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KF #38. Optimizes Work Processes

1175: Reclaiming Time through Effective Delegation to Humans and AI with Ari Meisel

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Ari Meisel shows you how to optimize, automate, and outsource your way into more time and freedom.

You’ll Learn

  1. How to build systems that don’t rely on you
  2. How to deploy AI agents to do work for you
  3. The rules of effective delegation

About Ari

Ari Meisel is a self-described, “Overwhelmologist” and founder of Less Doing. He helps entrepreneurs who have opportunity in excess of what their infrastructure can support, find focus, flexibility, and freedom in their business. His leadership skills, his coaching prowess, and his ability to inspire leaders to become more agile, have earned him the reputation as the preeminent Entrepreneurial Strategist. 

Resources Mentioned

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Pete Mockaitis
Ari, welcome back!

Ari Meisel
Thanks, Pete. Good to see you.

Pete Mockaitis
Well, I’m excited to dig into your story and what you’ve been up to for the last seven years since your last appearance on How to be Awesome at Your Job. For starters, could you perhaps orient listeners who didn’t catch that one seven years ago, what is Less Doing and what’s that all about?

Ari Meisel

So Less Doing is the productivity methodology that I created, gosh, like 15 years ago now, and it is my company where I do productivity and business coaching for entrepreneurs, founders, executives, all over the world, and have been doing that for about a decade and a half now.

Pete Mockaitis

Yeah, beautiful. And so last time we talked about optimizing and automating and outsourcing. And so we’ll talk about some of that again with some new insights and tools and goodies. But, in your life, this notion of less doing took on a not just sort of a nice to have, but an absolutely critical must-do kind of a vibe. Can you tell us the story?

Ari Meisel
So when I got out of college, I was working in real estate development and construction, and built a big project in upstate New York. But I was really hands-on. I was working my butt off and not living a particularly healthy lifestyle and under a lot of stress, and ended up finding myself in quite a bit of debt when I was 23.

And I was diagnosed with Crohn’s disease. And Crohn’s is considered to be an incurable illness that affects the digestive tract. And I was able to overcome that illness and have been free of it for a long, long time now.

But the main constraint that I was faced with was I went from working 18-hour days to barely being able to get an hour of work done a given day. And that extreme restriction on my time is, honestly, what has led to everything that has come since then because, and it’s an exercise that I take people through, which is, “What would you do if you could only work an hour a day?”

And the question at that point, really, isn’t, “What would you do?” it’s, “What wouldn’t you do?” because if the things that you need to do have to get done by something or somebody, you’re going to have to figure that out so that that hour becomes a thing that only you can do.

Pete Mockaitis
Well, that’s powerful. And can you share with us, so you said you could only do one hour of work for those who are not as familiar with Crohn’s disease and its impact, like what would happen if you tried to push more than that?

Ari Meisel

So it was both a physical and, I’d say, a psychological barrier that I was dealing with because, first of all, any autoimmune disease, you’re, essentially, like at war with your own body, which is challenging in itself.

Crohn’s, again, it affects the digestive tracts. So not only is it difficult to eat and enjoy food and benefit from food, but there’s also like a nutrient deficiency thing that kind of happens because of it. And it just creates all sorts of problems.

So there was, literally, the physical weakness where there were days where I just didn’t even want to get out of bed. And then there were other days where, you’re diagnosed with a chronic and incurable illness, it’s like, “Well, what’s the point of doing any of this other stuff?” So it’s really challenging.

Pete Mockaitis
Absolutely. That’s brutal. So what did you do, precisely, in order to make work fit in an hour?

Ari Meisel
So, at the time, it was very different than things we can do now, of course, with AI. But the framework that I came up with was optimize, automate, outsource in that order. So we have to optimize and look at what we are actually doing and sort of do a bit of an audit, which sounds kind of basic, but most people just don’t do that.

The second step is, once we’ve done that, we look at automation. And, again, automation, the tools at our disposal have changed quite a bit over time, especially in the last year. But we automate what we can and then whatever that’s left over is the stuff that we give to a person that we might outsource or delegate to help with that, whether that’s a virtual assistant or a graphic designer or a coder or whatever it might be.

So it was really the sort of systematic approach to doing that, and that was the personal methodology, the Less Doing, More Living was what it was really called. And then over a few years, that morphed into a bit more of a business-focused methodology, which I would call the replaceable founder.

And the idea there is to make everybody in the business, including the founder, as replaceable as possible by creating systems and processes that stand in for the things that you do at a level that is not at your level of genius, essentially, everything else. And it, again, became this really systematic approach at making yourself more replaceable.

Pete Mockaitis

Okay. Well, could you walk us through some of those steps in terms of the questions, the prompts, the activities that you do when you are optimizing and automating and outsourcing, and maybe share some specific tasks that you, with the condition, ended up working through those three steps?

Ari Meisel
So I’ll give you an example that’s going to sound like a really weird one, but anybody who’s got a family, in addition to their work and their business, and kids might be able to appreciate this. So I have five kids, and I have five kids right now that are in different camps, and camp requires lots of forms to be filled out.

And I can’t tell you how many times I’ve encountered this where there’s entrepreneurs who are also parents and they feel like they have to be the one to fill out the form. Nobody else could possibly do that, “Oh, there are so many questions that I have to answer. And, also, like, it’s for my family, so I’m going to do it.” And there’s a lack of knowledge there and, first of all, in terms of like what actually could be done by somebody else. There’s also an ego thing and, like, a value thing, right?

And the problem with that is, if you’re working, and you’re efficient, you’re making money and you’re supporting your family, great, and then you come home and you have to spend an hour doing paperwork.

Like, there’s this weird stigma, it’s like, “Oh, I couldn’t outsource something like that. It’s personal. It’s for my family. And there’s also no ROI on it.” It’s like, well, there actually is because that hour is something that you could be doing with your family and having the human element there as opposed to sitting and filling out paperwork.

And I promise you, you’re not the best person on the planet to fill out paperwork. There are other people who can do that better than you. And now there’s, you know, AI agents that could do that as well or better.

So that, again, that sounds like a really trivial example, but you have things like that in business all the time where people feel like, “I have to be the one to do it. Nobody else could possibly check the boxes like I do.” And it sounds like I’m being facetious, but that is, literally, like the mindset.

I can’t tell you the number of companies I’ve dealt with where you have a COO of a multimillion dollar company booking travel for the CEO, because that’s the only person they trust to do it, right? Because you couldn’t possibly codify your seat preference and your, you know, the how many hours.

It’s true, though, and it’s crazy. Like, I actually just got off the phone with a client who runs an eight-figure company and he’s got a full-time executive assistant. He books his own travel. He’s got the apps on his phone. He just does it himself. And it’s like, “Okay, sure.” But it’s just so crazy. And that’s the one that comes up a lot.

And then you have the things where people have just been doing it a really long time, and they feel like the reason that they’re able to do it is because they know it better than anybody else. But if you know it that well, you should be able to teach it. It’s a really good sort of, you know, litmus test for how well you know something.

And if you can teach it, not only are you enabling yourself, you get to remove yourself as a bottleneck, but you’re doing something that a lot of people miss out on when they try to delegate something, which is empowerment.

A lot of delegation for people who do it is, “Here’s an annoying thing that I don’t want to deal with or I’m not good at, so I’m going to give it to somebody else who has less context, less information, and, at the same time, I’m expecting them to produce a superior result to what I was going to produce myself. So I’m literally just setting everybody up for failure and then I get to reinforce the idea that outsourcing and delegating doesn’t work for me.”

Pete Mockaitis
Well, I love that so much in terms of, one, getting over yourself. And we had Dave Kerpen on the show who talked about that concept, and has a book with a similar name, in terms of like, “No one could possibly do the camp forms or do the travel the way I like,” or there’s like a hang up, like, “Well, that’s just what a good dad or a good mom would do for their kids. They wouldn’t dream of outsourcing.”

And so you’re directly challenging these internal narratives, which I think is excellent, in terms of, “Well, no, if you took the time to really speak what it is you need in a seat…” because, in a way, I get it a little bit in terms of, like, when I’m choosing between three different flight options, there are trade-offs.

And how do I articulate to another person, “I’m willing to pay an extra $60 dollars if it means that I don’t have to hang with a two-hour layover. So what’s my layover minutes per dollar conversion rate?” Like, how do I algorithmically, contextually convey that? That’s kind of tricky. I don’t know. Ari, how do I do that?

Ari Meisel
So this is going to sound really reductivist, but a lot of times, people don’t convey the outcome that they’re trying to achieve.

Pete Mockaitis
Okay.

Ari Meisel
So I’ll give you a good example. Actually, it’s one of my favorite outsource, one of my favorite virtual assistant stories ever. I was going to Canada. I lived in New York at the time. I was going to Canada for the day to go to an event, that I had to be at the event, I think, at about 8:30 in the morning. And I go to this event somewhat regularly.

But I was sitting in the airport at 5:00 in the morning, or 5:15, whatever. And I get a text on my phone from my virtual assistants at the time that says, “Your flight is getting canceled, but we re-booked you on United Airways. Go over to gate B6.” And I’m like half awake. There’s a bunch of people around me. Nobody’s reacting or saying or doing anything. And I’m like looking around, “Okay.”

So I get up and I start walking, and I get about 100 feet away from the gate and they made the announcement that the flight was canceled and there was, like, pandemonium. And I just walked to the gate, got on the other flight.

And so the virtual assistants had booked the flight for me, and the outsource, what I had delegated was like, “I need to be there by, you know, 8:00 o’clock.” So because my flight got canceled, they didn’t stop and ask me, “Do you want to get on this seat or that?” No, they immediately, going with the goal, they re-booked me on a flight that would get me there and meet my requirements. And that was done.

So, that was amazing. That was like such an awesome experience. But, so, a lot of times we just say, “It’s like, oh, you know, update this spreadsheet with these 150 lines or, you know, sort this email.”  But we’re not conveying what the actual outcome is. Like, “Why are we doing this? What are we trying to achieve?”

And to some extent, yeah, sure, sometimes I just need something to get done and I can tell you that. But when there’s any variability and you need to create sort of this sandbox within which a person can feel like they have some autonomy and, actually, not even autonomy, agency to overcome problems and get to that outcome, people engage with that work much better, first of all, because, again, it’s empowering. It’s not just like sweeping crap under the rug.

But what’s really amazing is that, a lot of times, the people who are delegating, the leaders, don’t even have an idea consciously of what that outcome is. They’re just sort of going through the motions.

Pete Mockaitis
Yeah. And with flights, you’re right, it’s, “So I want to appear no later than this time in this location, with the minimum amount of stress and fuss and headache and rush at a reasonable price point for the fare. That’s what I’m up to.” And I guess you can elaborate a little bit, “Here’s what I mean by reasonable. Here’s what I mean by fuss.” And then go at it.

And so, in your case, what I love about that is your delegation resulted in an outcome far better than you could have achieved on your own if you were like out of it in the morning, and then everyone else was in trouble because they didn’t get the memo quick enough because your folks were on top of it. They were watching it and they knew what you needed and, bam, that’s fantastic.

And I felt that in my own world with regard to, I’ve been reluctant to let go. And then when I did, I was like, “Oh, this is just so much better. I should have just done that earlier.” Very true.

Ari Meisel
Exactly. Yeah, and that’s truly the power of delegation, right? It’s really supposed to be a multiplier in that way when you do it correctly.

Pete Mockaitis
Yeah, okay. Well, let us know. So if someone is listening and they don’t want to fill out the camp forms, what’s the trick on this one, Ari?

Ari Meisel

Well, now it’s AI agents. So I’ve built an AI Chief of Staff framework that I share for free on my website, anybody can get it, that is based on my years and years of experience, not only working with hundreds of virtual assistants personally, but running my own VA company. And I really think this thing that I’ve built is better than any of the ones I’ve ever worked with.

And so, actually, I think it’s doing something right now. So this was another good story. So I was on a call yesterday, on a Zoom call, and a text message came in from camp and said, like, there was some waivers missing or something for two of my kids for some place they were going to go next week. And I saw it pop up, I was like, “Okay, whatever.” I got off the call about 20 minutes later and it was already taken care of.

So my iMessages are connected to my agent through a tool called BlueBubbles, and, basically, the agent saw the message and felt like an action needed to be taken, and it logged into the camp website, found the waivers, signed the waivers, which it had done before, so it wasn’t just going completely off the rails, like I had asked it to do that before, and then updated the camp with a text message back saying, like, “These waivers are done.” So that was all done before I even got off the call.

Pete Mockaitis
Well, that is stunning. Wow! Okay. So we just go to LessDoing.com and we can get ourselves Chief Staff Agent like this?

Ari Meisel
For that one, you go to LessDoing.ai.

Pete Mockaitis
Okay. Well, that’s wild. So many questions from that. It’s like, “How do I know it’s not going to go rogue and do something horrifically bad that I don’t want, that I can’t undo?” How do I do that?

Ari Meisel
And I’m not, like, gatekeeping here because it’s free, but there are actually, like, 18 foundational rules that I’ve developed that are in that AI Chief of Staff framework. So it’s actually not that hard to achieve. Everyone worries about, like, hallucinations, all this stuff.

One of the most basic things, there’s two really, really basic rules that I have for the AI agents, which, the fascinating thing about this for me is that you have all this stuff about like, “Oh, this is the 30-word prompt that’s going to turn your business into a billion-dollar company and, like, all these perfect prompts,” and it’s all total BS. There is no such thing as the perfect prompt. You need to have good structures and foundations in place, and then you don’t need prompts.

So, basically, two of those really important foundational rules, which are, well, so this is what I was going say. It’s not an AI skill. It’s delegation is the skill. It’s the same stuff I’ve been teaching forever. So two of those really important rules, which again, I would give these to a human also.

The first one is, anytime you do something, the next step is to verify that you did the thing that you were supposed to do. It sounds really silly, but most people, it’s like, “Have my AI send a whole bunch of emails.” And then the AI comes back and says, “I sent all the emails,” but it didn’t, or the emails were blank, or it wrote them but didn’t send them, or it sent them to the wrong address, you know, all these things.

So every single action that I have an AI agent do, the next step is now go, “You sent an email? Next step is go look in the sent messages and compare what was sent to what you were supposed to do. You’re supposed to put a Slack message? Now go read the Slack message. You’re supposed to write a document? Now go read the…” Again, it sounds basic, but people don’t do that.

Pete Mockaitis
Well, I think that, so people, when you give this duty to a human, I’d say people do it so automatically they don’t even realize that they’re doing it. Because I think about that with Slack, is like I type it, I push enter, you know, I do spend maybe a tenth of a second looking, “Oh, did that text show up in Slack such that it’s sent?”

Likewise, with my emails or attachment, “Did I attach the correct version to this email, and that’s the new updated, freshly saved version to this email? Oh, did this hyperlink that I pasted in, in fact, point to the URL I intended it to point to?” So, in a way, I think many of us are doing it so instantly, automatically, we forget that we are doing it.

Ari Meisel
Some of you are. I am not one of those people. I am not one of those people. Attention to detail is not one of my strong suits. And I’m aware of that. And that’s why I often hire for that when I would hire people. I’ll send it, and then I’ll move on to the next 16 things. And then someone is like, “Hey, you forgot the thing.” And I was like, “Oh, right. Okay.” So, yeah, you’re right.

Pete Mockaitis
Okay. Well, that’s great. Verify that you did the thing. Human or AI, verify that you did the thing. Cool. Next.

Ari Meisel
So that’s one. The other one is I do what’s called a nightly knowledge card. So you can do this kind of anywhere you want. It could be a Google Doc, it could be Notion, it could be Evernote. It doesn’t really matter. I use Trello just because I love Trello.

So every one of my agents, and I’ve got 32 active agents right now, every single night at 11:00 p.m., it updates a Trello card with a comment. And the comment is, “What you accomplished today, what automations ran, what blockers were encountered, what solutions were developed, and what is the plan for tomorrow,” every single night.

I have a couple agents that have been running nonstop for over 160 days now, and so there are over 160 comments on that card. So what that means is two things. One is it never, ever loses track because, every morning, it’s supposed to check that card and know where it’s off to.

So that’s first, like, that’s a very basic sort of cron job, you know, “Check your nightly knowledge card to see what you should be doing and where you’re at and compare that against the instructions that you already have.”

The other one is that, if I ever want to move to a different AI platform, agent platform, or I want to build that into another agent, or have a new agent spin up that’s based on another agent, that entire history is there. So it becomes really difficult, at that point, to sort of go off the rails. It’s not impossible, but it’s very difficult.

Pete Mockaitis
Okay. And so, we’ll drop by LessDoing.ai, but when you talk about an agent platform. For folks who just say, “I just know ChatGPT, I type some things, it’s like a better Google,” what do you even mean by an agent platform? Is that some software we go download or buy somewhere?

Ari Meisel
Yeah, so ChatGPT is an LLM, right, so that is a great resource for getting information, maybe compiling some documents, putting together an image or a presentation. It’s very much a push-pull, right, “I want something. You give me the thing.”

Agents are proactive, where it’s like, “Here’s the outcome. Here’s the goal. Now figure out and go do those things and run all day every day without having to bother me for things.” So a lot of the LLMs have agent platforms, but the most popular ones right now, I would say, are probably Claude Code and Hermes.

And the one that I use, which is Tasklet.ai. So Tasklet is a web-based platform. And, for example, you can take, if you go to that LessDoing.ai, you’re going to get a PDF with the whole framework of the whole Chief of Staff thing. You take that document, drop it into Tasklet and it will build it out for you and start asking you some questions of like, “Connect me to your GMail, and connect me to your calendar and let me get to work.”

Pete Mockaitis
Okay. And you haven’t witnessed anything catastrophic happen to you or any of you the people you’ve hooked up to this?

Ari Meisel
Nothing.

Pete Mockaitis

Okay. Good news. All right. Well, that was a fun deep dive, a little treat. But zooming back out, optimizing, automating, outsourcing, so you’ve got two great rules that you shared with us with regard to when you’re delegating stuff to humans or robots. Any other powerful questions, guidelines, principles you’re using as you consider optimizing, automating, and outsourcing?

Ari Meisel
Yeah, so at a very fundamental level, sometimes we really need to ask why we do things the way that we do them, which again, sounds sort of basic, but they’re the most common answer to why in a business, you know, “Why do we use this accounting software? Why do we use this landscaper that mows the front lawn of our store? Why do we do anything?”

The answer most of the time is, “Well, that’s how we’ve always done it.” And that’s a really, really bad reason to keep doing something. Now, to be fair, a lot of smaller businesses, a lot of bigger businesses, simply don’t have the bandwidth to re-examine those relationships, those tools, consider the migrations. It becomes a very big headache very quickly.

But now with AI, we can do that in such a bandwidth, you know, unlimited way in some cases. So, for example, right now, I’m sitting in the Princeton First Aid & Rescue Squad. We are the EMS provider, the ambulance provider for the town of Princeton, New Jersey, and I am the executive director here. It’s one of my side passions. I’ve been an EMT for about 15 years, and I was a volunteer here for about five years, and now I’m the executive director.

So this is an 86-year-old organization and there were a lot of things in place where it’s like, “Well, that’s the software we always use. And this was how we did these. And this is when we had our meetings,” and every single thing I’m able to say, “Hold on, let me take that bill and give it to my AI agent. I have a
Chief of Staff Agent that I built here. I also have a bookkeeper agent that I built here. Go out and get three quotes. See if this is competitive.”

“Oh, it’s not? Great. Send an email to this person with a negotiation and see if they can match it. Otherwise, let’s switch. Cool.” And that’s been huge for us here. Billing. “We’ve been billing at this rate for about six years now. We probably should bill more, but can we justify that? Well, let’s take all that data and crunch it and see what number we really should be billing at. Here it is. Okay, that’s what we’re going to do now.”

Again, none of this is, like, rocket science. It’s so much easier to just keep going than to be like, “Hold on a minute. Let’s figure out if there’s actually a better way.” It takes more work initially to do that.

Pete Mockaitis
So when you say have an agent go get quotes, that sounds pretty sophisticated in terms of how much guidance do you have to offer? I mean, does that just consist of, “Look up vendor. Find email address for vendor. Email vendor. Describe situation. Ask for price,” and like that’s the series of tasks that they’re up to there?

Ari Meisel
Yeah, I mean, it’s not much more, but that’s the thing, right? Like, it’s not much more complicated than that. And, again, that’s just the thing where people are like, “I couldn’t possibly make that into a binary decision.” It’s like, “Yeah, you can.” “This is what we pay for this thing now. Do you offer this thing and how much do you charge for it? Is that number bigger or smaller than the number that I’m paying now?”

But, seriously, you have people that are like, “Nah, you know, you don’t know these guys and, like, I got to talk to them and explain the whole situation.” No, you don’t. You don’t. And you’re not the best person in the world to do that. No person that I’ve ever met is the best person at describing the situation that they’re in so that somebody else can give them a price for it.

Pete Mockaitis
Oh, I love it. Oh, man, these are some hot takes. Well, I guess, though, the flip side is, sometimes, it’s annoying. When you’re trying to purchase services and you want a price, sometimes the sales folks are trained, “Oh, we don’t give that away without a call. You got to hop on the phone or the Zoom to get that info.”

Ari Meisel

My AI agents can make phone calls.

Pete Mockaitis

Okay. It’s like, “Hello, Ari. What is the price for your coaching services?”

Ari Meisel
So, you know, it’s funny, they’re actually quite good now, because I’ve listened to the recordings of some of the calls, and this is just my anecdotal take. It’s kind of a known thing, I think, in the call center industry, this shouldn’t be shocking to anybody.

But a lot of times, for better or worse, when somebody picks up the phone, if they hear somebody say something with an accent, it’s like, “Well, it’s a telemarketer,” and they hang up. We know that that’s a thing. Same thing with agent. You have people like, “Human. Human. Human.”

So my anecdotal take on this, from my own personal experience, but also from hearing a bunch of these calls, is I don’t think people have a problem with the accent or with the AI, with the automation. I think they have a problem with bad ones where there’s a lack of understanding. There’s a delay. They have to repeat themselves.

The AI that I have right now work, and it’s not my technology. I use Bland.ai and RetailAI, they’re really, really good. And I’ve had people have full-on conversations with the AI where it’s, like, I really can’t tell if they can tell. And if they can tell, they don’t seem to mind.

Pete Mockaitis
Okay. They’re not saying, “You stupid clanker.” You’re not hearing that on the other side?

Ari Meisel
No, I had my AI Chief of Staff call the vet to get, like, a bill. We needed a bill that they hadn’t sent me, whatever. And the AI voice agent spelled our cat’s name for the person at the reception, and it’s a French name.

So, like, they did it perfectly and did it clearly, and the person heard it and they didn’t have to repeat it. The person gave some information back, the AI understood it, didn’t have to repeat it back, like it was a very fluid conversation.

Pete Mockaitis
Okay. Well, this is pretty mind-blowing stuff in that I’ve heard, like, enthusiastic hyped tech bros claim that this is what the future is going to be, and you’re telling me, “Oh, no, I am doing it right now easily without worry or catastrophe or trouble, and it’s been a delight.” That’s what I’m picking up from you, Ari.

Ari Meisel
It’s been the greatest thing I’ve ever experienced in my entire career.

Pete Mockaitis
Okay.

Ari Meisel
Let me just give you just some context to this, right? So do you know what the Jevons Paradox is?

Pete Mockaitis
Oh, I’ve heard of it, but I forgot. Lay it on us.

Ari Meisel
So the original one was from the Industrial Revolution when there was coal production. And, basically, Jevons Paradox says that while we would assume that when something becomes more efficient – a process, an engine, whatever – you need less of it.

In a Jevons Paradox, the opposite happens, and we have this explosion. So coal production was an example of that, right? We could suddenly power all of America with a tenth of the factories, but now we quintupled the number of factories because we wanted to expand so fast. AI is another example of that. I am an example of that.

So I have, you know, famously, I mean, I’ve been quoted for this a bunch of times, but I spent several years where I was probably working 20 minutes a day doing all my coaching and everything, and that was legitimate.

Now I am busier than I’ve ever been in my entire life. And it’s amazing, though, because I think that I’m accomplishing more than a hundred people could accomplish. I have my company, so my coaching business. I am here as the executive director of the Princeton First Aid & Rescue Squad.

I have two other W-2 jobs because people now don’t want to just have me be a coach. They want to hire me on as an employee. For some reason, that’s been a new experience for me. I also sit on several boards. I’m on the school board here in Princeton, which is an elected position. I have five kids, three cats, two dogs, and I’m still able to sit here and have a really great conversation with you, Pete, because of all of this stuff. I have 32 agents working on stuff for me.

Pete Mockaitis
That’s wild. Well, thank you for giving us a taste and a glimpse of that whole world. I wanted to hear about your profound love for asynchronous voice or voicemails. Because if you’re on LessDoing.com, that shows up pretty front and center that you love these voicemails. Tell us what’s so great about them.

Ari Meisel
Okay, so there’s a number of platforms to this. A lot of people are probably familiar with Voxer. You can do this with WhatsApp and iMessage, but they just don’t work as well, in my opinion. So I use Carbon Voice now, that’s my platform of choice. And it is, primarily, a voice platform.

And what I like about that, it’s funny, this actually came out of a weird, specific thing to me, and now this is such a different issue entirely. For so many years, I was known for all the virtual assistant work, I was doing all the outsourcing stuff, so it was always a constant thing where I would have to convince people that they were actually talking to me.

So it would be like, “Hi, Ari, or Ari’s VA, or Ari’s automation.” I was like, “No, no, it’s really me. Like, here’s today’s newspaper, I swear.” And with voice coaching, particularly, I don’t have to say, “This is not a VA. It’s not an automation.” And, of course, now we have voice cloning, but it’s not quite there. People can still tell.

So I don’t know, five, six, no, maybe seven years ago now, I switched from the traditional coaching model of meeting with clients one hour a week, every week, and talking through stuff to fully asynchronous.

So now, instead of a client having to wait till next Wednesday for us to talk for 45 minutes and get the three-minute answer that they need, now they can walk out of a fight with their co-founder on a Friday afternoon, send me a voice message. A couple hours later, I can listen to it, think through my answer and respond to them with like that 90-second silver bullet answer that they need to get through their weekend and focus on other things.

And it’s such a more effective form of coaching, but it also allows me to never miss a soccer game and take my kids to school and pick them up every day because I’m never on someone else’s schedule. Everything is, I mean, 99% of my communication is asynchronous.

Pete Mockaitis
That’s cool. And so, as opposed to email or text message, I mean, you’ve got the richness of the voice and the emotion and the nuance and texture and tone. That’s cool. I guess you also do it faster than you type words. How else are you thinking about this versus email? And how do you deal with email, generally?

Ari Meisel

Yeah, so people, generally, speak four times faster than they type. I certainly do. I’m also a very audio-visual kind of person. So I’m not a great reader. I’ve never been my whole life. It just, I’m that person that reads a page and then they’ve been thinking about something else all the time and have to read the page again.

But, like, I can remember lines from movies that I saw when I was 15. Like, I don’t know that’s a good thing, but it’s just how my brain works. So I can listen and think through a problem with a client and then respond really well.

The other thing is, and this is another limitation I recognize in myself, my initial response sometimes is probably more aggressive than I want it to be because I can get annoyed very quickly because I’ve seen these problems so many times.

So having me have the ability to take a little space and be like, “Yeah, that’s not going to come off right. Let me think through that again.” And even, in some cases, record the voice message and then recall it because I was like, “Nah, that wasn’t what I wanted to say,” it ultimately ends up being a much better experience for the client, and it’s a really incredible, like, sort of learning experience for me as a coach. I get a do-over sometimes.

But I often will say that I can tell more about a situation from the way a client says something than what they actually say. And you just lose that in an email. Plus, at this point, so many, there are so many tools, so many AI tools for writing emails for you, imagine emails for you.

Like, when you’re dealing with voice stuff, you really know that you’re talking to the person. And, again, like, I have voice cloning on the app because it’s built in. So if I type something, it will speak it in my voice, but still, it’s more natural, but you know it’s not actually me. So there’s just something very intimate about that.

And also, one more thing about that, too, is it’s such a common practice, I feel like, for people to outsource their inboxes, which I have never ever been a fan of because I think it’s a real breach of trust, honestly.

And if somebody knows that they’re communicating with someone’s assistant through that person’s inbox, I think it just creates a very weird sort of scenario. This is always private and always like me and them, which is hard to achieve nowadays.

Pete Mockaitis
Right. Well, tell us, what do you have running on your own inbox? I like Superhuman as an app, although it’s still me, Pete Mockaitis, the person, typing out the things. What are you doing there?

Ari Meisel
Just good old Gmail and some good habits.

Pete Mockaitis
Well, but, I mean, so super automation, outsourcing, you know, optimizing, you’re just like tapping away in Gmail?

Ari Meisel
Yeah, yeah. Well, yes, with one caveat. So I actually, unfortunately, I have to use Outlook also for a couple of organizations I’m involved in. I hate Outlook. But, basically, well, yeah, mostly in Outlook. So for certain emails from certain people with certain topics, my AI Chief of Staff will draft emails for me in response. And then I’ll usually just go in.

Pete Mockaitis
Okay, so you review and then send.

Ari Meisel
Yeah, and they’ll send them. But there are also quite a few where it can autonomously just send it without having to draft first. So, like in Slack, for example, this has actually been so fun. So I use Slack with a few different companies, too.

And, for example, I have an AI agent that was building a website for the company because I don’t have the attention to detail. I put it into the Slack channel with six people on the team and like, “Hey everybody, can you check on the website and make any comments of things that you see that are wrong?”

And what was so fun was, so someone would make a comment, “Oh, this page doesn’t load, this link’s broken.” The AI is in Tasklet, the agent, sorry, Taslet is in Slack, so it would immediately be like, “Oh, thanks for catching that. I’ve already rolled that into the next version and deployed it.”

So then the next person is like, “Oh, well, I see this thing and this thing. It would be great if this was here.” “Oh, great idea. Thank you.” So what ends up happening is you go through, you get to like v7 within 20 minutes and each person, we don’t have six people looking at v1 and giving comments. Every person that looks at it is seeing a better version than the last person that looked at it.

And so in a matter of 20 to 30 minutes, you’ve gotten this incredible iteration, and the website is fantastic now. And in that case, I’m not drafting anything. I’m not approving. It’s just going and it’s taking feedback, fixing it, and doing it again.

Pete Mockaitis
That’s really cool. So that was fun for that particular project, rather than we’re emailing a designer or a robot designer, and then waiting. And so, inside your Gmail or Outlook, you are just like a normal person, reading messages and replying to messages that don’t fit into the narrow AI autopiece. Well, you mentioned the AI is drafting kind of logistically, tactically. How does one get an AI up in their Outlook and/or Gmail reading and drafting replies?

Ari Meisel
So a lot of the agent platforms can just do that. You just say, like, “Connect to my Gmail,” and it’ll do that through whatever means it uses. But the key, of course, I would say, is to have it look back through a lot of the emails that you’ve sent to get your style and that sense of style.

The other thing that I’ll do, so I do manage my own inbox for the most part just because I have a whole methodology around this. I’ve been teaching forever called the 3Ds for Inbox Zero. But what I will do is, if I’m unavailable for some reason, like tomorrow, for example, I’m going to be at this event with one of my kids and I will not be on the phone at all for like six or seven hours.

What I’ll usually do in that case is if I get back on my phone and there’s like 60 emails, I’ll just go to my Chief of Staff and be like, you know, “Just triage the inbox.” And so then what it’ll start doing is it can draft, it can archive, it can answer things that it needs to.

And the example I gave of the camp waiver, like if it knows that an action needs to be taken and it knows that it can take that action, it is instructed to just do that and get it done.

Pete Mockaitis
Okay. That’s cool. Well, Ari, tell me, anything else you want to make sure to mention before we hear about your favorite things?

Ari Meisel
People should go to LessDoing.ai. There’s a free, like, five-day boot camp thing. It’s not an upsell or anything. You get this document and you don’t do anything else with it. I think that’ll probably be really eye-opening for people.

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

Ari Meisel
It’s a Robert Heinlein quote, and I look at it every year. So it’s, “A human being should be able to change a diaper, plan an invasion, butcher a hog, con a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.”

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

Ari Meisel
So I’ve been very interested in how environments affect our productivity, mood, all sorts of things, so whether it’s lighting or temperature, or even an interesting one. So I have a thermostat in my office here that doesn’t do anything. Actually, the building temperature is controlled centrally. So I’m not even sure why they set these up when they do this.

But if you give somebody a thermostat in their office and they think that they have control over their thermal environment, they will be more productive and actually happier. So I find a lot of that stuff very, very interesting, how you sort of set up your environment for greater productivity and happiness.

Pete Mockaitis

Okay. And a favorite book?

Ari Meisel
Emergency by Neil Strauss.

Pete Mockaitis
Okay. And a favorite tool?

Ari Meisel
Tasklet.ai probably would be my favorite tool.

Pete Mockaitis
Okay. And a favorite habit?

Ari Meisel
I’ve gone through so many different seasons of exercise in my life, but I’m 43 now and I’ve got kids and it’s busy. Every morning, I do a kettlebell workout before 6:00 in the morning, basically, and sometimes it’s five minutes. But every morning, I pick up that kettlebell and I do something. And I think that that has a really measurable effect on how the day goes for me and mobility and just how I feel.

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

Ari Meisel
“You can’t read the label from inside the jar.” In seven years, you can say that back to me.

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

Ari Meisel
LessDoing.com.

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

Ari Meisel
Yeah, try to become more replaceable. So, try to take a list of the things you do on a regular basis, 10, 20 things, and then try to pick eight, or 80% of the things. So if it’s 20 things, 16 things from that list that, in six months, you will no longer do anymore. And then figure out if you’re going to optimize, automate, or outsource that thing so that you’re not doing it.

Pete Mockaitis
All right. Ari, thank you.

Ari Meisel
Thanks, Pete.

1157: How to Improve Processes, Remove Friction, and Accelerate Innovation with Jon McNeill

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Tesla’s former President Jon McNeill reveals the five-step framework behind one of the world’s fastest-growing companies.

You’ll Learn

  1. What most miss when designing processes
  2. How to identify outdated requirements that slow things down
  3. Why automation should be your LAST step

About Jon

Jon McNeill is the CEO and Co-Founder of DVx Ventures. With a track record of founding and scaling companies, Jon has led teams that generated tens of thousands of jobs and delivered multi-billion dollar returns for investors.

Previously, Jon served as President at Tesla, where revenue grew from $2B to $20B in under 30 months, and later as COO at Lyft, helping double revenue and take the company public. He currently sits on the boards of General Motors, Lululemon, Asurion, CrossFit, and Stash.

Resources Mentioned

Thank you, Sponsors!

Pete Mockaitis
Jon, welcome!

Jon McNeill
Thanks. Nice to be here, Pete.

Pete Mockaitis
Well, I’m excited to discuss The Algorithm and I’d love it if you could kick us off with a story you shared, which I found riveting, in which when you were just getting started at Tesla, even actually before you had the job, you took it on yourself to tackle a project. Could you tell us the story?

Jon McNeill

Yeah, I was talking with Elon about joining Tesla and I kept saying to him, “I think you need a big company guy to come in.” And he said, “No, that’s exactly what I don’t need. I need a fellow entrepreneur.” And I said, “Well, I want to make sure I can be helpful to you. So, like, what’s your biggest problem right now?”

And he said, “We have a demand problem.” And I said, “Okay, like frame that for me. They’re public companies. So what’s your commitment to the street this quarter?” He said, “Roughly 12,000 cars.” And I said, “How are you doing so far?”

It was about a month into the quarter. He says, “It’s a month into the quarter. We’ve sold like 2,500 cars, short of 3,000 cars.” I’m like, “Oh, now I understand your demand problem. You’re going to miss your quarter. Let me go to work on that and see if I can help.”

So I went to, just in the travels with my own business at the time, I went to eight different cities over the course of about 10 days. And I went into eight different Tesla stores and did what I was told was the pinnacle of the sales process and sales funnel, which was taking a test drive.

And the whole idea was that people would come in, they would get in an electric car for the first time, hit the accelerator. And the accelerator in an electric car is way different than a gas car. It’s instant torque to the wheels, and so you take off like a rocket. And so a lot of people experience that. And then they can’t stop thinking about it until they’ve got a car.

So I went in eight stores, I did a test drive. And then, oddly, like a few days later, I hadn’t heard from any of them. So Elon had put me in touch with his head of sales ops. And I called him and said, “Like, am I blacklisted in the system or something? I used eight different email addresses so people wouldn’t know who I was. And people don’t know who I am anyway. And I’m not getting any callbacks. Why?”

And he looked in the system, he’s like, “No, you’re not flagged or anything.” I said, “Can you do me a favor? Can you tell me how many test drives you’ve given in the last 30 days that haven’t been followed up?” And he’s like, “Sure, give me, like, an hour. I can go run that.”

So he calls me back in an hour, and he said, “Nine thousand, 9,000 test drives, no callbacks.” I said, “Well, congratulations. You’re going to miss your quarter because you haven’t called anybody back. And no wonder you’re so far short of orders.”

So then I said, “Can you shut off a store rep’s ability to take any new leads until they’ve called all of their previous test drives back?” He said, “Yeah, I could do that.” I said, “How fast?” He said, “Globally? I could do that in a few hours.” I said, “Awesome. Do it, because we got to force-change, like, super fast or, otherwise, you’re missing your quarter.”

So he does it. Calls me back the next day, he’s like, “You won’t believe the orders are flowing in like crazy.” And I said, “Yeah, because you’re just calling people back. It’s the easiest thing ever. You’re asking for the order.” And then it dawned on me that I didn’t work for Tesla yet. And so I kind of gulped, and I said, “Hey, I got to call you back, because I got to call Elon and beg for forgiveness.”

So I called Elon and said, “Hey, look. Here’s the situation. You’re demand-challenged. Here’s what I found out. You’ve done 9,000 test drives with no callback. And so here’s what I did about it. I was on the phone with your head of sales ops and we shut down any new leads into the system until everybody called their previous test drives back.”

And I said, “But I got to ask your forgiveness. I was acting like this was my company because I’m a CEO in my day job. But this is not the company I’m the CEO of. You are. This is your company. And I did something and I didn’t even ask your permission. And I’m really sorry. I got to apologize.”

And I didn’t know it because we were just getting to know each other. But I had this long period of silence on the other end of the phone line, and I thought, “Oh, my God, what have I done?” And it seemed like forever. It was probably 60 or 90 seconds of just dead silence.

What I’ve learned since is that’s how Elon processes. He, like, shuts off all other sensory input and just thinks. And so I was about to ask him if he was still there, and he hopped on and he said, “You know what? That’s exactly a rational decision, and I’m so glad you made it. I think you’re going to fit in here just fine.”

And that was the last hurdle. I said, “Well, I think I’ve proven myself I can be useful. So I think I’m ready to sign on, too.

Pete Mockaitis

That’s a lovely story on many dimensions. But when I reflect on it, what I’m stuck with is, “All right, Tesla, great, great brand, tremendous company, tremendous leaders, lot of smarts there.” How is it that we find ourselves in a situation where one of the most fundamental things one can do in a sales operation – call people back – isn’t happening?

Jon McNeill

I think I see this over and over again. People look at a lot of data and miss the obvious. And when you just go and see a process with your eyes – this is going to sound completely old-fashioned – but it’s actually the case.

Like, I believe that the strongest analytical instrument you have as a leader are your eyes and ears. And if you go to the front line and eat your own dog food and experience the product or the process for yourself, you’ll often see exactly what’s wrong. But unless you know the exact piece of data to look for that would give you the clue, you don’t know that.

And so this is a complete hack I’ve found in leadership is just go to the front line, go experience the process yourself. You’ll understand really rapidly exactly what’s wrong. And it doesn’t always work, but it works a lot of the time. And this was an example of that.

So a bunch of really smart people looking at data missed it because they didn’t leave their offices. And my encouragement to people, and those people, as I then became their leader was, “You’re going to leave your office at least one day a week, and you’re going to go to the front lines because you’re going to see stuff way faster than the data will show you. And, hopefully, we’ll miss a lot of these potential big divots in our plan if you do.”

Pete Mockaitis
Yeah, that’s tremendous. We had Marina Nitze on the show, who was the CTO for the United States VA, and that was one of her core recommendations, is follow the thing all the way through the process and then you’ll say, “Oh, that’s why it’s taking forever because so-and-so is waiting for something to be faxed. Well, let’s stop that. All right, now we know. Understood.”

All right. Well, so then zooming out a bit, your book, The Algorithm, any particularly surprising or fascinating discoveries you’ve made in your career or while putting together the book that you’re putting forward here?

Jon McNeill

I think this is, like, I had gone into Tesla having been a student of the Toyota Production System and Lean, and what I found was those frameworks were awesome for incremental improvement and optimization, but not awesome for quantum growth.

And so what we tried to distill in The Algorithm, this was the whole team at Tesla and, really, the leadership team that came up with this framework, was to distill a framework for quantum growth into some digestible steps that we could push to the edge of the organization.

And the edge could start to innovate super fast, because that’s what doubling a business every eight months at scale requires. And that’s exactly what the team was pulling off. They were doubling a business every eight months.

Pete Mockaitis

All right. So the classic Toyota manufacturing, Lean, Kaizen, Kanbans, etc., is great for your small incremental growth and you’ve got a whole another thing for hyper growth. And can you unpack sort of basically what is the algorithm?

Jon McNeill

It’s a five-step process that we used on a weekly basis to drive innovation. And this is used at Tesla. It’s used at SpaceX. And I think, as leadership experts or academics go to study Elon 20 or 30 years from now, and ask the question, like, “What made this guy such a successful entrepreneur and industrialist? Like, what was it?” I think they’ll come down to this, like, weekly cadence of deploying this framework, because that’s exactly what he does.

He determines the one or two issues that are existential to the business. In other words, the two things that could kill you if they don’t come true. And then he just devotes his time to that. He delegates everything else to the team. And so you have great agencies as a leader because you’re running the business and he’s really working on two existential issues, but he’s doing it on a weekly basis.

And what that does is that keeps the organization innovating on a weekly basis. So if you’re doing that every week, you’ve got 52 opportunities to build advantage versus your competition. And that’s exactly what that delivers.

Pete Mockaitis

Okay. Well, so could you maybe walk us through a couple examples of, all right, grab existential issue and then work through the steps?

Jon McNeill
So I’ll take you through one to make this super simple. So the first step is question every requirement. Second step is you delete every step and you simplify. The third is you optimize. The fourth is you speed it up because no process can get faster and have high quality with speed unless it is like optimized, so that’s a test. And then you automate last, which sounds kind of nuts especially coming from a technical company or Silicon Valley company to say automate last, but I’ll kind of illustrate that.

So let me start with the first, the negative example. So we started to prepare for Model 3 production. And the idea of the teams was, “We’re going to have a fully automated line, the most automated manufacturing line ever in the history of automobiles.”

And so you might remember this phrase, “We’re going to build the alien dreadnought,” or, “the machine that makes the machine.” That was this whole era. And so teams went to design the Model 3 production line in digital simulation. Today they would call it a digital twin. And they designed all the machines, the flow, the conveyors, the people, everything. They didn’t lay it out manually and do it manually first.

And so when we were down to the wire in terms of, “We got to produce Model 3s because we’re going to be out of cash if we don’t,” they went to start that line, and the line wouldn’t work for a thousand reasons. There were major, major mistakes that were made in that digital SIM.

And digital SIMs usually don’t work because they can’t think of everything. And cars were falling off the conveyors, falling off the line. And that then led to a radical step, which was one of the leaders, Jerome Guillen, said, “I’m actually going to scrap this whole process and build a tent outside. And we’re going to do what we should have done from the start. We’re going to build cars by hand.”

And so we started, over the weekend, building Model 3s by hand. And we simplified the entire process because we didn’t have conveyors, we didn’t have a lot of the machines that were necessary, and we did the bare essentials to produce that Model 3.

So we simplified the process, we deleted all the unnecessary steps, we didn’t have the luxury, really, of having many steps. And then we started to optimize the process, and we started, we produced 50 cars a week, and then we produced 100, and then we produced 500. And the goal was to get to 5,000. And we kept creeping up, creeping up, creeping up by optimizing the process and applying speed to it.

Once we finally had the process nailed, then we automated at the very last step and moved from the tent back into the factory. We had rebuilt the factory production line by this time so that it could actually produce cars.

And when we went to do the postmortem, we said, “How would we have avoided this? Number one, we automated first, not last, and it almost killed us. We did not run the process manually first. We did not delete a bunch of steps. We did not optimize the process. We automated before we had done any of that work, and we almost killed the company.”

So it was, really, at the end of Model 3 production, that the algorithm came together, and we said, “Here are the steps we’re going to follow from here on out. When we go to launch a new product, when you go to invent a new product, we’re going to follow these steps.”

And so that’s an end-to-end example of how not to do it, but then it led us to a framework of how to do it.

Pete Mockaitis
Okay. So maybe digging into each of these in some detail, with “question every requirement.” I have a feeling many of us, it doesn’t even occur to us to question the requirements because the requirements, they’re just like the air we breathe or the water we swim in. It’s like, “Well, this is just how it is.”

So could you maybe surface for us some prompts, or some examples, or some perturbations so that we can identify some requirements that maybe need to get questioned?

Jon McNeill
So when we started to sell cars online, we figured out it took 64 clicks to sell a car, but 44 of those clicks were in the financing process. And that’s because a loan doc or a lease doc for a car has 12 pages of paragraph after paragraph after paragraph. You’ve got an initial sign, all this stuff.

And so a question on requirement step that we did was I took that loan doc to our general counsel at the time, his name’s Todd Maron. I said, “Todd, out of these 12 pages, I need to get rid of some clicks. Can you tell me how many of these paragraphs are a requirement of law or regulation?” He came back about 24 hours later and he said, “None.”

I said, “Well, how does a 12-page document exist then?” He said, “It’s the result of a bunch of well-meaning corporate lawyers at banks trying to protect their client. And so they insert paragraphs for all these uncertainties or these edge cases that could come up to protect the bank.”

But he said, “None of these are required by law or regulation. And, actually, the bank has case law on its side. Like, they don’t need all this stuff because if somebody cheats in a certain way, that’s already been decided by case law. So it’s not like you need to make somebody acknowledge something that the courts have already acknowledged as being out of bounds.”

So I said, “Todd, you’re telling me we could have a one-paragraph loan or lease that says, ‘Here’s the price of the car, here’s the interest rate, here’s the term, and here’s the monthly payment?’” He’s like, “I’m telling you, you can do that.”

Nobody in the industry had questioned whether or not the loan doc or the lease doc should exist. We were just crazy, silly enough to make that, to raise that question. We discovered something that none of our competitors had discovered, which is you didn’t need to put customers through a 44-click process. And as you know, if you had to buy anything on Amazon, and it took 44 clicks, you’d probably opt out a lot. And that’s true in e-comm, and it’s certainly true when people are buying a $100,000-car online.

So we went to talk to banks to see if we could get anybody to go along with us on this one-click loan release, and we got the door slammed in our face by everybody, even though they would intellectually acknowledge that they didn’t need all these paragraphs.

They said, “I would never take the risk of doing this. I would never take the career risk of going to my CEO and suggesting we do this.” Finally, we found a very enterprising CEO at US Bank, and he said, “We’ll do it. In fact, we’ll talk to a CrossTown digital bank called Ally. They’ll probably do it too. We’ll take your loans, they’ll probably take your leases, and we’re off to the races.”

All that started because we questioned why a 12-page loan doc had to exist. And that’s probably the clearest example or the best prompt I can give you on questioning requirements. There’s a lot of stuff that nobody ever questions and takes as a given. If you question that stuff and it turns out it’s not a given, now you’ve got an advantage.

Pete Mockaitis
Yeah, I like that a lot. And I’m thinking about, well, the phrase that comes to mind is checkbox marketing, or really checkbox anything. If your mindset is, “Well, that’s just what’s done. It’s just what needs to happen.” And I’m thinking about, well, I have a one-page guest release form.

And I think lawyers tend to want to put a lot of intense, you know, things in there. It’s like, “I own all of these forever, no matter what.” And I think, “Well, actually that’s not the vibe I’m trying to put out there when I’m just meeting somebody. I’m just sort of like, ‘Hey, you and I are both cool to do what we want to do with this thing, okay? So no pressure, it’s all good.’” And that’s kind of what I’m trying to convey.

So it was not the default. We had to shift and adjust and then it is, well, it’s much smoother because then I don’t have a lot of people say, “Whoa, whoa, hold on, buddy. What, what is this? I don’t know. Wait. Time out. I got to talk to my lawyer. I got to talk to my agent. I don’t know if we can do this, you know?”

No, that just about never happens because it’s very quick and it’s simple and it’s handy. And I liked that example because the law, in particular, feels like something that’s immovable, like, “Oh, ‘legal’ said, we just have to have that. And end of discussion. It was like, “Oh, well, maybe legal would be willing to have a follow-up conversation and see what can be done here.”

Jon McNeill

Totally. And it takes a certain mindset. So, like, Todd, as a leader of the legal teams was willing to come along on that journey with me and question requirements, and that’s pretty rare in that kind of a leader in that function, but he was super commercial and business-oriented.

And so he would start that journey without having a bunch of hesitation. Like, he’d say, “Yeah, let’s go, like, look into this and see if this is really true and if we really need this.” I don’t experience many general counsels like Todd because they largely go into that career to mitigate risk. And so that’s where their position starts.

Pete Mockaitis

Well, and as a point of curiosity, I mean, I understand frictions and clicks are, you know, undesirable. They slow down the behavior you want, and this is cool and convenient and nice and pleasant to have fewer clicks.

But, you know, Jon, really, lay it on me, is a few dozen clicks for signing an initialing a hundred thousand dollar vehicle enough to move the needle so that folks are like, “You know what? I wanted that Tesla, but this is too much effort. I’m done with this document. I’m abandoning my cart”?

Jon McNeill

It happened a lot, and when we eliminated it, the opposite happened. People started to buy like crazy online, and our digital sales went through the roof, which is because it’s just science. In e-comm, clicks equal anti-conversion. So you get rid of clicks and your conversion rate goes up. It’s just math.

So this is why when you get to the cart in Amazon, the search bar disappears. They want to take away any potential click that you’re going to do other than hit order, because they know how hard it was to get to that point and how hard it is to get you to actually click the order button.

Pete Mockaitis

Yeah, and I believe they’ve litigated the one-click ordering.

Jon McNeill

Exactly.

Pete Mockaitis

It’s like, “No, this is ours, we own it, no one touch it.” And it’s like, “Very touchy,” and because the stakes are huge.

Jon McNeill

Because of that, because it’s powerful. Yeah.

Pete Mockaitis
All right. Well, can you chat with us about deleting the steps in the process?

Jon McNeill
Yeah, so here’s another example, and Elon actually cut a little video in this early on, but he had taken on this challenge in manufacturing where there was this separator between the battery and the car. And so it’s basically along the floor of the car.

And we could not produce this separator, big piece of plastic. We couldn’t produce it to save our lives. It was warping and it wouldn’t fit right, etc. And so this is one of the chapters where he’s literally sleeping in the factory trying to solve this problem.

And, eventually, he asked the team, “I got to talk to the engineer who spec’d this part. Who spec’d the part?” And the closest people around are the battery people, and they said, “Oh, it’s the auto dynamics team. They wanted a noise dampener in between the battery and the passenger compartment.”

So he grabs the guy that’s the head of the auto dynamics team, and said, “Why did you spec this part?” He said, “I didn’t spec the part. It was the battery team. The battery team told us they needed a heat shield between the battery and the passenger compartment.”

He’s like, “I was just with the battery team and they said it was you, not them.” He said, “Give me the name of the person who spec’d this part.” So they go look for the name. And it turns out the name of the person that spec’d the part was a summer intern that didn’t even work at Tesla anymore.

Elon had spent weeks in the factory trying to solve this problem, all for a part that didn’t need to exist. And so, at that point in time, “We said, nobody claims ownership of this ‘requirement.’ So we’re going to delete it out of the car. And, therefore, we’re solving a whole production problem that was holding us up.”

And you will find, over and over again, that there are steps you can delete from your sales process, from your delivery process. And the hack to finding those is, essentially, map your process on a wall with a bunch of sticky notes. Then have your team go circle those steps that the customer pays you for. It turns out there’s very few of those.

They don’t pay you for the order sheet. They don’t pay you for the PO. They don’t pay you for, in our case, the bill of lading. They don’t pay you for all this stuff. And the things they don’t pay you for are immediate candidates for deletion, because you’re doing those for internal reasons, and you’re creating cost for internal reasons.

Now some of the stuff is necessary to track dollars and cents. I totally get it. They don’t pay you for accounting. They don’t pay you for tax. I get that. But there are a bunch of steps you can cut out when you start to say, “Hey, the customer really doesn’t pay us for this. And we don’t really get anything out of it. So why are we doing this?” And those are good candidates to delete.

Pete Mockaitis
That’s good. Well, I was curious, did Elon get on the phone with the intern? Like, “Hey.”

Jon McNeill
The intern didn’t even work there anymore. Like, didn’t even work there.

Pete Mockaitis
Well, mean, hunt him down wherever he is.

Jon McNeill
He was like, “I don’t need to waste time talking to the intern, like, it’s gone.”

Pete Mockaitis
Okay. So then simplify and optimize.

Jon McNeill
Yeah, so once you delete steps, now you’ve got way fewer steps. So you’ve got a simplified process and now you can start to optimize that process and make it go faster and faster and faster and faster. It’s a little bit like starting any skill, whether that is playing a musical instrument or a sport, where you start and you’re like, “Man, I can’t go very fast.”

And then you practice and practice and practice, and it turns out you get faster and faster and faster because you get more and more efficient and optimized. And that’s the idea here is you keep speeding the process up and speeding it up.

Now you’re still in manual mode. So you’re learning a bunch about what’s causing, what’s getting in the way of speed, and the stuff getting in the way of speed is usually a quality issue. And so you eliminate these quality issues. And then once you’ve got the target speed achieved, now you know you’re optimized and you can then start on automation.

Pete Mockaitis
A quality issue in terms of something needs rework or is outside of the spec we’re looking for?

Jon McNeill
Exactly.

Pete Mockaitis
All right. And then with the acceleration, so there’s practice. What are the other drivers of accelerating?

Jon McNeill
Mainly, it’s putting speed goals that are double the current speed. So you say, “I want to either double the output at current speed or I want to double the speed at current output,” either one of those works in my book, just try to double.

And it starts to reveal, “Oh, here’s all the things that are in the way of doubling. So maybe we can delete more steps. Maybe there are more requirements that we should question. Or, maybe there’s a better method.”

And as you do those, then you start to identify, “Ah, there are a bunch of things that we didn’t see at first that we now see now, that we can either delete or simplify to help us speed this process up.”

Pete Mockaitis
So the doubling of the speed is not so much a, “Hey, it turns out we can just double the speed, it’s all good.” But rather, it’s sort of like a magnifying glass to identify, “Oh, that’s what’s holding down the speed doubling.”

Jon McNeill
Totally. There’s this great series of scenes in the Hulu series, “The Bear,” which is about this super high-end restaurant in Chicago. And it’s turned from a roast beef cafe with the same team in the back that is now trying to earn its Michelin star.

And there’s a woman that’s at the pasta station, and she has two minutes once an order comes in to cook pasta. And she starts at five minutes. And then she does things like she portions each serving of pasta in a little plastic container. So she’s pre-portioned.

And she starts to do multiple boiling water pots to drop the pasta into so she can do more than one at a time. And then she’s got a saucier step that she realizes, if she preheats the sauce, it meets the pasta at the right time, she can speed it up. And she gets the process down from five to two and a half minutes by just eliminating all these steps, but she’s still not at her two minute target.

And then the sous chef, who really runs the kitchen, comes over and is just helping her. They have a busy night. And so the sous chef comes over and does a few things that experienced chefs know to do. Bam! Bam! Bam! Order comes out in a minute and a half.

And the woman who is at the pasta station says, “I’ve been working this problem for like 90 days and I got it from five minutes to two and a half. And you walk over and you do it in a minute and a half.” And she’s like, “Yeah, I’ve done this before. So just watch me and you can see the extra steps you can take out of your process to make yourself faster.”

That’s what we’re talking about is just optimize, optimize, optimize until you get to a really different output than you’ve had before.

Pete Mockaitis
And then the final step is automation.

Jon McNeill
Yeah, and then you can automate it. Because automation is like wet cement. When you put it around a process, it sets up really hard and you got to get jackhammers to get rid of it. So you don’t want to automate until you’ve really got the process nailed. Otherwise, you’ll be suffering with the cement that’s already solidified the current process where it is.

Pete Mockaitis
Okay. So now, as we were talking about this with the restaurant example and manufacturing examples, I’d love to change gears a little bit and hear about, let’s say there’s someone who’s in the middle of an organization and their output is not physical, but, nonetheless, there is a process that’s cranking out something on the other end. Could you give us an example in that domain of working through those steps?

Jon McNeill
Yeah, so, like, whether you’re producing software or whether you’re producing marketing or you’re producing financials, I think the same steps apply. If you step back and say like, “Hey, look, I produce financial statements for the business,” or, “I produce a budget for the business.”

If you step back and say, “Okay, let me just map the process that we use today to do that. And maybe I should question some base assumptions here. And do we have to do all these steps? Like, are all these things really required?”

And so an example of that is Tesla, when I joined, was doing standard annual budgets. And the senior management team and the CEO would set the target for sales, and the target for gross margin, the target for cash flow. And so these annual budgets were being done in the way they’re done at almost every company.

The challenge was we were doubling the business every eight months. And so, like, if you’re trying to project out a budget for a year, it was horribly inaccurate by, like, month three, because things were changing so fast. So all that was essentially wasted effort, all that planning and budgeting.

So we asked ourselves a question, like, “Time is super, super valuable in this company. How could we improve this process? And rather than going through a big planning cycle every year, what actually needs to get done?”

And where we ended up was, we questioned the requirement of having a year budget. It turned out what we did was we had quarterly budgets because the business was moving on a quarter basis, not a year basis, and we would have these rolling four quarter budgets.

We would spend less than two days setting targets in the budget because it was only going be good for a quarter. So you didn’t want to spend a week of the quarter, a huge chunk of the quarter doing it. And that finance team evolved a whole different way to do financial planning and budgeting.

And they did it, not on an annual basis, but a quarterly basis. They did it on a rolling basis, and they just used the key inputs that everybody was looking at in the business anyway, “What’s the sales rate? What’s the production rate? What’s the margin?”

And we can build a budget off of that, and rather than taking the whole company’s time planning, we’re just going to keep rolling this and rolling this, and we’re absorbing everything that we’re learning from the market as we double.

And so you can apply this whether you’re sitting in a finance department or a marketing department or a sales department. You can apply these principles to your advantage, too.

Pete Mockaitis
Okay. Well, Jon, tell me, any final top tips, do’s or don’ts, for folks looking to implement this stuff?

Jon McNeill
As we talked about, like one of the principles that is a complete hack is eat your own dog food. I learned this from Sam Walton in his book, Made in America, where he would tour stores on a weekly basis to find out what the customer wanted that they didn’t have, what they had too much of that the customer didn’t want, and what were the things that store managers were doing that were super good that he could spread across the company.

And I learned from that and started to see that, “Oh, he’s onto a complete hack.” Like, if you use your own product, if you experience the customer experience, you’re going to see all kinds of areas of improvement. And if you teach your people to see it before you, they’re going to move even faster than you can.

And so I would say, like, the secret hack is go experience your own product and use it. We even went so far at Tesla to have a rule that you couldn’t present product in a PowerPoint. We didn’t want to see, like, some rendering or rendition. We wanted to see the real thing. So if you’re presenting product, you had to do a live screencast onto the screen so we could see the product, we could play with the product, and we could see how it actually worked.

I was with a group of bank executives a few months ago. I asked them to raise their hand if they actually use their own bank’s consumer app. No hands went up. And I said, “I could have guessed that because I’m a consumer of two of your banks, and your app sucks.”

“It’s so bad that if you used it, you wouldn’t live with yourself for another day without fixing it. You would call up the head of engineering and you say, ‘We got to fix this, this, and this.’ But you don’t use it.” So the organization gets the sense that nobody cares. And if you can live with it, they can live with it.

And eating your own dog food changes all that. It creates an immediate feedback loop to the top and it allows you to set the bar of acceptability with your organization.

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

Jon McNeill
I think this whole approach is about simplicity, and so I love the Mark Twain quote, “I would have written you a shorter letter if I would have taken the time.” It speaks to how hard it is to simplify. Humans, I think, we are naturally complicators. We’re not natural simplifiers, and it actually takes work to simplify.

And I love that quote, because it reminds me, each time I read it, of the fact that simplification is work. It’s super valuable and rewarding work, but it’s work.

Pete Mockaitis
All right. And can you point to a favorite study or experimental or bit of research?

Jon McNeill
I think, if you want to understand AI and the current version of AI that we have with LLMs, the best piece to read is the original DeepMind paper.

Pete Mockaitis
“Attention Is All You Need”?

Jon McNeill
Yup.

Pete Mockaitis
All right. And a favorite book?

Jon McNeill
Favorite book would be, I’ve got two right now, one is The Goal, which taught me a completely different way of looking at business, by Eliyahu Goldratt. And the second is Unreasonable Hospitality by Will Guidara. I think it applies to every business. It’s so good.

Pete Mockaitis
Okay. And a favorite tool?

Jon McNeill
Reading. Like, if I could answer the question that way, I’d start every day reading for an hour and a half, and I read variety of things. I read books, I read, obviously, the news. I read Twitter, I read Reddit, Hacker News sometimes. Reading for me is a tool.

Pete Mockaitis

Okay. And is there a key nugget you share with teammates, audiences, that they quote back to you often, a Jon original?

Jon McNeill
We had the standard for service at Tesla that gets quoted back to me, it got quoted back to me today actually, and that is, “Make them talk about you at dinner tonight.” Do something that is so awesome that they’re going to talk about you at dinner tonight.

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

Jon McNeill
I’d point them, you can find me at DVX.ventures.

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

Jon McNeill
Become a simplifier and you’ll stand out.

Pete Mockaitis
All right. Okay, Jon, thank you.

Jon McNeill
You bet. Thanks, Pete.

1156: How to Make Great Meetings that Stop Wasting Time with Rebecca Hinds

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Rebecca Hinds discusses the simple shifts that turn meetings from time-wasters into value-generators.

You’ll Learn

  1. Why most meetings don’t feel like “real work”
  2. Why every organization needs a “meeting doomsday”
  3. The easy agenda fixes that save so much time

About Rebecca

Rebecca Hinds is a leading expert on organizational behavior and the future of work. She holds a BS, MS, and PhD from Stanford University. Rebecca founded the Work Innovation Lab at Asana and the Work AI Institute at Glean, first-of-their-kind corporate think tanks dedicated to conducting cutting-edge research on the future of work.

She is a trusted advisor to companies navigating the challenges of modern work—from meeting overload and hybrid dysfunction to the messy realities of AI adoption and organizational change.

Resources Mentioned

Thank you, Sponsors!

Pete Mockaitis
Rebecca, welcome!

Rebecca Hinds
Thank you so much for having me, Pete. I’m looking forward to chatting.

Pete Mockaitis
Me, too. Me, too. And I am excited about making meetings fantastic. Could you share with us perhaps one of your most surprising, fascinating, counterintuitive discoveries you’ve made while you’re putting together Your Best Meeting Ever?

Rebecca Hinds
I’ve long been fascinated by this phenomenon that’s called the Babble Hypothesis. Research shows that, when people talk more, talk more in a meeting, outside of a meeting as well, we perceive them to be a leader more than they are regardless of what they’re saying.

And I think, you know, so much of our meetings are performative, they’re skewed by status dynamics and power dynamics within the organization, and I think this Babble Hypothesis really speaks to the fact that we need to be much more intentional about how we show up to meetings because talking, hogging the airtime isn’t just annoying. It isn’t just frustrating. It actually skews our perception of the people in the room.

Pete Mockaitis
That is so fascinating and, boy, you’re bringing back memories of high school. I remember Robbie Klaver – shoutout to Robbie, wherever he is – told me, I was starting up a Model United Nations chapter at my high school.

And he said, “If you want to win awards, all you have to do is talk a lot.” It was like, “That’s it. It doesn’t have to be good, it doesn’t have to be insightful, it doesn’t have to be helpful. Just get in front of that microphone a lot, and that’s how you get awards.”

And it’s like, “Robbie, surely not.” But, no, it really was exactly what I witnessed. And, whatever that had implications for, I guess, people’s college applications and all that. But this high school Model UN principle rings true decades later in workplaces all over the world.

Rebecca Hinds
As does so many other things, so many aspects of high school, you know, the homogeneous people coming together and sticking together, birds of a feather and, you know, jargon, too. We’re often told to use fancy words.

I talk in the book about how that’s often counterproductive because using jargon, using big words, using technical words, as I often see in meetings, it alienates other people, and we actually trust them less because they’re not speaking our language and they’re less relatable.

And I think that the science behind all of this is incredibly fascinating, in part, because it’s incredibly human. And probably what happened in high school is still showing up in some way, shape, or form in our meetings as well.

Pete Mockaitis
Well, thinking about high school jargon, if I may attempt, as I’m 41 years old, jargon-maxing is not good, but talk-maxing is good from your perception as being a leader, and wise, and all those things, but it’s not great from the meeting experience or the outcomes.

Rebecca Hinds
And I think maxing is such an interesting word. We’re seeing it everywhere now, certainly with token-maxing and more is better. My colleague and mentor at Stanford, Bob Sutton, will call this addition sickness, right?

We are hardwired as humans to solve problems through addition. We have a problem, we throw more money at it, we throw more people at it, we throw more meetings at it, we throw more people in the meetings, more meeting minutes, and it’s very dangerous because, often, we don’t take time to subtract.

And there’s also a great research from my colleague, Leidy Klotz at University of Virginia that shows, “If you do prime people to subtract, it dislodges that addition sickness and they start to adopt a subtraction mindset.”

It’s often not that we dislike subtraction. It’s often, it doesn’t even occur to us as an option. It doesn’t even occur to us that, as we add another person to the meeting, what we should probably think about, “Is there someone we can remove where the meeting is no longer relevant to them or as relevant as it once was?”

Pete Mockaitis
Well, I’d love to get your take for this notion of the person who speaks more is perceived as the leader more. Are there any compelling studies or experiments or data points to highlight just how substantial an effect this is?

Rebecca Hinds
Interesting. So I think that the study that I anchor, and in the book, I believe it was for every 34 seconds of talk time on that order, people gained an extra point as a leader.

Now this was done in a context where there was no natural leader in the meeting in terms of having a bigger title than anyone else. But it skewed the perception in the room. And what’s also fascinating is, in this particular study, and there have been other studies where they didn’t find this effect, but in this study in particular, men automatically earned an extra point for being a leader, just for being male.

And I think that’s also a key part of the power dynamics is, you know, the gender, the diversity in the room, how quickly you speak as well. If you speak more quickly, in general, you’re perceived to be more competent.

And a lot of these cues, and we’re seeing it with AI as well right now, you know, depending on the way an AI tool is framing the output, how sycophantic it is, we also know that if people agree with us, we tend to view them as more intelligent and more capable. And all of these biases, you know, they are front and center in meetings and something that we need to pay very close attention to.

Pete Mockaitis
Okay. Well, these are tantalizing tidbits. But maybe we should zoom out and say, what’s your big idea, main message, key thesis of Your Best Meeting Ever?

Rebecca Hinds
So the big idea is meetings are a product. Meetings are the most important product in our entire organization. They’re where decisions get made, culture gets built, alignment gets set, and yet they’re also the least optimized. They’re the least optimized product in our entire organization.

And when we think about great products, great everyday products, well, they have certain product design principles. We should be applying those same product design principles to meetings. So the seven chapters of the book each walk through a product design principle applied to our meetings.

Pete Mockaitis
Okay. Well, so when you say product, I can read that word in multiple ways. Like, a product might be a physical item that I can purchase at a store. Or, in the tech world, products are not so much physical. They’re software things with features and experiences and a user interface. So how are you using the word product here?

Rebecca Hinds
In a few different ways and with a few different dimensions. Meetings are a communication tool. They’re a communication and coordination and collaboration mechanism within our organization. So they’re intangible in that way.

But what I’m getting at with the idea of product is intentionality. Just as we would think very carefully about how we build products and services for our customers, well, we need to approach meetings with the same discipline.

We would never launch a product to our customers without design, feedback, refinement, iteration. We do that with meetings every single day. We throw them on the calendar and they’re often our default reaction to any sort of uncertainty or ambiguity within the organization.

We don’t treat them like a product we would sell or give to our customers, which, in the context of meetings, those are the attendees in the room. They are not ourselves as organizers of the meeting.

Pete Mockaitis
Okay. So the product is something that needs to be thoughtfully, carefully considered and not just knee-jerk default, “Here’s meeting,” and to put some upfront effort into crafting how that’s going to be effective. Can you share with us some additional implications of the product mindset toward meetings?

Rebecca Hinds
Countless. You know, countless implications in terms of employee engagement. We know that meeting effectiveness is a strong predictor of employee engagement within the organization, even controlling for the factors that you would think to be important, your manager, your role within the organization.

Real business results, right? I think I often work with organizations where you’ll go in and you’ll start to hear people talk about meetings as if they’re not the real work, you know, “Oh, I have to get through all these meetings and then I can finally get to my work,” right?

If we design meetings correctly, they should be the real work, right? They should move work forward. So often, it’s not the case because they’re used performatively. They’re used as a box-checking exercise and not a mechanism, not a product that moves our work forward.

And so key business results, you know, moving work forward, better engagement, better cooperation, better relationships between the manager and the direct report, you know, meetings are the most common form of collaboration within our organizations.

As knowledge workers, as desk workers, we spend 90% of our time collaborating. There is nothing that we can do as leaders within organizations that is more impactful in boosting collaboration, improving that 90% of time than meetings because they’re so ubiquitous, they’re so common, and they’re so dysfunctional.

Pete Mockaitis
Okay, well said. So I like that notion of box-checking versus moving the work forward. And, boy, that’s a really good, bright line of distinction associated with, “Is the meeting real work or is it not?” You’re thinking about effectiveness on these dimensions over the relationship, as well as moving work forward.

Can you give us some more clarity on how I can assess, “Is this meeting amazing, terrible, okay, pretty good?” How do I get a gauge on how effective or ineffective a meeting is?

Rebecca Hinds

It’s such a great question, it’s a hard question. And the reason why it’s a hard question is we have what I call a meeting-suck reflex. Meaning we are conditioned to dislike meetings, and we are conditioned to believe that that’s how we should behave, right?

There are a few things that bond coworkers more than lamenting over that meeting that could have been a two-line email. And because of that, you can’t just go into an organization, your own organization, and ask people, “Are your meetings effective?” because you’re going to trigger that reflex and not the reality. And that’s why we need to be very careful about meeting measurement.

One of my top recommendations is, if you want to gut check into how effective your meetings are, the ones you run, after about 10% of those meetings, ask attendees, “On a scale of zero to five, was this meeting worth the time you invested?”

My colleague Elise Keith calls this ROTI, return on time investment, and it does a couple things. One, it’s usually, in almost all cases, anonymous, so it avoids that temptation to either inflate or deflate the ratings.

Two, unlike meetings, which are socially loaded, everyone has some intuitive sense of the value of their time, and they know more or less whether this has been a good investment of the time. So you avoid that sort of meeting-suck reflex and it’s simple, you know, it’s not after every meeting. Survey overload is real with an organization.

Finally, it’s coming from the attendees and not you as the organizer. My colleague, Steven Rogelberg has done fantastic research to show there are two people that tend to leave the meeting most satisfied, two types of people. One is the organizer and, two, as we’ve talked about, is the person who has spoken the most in the meeting.

And so we can’t ask those two people whether the meeting has been effective. Their ratings will be inflated. We need to ask the users, the attendees of the meeting, whether this meeting has been worth the time.

Often you see split ratings. Often you see a cohort rating the meetings five and four versus zero and one. And that can also be very helpful information to understand, “Okay, this meeting was worthwhile for some cohort of folks, but not for the entire attendee population. Well, now we can redesign the meeting and design it to be much more effective.”

Pete Mockaitis

Worthwhile. And I hear what you’re saying that it’s tricky because meetings have different objectives and that’s a handy gauge. I imagine every potential measure of meaning effectiveness could have some limitations.

This one is like, “Well, hey, you didn’t think it was effective, but, by golly, you needed to know that. And now you do. And it was essential that that occurred,” and emails get ignored. So I suppose there’s a big gray zone, too.

Rebecca Hinds
There is, and that’s why the agenda is also very important. I recommend framing every agenda item as a combination of a verb and a noun. So it’s not just budget discussion, it’s “align” or “decide” on the Q2 budget.

You’re being very clear about, “What is the verb we need to accomplish?” because then you can assess or you can now use AI to assess, “Have we done the thing?” because that is now a measure of effectiveness within the meeting. If you’re unclear on what you’re trying to achieve, well, it’s impossible to determine what it even means to be effective in terms of the meeting.

Pete Mockaitis
And I’m curious, if your verb is “inform,” what do we think? Some schools of thought would say, “Well, if all you’re doing is informing and it’s not a collaborative back and forth, then you should just do an email or some alternative medium.” What’s your take on that?

Rebecca Hinds

Exactly that. Information exchange is not a good purpose for a meeting. In the book, I talk about the 4D CEO rule, a two-part test to determine whether that meeting deserves to exist. First test, a meeting should only happen if the purpose is to debate, discuss, decide, or develop yourself or your team.

Information exchange, status updates, boss briefings, often these meetings are designed for the organizer, often for the powerful person in the room who either needs to consume information or disseminate information. In those settings, it is far more effective to communicate asynchronously through email, through Slack, and let attendees self-serve the information.

Pete Mockaitis

I think that’s very handy and sensible and that feels true. I’m wondering about this tricky challenge of, when folks have overwhelming inboxes and too much just flood of information coming at them, but it is essential that something gets to them, I think that’s one of the top reasons folks are tempted to do meetings, like these town hall meetings.

It’s like, “No, everyone really needs to know this. So we’re going to, by golly, put it on the calendar to make sure it gets there.” I’m curious, what’s your thought on making sure, in a world where that is not communicated via meeting, how do we make sure that the memo is sent and received?

Rebecca Hinds

It’s a great point and, you know, there’s the ideal case in organizations, there’s always the ideal case, and then there’s the reality. And the reality in many organizations is workers are overwhelmed. They’re overwhelmed with information and, often, the meeting feels like the most reliable way to get people’s attention to share the information.

There are certainly cases where that makes sense and that’s the unfortunate reality of our organizations, but in the best cases, we’re designing a communication system so that employees get the information they need and are able to distinguish between what’s important and what’s urgent.

And that requires being very clear in terms of, “What is the purpose of a meeting? What is the purpose of an email?” Ideally, you’re designing the asynchronous channels to be consumable and digestible, right? It’s not a memo that’s 20 pages that employees are needing to sift through.

You make it engaging. You make the asynchronous update a video. You make it a video where the CEO or executive team is in a location that has some personal relevance and it’s engaging to people.

Pete Mockaitis

There’s TikTok dancing.

Rebecca Hinds
There’s TikTok dancing, there’s family. One of my favorite all-time sales leaders would record videos after a run, dripping in sweat.

And that’s so important right now, that connection to leaders, not feeling like they’re on a different pedestal than the rest of the organization, which is often what happens in town halls or all hands or all staff meetings is you get this very rosy picture of reality in a way that does very little to strengthen the relationships between individual contributors and the people at the top of the organizational totem pole.

And even in the context of town halls, it’s usually significantly more effective to do those in smaller group settings. We know that as soon as a meeting or any team size gets above seven, eight, nine, 10 people, people start to check out.

Social loafing kicks in, people feel less supported. And so even if you’re doing far fewer town halls, but you’re doing them very intentionally in a way that can encourage back-and-forth dialogue between the individual contributors and the managers, well, that’s going to do so much more to boost the relationship.

Pete Mockaitis
When you say designing a communication system, that sounds very sophisticated, could you give us some examples that maybe we’re not thinking of, like, “Sure, I could say an email, maybe a loom video”? Are there other elements of a communication system that are super effective but underutilized in your view?

Rebecca Hinds

So there’s a really important delineation between synchronous ways of communication and asynchronous ways of communication. And a common misconception is inherently technologies are either asynchronous or synchronous.

We often think of Slack as an asynchronous communication channel, right, because it doesn’t require real-time communication – similar, email. But the reality is any technology can either be used asynchronously or synchronously, right?

We can, and we often do, operate in a world where Slack is treated like a synchronous communication. We get the ping and we’re immediately either drawn to it or respond to it. There is an implicit expectation that you are always available and responding. It’s far more important for organizations to think not so much about the technologies but around the cultures and practices and norms associated with asynchronous communication.

In order for asynchronous communication to work, in order for you to be able to transmit, convey information through asynchronous channels, there needs to be strong, strong documentation culture, right? There needs to be single sources of truth for this information, for the meeting transcripts, for the memos. There needs to be very strong written communication cultures.

And this is something that remote-first organizations tend to do really well. They even train their employees on, “How do you communicate in an effective way asynchronous?” That often requires significantly more context than in face-to-face interactions when you can ask the follow-up question.

I worked with an organization a couple years ago where they had a norm, a company-wide norm, that employees were evaluated on around “No lazy asks.” If you’re going to ask someone for something, it can’t be a lazy ask. You can’t remove context, fail to include context, include the deadline, include the why, include the what, right?

All of these things ensure that we can communicate more efficiently asynchronous, because if there’s ambiguity, if there’s uncertainty, well, people are going to schedule that meeting to get the information they need to move the work forward.

Pete Mockaitis

You know, I can’t help but think of the episode of “The Office” where the new boss asked Jim Halpert for a rundown, and he’s like, “Okay,” and so he spends the whole day worrying, “What does that even mean? What is a rundown?”

Rebecca Hinds

Yeah. And that’s the jargon, those are the acronyms, right? And we’re alienating people, in addition to adding ambiguity within the organization. And we see this all the time, you know, with the office jargon, the synergies, the circle backs.

Now with AI, people are, you know, it’s AI everything, “What are you talking about? And do you even need to include AI in what you’re saying?” It’s very important. I think written communication has never been more important, as well as verbal communication, right now.

Pete Mockaitis

And are there certain key things you’re looking at to ensure you have clarity and comprehensiveness or completion when you’re making an ask or trying to communicate a thing?

Rebecca Hinds

Deadlines are very important and, especially, I work with lot of global organizations being clear on what time zone. It sounds simple, but end of day Friday means something completely different in Japan versus San Francisco, as well as depending on your culture.

The why is very important, and we continue to see the why is significantly impactful in helping employees feel bought in to the ask. I see this especially, too, with policy, any sort of policy within an organization. We saw it with remote work, with remote and hybrid policies. We’re seeing it with AI right now.

One of the biggest predictors of whether people get on board with a policy is whether they understand the rationale behind it, even more so than whether they agree with it. And that helps them understand, “Is this worth my time? Is it worth my time to invest in this ask?”

If they can understand the why, the rationale behind it, and it’s something bigger than themselves, that’s going to motivate them to complete it, complete it well, and complete it on time.

Pete Mockaitis

And you’ve got a couple interesting concepts in your book I’d love to hear about. What is your meeting doomsday?

Rebecca Hinds

Meeting doomsday is my favorite meeting strategy to improve our meeting culture. It’s a 48-hour calendar cleanse. Employees delete their recurring meetings for 48 hours and then they re-add meetings back to their calendar in a way they think is going to be most effective.

So many meetings never make it back on the calendar. They’ve outlived their purpose. Perhaps they never had a purpose. For the meetings that have some value, they are redesigned. So thinking about the length, the cadence, the attendees, the agenda items, every meeting on our calendar can be redesigned to be most effective.

And we see significant benefit of this doomsday activity as opposed to a traditional meeting audit. We talked about addition sickness at the beginning and strategic subtraction. Well, what the doomsday does is it jolts you out of the status quo and makes subtraction the default.

When people are doing a meeting audit, they tend to justify the meetings because the meetings are still on their calendar. Whereas, the doomsday, it forces you out of the status quo and it gives employees social permission to delete the meetings in a way that removes that social guilt we all feel when we think about canceling meetings or think about not showing up to meetings.

Meetings are so personal that we often think people will take it personally, and they often do, if we cancel or don’t show up to the meeting. And so I recommend every organization do a meeting doomsday at least once a year. And, again, not just to save time, and we do see big time savings, but to reset our assumptions about what actually deserves to be a meeting.

Pete Mockaitis

So, okay, can you walk us through step-by-step in practice, if we’re saying, “Ooh, we like meeting doomsday. We’re going to do it”? How do I execute that step-by-step?

Rebecca Hinds

Lots of planning. It’s a radical effort. It requires lots of planning. It requires understanding, “Are you going to do it at an organizational level?” That’s ideal. Or, “Are you going to do it on a team level, department level?” I’ve done both. I’ve done as small as a nine-person team.

And then it’s about preparation, making sure there’s leadership buy in. The leadership is communicating the why behind this. There are clear instructions in terms of, “When are we going to do this? We’re not going to do this at the busiest time of the year. We’re going to do it in a lull period.”

How are people going to assess whether the meetings should be brought back? What dimensions are they going to use? Increasingly, I’m working with organizations to use AI to identify, flag those dysfunctional meetings. That becomes very exciting.

And then how are we going to celebrate? How are we going to celebrate along the way the success stories? This needs to be something that is fun. There’s a reason I call it meeting doomsday, right? There needs to be a rallying movement around it.

Meetings need to be the enemy. It’s not the person who scheduled the bad meeting. And we need to create a sense of energy around it. Get people bought in. And you start to see this becomes a big culture-building movement when done right.

And people become very excited about not only doing the doomsday, but also sticking to it. And meetings never are set in stone in terms of being effective. This is something we need ongoing maintenance to do. And, again, doing it at a consistent cadence every year is a way we continue to instill this practice of meeting hygiene.

Pete Mockaitis

All right. So then, when they are executing this, “It’s on this day,” I guess that’s the doomsday, “On this day, all recurring meetings, organization wide are deleted.” And then the hope, and with your prep and your communication and your pre-work, is that the new meetings that are established will be good and better ones, as opposed to just, “Oh, hey, I need that meeting. Let’s put it back on the calendar.”

Rebecca Hinds
Exactly. And there’s a big difference. I’ve studied two types of organizations. One, they’ll do this doomsday top-down. They’ll write a script, the IT team will come in and do a massive wipe of the calendar. I’ve seen that. You know, Dropbox did that. Shopify did that. Slack did that.

The meeting doomsday is explicitly designed to put that determination in the hands of employees because we know that, when employees do something themselves, they feel significantly more valuable. It feels significantly more valuable to them, and they’re more likely to stick to it.

Sometimes this is called the IKEA effect, right? When we build something ourselves, whether it’s an IKEA desk, a newly built idea, a newly built calendar, we’re much more likely to stick to it and value it even if it’s a little bit wobbly.

Pete Mockaitis
And what is your rule of halves?

Rebecca Hinds
The rule of halves, inspired by two folks I’ve talked about, Bob Sutton and Leidy Klotz, it’s essentially look at the four dimensions of your meeting – the length, the cadence, the attendees, and the agenda items – and decide one, two, three, or four dimensions you can cut in half.

And often this is a valuable practice as you’re doing the doomsday, but you can take any dysfunctional meeting or any meeting that you know isn’t fully optimized, and pick one dimension, cut it in half, take that 30 minute meeting, try to run it for just 15 minutes, take that six person meeting, “What if it’s three people?”

And what you often find is you didn’t need all that time, you didn’t need those attendees. You might cut too deep, but it’s also often in those moments where you go one step too far, do you realize what was actually essential and what was dead weight.

And so I think that’s, you know, whether you’re doing it one, two, three or four dimensions, the rule of halves can be another effective way to jolt us out of the status quo. I think we often, in organizations, suffer from what’s called Parkinson’s Law, too, meaning work expands to fill the time allotted.

If we give a meeting 30 minutes, if we give a meeting 60 minutes, which is what our calendar tells us should be a meeting, well, it’s probably going to take that 30 minutes, 60 minutes because of this Parkinson’s Law. Whereas, if we cut it to 15 minutes or 30 minutes, it’s more diligent in terms of encouraging us to stick to that time. We’re more diligent because we only have that time available.

Pete Mockaitis
And what are those four dimensions again?

Rebecca Hinds
The length, so the duration of the meeting; the cadence, so thinking about weekly versus monthly, quarterly meetings; the attendees, only inviting stakeholders, not spectators or meeting tourists; and the agenda items. So thinking about, very carefully, “What are the agenda items we want to include on the agenda?”

We also know that agendas suffer from what’s called the law of triviality, meaning, we will disproportionately spend more time on the agenda items that are the least important, the most trivial. And so it’s very dangerous to add agenda items that are trivial, much less important than the higher stakes one, in part because they feel safer.

They feel safer for people to weigh in on. In general, most people want to hear their voice in the meeting, as we’ve talked about, and everyone feels more safe to weigh in on the trivial topics as opposed to the higher stakes one.

Pete Mockaitis
Yeah, I’m thinking about this a lot when it comes to, like, color choices or names of something. And it’s kind of, like, “You know, if people like it, they’re going to buy it no matter what colors on the website or what we call it within reason.” And so, yeah, that is a great observation.

Rebecca Hinds
Naming, font sizes, what do we do over the weekend, what are we eating at the offsite, you know, all of these things. And we see it all the time in meetings, and it’s a reflection of the law of triviality. The other bias is the primacy effect, meaning we will also spend disproportionately more time on the first agenda item. And so agenda design is very, very important as well.

Pete Mockaitis
Okay. And you also talk about injecting delight into meetings. What are your favorite approaches for this?

Rebecca Hinds
Yes, delight. Now, delight is interesting because delight is a combination of two things. It’s a combination of joy and it’s a combination of surprise. So, delight needs to have an element of surprise. Employees, attendees can’t be expecting it for it to work.

And so, this is something that I recommend it be 10 seconds, a minute in the meeting, an unexpected shoutout for an employee that has done something well. You’re bringing some, you know, food item. Food is a great engagement booster in the meeting that has some personal connection.

Something that is going to leave employees remembering the meeting and wanting to show up the next time. It sounds trivial, but so much of our meeting dysfunction is driven by the fact that employees dread meetings and they’re largely rinse and repeat.

Delight ensures that there’s that moment of surprise that’s positive and joyful that employees will keep coming back to and keep wanting more of.

Pete Mockaitis
Okay. Well, Rebecca, tell me, anything else you want to make sure to mention before we hear about your favorite things?

Rebecca Hinds
No, I think that the common thread through all of this is intentionality and intentional design and how do we ensure that we are treating meetings as that important product.

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

Rebecca Hinds
I’ve always loved the quote, “The harder you work, the luckier you get.” And I really believe that.

Pete Mockaitis
All right. And could you share a favorite study or experiment or bit of research?

Rebecca Hinds
So we’ve done some research over the past few years looking at the mental models through which employees approach AI.

And what we’re starting to see, we’ve seen it for years, we’re still seeing, is depending on whether people are approaching AI from the mental model of a tool versus teammate, they interact with the technology differently and they’re significantly more likely to be productive when they approach AI with the mental model of the teammate because they’re not just asking, “What can the technology do for me in a really transactional way?”

They’re asking, “What can I do with the technology?” They’re also recognizing that AI is not perfect. They’re not giving up after the first prompt. They’re pushing the technology to think and act deeper. And I think that’s at the core of a lot of the failures of AI transformation right now, is not recognizing how important the psychology is and how important that relationship between humans and AI is.

Pete Mockaitis
Okay. And a favorite book?

Rebecca Hinds
So I’m a massive fan of both Bob Sutton and Adam Grant’s books, so Give and Take is a key one that has influenced so much of my life, as well as Bob Sutton’s book, Scaling Up Excellence, The Friction Project.

I think “The Friction Project,” in particular, is so relevant right now in terms of, “How do we ensure that we are injecting good friction into our organization through the use of AI,” for example, “and removing the bad friction from our organization’s dysfunctional meaning?” are one great example of negative friction.

Pete Mockaitis
And a favorite tool?

Rebecca Hinds

So I work at Glean. Glean is my new favorite tool. I use it for all things AI. It’s my first pane of glass into my work in the morning, and it’s a highly intelligent teammate that helps me do my work.

Pete Mockaitis
And is there a key nugget you share that seems to really connect and resonate with audiences, they quote it back to you often?

Rebecca Hinds

You know, I think I work with a lot of organizations on change management, and I think my mantra is always “Change doesn’t fail because of the technology, it fails because of the humans.” And as we think about AI, in particular, but also meetings and everything in between, making sure that we’re designing for the humans involved is super important.

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

Rebecca Hinds
I’m on LinkedIn. My book, Your Best Meeting Ever is at all your favorite bookstores. And my website is RebeccaHinds.com.

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

Rebecca Hinds
Do that meeting doomsday. I think it’s the single most effective way to jolt you out of the status quo and get a small team and do it together.

Pete Mockaitis
All right. Rebecca, thank you.

Rebecca Hinds
Thanks so much, Pete.

1155: How to Escape the Procrastination Trap and Achieve Your Goals with Jon Acuff

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Jon Acuff talks about the hidden fears, assumptions, and overwhelm that are keeping you stuck in the procrastination trap.

You’ll Learn

  1. 
What it really means to have “more executive presence”
  2. How to “make tomorrow easy today” with simple preparation
  3. How to go from stuck to unstuck in 4 steps

About Jon

Jon Acuff is a New York Times bestselling author of 11 books. His titles, including Soundtracks, Finish and All It Takes Is A Goal, have sold more than one million copies. Named one of Inc.’s Top 100 Leadership Speakers, he’s delivered keynotes to companies such as Microsoft, Walmart, and Comedy Central. Host of the popular podcast All It Takes Is a Goal, Jon has inspired hundreds of thousands of people to overcome overthinking and finish what matters most. Jon lives outside of Nashville with his wife and two daughters.

Resources Mentioned

Thank you, Sponsors!

Pete Mockaitis
Jon, welcome back!

Jon Acuff
It’s good to see you again, Pete.

Pete Mockaitis
Well, I’m excited to talk about procrastination. You got a whole book about this. Tell us, what do you know or have discovered about procrastination that’s new and fresh and surprising and interesting that we should know?

Jon Acuff
Well, I think the really interesting thing to me is that it’s not necessarily a problem. People use it as a solution. It’s just not a good solution. Meaning, if they don’t want to tell their mom they’re not coming home for Thanksgiving, procrastination goes, “No problem. We don’t have to do that for, like, seven months. We can wait until the last second.”

Or, I’m afraid of getting negative reviews of my book. Procrastination says, “No problem. I’ll solve that. You’ll never get a negative review. I mean, you won’t get to write a book, but you’ll never get that.” So it’s not a laziness problem, which is why so many of the willpower discipline things we do don’t ultimately work.

It’s really more of a figuring out how to give yourself permission to do those things that you really want to do or really need to do.

Pete Mockaitis
Permission to do the things you really want to do or need to do. I’m also curious about the things we don’t want to do. I guess we need to do them, but we don’t want to do them. I think that’s where it gets me. It’s not so much…

Jon Acuff
Like what? What do you procrastinate on?

Pete Mockaitis
Oh, boy. Well, I think there’s tax things. It’s a joke, every year, my accountant is like, “Yeah, we’re deferring, right? Yeah. Didn’t need to ask.”

Jon Acuff
Yeah, that’s funny.

Pete Mockaitis
So, yeah.  there’s plenty of things in terms of, “Oh, it would be good to have…” I think that’s for me, like, “It’d be nice to have the result of that thing, but, ugh, doing the work seems exhausting and overwhelming, and I just don’t want to right now.”

Jon Acuff

Yeah, I think that’s 100% fair. I love that you admitted having the result would be great. I think a lot of people won’t admit, “You know, I’d really just like to have done the thing, but I don’t want to do all this.” For me, entitlement is when I go, “I wish my LinkedIn profile, and I had a better LinkedIn presence.” And you’re like, “Yeah, you haven’t used LinkedIn for, like, five years.” Like, “Yeah, it’s really suffering somehow with my complete lack of effort.”

Pete Mockaitis
“Yeah, go figure.”

Jon Acuff

And to me, that’s entitlement is when I go, “I want blank, but I haven’t done any of the work.” I just think, as far as doing stuff you need to do, but don’t want to do, it’s about selling yourself into doing it. Like, in the book, one of the ideas is, like, you’re the greatest, Pete, salesman in the world because, before every decision you’ve ever made, whether it was good or bad, first, you sold yourself into it.

So I think a lot of goals comes down to your ability to sell yourself into doing something you want to do or need to do, but you don’t feel like doing.

Pete Mockaitis
Well, we’re going to need to talk about that at length, but I want to zoom out a smidge and get the big picture. What’s your overall message about procrastination and the latest insights from your in-depth research here?

Jon Acuff
Yeah, so the overall is there’s four permissions you need, and if you do these permissions in this order, it’s almost impossible to not be successful. And I want to say very clearly, I couldn’t have written this book as book two.

If, at 36, Jon Acuff wrote a book called Procrastination Proof: Never Gets Stuck, I’m an arrogant guesser. I’m going, “Maybe, I don’t know. I’ve written one book before. Clearly, I’m great at not procrastinating.”

But by book 11 at 50, I’m like, “Yeah, for someone as distracted as I am, for somebody who has such a hard time focusing to have written 11 books, I figured out how to kind of do some difficult things that maybe you shouldn’t put off.”

So the ultimate idea behind the book is permission, and the four types of permission are permission to dream, permission to plan, do, and review. So those four actions – dream, plan, do, review. And if you do those in that order consistently, everything gets really easy and often really fun.

Pete Mockaitis
Okay. Well, yeah, I want to hear about these permissions. And can you tell us a bit about the research process by which you landed there? So you did some substantial surveying, right? And talking to folks and identifying some real themes and patterns that appeared at high frequency.

Jon Acuff
Well, the benefit to my job, Pete, is that the way I write a book is I find a problem in my own life and I figure out if there’s a solution for it, and I spent a few years doing that. And then I ask, “Do other people have it?”

And if a lot of other people have it, then I go research to figure out, “Okay, how does it apply to other people, not just me?” It’s not a helpful book if it’s, essentially, how Jon Acuff beat Jon Acuff’s procrastination. That’s not a good book. That’s a manual for me.

So what happened with this book, I worked with this PhD named Mike Peasley, he’s a professor at MTSU. And so it started with, we did a study on, “How many people think they’re living up to their full potential?” meaning there’s something they really want, but they’re not doing it.

And we asked 3000 people and 96% of them said they were not living up to their full potential. So then I go, “Okay, there’s this huge audience.” And then the research kind of goes from there into testing it in a community online, testing it with real live audiences. Like, it’s one idea.

It’s one thing to have an idea in this office, it’s another thing to take it to a Fortune 500 company and go, “Hey, here’s how this permission works.” And you can tell instantly, “Oh, no, that’s not their world at all,” or, “Oh, no, the permission to dream is not helping the cattle ranchers,” or, “Permission to plan is not helping the engineers.”

So a lot of what I do is then go test it on the road and then, eventually, it ends up in a book. So it’s a longer process than my other books used to be, but I think it turns out a better product.

Pete Mockaitis
Okay. So then could you speak to us about these permissions?

Jon Acuff
They’re really, really simple. I mean, the first one, permission to dream, you have to have a reason to change. No one ever changes just because. I’ve helped a million people with their goals. I still haven’t met somebody that said, “I woke up today and decided to have grit. I just woke up today and decided to sacrifice.”

No one willingly leaves their comfort zone, and they shouldn’t. It’s comfortable. The only reason people leave their comfort zones is there’s something outside it worth being uncomfortable for. And it’s usually one of two things – desire or disappointment.

Desire, meaning they bumped into something they really want. Disappointment, they woke up at 42 and their career wasn’t where they wanted it to be. They lost their job to AI and they don’t have much of a choice. The disappointment finally got loud enough to go, “I got to change some stuff or this isn’t going to work.”

So that’s the dream. You got to have a sense of why you want to do something and what you want to do before you even move it into planning. And planning is you answer the question, “How will I do it?” Doing is, “Are you doing it?” And review is, “Did it work? Are we headed in the direction we want to go?”

Pete Mockaitis
Okay. Well, now let’s talk about the word permission in terms of it’s just me. I don’t have to appeal to some authority as the principal or a government official for the permission, the access to do any of these things. So can you unpack this word here?

Jon Acuff
Yeah, so I’ll give you an example. Somebody the other day told me they had a weight loss goal, but if they lost weight, they’d be breaking family norms. Because in their family, they grew up in their family of origin, food was comfort. Food was security. Food was family. Food was tradition.

Big Southern family, like you had big Southern plates of food, and to be health conscious felt like divorcing the family you were from. And so he needed permission to go, “No, I have permission to love my parents where they are, but I don’t have to repeat my childhood. I don’t have to. I get to lose weight. I have permission to have a healthy lifestyle. I have permission to care about what I eat and how I look and how I exercise.”

So a lot of times, even if you’re an individual, that doesn’t mean you’re free of kind of hangups that are getting in the way. So a lot of times it is that sense of like, “What are some of the broken soundtracks I believe?”

Take money for instance. Money is the last taboo we have in our country. Like, I know men that’ll tell me the worst things they’re dealing with. But if you go, “Hey, what’s the financial number you’re thinking about retiring with?” “Whoa, whoa, whoa, no, we don’t talk about that. That’s super sensitive.”

And some of them have hangups about money because they grew up in a family where money was considered evil or must be nice or, “They’re rich, we’re not.” And if you get to a certain level of success, you therefore, become greedy.

So they need a permission to go, “No, I have permission to do. I have permission to go as hard as I want at this business on this job.” So there’s so many different areas where the lack of permission holds you back.

Pete Mockaitis
I hear that. And talking about money, I guess, I’m thinking in terms of you hear so much, at least I do, in terms of scams, and scandals, and swindles, and crypto rug pulls, and extractive private equity yuckiness that feels gross to me, such that I think I’m vibing with what you’re saying is I do feel a little bit of resistance internally in terms of really going after some money-making opportunities, because it’s like, “You know what? I’m doing fine. And I don’t want to be like those mean private equity dudes. Hmm.”

Jon Acuff
Yeah, “I don’t want to step on next. The only way to get ahead is you have to take advantage of people.” Or, the one that I saw somebody asked the other day, it was like, “Why is it binary where I can either have a really great business or I can be a great dad? Why does our culture present it as like…?”

Because I’ve had friends, and I’ll go, “I think you should really start that business.” They go, “Ooh, I don’t want to, like, forget my kids names. I’ll never see them.” As if there’s only two options – not pursue your dream or get a divorce and not attend your daughter’s first communion.

And it’s like, “Whoa, there’s a lot of options. It’s just you’ve made it very binary.”

Pete Mockaitis
Okay. So how do we grant ourselves or acquire this permission if we’re feeling some of this conflictedness?

Jon Acuff

Well, part of it is identifying it. Some of it’s just labeling it. Like, there’s a really great exercise that we talk about a lot where it’s like you write down a goal and then you write down your reaction to the goal. So you write down, “Okay, I want to retire with $5 million.”

And you write down like, “Oh, that would be impossible,” or, “Oh, I don’t have enough time for that,” or, “Oh, I’ve already made too many bad decisions,” or, “Oh, somebody who has that amount of money is always like this.”

And you start to identify, “Oh, these things are going to hold me back.” Most of the things we wrestle with in life are mindset issues. They’re not physical problems. Where we live, like at least in the Western world, I never have to fear a tiger.

I never leave my house and I’m like, “Just, hey, be careful. There’s a lot of physical predators out there.” It’s only things like procrastination, imposter syndrome, inner critic, overthinking, you know, perfectionism.

And so a lot of times, it’s identifying those things so that you can actually start to work with them. That’s a great first step to go, “Oh, this is holding me back. I’m overreacting in this situation because I have something that’s holding me back. Let me identify that so I can actually deal with it.”

Pete Mockaitis

Okay. Well, let’s talk about that weight and big Southern cooking plates situation. Let’s say someone has identified that, “Okay, I would like to be slimmer, but, ooh, that feels hard, that feels risky because of these beliefs, these associations, this history,” what do I do with that?

Jon Acuff

Well, I mean, I guess it would depend on, like, if it’s an event you’re talking about, meaning, “I’m trying to be in shape, and I’m going home for Thanksgiving,” or, “I’m going home for Christmas, and I know that there’s going to be a lot of food, and a lot of food discussion.” Like, having a game plan and going, “Okay, what do I want to do with that?”

My favorite definition of discipline, which I put in the book, is “Make tomorrow easy today.” Make tomorrow easy today. What can I do today that makes tomorrow easy? That’s constantly how I’m thinking, “What can night me do to hook up morning me?” “What can Monday me do to hook up Friday me?”

So in a situation like that, if somebody said to me, “Okay, I’m trying to break these family norms,” I’d go, “Okay. Well, is it, like, related to a specific thing? And if it was, then we’d come up with a plan for that thing.”

If it was related to the decisions you were making of like, “Oh, man, every time I feel stressed, I do this and I know it’s a short-term solution.” Well, let’s change that. You know, like, let’s change the rhythm of that. Let’s find a different way to deal with stress than that. Like, if you know that’s where you tend to go, you have permission to make different choices.

And then maybe it’d be, let’s get some community. So now you have a communal sense of it. Like, for me, I worked out alone a long time, and I joined a community called F3 where it’s a free men’s workout in the morning.

Pete Mockaitis

Oh, yeah, that’s fun.

Jon Acuff

And I love it. And that changed my approach to working out. Like, that gave me new norms. Now I’m with a bunch of other dudes at 5:30 in the morning. That’s a new norm for me. What’s fun is if you do this long enough, not doing it becomes weird.

Meaning, when you first work out, when you first write, when you first build a business, whatever, it’s hard and it’s uncomfortable. But then you get into such a rhythm that, if you miss a week or two, you’re like, “Oh, this isn’t right.” There’s this really sweet spot where the good habits, when you miss them become weird and it flip flops.

Pete Mockaitis

Yeah, I totally feel that, experientially. And I think about it almost, like, a dirt road when you got the groove established. It’s easier to be in the groove than out of the groove. Like, today, I had an odd early meeting. And I knew, and actually set multiple alarms because it deviated from my regular schedule so often.

And so I dropped the kids off, and I knew I got to get right to the office for my early meeting. And, mindlessly, I’m driving to the church for, because that’s usually what I do is I hang out in the chapel for some prayer, post-kid drop off.

And I was like, “Wait, no, no, not today. That’s not…We do that almost every day, but today, I have an early meeting. So I got to get to the office right away.” And so it’s so funny how the autopilot move is just, “Oh, I turn here toward the church.”

And I think that is the case with, well, almost everything in terms of, “Oh, I’m working out in the morning, so that’s what I do.” And then it’s like, “Oh, no, no, today is a different day. We don’t do that.” And so it really tracks that, like, the first one or two or three times it’s like a force of will, effortful, intense. And then it’s easier and easier.

And I guess different people put different numbers on it. But, Jon, if I may, when do you think the groove has more momentum than the new groove?

Jon Acuff

Yeah, like, I love if you Google “How long does it take to start a new habit?” there were nine million answers, and it’s like 30 days, 90 days. I mean, for me, I think, at least, it takes a season, meaning like it takes a fall, it takes a summer.

Like, it takes a, you know, for me, three to four months chunk of time of like now F3 for me, like getting up at 4:55 is crazy. For, like, the first eight weeks, I was like, “This is the dumbest thing ever.” Now, I’m like, “Oh, yeah, I’m looking forward to it. Now I’m into it.” So, for me, it usually takes at least a season.

Pete Mockaitis

Okay. Got you.

Jon Acuff

How does it take you? I mean, what’s your number?

Pete Mockaitis

Yeah, you know, well, it’s not binary, you know? It’s hard for me to, like, establish the cutoff because I’d say the second day is easier than the first, and third’s easier than the second, and the fourth, and so on and so forth. So I don’t know where I would draw the line. But, I don’t know, maybe 40-ish.

Jon Acuff

Yeah, that feels good. I’ll hold you to that, 40-ish.

Pete Mockaitis

At this point, it feels harder to not do the thing that I started doing 40 days ago.

Jon Acuff

Yeah, yeah, I can see that.

Pete Mockaitis

Okay, so permission to dream. And let’s talk about planning.

Jon Acuff

Yeah, so where people get stuck there is dreaming runs on optimism, planning runs on realism. So dreaming, “Anything is possible. This is going to be amazing. It’s going to be huge.” And then you have to transition kind of into the real world, into reality.

And one of the simplest tools you can do is really just be honest about your calendar. I meet people all the time that’ll go, “I have these 30 different goals. I have 10 different dreams.” And I’d go, “Well, let’s put a number associated with them.”

And then they put an hour or timeframe with them, and I’ll go, “Well, how many hours of free time do you have in your week?” And they go, “Free time? What are talking about? I’m very busy. I’m slammed right now.”

And you go, “Well, you have a 12-hour goal chunk and a week that has zero hours, like that’s why you’re going to keep procrastinating. It’s not because you’re just delaying. It’s because you don’t have the time to pay that bill. Let’s figure that out.”

So that’s a big part of it for people with planning is, “Okay, how do you actually pay the price of the thing you want?” And maybe you don’t want the thing. Like, I would argue, if you won’t spend half an hour with Claude or ChatGPT having it interview you about the thing, you probably don’t really want the thing.

And maybe you’ve just carried that goal along for a long time of, “I think I need to write a book,” “Someday I want to start a business,” “I’ve always wanted to run a marathon,” but if you won’t even spend, like, half an hour kind of just investigating what would that take, maybe it’s not a goal you care about. And that’s fine. Like, I love getting rid of fake goals.

Pete Mockaitis

Tell us about this half-hour AI interview protocol. How does this go down?

Jon Acuff

Yeah, so, for me, if I have something I want to do that’s new, that I don’t know how to do, I often will say, “Okay, one, I love the whole, like, tell me how to write the best prompt to get the thing I want.” So then I’m not even really writing the prompt.

But if I might say, okay, like, an example for me is I’m doing something called Stage & Page, where it’s a one-day intensive for speakers and a one-day intensive for writers. So I might say, “Hey, you know, I’ve been doing this for 18 years. I want to be able to help people that have just started. Interview me about my first year of public speaking because I know these things, but it’s been a while.”

“You’re the best journalist in the world. You write for a magazine called Stage & Page, and I want you to ask me 10 really insightful questions about my early experience as a speaker.” And then it interviews me, and then it’ll summarize that, it’ll create content out of that. But it’s a really easy way versus just a blank piece of paper.

So if I was going to run a marathon, start a business, you know, figure out how to lose 10 pounds, I would say, “Interview me,” so that I really have a sense of why I want to do it, what I want to do, what are my limitations, “Oh, you’ve got a couple injuries. Let’s figure that out.” Like, the interview format is so much easier than just trying to willpower your way into a blank piece of paper.

Pete Mockaitis

I hear you. So you are engaging in that conversation to get the beginnings of some kind of plan going. Is it fair to say, you don’t expect the AI to spit out the perfect plan, but rather it gets you going so that the planning has begun and the ideas are multiplying?

Jon Acuff

Well, and, no, the problem with AI, the fatal flaws, I still have to do it. Like, I keep working with people and they’ll like give me like, there’s like this AI document arms race that happens in small businesses where I go, “Hey, I think we should try blank.”

And then somebody comes back with a 30-page document that they haven’t even read. Like, AI just created it and now we’re going back and forth on documents. So, yeah, I don’t expect AI to come up with the plan because it’s never really been a lack of information.

Like, if you don’t do the thing, you have a great library in your town. Every town has a great library. So I still have to do it, but it gets me from stuck. The book is designed deliberately to move people through it quickly, meaning it’s 71 short chapters.

And I did that deliberately, and they’re short and they’re punchy and they’re all connected. I did it deliberately because nobody wants to read a thousand-page book about procrastination. Like, if your procrastination book has 90 pages of notes, you’re not a procrastinator. You’re a monster.

Like, that’s Jane Goodall writing about monkeys. I’m a monkey writing for other monkeys. So I just want the person to get started. And if they go, “I have to figure out the perfect plan for this goal,” they’re never going to do it.

But if they say, “Can I be interviewed for a half an hour?” even a podcast, they could take you and go, “I really like Pete’s show, and here’s an episode. I like his style of asking questions. Interview me about a book that I want to write as if you’re Pete.”

And then, like, that’s the easiest, most casual way to go, “Oh, okay. Now I’m feeling a little bit.” It’s not that intimidation of like, “I got to figure this out.”

Pete Mockaitis
And then, so that gets you started. How far do you go with the plan before you do?

Jon Acuff

Yeah, so, for me, I like to do what I call audition a goal. I think a lot of goals fail because people try to commit to something for a year they’ve never done for a day. That’s like marrying somebody you just met at speed dating.

So if you told me, “Hey, I have this thing I’ve been putting off that I want to do,” and it was sizable. Like, we’re not talking about, like, you got to clean out one closet. Like, we don’t need to roadmap that. It’s like one closet. Like, I don’t want you to interview yourself. Like, “You run California closets and are asking me about how I store my socks.”

But if you had a goal that was at least a month’s worth of time, I would say, “Hey, let’s do a one-month audition. Like, what if we just tried this thing for 15 minutes a day for 25 for the next 30 days?” Because I don’t want to trigger perfectionism.

But if we tried that and it was like, “Let’s just see.” And then at the end of the 30 days, you can double down and do half an hour. And at the end of that next 30 days, you can add more time, more time, more time.

I would try to ease you into it. I wouldn’t try to get you to plan an annual thing, like, right out of the gate. Or, “From start to finish, here’s how I’m going to write and publish and market my book.” Like, no way. No way. I’d try to get you to write for 15 minutes a day for 30 days in a row, and see if you even like writing, and see if you even like this exercise at all. So, yeah, that’s the next thing I would do.

Pete Mockaitis

Audition a goal. So, like, the goal is auditioning before you, the director, who will determine if it gets the role.

Jon Acuff

“You’ve made it through. You now get to be part of my summer. Like, I gave you May and, congratulations, I just picked you up for the summer. You’ve now made it for the next summer. And not only have you made it, resources will be dedicated to you. I’m going to give you time and maybe even money. Like, oh, that’s exciting.” You’ve won the audition.”

Pete Mockaitis

Do I need to have a director’s chair and beret when I’m auditioning a goal?

Jon Acuff
I don’t think a beret ever makes a situation worse. Like, maybe a funeral. Like, if you don’t own a beret and then, all of sudden, at your mom’s funeral, you show up in a beret, lot of questions, lot of questions.

Pete Mockaitis
These are the key insights, Jon, that we count on you for. Thank you.

Jon Acuff
Yeah, I hope people are taking notes right now. I hope they pulled over. Probably pulled over on that one, like, “Wait a second. We’re going into berets now, Pete.” And you probably didn’t even put that in the description, if I know you. It’s just a surprise.

Pete Mockaitis
No, not yet. And let’s hit the permission to do now.

Jon Acuff
Yeah, so the first two are great, but if you don’t actually do it, it ultimately doesn’t matter. So the thing that I like about doing that I think people have a hard time with is maintaining motivation. We tend to think motivation will grow as we work on a goal. That’s just not how it works. Motivation is often the first thing to leave.

So I spend a lot of time helping people make it through the middle, or what I call the montage. Like, we love a montage in a movie. We don’t like being in one in our own life. Meaning, we love to watch Rocky IV, and there’s an eight-and-a-half-minute scene where he trains against Drago.

A prize fight training camp takes eight to 12 weeks. So we saw 1% of the experience, but when we try to write a book, start a business, you know, parent teenagers, whatever this big goal is, there’s a lot of middle.

And so a lot of what I do is teach people how to build a motivation portfolio. Meaning, collect enough motivation so that when you’re discouraged, which you’re going to be, you have a long robust list, not just one thing.

If you only have one why, like that why won’t show up most of the days, and you’ll go, “Ugh, I’m not even going to do the thing.” But I’d much rather you have a whole list where you can go, “Oh, it took me till number nine.”

And here’s a silly example, because you said, it seemed like you were familiar with F3. Like, one of my motivations for doing it is, the night before I text three friends and say, “I’ll give you a ride tomorrow,” because I’ve just put myself into a corner.

And I know in the morning I’m not going to text three guys and go, “Hey, it turns out I’m a wimp. Never mind.” Like, I now have some accountability there. I now have that motivation to fulfill what I promised to those three guys.

So that’s what I try to help people when it comes to doing. I’m never, like, anybody who listens to this show or reads the kind of books I write, it’s not a question of whether they’ll do it. It’s a question of whether they’ll keep doing it. And that’s where you really have to lean in.

Pete Mockaitis
So I like that. A motivational portfolio, we’ve got multiple sources of support pulling upon you. One was some of that accountability. People are expecting you to show up and give them a ride there. You said nine. Give us a quick rundown of maybe a bundle of things that might go in a portfolio.

Jon Acuff
A couple others? Yeah. I mean, for me, like, I wrote this book, Soundtracks, and we ended up turning it into a Soundtracks card deck, so it’s 52 cards. So sometimes I’ll have these in my pocket, and one will say “Hills pay the bills.”

And it’s a reminder to me of, like, when I have to do the hard things, if I do them and if I climb the hills, other people don’t, I get to see vistas other people won’t. And that could be something like a canceled flight in Chicago in January, where I had to spend the night, like, at the worst airport next to O’Hare. Like, nobody wants that. Nobody.

But, it’s like, “Oh, yeah, hills pay the bills.” So sometimes it’s a soundtrack. Sometimes it’s a literal song where I know when I hear this type of music, I always feel this type of way. Sometimes it’s a movie clip. Sometimes it is a friend that I go, “This is my most uplifting friend. And anytime I’m stuck, if I call so-and-so, 30 seconds of conversation, I feel like I can conquer the world.”

Sometimes it’s 10 minutes of walking around the neighborhood because I need some endorphins and some sunshine. Sometimes it’s caffeine. Sometimes it’s like, yeah, an espresso would really help at two o’clock when I’m struggling.

So I think everyone should be a great note taker about themselves. I think you should be the best documentary filmmaker about your life because, then, you figure out how you work best, and then you can repeat that. And so that’s what I mean by a motivation portfolio.

Pete Mockaitis

Oh, I like this a lot. We had Dr. Ethan Kross on the show, who wrote a book, Shift, about your mood, and so this is kind of reminding me of that because he mentions music specifically as a tool. So when you say portfolio, you just have a big old list of options in terms of, “This is the thing I could remember or do to take the action.”

Jon Acuff

Well, because I know I’m not going to want to. Like, why pretend I’m always going to feel motivated to write a book? I’m not going to. Someday, the financial motivation will motivate me, I’ll go, “Oh, it’s how I pay the bills. It’s how I put my kids through college. Great.”

Some days, I won’t care about that. Some days, showing my kids an example of hard work will motivate me. Someday, it won’t. Like, sometimes I’ll be like, “They’re not even really watching. Like, I can take it easy on this,” you know?

So, yeah, collecting those and that’s, to me, part of that is just self-awareness. Like, if you have self-awareness, it’s a lot easier to accomplish your goals, because then again, you figure out, “This works. This doesn’t work. I should repeat this thing that does work. I should stop doing this thing that doesn’t work.”

Like, a simple example. Pete, if my phone is in my bedroom, I stay up later. I don’t need another test of that. I’ve checked that box. I know that. So a simple hack for me is I leave my phone downstairs when I go to bed.

Like, imagine me going, “Man, I found a sleep hack. It’s unbelievable. Here’s how to like…” It’s the simplest thing. I just realized over and over and over again, if I have my phone near me, I’m going to look at my phone, and I’m going to stay up later than I really want to.

So I found a workaround, which was leave the phone downstairs. Like, it’s not complicated. That motivates me to go to bed earlier. Like, “Eureka!”

Pete Mockaitis

You know, Jon, I love that specific example. I was once, true story, in Vanderbilt’s Sleep laboratory, having all sorts of things attached to my body. And I said, “So what are the top sleep tips?” And she’s like, “Oh, yeah, it’s don’t bring your phone in your bedroom, but no one wants to hear that,” as she continues strapping electrodes to me.

Jon Acuff

Yeah, yeah, exactly.

Pete Mockaitis

Simple as that, “Okay, that was that.”

Jon Acuff

Yeah, jeez, that’s so funny. Were you doing it for money or to fix your own sleep? Like was this a…?

Pete Mockaitis

Well, we were curious if I had sleep apnea. It turns out I had mild sleep apnea. I’ve since overcome that. That was fun.

Jon Acuff

Survivor. Survivor.

Pete Mockaitis

I am. So that’s really cool. The motivational portfolio, it’s like layers upon layers upon layers of backup systems.

Jon Acuff

Yeah, I want it to be easy. I want, like, again, make tomorrow easy today. So I know, like, because nobody’s job is easy. Like, writing a book has a lot of, like, identity and emotion around it.

I’m right now in the marathon part of the book release, meaning I’ve already released the book. I sprinted to the finish line and now I’m in the marathon part, and I need to talk about it constantly and I need to promote it.

And every author loves writing a book. Most hate selling a book. But guess what? If you don’t sell it, you don’t get to write other books. And so now I’m like, “Okay, for me, in the next six months, how do I motivate myself to do 500 different types of promotion around Procrastination Proof versus I hide from it. I hope Oprah discovers it in her dentist office, whatever.”

And I was like, “No. For me to do that thing will be difficult, how do I make it easy? How do I motivate myself to stay on top of this book?”

Pete Mockaitis

Well, I think this is so good, if I may. Could you give me three more things that can go in a portfolio to get motivation cooking?

Jon Acuff

Oh, yeah, 100%. I mean, an item you want to buy can go in a portfolio. There’s a woman I know that grew up in Indiana, kind of small town, and she always wanted to buy a Louis Vuitton purse. That was her thing, like, “When I make it, when I become an executive…”

Like, that was her symbol to the point that when she went to Paris, France with her husband, he tried to buy her one, and she said, “No, no, no, no, no, no, no, no, no, no.” She was like, “I don’t want you to buy this for me. I need to do this. This is something I’ve thought about.”

So sometimes it’s okay, “I want to buy this thing,” or, “I want to be able to give this person this thing.” That’s a great one. Another one can be, “By this date, I want to accomplish blank.” Everybody has had the vacation moment where you get a lot of work done right before vacation.

Because you’re going, “How do I make tomorrow easy today? I want to have a really peaceful vacation. So if I clear these things off my plate, I will.” So you get a boost of energy. You could just say, “Where are some deadlines like that that I want to say before I go to this, I’ve done these three things before I go to this. I’ve done these three things?” To me, that’s another one.

And then the third one, I’d say, is like this principle of do difficult things in beautiful places. Meaning, if there’s something you’re putting off, go do it somewhere beautiful. Like, don’t try to crank on something in your office. If you’re stuck, go to a coffee shop.

Don’t run somewhere ugly. Like, make that part of the reward, like, “Oh, I’m going to go to, you know,” I don’t know, “Pinkerton Park, because I love that park,” versus, “I’m just going to run around this treadmill.” You’re already doing a difficult thing. Why add more difficulty?

And so, again, you just get creative and curious about yourself, and you’ll start to notice. Like, last one I’ll give you, I bought a Timex watch. I don’t mean to brag, but, obviously I’ve achieved some success. I bought a Timex watch that has Snoopy on it jumping into a pile of leaves.

So on the days when I feel tempted to write a boring, serious book devoid of humor, I can wear that watch and be like, “Oh, that’s charming. That’s delightful. Like, look at Snoopy having so much fun. He’s with Linus. They’re jumping in the leaves.” Very silly trigger for me. Wouldn’t work for most people. No problem.

One year, I wanted to write a book faster, so I bought carbon fiber Nike running shoes. Bright green. Obnoxious. The most expensive shoes I’d ever owned from a running perspective. Wore them every time I wrote that book. Ridiculous? Totally. Totally ridiculous. But it was another one of those things.

And the more you study high performers like you do, the more you find they’re playing games like this all the time. They’re playing little games behind the scenes to do the things that most people don’t do.

Pete Mockaitis

So if I perceive that I have many lucrative opportunities and I just need to go to work, I should put a large pickaxe in my office because there’s a gold mine that just needs me to go to work on it.

Jon Acuff

Gold, you could do that. Yeah, or get rid of your chair and do a little cart, like one of those carts they carry the gold in. Maybe you just sit in that. Maybe you, overalls, like Yosemite Sam or something. I don’t know, we’re just spitballing, Pete.

Pete Mockaitis

That’s good. That’s good. Well, I want to hear the one-minute version of permission to review and then how procrastination is the most well-funded fear in human history.

Jon Acuff

Yeah, so the one minute is, I’ll give you the soundtrack for it, “Data kills denial, which prevents disaster.” Data kills denial, which prevents disaster. All the review is telling you is what’s really going on. And we hate a review, dude. We hate it.

The first time I saw this, I was at a restaurant in New York, everybody was going to get a crazy meal. They opened the menu and they had put the calories next to the menu. And everybody’s order changed. Everybody changed their order to sad grilled chicken salads with dressing on the side, not the side of the plate, the side of the restaurant.

So all that to say, if you want to go the direction you really want to go, become friends with data, become friends with a review.

Pete Mockaitis

Okay, understood. Now this well-funded fear, what’s the scoop?

Jon Acuff

Well, yeah, so Netflix doesn’t fund perfectionism, Hulu doesn’t fund inner critic, but every single one of those modern-day services funds procrastination. In 2017, the CEO of Netflix said, “Our number one competitor is sleep.”

They are actively funding procrastination, meaning they don’t want you to go to sleep. They don’t want you to get in shape. They don’t want you to write your book. They don’t want you to publish your podcast. They want to turn your time and attention into ad revenue.

And I like those services. That’s not a criticism of them. Just know the score. Like, it’s easier now to procrastinate than it ever has before because you have a pocket casino. Like, that’s a real thing. And in the same way that Dr. Vanderbilt told you, “Yeah, the trick to sleeping is to leave your phone in another room.”

If you said to me, “What’s the trick to writing a book?” I’d go, “Well, why don’t you open your screen time and take an hour back from your greediest, hungriest app, and apply that to writing.” Like, that’s not, even the busiest people, if you ask them to open their screen time will go, “Oh, my gosh, I had no idea I spent six hours on Facebook last week. I would have said, I would have guessed an hour.” Like, that’s what I mean by it’s the most well-funded.

Pete Mockaitis

Okay. Got you. Well, Jon, tell me, anything else you want to make sure to mention before we hear about your favorite things?

Jon Acuff
Yeah, so we have a quiz. If you go to JonAcuff.com/quiz, that’ll show you where you might be tempted to get stuck and what to do about that. So it’ll put you into one of the four categories. You’re a dreamer, you’re a perfectionist, you’re a hustler, you’re an analyst. So JonAcuff.com/quiz will be a whole lot of fun.

Pete Mockaitis
All right. Now, could you share a favorite quote, something you find inspiring?

Jon Acuff
I love Jim Rohn’s quote, “Don’t wish it was easier. Wish you were better. Don’t wish you had less problems. Wish you had more skills.” Like, that’s one of those, that’s in my motivation portfolio. Like, when I go like, “It’s so hard.” Like, “No, I wish I had more skills to deal with this challenge. Am I being invited into a skill?” That’s one of my favorite quotes.

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

Jon Acuff
Daniel Kahneman wrote about it in Thinking, Fast and Slow, where they had college kids make sentences out of words. And one group of college kids had words related to being old in their collection: slow, retired, bald, Florida, etc.

And when they tested how fast they walked later, the students who had read the words about being old physically acted old. They, unknowingly, acted like old people just from reading the words. My favorite study because it speaks to the power of your mindset.

Pete Mockaitis

All right. And a favorite book?

Jon Acuff
I always say War of Art, Stephen Pressfield. That book, for me, really kicked off my own writing journey.

Pete Mockaitis
And a favorite nugget, something that Jon Acuff shares that gets quoted and tweeted a lot?

Jon Acuff
I often say, “Starting is fun but the future belongs to finishers.” So starting is fun but the future belongs to finishers is one of the things. And then the other one that gets tweeted a lot is, “Be brave enough to be bad at something new.”

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

Jon Acuff
JonAcuff.com is my site. I have a podcast called All It Takes Is A Goal. And I’m big on LinkedIn now. If you listened to the whole episode and just didn’t skip to this, I’m big on LinkedIn. Hit me up.

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

Jon Acuff
Yeah, so I would find somebody 10 years ahead of you and 10 years behind. The 10 years ahead, we know. It’s a mentor. It’s a time machine. Somebody who’s been to the future you want to get to, and will tell you how to do it.

Person 10 years to 20 years behind, they grew up in the new way and can teach you the new way very quickly. I grew up in the old way. I’m 50. For me to do the new way, I have to unlearn the old way first. When I connect with a 27-year-old and they show me something about AI, like, it speeds me up.

So I would just encourage you, know somebody 10 years ahead of you, somebody 10 years behind you.

Pete Mockaitis
All right. Jon, thank you.

Jon Acuff
Yeah, thanks for having me.

1143: How to Build a Career that AI Can’t Replace with Aneesh Raman

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Aneesh Raman guides you on how to use AI and turn it into a competitive advantage.

You’ll Learn

  1. Why you shouldn’t see AI as competition
  2. How to make the most out of AI in your workflow
  3. What AI can’t replicate–and how you can double down on it

About Aneesh

Aneesh Raman is the chief economic opportunity officer of LinkedIn, where he works with leaders across societies and sectors to shape the global response to the historic changes hitting work. 

Previously, he served as senior adviser on economic strategy and public affairs to the State of California, led economic impact at Facebook, worked as a presidential speechwriter, and was a war correspondent. 

A graduate of Harvard College and a former Fulbright Scholar, he serves on the boards of the College Futures Foundation and Shanti Bhavan Children’s Project

Resources Mentioned

Thank you, Sponsors!

Pete Mockaitis
Aneesh, welcome!

Aneesh Raman
Thanks for having me.

Pete Mockaitis
Well, I’m excited to hear your insights about AI and economic opportunity. Could you maybe kick us off by sharing what’s the most surprising or counterintuitive thing you’ve discovered about us career professional folks and AI?

Aneesh Raman
Ooh, it’s a big one. It’s an existential one that we have internalized this diminished sense of self as humans at work across the industrial age. When AI broke out, what now three, four years ago, immediately, there was this great fear.

Immediately, the conversation was, “We’re done. We’re at the end of the road for humans at work. We’ve got this thing that can beat us at these things. It’s going to beat us at those things next. It’s going to beat us at everything soon.”

And I just sort of, like, intrinsically, didn’t believe that. I was starting from a place where, for a long time, I had thought the labor market did a horrible job matching talent and opportunity, indexed on pedigree signals like your college degree, “Where did you work?”

So I just knew there was so much human potential out there that had been blocked out or locked out of economic opportunity all over the world. And so I just didn’t believe that humans were done. I kind of felt like we hadn’t even begun yet.

And the more I sort of thought about it, the more our CEO and I talked about it, what led to the book was this realization that humans are more than we’ve been at work for a couple hundred years now. For a couple hundred years, we have been about one thing above all else – efficiency.

And we sort of told ourselves a story that the knowledge economy moved us out of the industrial age, of people working on factory floors on assembly lines. But it didn’t. Even if you were with a laptop in an office, you were doing more, better, faster, more, better, faster, more, better, faster. Everything was about efficiency and productivity.

And we had derided almost these skills that make us, us. We called them soft skills. We said they were nice to have, not must have. And all the math worked in terms of the industrial age and what the economy valued in terms of technical and analytic abilities.

But I think what’s been most surprising to me is that AI is forcing us to reassert ourselves because it is going to out-machine us, it’s going to out-efficiency us. And yet, our human brain, which is I think still the most incredible object in the known universe, it’s been around for tens of thousands of years, long before the steam engine arrived, and the industrial age descended upon us.

And so we’re going to pull from these strengths that we’ve had for millennia, that we talked about in the book, and it’s going to be a moment to reassert ourselves and our capability, I think.

Pete Mockaitis
Oh, wow! These are big ideas.

Aneesh Raman
Welcome to my brain.

Pete Mockaitis
“Internalize the diminished sense of self.” My goodness. You know, it’s funny, I was just chatting with Claude last night because I think the First Lady was with a robot doing an education event. And I was like, “Oh, can that robot finally load my dishwasher for me? And when can I buy one?”

And so, I was looking at that, and it said, “Oh, this robot is impressive because it could figure out how to fold a towel with just 80 hours of video.” I was like, “Oh, well, my five-year-old figured out how to fold a towel in about four minutes of instruction with a hug.”

So, yeah, I’m with you, our brains are spectacular. But, yeah, there are some domains in which we are being out-efficienced by the AI.

Aneesh Raman
Yeah, and I think that’s okay. It’s not okay right now because it’s causing a massive disruption to work. It’s changing the rules of the game, which are hard to manage if you’ve been playing the game the old way and you’ve done everything right and, suddenly, you know, old math won’t solve new equations. But I think it’s an opening for people that see it.

We were never meant to be machine-like. We were never meant to spend our days doing the work of efficiency and more better faster, more better faster, more better faster. I mean, at one point, as we were reporting in the book, you know, thinking about those people on assembly lines who are fastening that one widget over and over again, or the knocker uppers that we talk about, the people who their job was to shoot peas at windows to wake people up as this sort of human alarm clock.

I looked up and they were just at this coffee shop, four people sitting next to each other, on their laptops, just slamming through emails. And it just connected for me that this is all still ever been efficiency work. And so, I think the real opportunity we talk about in the book is to see this as a big change to everything, to be understanding of the fear that that’s going to cause, because the human brain is wired to fear change. It is not wired to get exponential change. We are in a moment of exponential change.

But then act despite that fear, push past it, because while it’s understandable, it’s also unhelpful. And if you start using these tools and using them not in ways that then just take all the work out of your day, but start to take away the stuff that’s mundane, routinized, efficiency work, free up time to do more cool things with these tools, to learn new things in new ways, to build new things in new ways.

And then to open up space to do the things we uniquely do, to give yourself time to think critically, to think about ethical implications of what you’re building if you’re an engineer, to spend time brainstorming or partnering with other humans.

The turning test started us down this path of AI versus human, and then it beat us here, it beats us there. But that’s not where the story goes. There’s no innovation. There’s no growth if it’s just all about AI. Humans are illogical. We’re unpredictable. What works for us requires someone to be us, to be human, to in-tune that.

So, really, the test we should be doing is human versus human with AI, versus humans with AI, because we always do the coolest stuff together. And that means think about yourself five years ago, think about yourself today, “What are you doing that’s new and better and energizing that you couldn’t do without these tools five years ago?”

And in the book, we talk about an easy way to start this. Put your job title aside. It doesn’t matter if you’re a CEO. It doesn’t matter if you’re a senior director. It doesn’t matter if you’re the newest hire at a company. Your job title is irrelevant for the purposes of this exercise.

Every week, you do about a dozen tasks, list them down, and then you’re going to put those tasks into three buckets. The first bucket are tasks that AI can now do or can soon do. So coding is in there, quick summary, quick analysis, first draft of content, meeting notes, like all that stuff’s in bucket one.

Bucket two is stuff you’re doing with AI that’s new. It’s not just additional stuff that you’re putting in bucket one. It’s, “Are you learning something new with AI?” “I’m on marketing, I got to talk to the sales team. They speak a different language. How do I close that expertise gap in what I’m trying to pitch them?”

Are you building something new? “I have to present. What’s a cool image I could associate with this idea? A video? How do I make this land in a more visceral way to the people I’m trying to convince to back this project?” So that’s bucket two.

And then bucket three is, with the time you’re saving in bucket one, with the cool new stuff you’re doing in bucket two, what are gyou doing that’s uniquely you? And that starts with what’s uniquely you as a human, your ability. We have the five Cs in the book, but with those, think critically, “What’s an ethical implication of what we’re doing?”

But then are you spending new time with people to try new things, to test something out as a partnership, to get advice on how to pitch something. And as you sort of move the tasks of your job away from bucket one towards bucket two and bucket three, you’re adapting your job. You’re redefining your job.

We have a statistic at LinkedIn, 70% of the skills for the average job will have changed by 2030. Now, the old way that disruptions hit meant that, at some point, in six months or a year, your boss, your boss’s boss would come to you and say, “Here’s how your job has changed by 70%.” Because old disruptions from the steam engine to electricity to the internet, they played out over years and they came top down.

This one is different. Your boss actually doesn’t really know how your job is supposed to change. Their boss doesn’t know how their job is supposed to change. CEOs are trying to figure this out at an organizational level. So we get to change our jobs now. We get to start figuring out where these tools come in and then what that opens up in bucket two and three, not just because we’re human, but because we’re us.

We have a chapter in the book, “No One Beats You at Being You.” That’s where it’s going, is that you’re going to shift your job and then re-center your career around your unique curiosities and capabilities.

Pete Mockaitis
No one beats you at being you. And it’s funny, I’m thinking about, you know, so me here now, here we are having a podcast about professional skills development, and there are a lot of places where you can get such things.

And it’s interesting how, if I talk to an AI about such a matter, I might get the answer, and it might be quick. And yet, it is not as satisfying, complete, thorough, giving rise to new ideas and connections, the way hearing a full blown conversation between two folks on a matter is. And I think that that really resonates.

Aneesh Raman
And I think that it’s really important. Yeah, I’m glad you’re saying, because right now there’s this sort of idea to AI or not AI, as if it’s binary. And if you AI, you’re doing everything AI. If you’re not, you’re rejecting it for righteous reasons, and that’s where you’re at.

And in the book, we have the story of Neil Pretty, whom really, he embodies this idea that you need to use AI, but you cannot misuse it, nor should you overuse it. And Neil starts using this tool to help him prepare for different presentations, and he overuses it and realize it doesn’t sound like him and it’s not going to distinguish him. And he dials it back and he uses it differently.

Instead of asking it to tell him what to say, it says, “What would this CEO say about what I said, or this academic? Give me 12 reactions to what I think.” And then he would use that to even get better at what he was going to say that would have taken much conversation with many people ahead of a meeting.

So you can overuse AI. And MIT has done cognitive scans and come up with this term cognitive debt. Like, if you’re sitting at work and your boss asks you something, you copy and paste it in the tool, then you copy and paste the answer back and send it to your boss, you might be doing efficiency work more efficiently.

But if you run into your boss a week later, and they’re like, “Hey, that was a great idea. How did you think of that?” you might not even remember that exchange because your brain is not tracking it, and you will have brought no critical thinking to it. So that muscle is atrophying. So you got to make sure that you are using this tool to do better things yourself. You cannot outsource to it.

Pete Mockaitis
So in the universe of more, better, faster efficiency work, how would you suggest is the contrast? If I’m thinking efficiency work AI stuff is in the land of more, better, faster, what is the land of our humanity?

Aneesh Raman
This is the first time someone’s asked me that. Because what’s crazy is we had to define what makes us us. We had to define what makes humans unique in the arena of work.

It turns out not much work had been done around that. As you started talking to neuroscientists, behavioral psychologists, behavioral economists even, when I’d ask like, “Who from companies or from the world of work comes and talks to you?”

One neuroscientist said, “Not many. Like, athletes will come because they want to push their brain to the limit. The military will come because they can’t hire from another military. Hedge funds will come because they want a cool like summit speaker. But you were not getting incoming from everyday practitioners of work.”

But now the mind is going to the center of work, not the machine. And so what does it all lead to? You know, in the book, we identify the five Cs that we think are at the core of human capability – curiosity, compassion, creativity, courage and communication. Those are what we offer up at the intersection of our IQ and EQ of our consciousness and conscience.

Then we say there’s some habits we all need – resilience, adaptability, handling hard well, failing fast, learning quick. And we sort of bundle it all into this idea of being entrepreneurial in our habits and in our thinking. And we know that in saying that, we lose a lot of folks who think being entrepreneurial means starting a business, and that is not for them.

Paul Cheek from MIT, who’s a professor on entrepreneurship there, has an amazing definition for it. “Entrepreneurialism,” he says in the book, “is doing more than is reasonable with the resources you have.” So every one of us every day has a task, has a project, has something we’re doing at work, what’s more than is reasonable that we could do with these tools and with others with the resources we have?

And then what that leads to is a flip. Instead of more, better, faster, I think we’re doing new, bigger, bolder. We are creating a whole bunch of new ideas, a whole bunch of new ways for businesses to grow, a whole bunch of new businesses to go after, a whole bunch of new areas from climate to healthcare to all sorts of stuff that we could create technology for businesses to address, at the local level for just a community, or at the country level, or at the global level.

So, to me, “more, better, faster” becomes “new, bolder, better” and not just in terms of work. Like, I think if we do this right, and it isn’t just us as individuals. Institutions need to completely redesign the systems of work from employment to education, entrepreneurship.

But, ultimately, we get to better work for each of us, better work for all of us, better defined by just more human work, more fulfilling, more high value, more impactful. But that all leads to greater prosperity and progress because of this sort of innovation explosion, this entrepreneurialism that can take root.

Pete Mockaitis
And to these notions of efficiency work versus newer, bolder stuff, I’d love your hot take on these AI layoffs. I mean, some say, “Oh, well, that’s just AI washing. They over-hired, interest rates are worse. It makes a better story for Wall Street to say, ‘Oh, it’s because of AI efficiency.’” But others say, “Oh, no, no, no. Sure enough, one person can now do what things that previously require two, three, or four, and thus it makes sense to shed those jobs.” You’ve got an interesting vantage point. What’s your take on this?

Aneesh Raman
I mean, we’re seeing jobs get added, one million plus jobs around AI. That’s not just the sort of like hardcore engineering jobs. That’s also the data centers. We know sectors are hiring, like healthcare. Look, there’s these two truths we have to hold at once that are somewhat inconsistent.

The first truth is we know at the other end of all of these moments of disruption from technology, we generally see an increase in employment, and the Fed is out there sort of repeatedly with that. Jobs change, new jobs emerge. MIT has a stat, 60% of employment in 2018 didn’t exist in 1940. Creator wasn’t a career 10 years ago. Data scientist wasn’t a job 20 years ago. So we, generally, do see employment go up.

That happens after a messy middle where a lot of lives get upended and it’s really hard for people. But we do see employment go up. That sort of thing one, truth one. Thing two, truth two that contradicts that is we’ve never been here before in terms of this technology. It is fundamentally different in terms of what it’s able to do.

And I think predictions are unhelpful right now. Anyone with absolute certainty about what’s happening to a job category or to all jobs or to jobs in this sector, let’s see how it turns out in five or 10 years. Like, I think it’s just impossible for anyone to know with certainty anything absolute.

The one thing we do know, to contradict myself a little, is the only thing that matters right now is what we believe, and what we choose to do, and what decisions we make, and what steps we take. And that is true for us as individuals. It’s true for us as organizations. It’s true for us as societies. It’s true for us as humanity.

If we decide that worse is more likely, and we make decisions that make worse more likely, worse is more likely. If we decide that better is more likely, and we make decisions that make better more likely, better is more likely.

So in terms of where employment goes, there’s so much in the air. I mean, we’re going from an old world to a new world of work. There’s so much macroeconomic muckup that’s going on on interest rates and geopolitics. Every company is going through its own moment of business transformation.

Some over-hired and now they’re managing that. Some are built with an org chart for stability, order, predictability. That isn’t going to help you innovate, be agile, and grow. They’ve got to manage that. There’s no one truth to everything that’s happening.

And so I think for folks who are looking for a single answer, who are looking for someone to tell them what to do, who are looking for an off-the-shelf playbook as an individual or as a company, like, that’s not this moment. It’s not like back when it was like everyone get a CS degree or bootcamp certificate in coding if you can find one, because that’s the ticket.

There is no “it” right now, but that’s it. We’ve all got to start to figure this out on our own, use these tools, and with these tools start to understand our own unique interest, capabilities, where those could go, where we would pitch ourselves across a broader set of job opportunities that we might, otherwise, have looked at. And I think that’s what we’ve got to do is look. It’s a metacognition sort of moment.

Pete Mockaitis
Understood. But you do have some interesting data. 85% of people are in jobs where AI can automate at least a quarter of routine tasks. Can you tell us a little bit about that data and what sorts of things we’re seeing automated now with AI?

Aneesh Raman
A big thing we’ve been trying to push people on is to look at jobs as a set of tasks, not as titles. A good example of how not to do it, I would say, is looking at software engineers. And for a bit coming out of the gate with AI, everyone said that title describes all software engineers in one way, and that one way is that they code. And as AI got better and better at coding, it became, in that line of argument, intuitive that software engineers were done.

We’ve actually seen recent data where the hiring for software engineers is going up because as AI is able to do more coding, more companies want to build tech, so they’re hiring. And the job of software engineer was never limited only ever to coding.

Some of those jobs, entry level jobs, even middle, they were, but the job doesn’t have to be just that. In fact, as AI is able to do coding, it shifts to reviewing the code, or talking to customers, or having those conversations about ethical implications of what’s being built. It’s the same three buckets and things move.

ATMs are a good example, we talk about in the book. When ATMs hit in the late ‘70s, everyone thought bank tellers were done. We have a quote from the New York Times. It basically says bank tellers are done. Bank teller jobs, like, doubled between that moment and 2010, and they doubled because you had more banks opening so you needed more tellers because ATMs allowed it. The job of the bank teller shifted to being more about relationship banking.

Now, there were some debate over whether the quality of the job went up, but in an absolute term, you know, the jobs went up. They came down after that because of the iPhone and the smartphone and all the banking we’re now doing. But you couldn’t have predicted that in the ‘70s.

So that’s all to say our data doesn’t look at job titles. It looks at jobs. It looks at the tasks people are doing. And it says, if you are in a job where a lot of your job is that bucket one, that’s worth knowing. That doesn’t mean that entire job is going away. And it doesn’t mean you are done at work. It means you’ve got AI coming for well over 50% of the jobs in that task. So you want to start on your own moving tasks in your day to day to bucket two and bucket three.

And if you do that, don’t worry about the job category or the job title you have. That’s all secondary now. It used to be job title mattered first because you’d reverse engineer from it. Job title matters last now because we’re going to be reshifting work.

And so depending on your number, and you don’t need us to tell you this data, you can do an evaluation of the tasks in your job and look at where you’re heavy. Anyone who is heavy in bucket one, okay, what do you got going in bucket two and three? How can you build out from that?

If you’re in a job category that feels really volatile, okay, what are the transferable skills you have across two and three that could take you into other job functions or job categories? But it’s not an overnight, everything is done end of day sort of thing. It’s a step-by-step incremental of, “How do I manage this change sort of thing?”

Pete Mockaitis
And we had a really good chat with Jeremy Utley, who suggested shifting perspective from AI is not the oracle with the answers, but rather like a collaborator, a teammate, and that’s been pretty helpful. I’d be curious to hear, for those whose AI use is limited to sort of an enhanced Google or enhanced Bing, where do you think are the most promising opportunities, like, “Hey, go do this right now with AI, and you’re going to see some cool career benefits”?

Aneesh Raman
This is another one where there’s no one answer for everyone. I’m sorry to tell folks. Like, you’re going to have to go to the gym. You’re going to have to try things out, test things out, and figure out what is the high value of AI for you.

It could be learning new things. It could be building new things. It could be coaching you on new things. You got to keep trying the tools. Like, to your point, I think too many folks either are afraid of AI and don’t want to touch it. Or, if they’re using it, they’re using it just for a better search.

We have five Cs I talked about, and curiosity matters most right now as individuals. And the first place to start is be super curious about these tools, because their capabilities are changing every day. It’s almost like a skill of tool dexterity.

I use multiple tools every day. Every once in a while, I shift to the dominant tool. I use them for all sorts of things. Every week, I’m trying to push a new task out to the tools so that I’m constantly testing what new things that I’m working on can it help with.

It helped with writing at first, and then that pushed me to realize, “Okay, I got to focus on how I elevate what I can get help with on the research or first draft side. But also how do I spend more time doing in-person communication?”

So I started studying, like, theater actors who have it down, who know how to command a room, command energy. What can I learn from them now that my bucket three is going to be more of this? Right now, I’m using the tools for a lot of coaching. I want to send this email. I’ve told the tools what I’m working on, which is sending less emails that are less lengthy with less ideas to people like Ryan, who I can bombard with ideas.

And so it’ll say like, “Hey, you just got yesterday, like take a day off,” you know, like stuff like that. So it’s not so much about the tool capability. It’s what is the human capability you’re working on in that moment? Because we’re all going to want to keep growing right now in new ways, which is fun. It’s hard, but it’s fun.

And then you’re going to use the tools differently based on what you’re working on. If you’re just doing search, that’s an issue. So the easiest way to do it is find the hardest part of your tomorrow. You got something at work tomorrow that you’re not looking forward to, that is either monotonous and drudgery or complicated and a hard conversation you got to have, or you’re suddenly going to have to come up with an idea and you’re bit freaked out about that.

Whatever is your hardest thing tomorrow, start going to the tools and asking them how they can help you with that. And they might not be able to help you. Okay, that’s like a good example of a tool that isn’t there yet, or a task that isn’t there yet, but they’ll give you something. And that’s the sort of rhythm you want to get in.

Pete Mockaitis
Okay. Well, could you give us some fun examples of folks who saw some really great tactical good things flowing from tools into what they’re up to tomorrow?

Aneesh Raman
My favorite from the book, probably, I mean, they’re all stories of individuals who are using these tools to get jobs, keep jobs, and change their career, build businesses, like, all of it. But Jonetta Gresham is in her 50s, and because of her age, she came to AI with, in her words, a “Hell, no to AI,” mindset, because she had seen Terminator and Terminator 2 and Terminator 3, and really felt like this was a robot apocalypse come to life.

Again, she had a task at one point, which was to get her resume ready. And she used a tool to just help her do that. And she was blown away at how the tool helped her articulate skills that she had and better organized experience that she had in a way that made her so much more employable for the job she was going after.

And so that sort of opened up her eyes to like, “Okay, maybe this can help me.” And a little bit later, she was taking an IT certification course. And she is someone who, in various moments of education, didn’t feel like she was being taught in the way that she would like to learn, in the way that her brain process information, and in the way that would feed her curiosity.

So she told the tools to help her learn all the stuff she had to learn in the ways that she likes to learn, with stories, with analogies. The tools did that, she passed the test, she got the certification.

It can personalize against your needs in a way that no technology has before. It can close learning gaps. It can close entrepreneurial gaps or building gaps. You just got to get in the rhythm with it.

Pete Mockaitis
Yeah, I like that a lot in terms of, if you’ve got a laser focus on, “This is the thing I need to go learn,” and then how can the tool facilitate that, I found that rather handy. Like, I found myself getting in the Mac OS Terminal bash command line, and I don’t know what I’m doing, but it’s like, “Hey, if you want to, you know, do this automatic downloading of stuff, you’re going to need this tool.”

So I was like, “Go to GitHub,” it’s like, “Okay, no, you’ve already lost me.” And so I say, “Explain it like I’m five.” And it’s really funny, it’s like asking the robot to go to a store. It literally explains it like I’m five. But that was very handy. And I’ve heard that theme from a number of people.

It’s, like, they know a little something about the domain that they’re after or looking to enter for perhaps the first time, but not nearly enough to actually achieve anything. But with this sort of mega-crutch, they’re saying, “Oh, okay, I can kind of fake my way through step by step.” And then afterwards, like, “Oh, hey, I guess I know how to do this now. How about that?”

Aneesh Raman
Yeah, we’ve got a great story of a guy named Diego, who’s in Texas and is trying to push for rural entrepreneurship with AI to really inspire more folks to realize they can build businesses. Often, folks who couldn’t afford to go to college for whom entrepreneurship is, as he calls it, this permissionless path, this ability to go build your career on your terms.

And he has a great line, which is, “We are no longer limited by what we know. We are only limited by what we can think to ask.” And just imagine what that means for all people all over the world who have access to these tools, who hopefully have electricity and AI infrastructure.

But you’re only limited by what you can think to ask. All of us as humans are innately curious about things, wildly different things. That’s what’s amazing. We all have different perspectives, different things that drive us. But imagine now having this tool that can sort of feed that curiosity and help us align it with the work we do and the impact we want to have and the purpose we want to bring to our jobs.

That’s where you start to get excited. I think we are collectively doing a horrible job telling that story and making it clear, that hiding in plain sight is this thing that is going to make all of our jobs more interesting and more fulfilling, and all of our efforts lead to greater impact for good in the world.

And that’s now on us to try and reset that story and that conversation, which is like the big reason we did the book.

Pete Mockaitis
I like that, “What you can think to ask.” Have there been some power questions that you found transformational?

Aneesh Raman

I think a lot of it is, right now, for folks around, “Where do I start?” or, “What do I do about? How do I think about AI? How should I use AI? When should I not use AI?” You can just dump that in as a voice memo into one of these tools, and it gives you a start. It gives you something to react to.

Again, it doesn’t give you the answer. It gives you an option. And it’s your job to push back on it or to pull from it, and then try and learn something here. Ask it to challenge your thinking over there. One of the things we talk about in the book is like the, I think, it’s a hundred to one rule.

I mean, “You pick your number, but give me like 80 versions of something,” and then you react to which of those you like. And then you can start to think about why and build from that. Or, “Give me the five best arguments against the thing that I think is true about what I’m going to do tomorrow.”

That’s where I think people are really starting to get good results from it. Not, “Give me the answer,” but, “Give me a way to get to a better answer.”

Pete Mockaitis
And I like what you’re saying with regard to the challenging is because it seems like that’s the default setting is sycophancy in these AI tools. It shows me a study. I was like, “Wow, that’s very compelling.” I was like, “Do we think this is real?” It was like, “Actually it has all the hallmarks of being a fraudulent paper mill submission.” I was like, “It’d be nice if you proactively shared that.” But, yeah, to ask it to do the challenging is great.

And you said voice memo and I think that’s a brilliant hack right there in terms of not just the one sentence, but the five minutes of verbiage can make all the difference.

Aneesh Raman

And you can just dump it all in and it’ll organize it. I know someone who does a call with AI every day. They do the chat functionality because you can also, without having to type in or do a voice memo, you can literally converse with these tools.

And they go out for a walk, and they just talk about everything on their mind, “I’m like thinking about this, I had a hard conversation with this person.” And over time, what these tools start to have is longitudinal data on us. They aren’t another person. They are just a collection of insights and knowledge that’s out there. And then, increasingly, if you give it context and give it info, insights, and thoughts on us over longer and longer periods of time.

And so in these conversations, the tool will start calling out, “Hey, you’ve talked for a few times now about wanting to learn more about neuroscience, or how that’s going to relate to work. Here are some, like, podcasts you might want to listen to.” Or, “I’ve noticed, like, anytime you have to have a conversation that’s tough, and it is how you end your day, it really upends your day. Like, have you thought about making those conversations happen at the start of a day?”

It starts picking up on stuff for us that we might miss in the day-to-day of just life being busy. So the key thing is, like, this is a tool that is the easiest technology humans have created for humans to use. It is literally like just talking to someone else at the most basic level. You don’t have to go learn AI. You just have to, like, sign up for a free tool or watch a couple of free videos on it, and then just start using it.

Pick a thing. It can be an exercise plan, a meal plan, or something at work, a project, or a set of tasks you’ve got going, and just start using it. Like, it’s sitting there for any of us to use. So you got to just start using it and keep using it but don’t outsource to it. Use it to then start building you into a better person.

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

Aneesh Raman
I think it goes back to your opening question. Like, it has been surprising how we have internalized a diminished sense of self, and yet it is a reality. And so the biggest thing I would tell people is, like, what matters most right now is your belief in yourself.

You’re going to have to bet on yourself. That’s the future of work and then push your leaders, and we’re pushing them, to build systems that make that bet pay off. But the thing that starts it all is going to be that you believe in yourself and you’re going to bet on yourself. And that’s going to take some work because we are all coming out of an era for work that wasn’t about betting on yourself.

It was turning yourself into whatever the job description needed, whatever the job category needed. So it’s going to be a flip for your brain. The good news is, and there’s a great book, Tiny Experiments, a bunch of them on neuroplasticity and how we can rewire our brain to become a different person.

The good news is you got a human brain and it is able to be rewired and you can become a different person. You can get to belief. You can get to a place where you know exactly how and why you’re going to bet on yourself, but it’s going to take some work. But that’s where it starts. That’s what I would say.

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

Aneesh Raman
I like the, “Some men see things as they are and ask why. I dream of things that never were, and ask why not.” That drove me for a while. I think, right now, it’s more “Be curious, not judgmental.” I think it gets appropriated to Walt Whitman.

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

Aneesh Raman
Mine, I mentioned at the MIT one, 60% of jobs in 2018 didn’t exist in 1940. That’s just like a good number for us to keep in mind.

Pete Mockaitis
And a favorite book?

Aneesh Raman
A bunch of them. My favorite hits at a certain moment in life, that sort of like hits me deep as it relates to this conversation, Sapiens. I read that in August 2023, GPT had gone global the prior year, and it is a brief history of humankind.

And so it just helps you have a sense of, like, how incredible the human brain is, but just also how much has happened across millions of years when we all focused on a few hundred years. So that really widened my perspective.

Pete Mockaitis
And a favorite tool?

Aneesh Raman
Copilot, I’m using it a lot because I work at LinkedIn. My co-author is working on Copilot. So it’s kind of a default because I can go tell someone if there’s something we should make better out of it. But it can really give me good advice on, “Should I send this email?” or, “What am I overspending my time on?” because it’s got my calendar, it’s got my email, it’s got the team’s messages. So, for me, right now, because a lot of my growth is growth I want to do at work, it’s been helpful.

Pete Mockaitis
And a favorite habit?

Aneesh Raman
This is probably controversial, because I don’t know if people would say this. My favorite habit is small talk, actually. I love small talk. I think every human is like a documentary unto themselves. There’s this great word, sonder, that I won’t do it justice, so people should look it up. It’s a word someone made up, I think, five, 10 years ago. But it’s that every human around you is living a life as complex and interesting as your own.

And that’s true across human history, or at least since we’ve had the brain we have with the ability for complex thought that we have. So I find small talk just amazing. I love meeting new people and just, I’m sure I’m awkward about it because I ask like deep questions sometimes really quick, but I just, like, love learning about people.

Pete Mockaitis
And is there a key nugget you share that people really connect and resonate with and quote back to you a lot?

Aneesh Raman
Hard things are hard. That’s a good one. You know, at one point, someone asked me, “What’s been the hardest part of your career?” And I was like, “You know what? All of it.” And I did it kind of, like, begrudgingly. And then as stuff has stayed hard in just figuring this story out, I revisited, you know, when I worked for President Obama, he had a “Hard things are hard” plaque on his desk because at certain moments when legislative victories were hard fought, people would remind each other hard things are hard.

And that just has led me to become a real believer in the bigness and value of hard. I have, like, an ode to hard things. It’s got, you know, quote from a stoic Marcus Aurelius, who’s like, “The obstacle is the way,” to “Hard things are hard,” to Carl Lassen, the Duke women’s basketball coach who has a viral video that’s amazing about how the whole thing in life is, “How do you handle hard well?”

Roger Federer had a commencement speech a few years ago about the mastery of hard things. Nvidia CEO Jensen was at Stanford Business School and said, “I wish upon you pain and suffering,” because his point to these Stanford Business students was, “You got to build resilience and you got to go through hard for that.” So, yeah, hard things are hard. I think I’ll take that.

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

Aneesh Raman
LinkedIn. The sleeper functions on Linkedin, I think, that people don’t know enough about is you can follow people without connecting to them.

You can go follow folks and they’ll be in your feed. So I am, I’d say, regularly, every three months, unfollowing some people where my curiosities have moved somewhere else, following new people who are talking about the things that I’m newly curious about.

So follow me until you get bored of me. Follow others. All the people in the book are on LinkedIn. And then the book, Linkedin.com/opentowork, that’s where you can go find out about the book.

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

Aneesh Raman
Bet on yourself. Find your way to betting on yourself and you’ll be okay.

Pete Mockaitis
All right. Aneesh, thank you.

Aneesh Raman
Thanks for having me.