic decision that has been made.

So, another person I interviewed for Move, Think, Rest is Carla Silver who is the co-founder of a really great nonprofit organization called Leadership + Design. And one of their taglines is “Be more curious than certain.” And when we are curious about how we are feeling, how we are doing, how others are feeling, how we are doing, that actually is the on-ramp to so much discovery. So, the emotional recovery component to work is essential now more than ever.

Pete Mockaitis
And that’s an interesting notion. And we might find ourselves emotionally taxed. Or, what would you say? What’s the opposite of being emotionally recovered? Emotionally drained, depleted?

Natalie Nixon
Burnt out.

Pete Mockaitis
Burnt out, yeah. Certainly. And I guess, as I think about that experientially for myself, so I’m thinking about just my young kids at home, in terms of, I mean, sometimes it’s just a delightful, wonderful, happy, joyous, relating communal experience. And other times it’s just brutally exhausting, like, oh, so much whining, so much, you know, “Oh, we got a diaper to handle over here, but, oh, there’s a mess over there,” and sort of all the things in rapid succession.

Natalie Nixon
How old are your children?

Pete Mockaitis
Well, so right now, they are seven, six and two.

Natalie Nixon
Wow, full house.

Pete Mockaitis
So, yeah, it feels like, I do, I feel like sort of activated in terms of like the nervous system and my emotions. And I could feel it, it’s like, “Oh, I’m still irritated about what happened 30 minutes ago over there.” And yet I need to be, you know, Mr. Insightful Curious podcast, you know, moments later.

Natalie Nixon
Yeah, I love that you referenced the nervous system just now, because the other part of emotional recovery, the gift that it gives us is a self-awareness. Instead of just pushing through, plowing ahead, if you don’t pause to have a personal check-in about how you are feeling, then you actually are not fully present. And if you’re not fully present, then you actually will not be able to do your job well.

So, it’s a combination of being able to check in with oneself personally, be really honest. It doesn’t mean that you’ll have a solution to be able to go from frustration to jubilation right away, but even acknowledging it is really important in order for us to be able to do our best work, in order to able to start to put things in perspective.

And when you mentioned the nervous system, man, there were so much. There’s so much more research on the neuroscience of how our brains work best that was so fundamental to how I was putting together this “Move, Think, Rest” framework. One of the experts that I really have enjoyed learning from, I’ve listened to her podcast interviews, read her book, is Dr. Lisa Feldman Barrett, who’s written a great book called How Emotions Are Made.

And it turns out that emotions are not reactionary thoroughly, they’re actually constructed. And the reason why that matters is a lot of the way we have thought about how to show up publicly, how to show up socially facing in the West and Western cultures is we really take our nod from Descartes, “I think therefore I am,” right?

The ways that you can judge me, evaluate me is by my thinking, which is true. And it turns out, based on Dr. Feldman Barrett’s research, that emotions are actually a bit more predictive than we give them credit for. They’re not just reaction, but they are predictive. So again, that ability to be aware of where our nervous system is at, how we are feeling, is really important.

And another thing I learned about is something called interoception. And the book that I wrote, prior to Move, Think, Rest is a book called The Creativity Leap. And the subtitle of The Creativity Leap is “Unleash Curiosity, Improvisation and Intuition at Work.” And when I wrote that book, that book came out in 2020, I just had this nudge, and through my interviews, I was piecing together my thinking that there are a lot of connections we can draw between intuition and strategic decision-making.

Now, there’s actually a lot more research that connects the dots between the two. And so, there’s something that all of us have, which is called interoception not “introception,” but interoception. Interoception is that self-awareness of how I’m feeling, “I feel sad. I feel excited. I feel tired. I feel hungry. I feel satiated.”

And it turns out the interoception, that awareness which is linked to the nervous system internally, is powered by the vagus nerve, which is the longest cranial nerve in the body. It extends from the brain down through the heart and the lungs, into the gut. It’s a really interesting complex system of nerves. So, when we say things like, “My gut is telling me,” it literally is. We have this superpower highway that helps us with sensemaking, that helps us with pattern recognition.

And I’ll just share one small research study that I learned about, which shows the connection between interoceptive awareness, intuition, and strategic decision-making, was as follows. The experiment was to ask people to sit on a chair with their feet planted on the ground and their hands on their lap, and to tap out on their lap the rhythm of their heartbeat, not by touching the pulse on your wrist, by just being still and beginning to tap out the rhythm of your heartbeat.

Some people found that ridiculously challenging. Other people were like, “Yeah, okay,” then they would just tap out the rhythm of their heartbeat. That’s called interoceptive awareness, and then also interoceptive accuracy. And that same research study was extended to show a link between people who have high interoceptive awareness, powered by the vagus nerve intuition, also have really great strategic decision-making, which was music to my ears.

Because every successful leader has this moment in their origin story where they will say something like, “Something told me not to do the deal,” or, “Something told me to work with her or not him even though her pedigree wasn’t as snuffy.” And that something is intuition.

So, the nervous system, emotional recovery, the ability to intuit and be self-aware is increasingly important in a time of ubiquitous technology.

Pete Mockaitis
That’s really interesting and totally makes sense in so far as, when we make strategic decisions, or really any decisions, there is an emotional dimension at work inside of us. And if we’re just blithely oblivious, unaware of that and its impact, we can very well, it makes sense, not have the fullness of the information set to consider and, thus, make suboptimal decisions, like, “Ooh, I did that thing.”

And I think few of us have this self-awareness or humility to admit, it’s like, “Oh, actually I did that because, in the moment of decision, I was really angry about this totally unrelated thing. And that probably wasn’t the move. Oops.”

Natalie Nixon
Yes, that’s right. That’s right. You know, athletes, for example, elite performance of athletes are very aware of their emotions. And a lot of what their coaches do is to recreate the feeling when you hit the ball that way, if you’re a baseball player, or if you’re a tennis player. During the Olympics, I love track, and you’ll see the sprinters, they’ve got their headphones on and they’re doing all this big envisioning work and self-affirming talk.

And they are envisioning that path of running around the track, or whatever, if it’s a shorter sprint. But we take it for granted that, “Okay, yeah, in their work of performance, they have to be attuned to their emotions and to visualize and to recreate.”

And it turns out that is an equally useful tactic as we strategically build leadership, “To remember what it felt like when I made that decision, to work with someone, to partner with someone or to not end up collaborating with this group, or to decide to go ahead and do this product development work.”

One of the other people I interviewed for Move, Think, Rest is Ivy Ross, who is the head of design at Google. Ivy is also the co-author of an incredible book called Your Brain on Art. She co-authored it with Susan Magsamen. And Ivy likes to share this statistic that 95% of our decision-making is happening at the subconscious level. Only 5% is happening at the conscious level.

And she shared that statistic in a meeting where she was challenged about deciding. She was proposing what color of story to be using in a product launch. And some of her colleagues, who were also in the C-suite said, “Well, where’s the data on that?” And she said to them, “The data comes from my awareness of culture. It comes from the signals that I’m getting.”

And then she shared, “You know, 95% of the sense-making that we do is at the subconscious level,” because, these are now my words not Ivy’s, we’re sentient beings. We do a lot of sense-making throughout the day. And to not be aware of that, to not acknowledge that, because it’s problematic. And neither Ivy nor I are saying, you know, throw out the quant, we need both, is really the point here.

The quantitative research and data show us patterns. It gives us the bird’s-eye view. We see an aggregation of data at point T90 and not over at point B3. Why is that? If you only make decisions based on quantitative data, you’re only getting part of the picture, because quant doesn’t tell you why people chose to behave in that way.

You’ve got to dive down to the worm’s eye view, through qualitative research, to understand the why. And I would even then take it another further. There’s a tertiary dataset, which we get through our sense-making and sentient intelligence.

Pete Mockaitis
Well, and I love that picture, that vignette there with going through a color story, presenting to executives who want data. It’s funny because colors and design, in general, is just that totally different part of the human experience in terms of. And so, you could, it’s like, “Okay. Well, hey, we have five color options. We presented them to a panelist of prospective consumers who meet the target demographic, and 71% of them liked the orange. So that’s why we’re doing orange.”

But you can’t just, unless you have a huge budget and timeline, just test everything with data. That’s the way I think about it. It’s, well, first you have to generate some outstanding finalists based on something else internally, creatively, before you can even get to that point because it’s impractical to test, “Hey, we tested 800 different colors. Yeah, it costs $8 million and it took us six years.” But rather than we’ve got someone who really understands the vibes associated with the colors, and the feels, and the associations, and the rich history of color theory, and all that design stuff.

Natalie Nixon
It’s both-and. Part of my background is working in the fashion industry. The fashion industry is excellent at incorporating the value and the role of beauty, aesthetics, and desire in consumer decision-making. And it has to because fashion designers, fashion buyers and merchandisers, the fashion sector knows that as soon as we launch this, it will be knocked off.

So, there’s always this level of urgency and need to discern what’s around the corner, what’s coming up next. And you can’t only get that through the quant. So, there’s a lot of shopping the market. There’s a lot of tapping into what’s called the street and the elite, and really understanding what’s happening among subcultures, and the way trends work.

Trends start as signals. And you get signals, as Ivy Ross says that you get a hit not by staying in your office. You get a hit, you identify signals by being in the world and observing, and being curious, and paying attention to that, I call it, the blurb on the radar screen, where something just catches your attention. You don’t know why, but that was interesting and just kind of following the breadcrumbs. So, it’s a combination of approaches that actually yield us the most innovative and resonating results.

Pete Mockaitis
Oh, now this is fun. Talking about breadcrumbs, we’ve gone down some fun paths. Maybe let’s zoom out. The book Move, Think, Rest, what’s the big idea, the big promise of it?

Natalie Nixon
The big idea of Move, Think, Rest is that we will cultivate our best work when we integrate what I call movement hygiene, which is the movement part, back-casting and forecasting, which is the thought part, and intermittent resting throughout our work days so that we can navigate ubiquitous technology, unprecedented burnout, and new rules for remote work.

The whole point of the, what I call the MTR framework, or the “Move, Think, Rest” framework is to build our capacity for creativity, is to build creativity as a strategic competency so that we can consistently and sustainably innovate. If we don’t have means, tools, ways in, to build creativity as a capacity, as individuals, as teams, and as an organization, we will be working in a very myopic way.

We will miss opportunities and we actually will not innovate in a way that’s interesting, that makes it exciting and cool to show up for work, and that actually delivers meaningful value to the clients and customers we serve.

Pete Mockaitis
Well, I think I’d like some more of that capacity. That sounds good. Could you share with us a story of someone who took on some of these approaches and saw a nifty transformation?

Natalie Nixon
One example would be my interview with Brendan Boyle, who is a toy designer. And I went out to the Stanford d.school where he teaches a course on play. Play is probably the ultimate MTR framework opportunity. And the challenge with play is that play has a horrible PR problem.

Play is dismissed, it’s thought of as an add-on, an addendum to the important things. But consider, and this is one of things that Brendan and I talked about a lot, consider that all the attributes of play, which are being able to actively listen, to being curious, having a great ability to negotiate, to collaborate. These are all of the same traits that we say we want in our leadership, that we say we want to hire for.

So, one way that Brendan has been really successful with the clients he works with to understand that, his definition of play is engagement. I mean, you want engaged employees, right? You don’t want them checked out because that’s a business cost. There’s a significant business cost when we don’t build these capacities through movement, thought, and rest. But play is the ultimate integration of movement and thought and rest.

So, when we are at play, we tend to be a bit more mobile. We have to think very differently. We have to be sometimes reflective, sometimes super imaginative, and the imagination and the curiosity and the dreaming is the forecasting piece I referenced. The reflection, the use of memory is the back-casting piece.

And it’s a rest. It’s a break from the typical cognitive load in our neocortex that we only associate with work. And someone I actually interviewed for The Creativity Leap, but her example was something I was reminded of in writing Move, Think, Rest is Gerry Laybourne, Geraldine Laybourne, who’s the founder of Nickelodeon.

And she would have recess, “No agenda. Step away from the desk and just come hang out for 30 minutes.” And Brendan built on that, and said, “You know, that’s really powerful and really important,” because you could have guard rails. Whenever we have things that sound pretty loosey-goosey or improvisational, remember improvisation has rules.

So, one of the rules could be, “No conversation or chat longer than three minutes so you don’t hog up the VP’s time,” right? But you begin to have just playful conversations about, “Oh, how did you prepare that sauce that you just described that you had for dinner last night?” You get to learn about another dimension of a person. Again, work becoming inside out.

And what’s happening when we are at play is that we are allowing the default mode network in the brain to take over. And the default mode network are those different neurosynapses that happen when we tap out of the world and we, as I like to say, get out of our head and into our body.

That might be through a walk. That might be through what I call, what I do every day, a daydream break. That might be through a rollicking, engaging conversation with an old friend, where you’re not thinking about the work at hand. But what’s happening is that different neurosynapses are at work, which are actually critical for what I call the juicy bits of productivity to happen so that when you then return to the screen, all of a sudden, that conundrum from this morning, some new ideas are shapeshifting into place.

All of a sudden, you have these lightbulb moments that happen when we’re awakening out of a really good sleep, that happens during shower moments. And I can share more about kind of the scientific terms for those too if you want.

Pete Mockaitis
Oh, that’s fun. Yeah, we had a sleep doctor, Michael Breus, on the show who described the “just waking up” creative zone as groggy greatness, which I thought was kind of fun. And it’s true, I’ve lived it and felt it terms of I wake up, it’s like, “Oh, of course, just do this.” I was like, “Well, yesterday, it was so hard. What the heck?” So message received.

Natalie Nixon
Yeah, I love groggy greatness.I love that. And the science, I mean, Dr. Breus knows this, but when we’re starting to drift off into sleep, that’s called the hypnagogic state. So, Thomas Edison, for example, started observing that when he would suddenly wake up, just as he was drifting off into sleep, he would have these lightbulb moments. No pun intended, Thomas Edison.

But he started to then, as if he took a nap in the middle of the day, he would intentionally hold a heavy ball or orb in his hand, and as he was drifting off, the orb would fall down, he’d wake up. And something that he was pondering would make sense.

Now what you can start to do is you can plant seed, a question in your mind, before you go to sleep. And a lot of times, the clarity will come as you awake.

Pete Mockaitis
Well, yeah, and I also think that holding orbs just sounds like a fun, awesome thing to do, speaking of play.

Natalie Nixon
Why not?

Pete Mockaitis

It’s like I’m a mighty wizard. That’s it, was it “The Wizard of Menlo Park,” right? That was the nickname, that he’s holding orbs just like a wizard does. Well, so what’s the movement hygiene part of this?

Natalie Nixon
So, we all know we should exercise, but exercise could be a little triggering to people, because when we think about exercise, we think, “Oh, I’ve got to go to a 50 minutes long Pilates class. Ugh,” or, “I’ve got to go for a jog that’s 30 minutes long.” No, movement hygiene is about incorporating movement throughout the day.

And it could be things like incorporating a standing desk. So, right now, for example, I don’t have a standing desk, but I actually need to figure out the brand of this contraption. It’s this cool little contraption I put on top of my desk. It can rise. I can lower it. So, when I want to stand just to stretch my legs, I can.

I’m also on this really cool platform by this company called Fitebo. And it kind of rocks. It forces me to practice my balance and to make sure that I’m not leaning too heavily to one side of my body, which is an example of movement hygiene, making sure that you’re incorporating microbreaks throughout the day so that you stand up, empty the dishwasher.

When we also think about exercise versus movement, there seems to be more pressure about how long it should last, how intensive it should be. I have walks, I work from home. I have walks around my neighborhood that I know some walks are it’s going to take me three minutes.

There’s another walk I have that takes me seven minutes. And there’s one short walk in the woods I can take that takes me 16 minutes long.

So, depending on the amount of time you can budget during the day, there are so many opportunities that you have to incorporate this movement hygiene. And the reason that matters is because, as humans, we are designed to move. The spinal cord is an extension of the brain. It’s an extension of the medulla oblongata.

And if we are sitting, for more than, you know, Dr. John Medina, who’s the author of a series of books called Brain Rules, his research suggests that we shouldn’t be doing one particular task for longer than 30 to 40 minutes. If we’re cramped at the laptop for longer than 40 minutes, for two hours, we are constricting blood flow to the brain and, therefore, restricting oxygen, and, therefore, we’re actually not doing our best thinking, which is not the goal.

Pete Mockaitis
Well, I’m curious with your research. Did you find any nifty random control trials associated with a modest amount of movement, hygiene, mixing it up, resulting in some cool thinking, creativity, smartness benefits?

Natalie Nixon
I mean, I can’t name a specific example right now, but over and over again, the research shows that when you are incorporating movement, integrate it throughout the day, and not waiting till you go to an exercise class, it affects more exponential creative thinking because you are activating the way the body is designed to work, and you are not treating the brain as a disembodied part of the rest of your body.

When you move, what’s happening? You do deeper breathing, right, which is important for alleviating stress. It reduces cortisol. It boosts serotonin and all the positive hormones that we actually need for these different neurosynapses to take effect in the brain. And one of the things you’re already hearing through, as I’m describing these examples, is that the MTR framework is not a siloed framework.

It’s not, “First you move, then you think, and then you rest.” A lot of the activity that I’m suggesting that we do more is integrative. So, when we move, we’re also taking a break. When we move and take a break, we’re also allowing the default mode network to begin to be activated so that our thinking is fresher and crisper and, dare I say, more innovative.

Pete Mockaitis
Beautiful. Well, tell me, Natalie, any key top takeaways you really want to make sure folks, looking to be awesome at their jobs, grasp when it comes to moving, thinking, resting?

Natalie Nixon
I want them to understand that the end goal here is to build your capacity for creativity. And the ways that I help people think about creativity is that creativity is our ability to toggle between wonder and rigor to solve problems. Creativity is not a nice-to-have. It’s not something that only artists are great at. When all of us dedicate and design more time and space to wonder and rigor, then we will be more creative, which means we will actually be more innovative in our work.

And so, movement, thought, and rest is one on-ramp to building up more wonder and more rigor into your day and into your life and into your work. Because wonder and rigor, which is kind of the umbrella category of my portfolio of work, movement helps you to be more wondrous. There’s so much that you can discover if you just go on a short walk.

If you take a daydream break, right, that is a wondrous time of your day for 90 seconds. When you decide, when you commit to rest, that’s a type of rigor, right? When you commit to be more imaginative and audacious in your thinking, that’s also a type of rigor. But also, it lends itself to greater critical thinking.

So, the movement, thought, rest framework is really an opportunity to build creativity as a capacity, which matters because people have been dying a slow death at work. They’ve just been kind of shut up in a copy-paste way. And so, I want people to shift the ways they’ve been thinking about productivity.

We have an either/or way of thinking about productivity. Either you’re at work or you’re not. And what I’m offering is a both-and model rooted in cultivation. So, I am provocatively saying we need to put productivity to bed. It doesn’t really serve us anymore. It’s rooted in the first industrial revolution where we only measure what we see. It’s based on speed, efficiency, output.

The cultivation model, which was really the MO during agrarian economies prior to the first industrial revolution, we have an opportunity to engage in cultivation 2.0, which is a both-and model. We value the solo practitioner and the collective. We value quick spurts of growth and slow. And we value, yes, we should measure what we see, but we also acknowledge that there’s a lot happening in the invisible dormant realm.

We need to sleep on it when we need things to percolate and marinate. So, the both-and cultivation model and understanding that all this work helps you to build your creative capacity.

Pete Mockaitis
And when you mentioned 90 seconds, was that 90 seconds for daydreaming?

Natalie Nixon
Yes, I will stand by it.

Pete Mockaitis
Okay, that’s all it takes

Natalie Nixon
That’s all it takes. Sometimes I can afford a five-minute daydream break. But your prompt can be just watching clouds drift down across the sky or watching ants crawl on the pavement. If you work in a high rise, stand by a window and just kind of zone out and watch all the little people and cars down below, and then go back to the work.

Pete Mockaitis
Well, yeah, I was going to ask, since you mentioned a number and time, so moving, thinking, resting, I imagine it’d be kind of easy to fall into a groove or rut of doing too much or too little of either of them. Do you have any rough guidelines for what’s the right rough proportions of moving, thinking, resting to really light up this creative capacity.

Natalie Nixon
The first place I start as I’ve been doing more workshops and talks about this, is for people to check in and identify, “Of the three, which is the one that’s most challenging for you?” And so, if you are deficient in movement, that’s where you should be starting. If you’re deficient on rest, which is different than sleep, right, but if you’re deficient on rest, that’s where you should be starting.

So, this is not a cookie-cutter model. It’s not a sequential formulaic model. It is very much a model that requires you to be self-aware about, “What’s missing in my work habits? And what are the new habits that I want to start to develop and start there?”

Pete Mockaitis

All right. And with that 90 seconds of daydreaming, do you, likewise, have any short prescriptions on the moving side?

Natalie Nixon
Yeah, I think walking is the easiest and best place to start, but I also, when I wrote this book, when I wrote The Creativity Leap, I wanted it to be as inclusive as possible. So, I interviewed, for example, Tyler Turner, who’s a paraplegic.

I wanted to talk about what does motor mean for people who are living with physical disabilities, people who may live in socioeconomic environments where they can’t just go out for a little jog at 6:00 p.m. because it’s actually kind of stupid. It’s not very safe. They don’t have access to parks and nature. So, what does that look like to them?

And so, one of researchers, whose research I learned about, is Dr. Yancey, who sadly died at age 50 of breast cancer, but her work, and her mission in her work, was to really catalyze movement in urban environments. She piloted a lot of programs, kind of micro movements that you could do in a small apartment, do it in the middle of a busy day, at UCLA and at UC Berkeley.

So, stretching, taking a dance break, maybe that’s not part of the culture of your team, but you can certainly do those sorts of dance breaks for yourself privately, if it doesn’t make sense for your team. If you can’t go for a walk outside, can you go up and down the stairs?

And, again, the author of the Brain Rules books, he talks about how the times that we are kind of static and doing more of that important work of the frontal neocortex shouldn’t be longer than 30, 40 minutes. And then peppering it with anywhere from five- to 15-minute breaks will really do the trick.

Pete Mockaitis

Lovely. Thank you. Well, now could you share a favorite quote, something you find inspiring?

Natalie Nixon
I think a lot about “Don’t let perfection be the enemy of good.” I think that’s a really important one for me to not overthink. And I also love the quote, “Comparison is the thief of joy.”

Pete Mockaitis
All right. And a favorite book?

Natalie Nixon
I’m reading right now Abraham Vergese’s The Covenant of Water. Do you know his work?

Pete Mockaitis
No.

Natalie Nixon
I remember it’s pronounced Verghese, it’s V-E-R-G-H-E-S-E. He’s a true polymath, he’s a super accomplished surgeon, a medical school professor at Stanford. And he decided to kind of take a sabbatical and got accepted into the Iowa Writing program, and has multiple bestselling books of fiction. The first of his book that I read was Cutting for Stone. I’m also a big fan of J. California Cooper, her book In Search of Satisfaction.

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

Natalie Nixon
Right now, I use Otter a lot. I love a good dictation app. I love being able to just download my thoughts verbally. So, Otter is one of my favorite tools for work.

Pete Mockaitis
And a favorite habit?

Natalie Nixon
Stretching. I try to stretch 15 minutes every morning just to remain limber.

Pete Mockaitis
And is there a key nugget you share that people really dig and quote back to you often?

Natalie Nixon
“Wonder is found in the midst of rigor. And rigor cannot be sustained without wonder.”

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

Natalie Nixon
Figure8Thinking.com. That’s F-I-G-U-R-E, the number eight, Thinking.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Natalie Nixon
Have some self-compassion. Tap into what makes you uniquely human and maybe start by reading my book, Move, Think, Rest.

Pete Mockaitis
Alrighty. Natalie, thank you.

1085: How to Find More Fun at Work Every Day with Bree Groff

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Bree Groff shares the simple but effective strategies for finding more fun at work.

You’ll Learn

  1. The mind shift that helps us find more fun at work
  2. The 5-minute team practice that drastically improves engagement
  3. How to find joy during even the roughest work days

About Bree

Bree Groff is a workplace culture expert and author of Today Was Fun: A Book About Work (Seriously). She has spent her career guiding executives at companies including Microsoft, Google, Pfizer, Calvin Klein, and Hilton through periods of complex change. She is a Senior Advisor to the global consultancy SYPartners, previously served as the CEO of NOBL Collective, and holds an MS in Learning and Organizational Change from Northwestern University. Bree lives in New York City with her husband and daughter.

Resources Mentioned

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Jeff DeGraff Transcript

Pete Mockaitis
Bree, welcome!

Bree Groff
Thanks for having me, Pete.

Pete Mockaitis
Well, I’m excited to talk about your book, Today Was Fun: A Book About Work. Could you share with us any particularly surprising or extra counterintuitive discoveries you’ve made about work and fun while putting this all together?

Bree Groff
I mean, the first, maybe most obvious is when I say work and fun, people are like, “So happy hour?” Like, a lot of times it, like, does not compute, “Wait, work cannot actually be fun. You must be talking about off sites, happy hours.” Or they think, “Oh, you’re going to tell me that fun is a driver of productivity and business performance in the bottom line.” That is true, but also not my point.

My point is that we should be valuing our days at work more highly, simply because they come from our finite bank of days that we get on this planet. And it is not only possible to have fun within the work itself, like when I’m actually creating or making something of value, but to do that is, actually, honors our brief time here, honors our lives in a way that I think we don’t often.

We often wish our way through the week, “Ugh, when can it be Friday?” So, I’m trying to correct that, swing the pendulum back a little bit, such that employee engagement and our own days at the office are seen as valuable just for themselves.

Pete Mockaitis

Okay, cool. And so, you say it should be fun and we’re trying to correct. Can you give us a sense of what percentage of folks experience regular fun during the course of work versus find this to be a foreign concept when you speak with them or you’ve done the research, like, “Oh, you mean the ping pong table or the happy hour?” Like, “No, I don’t mean those things.”


Bree Groff

Yeah. I mean, the data is staggering on things like burnout, overworking. I’ll try and cite it correctly, but I believe it was 89% of employees have felt a sense of dread within the last month at work, 49% have felt a sense of dread within the last week. And like dread, that is such a big word. It’s not like, “Oh, I’m not having the most fun of my life.” It’s, “I’m actually dreading something.”

So, there’s a lot of headroom for us to go from what’s currently the state of affairs at work, which is something often work is something that we show up to that we get through. We almost show up assuming it’s not going to be fun and that’s not the point of work. So why even try to make it so? But I think it is. I think if we are going to be spending, they say one third of our lives or five sevenths of every week at the office or at the virtual office, well, that’s worthy of us figuring out how to have a better time doing it.

Pete Mockaitis

And I’d love it you could drop even more stats on us, I’m shameless here, because I guess I imagine that both things are true for me in the sense that, “Yeah, you know, I have fun at work and also there are elements that I dread.” And I think that is probably the case for nearly even the most dreamy of dream job havers in their lives. So, I guess I really want to know, like, how many folks experience, you know, near zero fun in the course of doing their work? Do we know that?

Bree Groff
Who experiences near zero fun? I mean, I imagine it’s kind of sizable. Anybody who’s looking for a new job is not maybe near zero, but is sort of approaching that asymptote of there’s very little to get from here anymore. I will say, though, like I’m not of the opinion that every day and all work needs to be fun. That’s just unrealistic, and it holds us to such a high standard.

Chapter one of the book is titled “Most Work, Most Days Should Be Fun.” And if we get most, I think, yeah, you’re killing it. Right? You’re doing a really good job.

Pete Mockaitis
And do we have a sense, very roughly, and maybe even just your gut sense of chatting with folks, if there’s not a perfect survey tool that’s assessed this, like, how many folks find themselves in that boat?

Bree Groff
Of most days most work is fun? My gut sense, and then I’ll try and whip you up some research, my gut sense would be 50% most work, most days is fun. Again, that’s off the cuff.

Pete Mockaitis
And I think, Bree, folks will likely push back on you, in terms of, “Well, you don’t know about my job. This is as dull as it gets.” So, could you perhaps share with us a story of someone who was not having so much fun at work and then made some adjustments and, behold, the very same job they were in became more fun?

Bree Groff
Yeah, I’ll give you a sitcom, “The Office,” right? Like, you’ve seen it, they’re selling paper during the advent of the internet. Like, the business is crashing. It’s probably the dullest possible job you can imagine. I love how the show was framed because it’s not at all saying that work is fun because it’s meaningful or purposeful. It’s to show that work can still be fun even when you have no purpose, no meaning, when your job is to sell reams of paper.

And the reason it was fun, the reason why people love watching it is because the humans in the office, the entry level employees, they made it so. They made their own fun. So, when I think about, like, “How can we as individuals make our days more fun?” there’s so many things that we can do at the local level.

So, for example, when I’m leading consulting teams, it’s me and, on average, maybe seven, eight people on a team for a client, we are our own little ecosystem. So, whoever out there is listening, is, “Oh, my job is terrible,” the question is, “Do you have a few people around you in your local team, or even like one work bestie, where you can make your own fun despite the elements of what’s happening out there?”

So, this could look like anything from, “Hey, we’re going to wear our animal print socks on Fridays.” It’s such a stupid example, but it’s a stupid example because, one, nobody at work probably cares about what socks you’re wearing. And, two, it’s a little bit of an act of mischief and subversion in a way. Like, how can you make your own fun there?

Or, let’s say you have to do expense reports or fill out some sort of soul-sucking spreadsheet. Well, you could do that under your fluorescent lighting hunched over your desk. Or, if you work in an office building where you can take a walk and sit on a bench outside. If you’re working from home, and you can go to a coffee shop and do it there.

There are always ways to get the same work done, but dressed in a little bit more fun. So, at best, we think of work like steak, like it’s juicy, it’s delicious. The work itself is interesting and captivating. But if it’s just not, if your work is broccoli, then your job is to get some cheese and smother it on. And, in the very least, find some camaraderie with the other people who are also suffering alongside you.

Pete Mockaitis
Yeah. Okay, cool. Well, I think “The Office” is a fine example because you can see all sorts of good times had in the midst of very boring circumstances. So, could you share some stories of real people who maybe did not have the luxury of a Jim Halpert with all those hilarious pranks and fun-making activities in the mix and how they found some creative ways to upgrade their experience of fun at work?

Bree Groff
So, there was one client that I was working with. The remit was employee experience and sort of like the process of this function. There were about 150 people in the function, and one person in particular, as we’re doing these interviews, was telling me like she was out, she was not having any fun. She was ready to leave.

We proposed many structural changes, process changes, sort of to try and like lighten up the workload and do all these things. But the one thing that made more difference than, and then anything else, for this one woman in particular, we started introducing the concept of a check-in, which is, at the top of a team meeting, you could do it at a standup or, you know, once a week, you simply start the meeting by saying, “How is everybody on a scale of one to five? Put it on your fingers. Three, two, one, everyone puts up their fingers, it’s a four, it’s a two, it’s a one.”

And then you go around the room in 30 seconds, everyone says how they are at work or in life. So, it could sound like, “Oh, I’m a four. We got a new puppy, which is amazing, but the puppy kept me up all night, so I’m kind of tired.” “I’m a two. I’m actually super nervous about this meeting we have later this week. I don’t know if we’re ready for it, so excited to talk about that in the meeting today.” Or, “I’m a five. It’s my birthday tomorrow.” And then everyone says, “Happy birthday.”

It’s a very simple practice. It takes maybe less than five minutes to do within a team. And once we started introducing this practice, so now I’d say most days she was doing this with her team, she was able to share, one, she was a new mom, so she was able to share, like, “Oh, God, this is really hard. I didn’t sleep much last night. And I’m really excited about this event that we’re putting on tomorrow.”

She was able to open her humanity to her team. So, she felt seen in a way that she wasn’t seen before. Nothing actually really changed about the work in that period of time. We were still working on more structural changes, but just the simple fact that she could go into work and she knew that somebody was going to say, “How are you?” and listen, like that was enough.

And so, we will often do, like, a pre-post survey of belonging and engagement and all those things, and the numbers were incredible, just like even when we pulsed on that one intervention. And then, just anecdotally, like her ability to say, like, “Oh, my God, I finally feel like I can be part of this team and not hide my exhaustion.”

Because there’s so much about work that tells us we need to be buttoned up and professional and sort of have like one sort of presentable persona to the business. But just being able to say, “How are you?” and then have someone say that to her made all the difference. So often, when I’m working with clients, it’s the first thing, the first thing I’ll do.

Pete Mockaitis
Well, that’s cool. Thank you. Yes. I remember when I was working at the Bridgespan Group, we did that practice of check-in, And it was so interesting because, you know, part of me was annoyed at first in terms of like, “Come on. Come on. We’ve a lot to cover, you know. I’m excited to get into it. And really like we’ve got, you know, 50 minutes scheduled for this meeting. How many minutes are we going to do with check-in?”

And it really fluctuated. Like, sometimes it was maybe a good third of the meeting was the check-in. I guess we didn’t have clear rules, but what was interesting is, in a way, that fluidity was kind of helpful. It’s like, “Oh, actually, that’s what was most needed. Go figure. It was not so much what was on the agenda proper, but spending some more time on this stuff.”

And what’s funny to this day, I mean, mercy, this was 16 years ago, but, like, I feel more, like, I don’t know, warmth, affection, interest, friendliness, and remembering of these people than I do like most other team settings. And it was interesting because there wasn’t that much to it. So, I came around to be a fan of the check-in, and it’s interesting.

And people can sort of choose just how vulnerable they are, how much they want to disclose with regard to their check-in. And I don’t think we ever were like derailed, even if it’s like hardcore, you know. I don’t remember what the most dramatic example was, but if someone were to say, “Oh, I’m distraught because my son has a…we thought he kicked his drug problem, but now he’s using cocaine again, and we’re really worried about his safety.”

Like, I’m just trying to imagine like what’s among the most intense things you might say in a check-in. So, one, folks tended not to share that, unless they felt comfortable enough in the team dynamic over time. And, two, when they did share bigger things, it didn’t tend to derail, you know, or take a long, long time. Folks just say, “Oh, that’s so hard. I’m so sorry. Please, let me know if I can support you.”

And it’s a little awkward to transition to the next person, “And I got a puppy.” But, you know, we get over it. In a way, it’s nice because, you know, these things are in the room, even if we’re not saying them, and just not acknowledging them does not make them disappear. Like, we are carrying the emotional whatever of that stuff into it.

And, in a way, it’s actually super helpful because it, like, demystifies stuff. Like, in ambiguous circumstances, I think we humans have a knack for just inventing stories as to what’s going on. Like, “Oh, she thinks my ideas are really dumb.” Like, “No, she’s super stressed about these life circumstances. That explains the low energy, the low mood, the short tip, any number of things.”

And it’s like, “Oh, well, I feel bad for them, but it’s a relief for me.” It’s like, “Oh, that’s just sort of what’s going on there.” And then it opens up opportunities for people to follow up, it’s like, “Oh, you know, hey, we got a new puppy last year, and we found this amazing YouTube channel, which was game-changing in terms of training or whatever.” And then, like, all these new opportunities for connection appear. So, I’m going on and on, Bree.

Bree Groff
I love it, yeah.

Pete Mockaitis

But just to say, yeah, I think check-ins, at first, I was skeptical, but I became a believer that they do a lot of good, and you’ve got hard numbers on the back end there.

Bree Groff
Yeah, so, totally. And they do feel awkward at first. I won’t lie. Even after doing them for years, I’ll sometimes be like, “Oh, team, wait, can we do a check-in before we jump in?” And I have like a little spike of like, “Oh, is it okay?” And it’s always worth it. Because I remind teams that the goal is not to have an efficient team. The goal is to have an effective team. And in order to trust people, you have to know them. In order to like people, you have to know them.

So, yeah, the research behind this is also really good, in addition to like our own experiences of like, “That felt nice.” But it promotes psychological safety, because if you risk saying something, even 2% vulnerable at the start of a meeting and you’re met with support, now you’re more likely to share whatever you need to share, you know, your business idea, whatever it is, later in the meeting.

It’s great for cognitive offloading. So, there’s research that says if you write or say whatever is running through the back of your mind, you can then focus better on the next task at hand. It’s sort of like shutting down all the tabs on your computer. So, instead of just ruminating on like, “Oh, how’s the puppy? How’s the puppy? So, I got a new puppy. I hope they’re not destroying the apartment right now. Great. I’ve said it.”

Priming contributions. So, once you’ve spoken once in a meeting, now it’s more comfortable to speak again, as opposed to, we’ve all been in those meetings where one person doesn’t speak the whole time, or maybe that’s you, and you’re like, “Oh, God, am I going to jump in now? Is this the one thing I’m going to say the whole meeting?”

And then thwarting any sort of miscommunications, as you said. So, if one person’s camera is off, and you’re like, “What a jerk!” but they’re like, “Oh, I’m a two. I threw my back out. So, I’m going to be camera off this meeting,” now there’s empathy where there used to be resentment. So, so many good reasons to do the check-in, to fight through that initial like awkwardness, and, “Oh, is this going to take a few minutes?”

Because every team that I’ve done this with, which I’ve been doing this now for over a decade, like I know things about their lives and who they are that made me feel, just as you said, like warm and affectionate to them. I’ve had teams, even as they disbanded, continue to check in years later simply because we, like, essentially bore witness to each other’s lives in that time, to the degree the person wanted to share. So big fan is the bottom line.

Pete Mockaitis
Well, that’s awesome. So, there’s one intervention, simple, powerful. I guess maybe one quick little footnote is like you mentioned the affirming, and maybe it goes without saying, but just to be explicit.

Bree Groff

“Don’t be a jerk.”

Pete Mockaitis 
During the course of a check-in, yeah, you would be affirming as opposed to, “A puppy. Why would you do that to yourself? You’ve already got three young kids. Are you insane?” Like, “Okay, that’s not how to respond to a check-in. Rather, you would…well, you tell me, someone shares a thing and then someone else is about to go, how does that transition or handoff work in practice?

Bree Groff
Yeah, if someone shares a thing, the rule is don’t be a jerk. Although, if you really like each other and know each other, and you know the person would laugh being like, “What the hell were you thinking? You got three kids,” you know, that’s cute. But, in practice, the way that it would functionally work, so I would usually start it off, or like a project manager could start it off, I’ll say, “How’s everybody?” Three, two, one. We put our fingers up in the air.

I’ll nominate someone to start. So, I’ll say, “All right, Pete, kick us off.” You would do your 30 seconds and then you would pass it to someone else. Like, “Okay, Bree, you go,” and then you just go around the room. It just avoids the whole, like, “Who wants to go next?”

And also, if you start at the top of the meeting, you end up getting into the meeting stuff around the same time as if you had just like chit chatted and done the whole, like, “Let’s wait for a few more people to join,” which is my corporate pet peeve.

Pete Mockaitis
Yeah. And so then, when someone shares, we mentioned acknowledgement or affirmation previously, they just stop and the next person goes, there’s no like, I don’t know, commenting or responding?

Bree Groff
Oh, yeah. I mean, maybe a little. So, like, “Oh, you got a new puppy. Like, oh, it’s so cute. Love it.” Something like that. If you’re on Zoom or remote, a lot of times people will just put things in chat to respond so that there’s a little bit of reciprocation, but, yeah, I mean, just no terrible back and forth, like, “Oh, I really threw out my back.” Someone would be like, “Oh, I’ll DM you my chiropractor later.” Something like that.

But I’ve had leaders ask me, like, “Well, what do I do with this information? Do I need to follow up if someone’s not doing?” I’m like, “No. The beauty of the practice is, like, this is literally saying, ‘How are you?’ and listening. Like, it’s so fundamentally human. So that’s all you have to do.” But, yeah, like a few, like, “Mm-hmm” kind of thing, that’s good.

Pete Mockaitis
Okay, lovely. All right. So, the check-in right there is simple, powerful, fun-building. What is another one or two of your top practices you recommend?

Bree Groff
Sure. Another one that falls in that camp is the user manual, which is a document you would keep for your team or maybe your direct reports or a couple of people around you. That’s just a series of questions about who you are and how you work.

So, functionally, each person would have their own page, and the questions would read something like, “Who are the humans and animals who are important to you? How can you be misunderstood? How can someone help if you’re stressed or stuck? What’s important to you on a team? What other responsibilities or joys do you have outside of work? What are you trying to get better at, at work?”

So, it’s just all these sorts of questions called a user manual, is my cheeky way. It’s, like, if you get a blender, you’re like, “What are all these buttons do?” Well, it’s like, “Well, you just go look at the manual. There’s like some quick start guide.” So, this is just the human version of that. Because how often do we work with people? Maybe for years, and then you’re like, “Oh, you have a brother?” It’s like, “Yeah.”

But we just, like, never sort of have the opportunity to, or think to, or maybe we’re nervous to share about those things. Also, like, we learn so much in working together through trial and error, but it doesn’t have to be that way. So, for example, like, if I’m stressed, I want someone to talk it out with me. I’m a very verbal processor.

But other people want to be left alone, like, “Do not go near me when I’m stressed out. Give me a hot second. It’s going to…” But, like, why should we guess who’s who or like try and get it right and then mess it up? So, there’s a question, “How can others help when you’re stressed or stuck?” And you can say, “Oh, just give me an hour or two and I’ll figure it out,” or, “Ask me how you can help.”

So, it’s a really simple document. Actually, I have a template on my website. If people want to go, it’s BreeGroff.com/usermanuals. You can download it and create one for your team. And it’s just another way to sort of like lubricate our social interactions such that we’re having more fun with the people we’re working with and we’re more supportive of them as well. We’re more seen and when we’re seen, we’re also better liked.

Pete Mockaitis
Yeah, that’s good. I also want to hear your comments. In your book, you mentioned a couple of the super tiny little things we can do to, like, give many treats to ourself or to enhance a very basic experience of drinking coffee or tea. Can you speak to these concepts?

Bree Groff
Sure. Yeah, so there’s something that I call thin-slicing your joy. If you are looking ahead at your calendar for the day, and you’re like, “Oh, God, this is going to be painful. Back-to-back meetings, I have to get this thing out, and my inbox is a mess.” Well, if you look at the whole day, sure, it might look hard and dreadful, but we don’t have to look at a whole day.

So, then thin-slicing looks like, “Well, is there one hour, is there one meeting where I know I’m going to have fun? That’s maybe a brainstorm meeting or there’s some people in there that I like.” Or maybe you’re like, “Nope, Bree, every hour looks rough.” And I say, “Okay, great. Thin-slice even further. Are there a few minutes throughout your day where you can squeeze a little extra joy from what you’re already doing?” So, things that take no time.

Smelling is a great one. So, if you’re going to go get yourself a cup of coffee, maybe you stash some cinnamon in the office or in your kitchen and put a little bit on your coffee or your latte, and then just take three seconds and, like, breathe it in. Sensation kind of things are really good for getting us out of our heads, out of sort of like ruminations and anxieties and your head spinning about work.

Another small thing, sometimes the best way to have more fun at work is to help someone else have more fun at work. So, you can send something I call a love bubble, which is just like a two-line text. It could be a text, a DM, an email to a colleague, to say like, “Hey, you totally rocked it in that meeting. I don’t know how you got everybody on the same page. It was so cool.” It’s just like a little note of “You’re awesome. Appreciation. Thank you. So cool that you did that.”

The trick is, like, don’t overthink it, don’t like craft the email. This is not like formal feedback. This is like, “I have a nice thought. I share a nice thought.” Because so often, I think we do have nice thoughts about our colleagues, like, “Oh, they’re so good at that,” we just keep them to ourselves. So, if you can spend 30 seconds shooting off a little love bubble, now you’ve made that person’s day and you sort of kickstarted this positive feedback loop. Now maybe they’ll think of doing the same.

Other, like, little silly things, like micro acts of mischief I really like because they get your adrenaline going a little bit almost office style. Once in a while, you could put Comic Sans in your presentation and see, like, who you can make twitch because it’s like such a terrible typeface. You could rearrange the office furniture. Maybe you play yourself some music. I will say, though, all of these things are, they’re like realistic hacks.

Like, “I’m not having a great time at work. I can’t quit my job and/or maybe I’m just having a bad day. Like, how do I find more joy?” And that’s fine. Like, sometimes we just need to get through things. But I will also say it’s also important to acknowledge, like, “Oh, am I just hacking it through my day every day?” In which case, then it’s a bigger conversation with yourself about, like, “Is there a different role that’s better for me out there?”

Pete Mockaitis
It’s funny, I’m thinking about the TV series “Severance” right now with their really lame, like sort of parties are fun acknowledgments, “And you get to select a style of music and an instrument. We’re having a melon party, and this melon party is not going to start itself.” And what’s funny is, I think that that’s kind of the joke, it’s like, “Oh, these are kind of lame incentives, but these people are like, in some ways almost like children, and so, they can appreciate them.”

But yet, I think there’s also great wisdom in there in terms of like, “We are kind of like children in terms of little things really can be quite delightful.” And I think, often, my sense is, sometimes the more that they violate norms or are weird, in some ways, the more delightful. I mean, I’m sure there’s exceptions, but like the silly socks, for example.

Like, I have, for instance, when I had to get through some stuff, and it was all kind of lame, I would say, “I’m going to celebrate aggressively even though I have very limited resources.” Like, it’s just me. I am in sort of a small office space here but, “I’m going to get a shot glass full of cold water and pour it over my head and pretend it’s like the Gatorade being dumped on the coach, you know, after the victory.”

It’s like, “Well, I had a victory,” and cold water just makes you go, “Ooh,” a little bit. So, I mean, it is so little and so silly, and yet, I guess our inner children, if you will, can find some delight and some fun in it such that it meaningfully transforms the experience of that day.

Bree Groff
Yeah, I mean, the trick here is just amuse yourself. Like, because it’ll look different for everybody. Like, some people are sitting and will be like, “I like my socks just the way I like my…” It’s like, “Great. Don’t do the sock thing.” That’s a very low-bar example. But I guess what I most hope is that people feel the confidence in the value of their days.

And when you feel like you deserve to have a good day, you’re in a position then to try and make that true, to amuse yourself. Because I think so many people will show up to work thinking, “This day is not even mine. I’ve sold it to some employer. I’m not expecting to have fun. I’m here to provide the shareholder value and get my paycheck.” And I get that that sometimes feels like a more honest assessment of work. And yet, I feel like, in that situation, we’ve given up too fast. We’ve settled.

Instead, I think it’s worthy to hold the belief that, like, “Today, whatever day it is, April 12th, this year, I get one shot at this day. This day is not coming back again. This is a day of my life, not just a day that I’ve sold to an employer. So then how do I want to take ownership of enjoying it?” And then it’s just a question of like, “What do you like? I don’t know. What amuses you? What do you find fun?” I think the Gatorade, like the little shot glass of Gatorade is hilarious.

It’s so good because it’s playful. I think there is something in that sort of childish sentiment. Because children realize that there’s value in play just because there’s value in play, not the corporate version of that, that there’s value in play because it drives innovation. No, it’s just simply fun. And now you’ve had that moment of joy and you’ve banked it and it’s yours in life.

I also think it’s important to amuse ourselves because it creates a culture where we give permission to other people to also amuse themselves. And so, sometimes this is sort of like accoutrement around the work, you know, like the socks or the Gatorade example, but also, I think it’s important to amuse ourselves in the work. So, even like when I’m doing client projects and we’re scoping work, I’ll often ask myself the question, like, “How do I want to shape the work or define the work that’s most fun?”

Because I could deliver like an 80-page client deck or like a PowerPoint deck to the client. I would probably do the job. Or, we could design this like two-day immersive offsite experience that’s way more fun to build and way more impactful. So, I think it even goes just beyond the day to day, but, like, “What’s the fun work we want to do and do we have enough belief in the fact that we deserve to be having good days to like risk looking a little silly or childish?” And I think it’s worth it.

Pete Mockaitis
That’s good. Well, Bree, tell me anything else you want to make sure to mention before we hear about some of your favorite things?

Bree Groff
I said a lot of things.

Pete Mockaitis
Okay, well, we’ll do it. That’s fine. Can we hear about a favorite quote, something you find inspiring?

Bree Groff
Yeah, I mean, on this topic, I love the Annie Dillard quote, “How we spend our days is, of course, how we spend our lives.”

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

Bree Groff
Yeah, I’ve always loved the Marty Seligman, he’s a UPenn researcher in positive psychology, the learned helplessness studies. He did this study probably decades ago now, where he would put dogs in this room, would shock their feet, I guess, low shocks that dogs were okay.

In one setup, the dogs weren’t able to escape the shocks. In another setup, they were, they were able to walk off the place where they were getting the shocks. They took those two sets of dogs and put them in yet another trial with shocks. But now, both sets of dogs were able to escape. The dogs that could escape the first time were like, “Yeah, I’m getting out of here,” and they did.

The dogs that could not escape the first time just sat down and whimpered, even though they could escape. They just decided, they had learned, essentially, had learned helplessness, “There’s nothing I can do here. I’ve just got to take it.”

And I loved that study for what it teaches us also about, like, happiness and joy in the workplace. Because I think a lot of us over time, I know I have, at times, have learned, “There’s no fun to be had here. There’s nothing I can do to change it. I’m just going to lay down and whimper and collect my paycheck.” When, in fact, there is so much that we can do.

And in fact, what sort of broke the trance for those dogs who had learned, “I can’t escape this,” was the researchers picking them up and walking their paws off of the shock area to actually teach them, like, “Oh, no, you don’t have to accept this.” So, in some ways I’m hoping to do that for the corporate world as well.

Pete Mockaitis
Oh, lovely. And a favorite book?

Bree Groff

Yeah. So, basically, all of Agatha Christie’s novels because they’re my version of being totally unproductive. In a world that teaches me that I need to be optimizing all the time, reading for pleasure feels delightful and subversive. And so, my favorite reading for pleasure is cozy mysteries, and I love all of hers.

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

Bree Groff
Yeah, I really love Trello.

Pete Mockaitis
And a favorite habit?

Bree Groff
Yeah. So, I love – would you call this a habit? – I love making a Moka pot in the morning. I really love the few minutes that takes me to make it. The minute I stare, I say, I’m just like staring at it, waiting for it to boil. It’s a good sort of sorbet palette cleanser for the start of my day and makes delicious coffee.

Pete Mockaitis
Okay. And is there a Bree original quote that really seems to connect and resonate with folks?

Bree Groff
“When you overwork, you underlive.”

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

Bree Groff
Yeah, come hang out at my website. So, it’s BreeGroff.com, B-R-E-E-G-R-O-F-F.com. And from there, you can order the book, you can subscribe to my Substack, you can find me on social media, but it’s a good first place to come say, “Hey.”

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

Bree Groff
My goal for you for today is to send a love bubble. Find one colleague or contact. You’re going to shoot them a two line note that says something like, “Oh, that design you did was so good. The plan you wrote up was awesome. Like, thank you so much for doing this thing. It really helped me.” And then make somebody else’s day. We’ll create a pay-it-forward kind of vibe for each other.

Pete Mockaitis
All right. Bree, thank you.

Bree Groff
Thank you. That was fun.