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1163: The Surprising Keys to Superior Team Performance with Ron Friedman

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Ron Friedman reveals the science behind unlocking extraordinary team performance.

You’ll Learn

  1. The three strengths that separate superteams from average teams
  2. Why managing energy and attention matters more than working harder
  3. The feedback approach that encourages lasting behavior change

About Ron

Ron Friedman, PhD, is an award-winning psychologist and the founder of ignite80, a learning and development company that teaches leaders science-based strategies for building high-performing teams. His research has been featured on NPR, Bloomberg, CBS, NBC, FOX, CNN, as well as in The New York Times, The Washington Post, The Boston Globe, The Guardian, The Globe and Mail (Toronto), Fast Company, Psychology Today, and Harvard Business Review. 

He is the author of The Best Place to Work, an Inc. Magazine Best Business Book of the Year, and Decoding Greatness. He lives in Pittsford, New York.

Resources Mentioned

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Ron Friedman Interview Transcript

Pete Mockaitis
Ron, welcome back!

Ron Friedman
Thanks for having me, Pete.

Pete Mockaitis
Well, I’m excited to talk about Superteams, and I’d love it if you could maybe kick us off with a particularly fascinating and exciting discovery you’ve made while putting this together.

Ron Friedman
Well, let me tell you how I did this research. So I polled thousands of workers and asked them two simple questions about their teams. Number one, “How effective is your team at achieving its goals?” And, number two, “Compared to other teams in your industry, how would you rate your team’s performance?”

And then we took the teams with a perfect score, a very tiny group, we call them superteams, about 8%, and we looked to see, “What are the superteams doing differently?” And we looked at everything, from the way that they structure their day, to how they run their meetings, to the basic ways in which they recover after work hours.

And what we discovered is that superteams share three key strengths. The first is they get more done by better managing their time, energy, and attention. The second strength is they don’t just collaborate well, they actively make one another better. And the third is even when things are going well, they’re not satisfied. They’re constantly building new skills and improving over time.

Now the great news is every single one of those strengths is learnable, which means, by building the right habit, any team can dramatically improve its performance. So you asked, “What are some surprising insights?” There are a ton.

And, honestly, like this book features so many surprising insights. It would take us a long time to get through them all, but let me just give you one. And this might be very counterintuitive to your listeners in particular.

Productivity tips, the ones we hear about all the time online, you know, maybe even on this show, about things like, “Okay, turn off your notifications if you want to get stuff done,” or, “Only check your email three times a day,” or, you know, “Put your phone in the other room.”

Those types of productivity hacks might be great for the individual, but they slow the team down. And it’s because one person’s deep work becomes another person’s bottleneck. And so when you’re looking at the team level, how do the best teams get stuff done? It’s by coordinating when they’re going to be on and when they’re going to be off.

They set dedicated focus blocks so that people can get work done during the day with nobody has to monitor their emails. And so I think productivity experts are solving the wrong problem. And the problem they’re trying to solve is, “How do we allow people to do real work during regular work hours?”

That’s a very noble pursuit. But when you tell people to unilaterally disconnect from their team, you actually make the workday longer both for the individual and for everyone else in the group.

Pete Mockaitis
Well, that’s intriguing insofar as what I’m not hearing you say is, “Forget deep work. Everyone should be always on and available to be notified and summoned instantly, constantly.” But rather, “Yes, preserve deep work, but, ideally, do that with the whole team’s unanimous consent, coordination, and understanding.”

As opposed to just like, “Oh, where’s Pete?” “We don’t know.” “We’d love that answer.” “Well, I guess he’s somewhere unavailable for a couple hours.”

Ron Friedman
A hundred percent. And I love what you just said, “Where is Pete?” That’s exactly what happens. I call it a focus free-for-all. Everybody comes up with their own rules for themselves, and the team, as a whole, ends up lengthening the workday and making work harder for everyone.

And so let me take a step back and give you some statistics. These are some jarring statistics, I think. The average worker loses 18 hours a week to meetings. They then lose another 11 hours a week, digging themselves out of messages. That’s three quarters of their week gone before they’ve accomplished a single task.

And so, you know, we often wonder, “Why is everyone getting burnt out?” This is the question, like, we’ve been trying to solve for the last five years, “Why is everybody getting burnt out?” A better question is, “How do they manage to get any work done in the first place?”

And so what you find on superteams, the best teams in the world, what they do is they have dedicated focus blocks, they carve out meeting-free days where no one has to attend meetings, except they don’t call them meeting-free days. They call them get-stuff-done days because they want to reinforce the purpose behind the initiative.

And so if I was to sum up how superteams get more done, it’s by minimizing distraction and maximizing focus, but on the team level.

Pete Mockaitis
Okay, that’s very sensible and sounds solid. Well, and I guess what I’m thinking is, with these 18 hours of of meetings and 11 hours of messages, like, ideally, you are getting stuff done in the meetings. Like, the decision, the brainstorming, the insights generated, the solutions, the creativity is happening in the meeting to drive forward the team’s objectives. And, likewise, with what you’re messaging about, but often, the reality is not so rosy.

Ron Friedman
Yeah. And, in fact, you ask people, “What is the number one time sink in your week?” It’s not commuting, it’s not social media, it’s meetings. And most people consider meetings to be the number one drain in their entire week.

One of the things I do in my keynotes is I ask people to stand up when they see the percentage of meetings on the board that feels like a good use of their time. And I start off with 80 to 100. No one stands up.

I just did a keynote where the CEO didn’t stand up until I showed zero to 20. And it’s pretty depressing, frankly, when you think about it. Half our week is gone towards an activity that feels like a bad waste of our time.

And what happens when you’re in a meeting that doesn’t feel like a good use of your time? You fight to reclaim that time, and you do so by multitasking. And that makes the meeting worse and reduces the decision-making quality and feels, frankly, counterproductive.

Like, you know what happens in these large meetings, and we’ve all been part of them, where the only person paying attention is the person speaking, and everyone else is either doing their email or waiting for their turn to speak so that they can feel like they’ve contributed.

What we find on superteams is they are 50% better at avoiding unnecessary meetings. They’re 54% less likely to schedule recurring meetings. And recurring meetings are particularly insidious because they’re so difficult to remove from your calendar.

Pete, if you and I have a recurring meeting every Tuesday, in order for me to cancel that recurring meeting, I need to have a very awkward conversation with you. I need to say, “Pete, I don’t feel like our time together anymore is valuable.”

Pete Mockaitis
It’s like a breakup.

Ron Friedman
And it’s almost like breaking up with someone. And so people prefer to avoid having that conversation. They keep the recurring meeting on the calendar, and it’s completely draining. So let’s get into solutions. So what should you do? What should the team do?

In the book, I talk about meeting guidelines. Meeting guidelines are simple rules where you and your team decide, “This is a good use of our meeting time. This is a bad use of our meeting time.” On most teams, just about anybody can call a meeting for any reason.

And the unfortunate truth is lots of workers use meetings as a crutch. It enables them to look productive to their teammates because they’re getting stuff done, they’re putting meetings on the calendar, but it gives them license to procrastinate because they’re waiting on the meeting. And so meeting guidelines prevent that from happening.

So let me give you some examples. On my team, we have a simple rule: “No decision, no meeting.” If you have an update, that’s an email or it’s a video capture. If you have a question, pick up the phone. Unless there’s a decision to be made, we’re not going to pull people away from getting their stuff done.

Another example, I talk about it in Superteams, it’s a company called Percolate. And at Percolate, they have a simple guideline: “No spectators.” If you’re not contributing to the meeting, you don’t need to be there. It’s not a criticism, it’s respect for your time.

What all these rules enable people to do, again, is to get real work done during regular working hours. Because if they don’t have that opportunity, what happens? They look for ways to create more time. They come in early. They stay late. They work weekends.

I can’t imagine how many of your listeners experience this all the time, where they’re constantly fighting to get their actual job done because the regular work hours prevent them from being able to do it. So setting meeting guidelines both on the team level.

But also it’s something for leaders to lead in terms of of a conversation with the teams, not something that’s supposed to come top down where the leader says, “Okay, we’re having a meeting. We’re having meeting guidelines from now on, and this is what it’s going to be.” It’s something for the team to co-create together because when they do, they set themselves up for way more productivity.

Pete Mockaitis
Yes, thank you. Well, I’m hungry to dig into many of these subcomponents, but I guess, first, I just want to calm the nagging questions inside me. So these 8%, these superteams, I guess, Ron, how do we know they’re not just delusionally overestimating their greatness if it’s just sort of like, “Yeah, I think we’re pretty great, and I think we rank very highly compared to other teams”? I guess, fundamentally, how do we feel good about that?

Ron Friedman
I love that you’re asking that. I’ve been on a hundred podcasts and nobody has asked me that question, so thank you. We have a lot of great evidence that one of the best predictors of actual team performance is the team’s perception of the team’s performance.

It’s not the same thing as saying, “How good of a driver are you?” because that’s a self-rating. This is a rating about the group. And people tend to be far more accurate in their performance reviews about the team. So there’s a lot of meta-analyses that have been done over decades showing that this is actually a great predictor.

The other thing I would say is we asked a lot of questions about these teams, or rather about of the individuals who took the survey that were not very positive in terms of the results. So I thought, for example, “Well, maybe their nutritional habits are better.” Because, as we know, if you eat right, you’re going to be sharper at work, and maybe they’re eating better.

No. We found no such evidence. We thought maybe their sleep habits are better. Not the case. We even asked them, “How likely are you to look at your phone before brushing your teeth?” The answers were not good, Pete. And so we know from the research that they’re not just saying great things about themselves, they’re actually saying some things that are not so great.

The other thing, the final thing I would say is that a lot of the insights and the recommendations that came out of Superteams are supported by other evidence. So it’s not like they’re coming out of thin air. Like, there’s a lot of reason to believe why a lot of these recommendations make intuitive sense.

Pete Mockaitis
Okay, fair enough. And I suppose you had multiple individuals inside a team as well.

Ron Friedman
That’s right. Yeah, so this is six thousand people, over six thousand, rather, with six rounds of research across a wide spectrum of different industries. So we had everything from attorneys, to medical personnel, to salespeople. Like, we just looked at, “What are the findings that are significant across the industry?”

Pete Mockaitis

Okay. Well, so when it comes to these practices, the meeting guidelines, I think, is swell. And it’s kind of intriguing how just the word guideline, it makes me think of budgetary guidelines. And so many times organizations will have very robust and precise and immovable finance processes for which a project gets budgetary approval.

It’s like, “Oh, hey, if it’s more than $2,000, you got to work it through the finance process, and then away you go.” And yet, a meeting very well could cost more than $2,000 of company money when we factor in the cost of all those human hours being expended within that gathering.

Ron Friedman
Yeah, the reason we’re calling them guidelines and not rules is because they’re suggestions and they can be broken. We don’t want to put handcuffs on people in the way they work, they do their work. We’re trusting people to work effectively.

And so even meeting-free days, if you look at the companies that are doing this right, they’re allowing people to break those meeting-free days if they so desire. And so they’re meant as recommendations for, “Here is typically how good work gets done. But it doesn’t work if you limit people’s ability to get their job done.”

I think this is the problem. I think, a lot of times, we look for simple solutions that restrict people’s ability and undermine their autonomy. So a great example of this is return to work. Return to office. Everyone after COVID, “Okay, everybody needs to get back in the office. This is how we could do great work.”

One of the other findings we looked at in our research is, “Where are superteams most likely to occur? Are they more likely to occur in office? Are they more likely to occur remote? Or are they more likely to occur in hybrid teams?”

There’s good reason to imagine that it’s hybrid teams because they get the best of both worlds, right? They get to be around each other, they get more focus time. That one might be best. It turns out it doesn’t matter where the team is located.

High-performing teams are equally likely to occur in office, remote, or hybrid. And it’s because how the team works is way more important than where a team works. You can have wonderful opportunities for gathering together in the office.

But if that also means that your best employees now need to commute for two hours just so that they can get to the office and fire up their Zoom and attend the same meeting they could have attended two hours ago if they were allowed the flexibility to work from home, that doesn’t lead to better performance. It leads to resentment and it leads to overwork and burnout.

Pete Mockaitis
Okay. Well, keep laying them on us, Ron. So work from home, work remotely, it doesn’t really matter. What else are some of the other biggest findings?

Ron Friedman
I’ll give you another one that I thought was really surprising. So this actually starts Superteam. So we asked people about the amenities they have at their office. And we presented a very long list of to 20 amenities.

We asked them, “Do you have a ping pong table? Do you have an office gym? Do you have collaborative spaces? Do you have quiet rooms where you can meet and have some privacy?” And there was only one amenity that predicted high-performing teams, and it was this: a quiet space to do focused work.

It was the only amenity that predicted high performance. It was twice as likely to occur in high-performing teams. And that speaks to how most offices are an attentional war zone. This is why so many people want to work from home, is because they can actually focus and get their work done.

Most people don’t underperform because they’re led by a bad manager or because there’s too much work. It’s because they’re not able to actually get their work done. They just want the peace and quiet to actually get their work done. And if your week is just being cannibalized by meetings and messages, there’s just no opportunity for doing that.

And so I think what that speaks to is how, if you’re looking to design the perfect office, don’t start with, you know, an office slide. Don’t start with the office gym. Start with giving people the opportunity to focus.

Pete Mockaitis
Okay, understood. Well, I’m curious, with these superteams, there’s some factors that matter, some factors that don’t. I mean, what about just having really smart, great folks on the team in the first place?

Ron Friedman
Yeah, I think that’s important. I think a lot of the books in my space start with, you know, get the right people on the bus. Like, that’s the message, “Get the right people on the bus.” And that’s great if you’re building a team from scratch, but most leaders are not building a team from scratch. They’re dealing with the people they have on the team.

And so this book is about, “What are the practices that can help you turn any team into a high-performing team?” And it starts with a very simple formula that I think most leaders and most teams overlook. And that is, “How do you turn a group of strangers into an actual team?”

Most people think they work on a team, but they don’t really have a team mindset. They’re just a group of people who happen to be working together. So how do you do it? How do you turn strangers into an actual team? Well, you need three things.

The first thing you need is you need a shared goal. You need one outcome that everyone is working to achieve together. Now that sounds obvious, but in most teams, you don’t have that single outcome. So, for example, Pete, if you’re trying to get promoted and I’m trying to go home at 5:00 o’clock so I can take my kids to soccer, we have different goals. And that leads to tension.

If you’re on a sales team and you have two different people, two people both trying to optimize their sales, they’re competitors, they’re not teammates. They don’t have that single goal because they don’t have a metric that unifies them in terms of a single outcome. So that’s the first thing, shared goal.

The second thing is you need role clarity. I need to know what I’m responsible for, I need to know what you’re responsible for, and I need to know how those two things intersect. If we don’t have clear roles, then balls get dropped or we have turf wars. Either of those is problematic.

The third thing you need is you need something called interdependence. Interdependence is just a fancy psychological term. All it means is we need to believe that we need each other in order to succeed. If we’re independent salespeople, not only do we not need each other to succeed, we’re competitors, “I need you to fail in order for me to look good.”

So if you don’t have those three things, you do not have a team, you have a recipe for dysfunction. And I think this is where most teams struggle, is they’re missing one of those three factors.

Pete Mockaitis
Okay. So, fundamentally, there’s these three components, make a group a team. I guess I’d love to hear back on the individual side, is there any sort of foundational thing that individuals must have or must not have in order for the superteam business to come together?

Ron Friedman
Yeah, I think you need to hire people who are great collaborators, who are actually interested, authentically interested, in helping to make the people around them better. And I’ll give you an example of how you can hire for this.

This is an example from the book about an airline that, during the interview process, has people get up in front of a crowd and talk about their background. They do this for all the recruits together. They hire, you know, groups of people together.

And everyone thinks that what they’re really testing for is how effective people are at speaking. Because, you know, if you’re going to be a stewardess or whatever, you’re going to need to speak to the people on the plane. But actually what they’re looking for is how people react when someone else is speaking.

Do they cheer them on? Or do they stay quiet and hope that they screw up so that they look better and they only hire the people who are supportive of others? And that’s actually what we find in superteams is they don’t just collaborate well, they make each other better. And they make each other better by supporting one another, both in and outside the office, but they also make each other better by raising accountability.

In our study, we asked people a simple question, which is, “When things go wrong on your team, who do you feel worse about letting down? Do you feel worse about letting down your boss or do you feel worse about letting down your teammates?”

And on superteams, not even close. Eighty percent of people say, “I feel worse about letting down my teammates.” And that’s exactly what you’re looking for, is you’re looking for a team that’s accountable to one another, not to the manager.

Because when they feel accountable to one another, they work harder, they take ownership and they look for ways to lift the team by doing tasks that, even if they’re not in their job description, they’re still going to do them because they want the team to succeed.

Pete Mockaitis
Okay. And also in your book, you make a distinction between effort versus energy and attention. Can you explain what is the distinction and why does it matter?

Ron Friedman
I think, a lot of times, people assume that if they just work hard enough then they’ll, you know, get everything done. And the truth is that how you recover is just as important to how you well you do your job. And if you look at the best athletes, they take their recovery just as seriously as they do the actual task at hand.

And what we find on superteams is a lot of people, you know, assume that if they’re not working, that they’re automatically recovering, but that’s not the case. Just because you’re not working doesn’t mean you’re recovering your energy automatically.

So scanning Instagram or bingeing Netflix, that can help you wind down at the end of the day. It doesn’t help you recover your energy. What does? Well, it’s mastery experiences. They’re activities that you do outside of work that stretch your skills and challenge you in new ways.

So depending on your interests, that can mean playing a new song on the piano. It can mean playing pickleball. It can mean trying out a new dish. The key takeaway here, and this by the way, is what you see on superteams, is they’re far more likely to invest their off hours in hobbies. And those hobbies refuel them and recharge them and enable them to show up more effective at work, which then enables them to sustain their attention more effectively.

And so the key takeaway here is, when it comes to your downtime, don’t try a slow down if you really want to recover. Try to accelerate in a completely different direction.

Pete Mockaitis
Can you give some more examples of these winning recovery hobbies or master activities?

Ron Friedman
Yeah, it really depends on your interest. I don’t know, Pete, can I interview you? What do you like to do for fun on vacation?

Pete Mockaitis
Sure thing. Well, swimming is fun.

Ron Friedman
Okay.

Pete Mockaitis
I’d say eating food and laughing are among the top things. Well, I’ve been having a lot of fun with Slay the Spire 2, the game, since it was released. It feels like some mastery is happening there, just like these decision-making.

Ron Friedman

Is that a video game?

Pete Mockaitis

It is. It’s kind of strategic decision-making kind of stuff.

Ron Friedman
Okay. You gave me three things that I think are key to those recovery experiences that we know from the research are effective. So you mentioned swimming. Swimming is exercise. Exercise restocks your mental injury and makes you smarter at work.

And it’s because when you exercise on a regular basis, you get more blood flowing to the brain, enables you to sustain your attention, makes you less distractable. It also activates the memory regions of the brain. So now you’re soaking up information more quickly. We find on superteams, they exercise 84 more minutes per week. So exercise is one element.

The other element you talked about was laughing and being with others. Social experiences are vital to to recovering our energy. You go out for a nice time with people you love and people who support you and like you, they don’t have to be your family, that will restock your energy.

The third thing you mentioned was video games. They get a bad rap. Truth is, video games can not only help us restock our energy. They also make us smarter because, as you mentioned, they require sustained attention.

And so a lot of people think that that recovery is like exercise, where if I’ve just spent all day exercising my muscles, I’m going to be tired. And so I should just slow down, let my muscles recover. It doesn’t work that way for recovery. You actually will recharge faster by doing something different that energizes you.

Pete Mockaitis

Okay. Well, now, that 84 minutes more per week of exercise is startling. I love these numbers. So 84 minutes, so what does that leave the exercising or the superteam group in exercise minutes versus the non-superteam group in exercise minutes?

Ron Friedman
That’s a great question. I don’t have it in front of me. But what I can tell you is that it’s a social norm on these teams. In other words, they tend to do it. They not only view themselves as exercising more often, they say their teammates exercise more often. And a big part of it is the leader.

The leader talks about how, when they exercise, they kind of socialize. They talk about the benefits and how they do it, and they take more walking meetings. And walking meetings are not just an effective way of getting exercise during the day, they make you more creative because now you’re taking your ideas and putting it in a different environment.

That leads to more stimulation, more idea generation than it would be if you were stuck in a windowless conference room. And this is another thing. I think you’ll appreciate this, Pete, is walking meetings make you more attractive.

And it’s because, when you take a walking meeting in the presence of another colleague, you get elevated heart rate. And elevated heart rate tends to be confused for attraction. And so this is something I say in my keynote. If you take nothing else away from this, at the very least I’ve given you a secret weapon for making yourself irresistible, is take walking meetings. People will find you more attractive.

Pete Mockaitis
Attractive in every sense or just romantically, Ron?

Ron Friedman
Man, you have a researcher’s mind. I love that. The attraction comes from the confusion around the elevated heart rate in the presence of another person. And so if you get elevated heart rate while looking at another person, this is why people look more attractive at the gym, because you have the elevated heart rate.

You look around, and you’re just more likely to interpret that as attraction. And it’s because of the elevated heart rate. It’s not because of how they actually look.

Pete Mockaitis
Okay. So we also could be attracted to someone in the sense of they are a rock star at a concert and they are attractive as opposed to, “I want to take this person on a date.”

Ron Friedman
That’s right, yes. And it’s more of a positive experience. And so if you tend to have a more positive experience around other people, a particular person, you’re going to interpret that person as more attractive.

Pete Mockaitis
All right. Well, Ron, this 84 minutes is startling. Give me some more eye-popping numbers you’ve discovered.

Ron Friedman

Eye-popping numbers. Meeting-free days. Let’s talk about the impact of a meeting-free day. And so this is research out of MIT Sloan. After a meeting-free day, people report 71% higher productivity and half the stress as a regular day. I mean, that’s remarkable.

If you ever come in on a Sunday morning without having people email you and just being able to like, for three hours, just do your work, you know how unbelievable of an experience that is, how restorative that is, how energizing, because you were able to just identify what you need to do and then you’re able to do it.

Now imagine if you had days like that during the week. How often do many of us go into the office or fire up our computer from home, and then eight hours later, stand up and be like, “What the hell just happened? What happened to my time? I don’t even…”

You go home, you have dinner with your kids, they’re like, “What did you do today?” I’m like, “I don’t know. I don’t know what I did today. I had meetings all day. I didn’t do any goddamn thing.” And so this is all about allowing people to just do their job effectively, and it’s got to start at the team level or it’s never going to be solved.

Pete Mockaitis
Okay. And with regard to this energy and attention stuff, are there some top strategies beyond the energizing hobbies and exercising and collectively discussing and agreeing upon when we are not meeting? Are there any other top strategies that go miles in helping us manage distraction and stress?

Ron Friedman
Yeah, so this book looked at both the habits of the teams but also the habits of the individuals on the team. And so one of the things we looked at is, “How do people on superteams structure their day?” And if I were to summarize a few of the habits that I think are worth noting, there’s three of them.

One of them is looking forward, the second is looking backward, and the third is staying present. Okay, so I’m going to go through each of those buckets. And this, by the way, is how people on superteams are experiencing work as more proactive than reactive.

And we find that on superteams, people say they’re twice as likely to feel more proactive during work. So if you want to stay proactive, these strategies will help, almost regardless of the team you’re on. And so the first strategy…excuse me. Okay, we’ll edit that out. The first strategy is looking forward. What does that mean?

It means, at the end of the week or on Sunday morning, looking ahead to your calendar and identifying blocks of time that you can utilize to get actual work done, and then time blocking. Setting an appointment with yourself, where you will achieve a particular task during a particular time slot. Time boxing by looking ahead.

The second strategy is looking backwards. What does that mean? It means, after a good day, people on superteams are more likely to say to themselves, “Okay, that was a good day. How do I have more days like that?”

And after a bad day, they’re more likely to say, “That wasn’t a great day. How do I avoid having days like that in the future?” So there’s this ongoing reflection and refinement and improvement in terms of how they’re structuring their day.

And the third thing is staying present. And if you think about when we’re most distractable, it’s typically between tasks. When we switch from one task to another, we become more distractable. So after exiting a meeting, what’s the first thing we do? We look at our phones. After finishing a memo, you go on your email.

And so if you can reduce the amount of transitions between tasks, you can make yourself less distractable. And so superteams tend to do that by batching similar tasks and by writing out concrete SOPs, standing operating procedures, that help them stay on task without being distractable.

And so those are the three strategies that will help you improve your performance regardless of what team you’re on – look forward, look backward, stay present.

Pete Mockaitis
Okay. And you also claim there’s a magical question that makes team decisions smarter by up to 30%. Tell us, what is this question? How do we even measure that?

Ron Friedman
The question is, and this is something that the best leaders will ask at their meetings, which is, and this is before making an important decision, “If this decision doesn’t work out, or if this decision backfires, why would that be?”

Simply asking that question empowers the people in the room to tell you you’re making a mistake. And it’s called a pre-mortem. We all know what a post-mortem is. A post-mortem is at the end of a project, we talk about what went well, what didn’t work well, what we’re going to do differently in the future.

This is a pre-mortem, and what the research tells us is that teams that conduct pre-mortems, which is imagining, “In the future that this project does not work out, why would that be?” that opens them up to new ways of thinking that improves the ultimate decision by up to 30%.

Pete Mockaitis
Okay, lovely. And any thoughts with regard to navigating disagreement, thinking through consensus, arguing, getting to good outcomes with our collective wisdom?

Ron Friedman
Yeah, there’s a lot of research, great research, about how to disagree more effectively. A lot of it’s in this book. I have a chapter on Scalia and Ginsburg, the two Supreme Court justices, that were incredible friends, even though they disagreed about just about everything.

And one of the strategies was, essentially, understanding that you don’t need to agree on everything in order to be a good teammate. In fact, the best teammates tend to view disagreements as a tool for making better decisions.

The worst teammates tend to view disagreements as a judgment on how people evaluate their competence. This is the problem that people have, is they tend to confuse people’s agreement for liking. And so it becomes, “If you don’t agree with me, then you don’t like me or you don’t respect me.”

And so the disagreement gets off course because now we’re fighting about whether I’m a worthy person as opposed to what the right course of action is. And so the best teammates disentangle this emotional component from the actual logical argument.

I talk about ways of doing that, but one of the critical pieces is recognizing that people, generally, don’t change their mind in the conversation. They change their mind after the conversation is over when they’ve had a chance to reflect.

And I think, in the movies, we’ve been taught to just kind of bash people up with arguments and they’re going to change their mind, and agree with you eventually. But, in fact, you are far more influential and effective if you lay out your ways of thinking, and then giving people the space to change their mind outside of the meeting.

Pete Mockaitis
I think that really rings true in my own experience, in that someone says, I don’t know where I heard this, but that someone said, “The truth will set you free, but, first, it will piss you off.”

And that is my experience in terms of someone says something and I don’t like it in regard to making a change when I was perfectly comfy, cozy, not making that change. And it’s just kind of annoying, like, “Eh, I don’t like it.” It’s just my default reaction, “I don’t like it.”

And then maybe the next morning-ish, it’s like, “But that’s probably the right answer. So we should do it.” Yeah.

Ron Friedman
You know, I often feel the same way, particularly when my editor sends me changes. And I have learned in my advanced age of 49, that often is the best indicator, when it makes you angry, the feedback makes you, it’s often a leading indicator that it’s probably a good idea. And I always wait 24 hours now before responding.

Because once you get past the idea that it doesn’t have to feel good, that you’re optimizing for the best possible outcome, you approach it with a different perspective. And it’s a perspective that is more amenable to making the changes you need to change to achieve your objective.

Pete Mockaitis
This reminds me, I think, Daniel Kahneman was chatting with Adam Grant, and said, “I love being wrong, because it’s the only way I really know that I’ve learned something,” which, I think, is just an amazing reframe.

And it speaks to your experience of the editor. It’s like that commentary, I assume the editor’s good. That commentary that gets onto your skin is all the more powerful and helpful because it’s challenging something fairly deep within you that just ain’t so.

Ron Friedman
Yeah, and, you know, there’s research on feedback. And what the research tells us is that, for people with high self-esteem, they actually prefer negative feedback to positive feedback. And it’s because they know you can’t improve from positive feedback.

Positive feedback just tells you to repeat the thing you didn’t before. Negative feedback offers clues about how you can improve your performance in the future. The challenge is most people aren’t very high on self-esteem, so you can’t give people negative feedback if you want them to improve.

In fact, one of the research articles I cite in Superteams is that 97% of feedback does not improve performance – 97. In fact, 30% of feedback makes people worse at what they were doing. And so the question is, “How do you get it right? How do you model your feedback after the 3% that’s actually effective?”

And one of the most important tips I can offer you is to focus your feedback on what people can do differently in the future. Don’t re-litigate the past. Don’t tell them what they did wrong. Don’t tell them how it made you feel and the impact on you.

Talk about one change that you’d like them to consider the next time they do the task. And that will lead people to be far more receptive to your feedback and is far more likely to improve their performance.

Pete Mockaitis
Yeah. Very good. Well, Ron, tell me, anything else you want to make sure to mention before we hear about some of your favorite things?

Ron Friedman
Well, one of the things I tried to do with this book is I really wanted people to apply the insights. And so I created a free masterclass. You can find it at SuperteamsMasterclass.com, and it gives you the book’s best insights in under 20 minutes, and – this is key – it gives you a discussion guide for sharing some of these ideas with the people on your team. It’s completely free, SuperteamsMasterclass.com.

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

Ron Friedman
So in the book, I talk about this general manager named Sam Presti, he’s the head of the Oklahoma City Thunder. And his office is filled with quotes. And it’s because, apparently, this is what he does, where he reads a book he likes, he highlights the quote, and he prints it out, and he slaps it on the wall so he doesn’t forget it.

So I’ve adapted that same approach. I’ve got quotes all over my office. Okay, I just picked out one that I thought was great. “Eighty percent out the door is better than a hundred percent in the drawer.”

Pete Mockaitis
All right.

Ron Friedman
And the idea is just get stuff out even if it’s not perfect because it’ll allow you to move on to the next thing.

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

Ron Friedman
The study that was the spark for this research on Superteams was a study by Sonja Lyubomirsky where she looked at what happy people do differently. And so the way she did the research was she found people, she had people evaluate their level of happiness.

And then she asked them about their habits. And then she separated out the happy people from the unhappy people, and looked to see, “What are the happy people doing differently that contributes to their happiness?” And it’s a classic study.

And some of the findings were, don’t compare yourself to people who you consider more successful because it’s wasted energy, it’ll make you unhappy. And so that is what led me to the research comparing high-performing teams against average teams.

Pete Mockaitis
Okay. And a favorite book?

Ron Friedman
So a recent book that I really enjoyed, it’s called The Award. And it’s about a guy who wins a literary award. And I don’t know how to describe this without ruining the book for people, but it’s not what you expect it to be. And it’s all kinds of shenanigans that is very funny to read about.

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

Ron Friedman
Yeah, waterproof notepads. They enable you to write down your best ideas in the shower, and it’s actually where I write my to-do list for the next day.

Pete Mockaitis
All right. And a favorite habit?

Ron Friedman
Eat dinner early. It is a complete life hack. It will allow you to fall asleep faster and get a much deeper sleep. And so you aim for finishing your dinner five hours before bed.

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

Ron Friedman
When I do workshops on superteams, I talk about taking what makes your vacation restorative and applying it to your everyday life. And so the mistake that I think a lot of people make is that they wait until vacations in order to recover.

But if you can identify what makes vacations restorative for you and schedule that onto your calendar, you’ll have way more energy. So an example of this might be, Pete, you like to swim. If you can find a way to swim once a week, maybe on weekends, I’m willing to bet you’re going to show up at work with more energy.

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

Ron Friedman
I would point them to SuperteamsInc. That is the name of my company. We do keynotes, workshops. We love to teach leaders how to apply these insights. And so that’s the best way to find me.

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

Ron Friedman
Yes. I would urge you, the next time you want to, if you happen to pick up an idea from this conversation, or if you read Superteams, and you want to apply some of those ideas to your team at work, but you’re not the leader, I would urge you to talk to your leader about running an experiment.

Don’t suggest a complete wholesale change. Say, “Hey, can we try this for one week and see how it goes?” Like, a meeting guideline or a focus block. Try it because, what often happens is when leaders are offered an experiment, they’re far less likely to reject it out of hand because it’s just something they don’t need to commit to forever. They’re just trying it for one week and seeing how it goes.

But then even, if they don’t agree with your experiment, they’ll appreciate the idea that you’re trying to improve the way the team operates and makes you look great.

Pete Mockaitis
All right. Ron, thank you.

Ron Friedman
My pleasure, Pete. Thanks for having me.

1162: How to Set Yourself Up for Successful Change with Eric Zimmer

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Eric Zimmer reveals the small steps that build momentum and help create lasting habit transformations.

You’ll Learn

  1. Why most change efforts fail
  2. How to talk yourself into choosing the right thing
  3. The six ways we self-sabotage—and how to stop them

About Eric

Eric Zimmer is an author, teacher, speaker, and the creator of The One You Feed podcast. At 24, Eric was homeless, addicted to heroin, and facing prison. His journey from those depths sparked his lifelong inquiry into human transformation and resilience. Through his behavior coaching, workshops, and mentorship, he has guided thousands worldwide in creating sustainable habits that last through steady change. His approach combines cutting-edge science with timeless wisdom, providing practical pathways to greater integrity and deeper meaning.

His story and his work have been featured in the media, including TedX, Mind Body Green, Elephant Journal, the BBC and Brain Pickings. His new book is How a Little Becomes a Lot: The Art of Small Changes for a More Meaningful Life.

Resources Mentioned

Thank you, Sponsors!

Eric Zimmer Interview Transcript

Pete Mockaitis
Eric, welcome back!

Eric Zimmer
Thanks, Pete. I’m really happy to be here, years later.

Pete Mockaitis
Yeah. Well, that was wild. A thousand episodes ago we chatted and, in the meantime, you’ve been doing some really cool stuff. So I’m excited to talk about How a Little Becomes A Lot.

Could you kick us off by sharing what do you think is among the most fascinating or surprising or counterintuitive discoveries you’ve made as you’ve been, you know, learning these lessons and researching and packaging them into this book?

Eric Zimmer
Well, I think the first one is the idea that small change is what matters. So I start the book with a story that I think illustrates it well. And if you were filming the movie of my life, you would see a really pivotal scene where I walked into a treatment center in 1994 in Columbus, Ohio, and it’s the dead of winter. I’m a homeless heroin addict. I weigh a hundred pounds. I’m jaundiced and I’m yellow from hepatitis C.

Prosecutor says I might be going to jail for fifty years. I’m just really broken. And I go in, and they say, “We think you need to go to long-term treatment.” To which I say, “Meh, no, thank you.” And I go back to my room and I have what we call in recovery a moment of clarity, which I could say was more like just being scared to death when I looked at what was coming, right?

Because I was just like, “I’m going to jail or to die, and soon.” And so I went back out, and I said, “All right, all right, I’ll go to your treatment.” And that would be the really big pivotal moment. The director would spend a lot of time there. You know, the music would swell in the background triumphant.

Pete Mockaitis
Push shot.

Eric Zimmer
Exactly. And it’s not that that moment wasn’t important. Of course, it was, but that moment has significance because it was followed by thousands upon thousands of little decisions, little actions that I made after that, to move towards recovery and away from addiction. If I didn’t do those things, that would just be yet another failed attempt.

And so I think when we think about changing, we all want to make the big change that will change things quickly, change them for good. You know, we think about the epiphany or the watershed moment or this thing. And those things are useful.

But a lot of big change efforts fail because nobody is really understanding that it has to happen little bit by little bit. And we could go into a thousand different examples of that. But that’s the core principle that underlies a lot of the book.

Pete Mockaitis
Yes, well said, in terms of if you had a moment of clarity, you showed up for a moment or a few days of of rehab, and then that was, you know, and then relapsed, then it’s interesting that that moment doesn’t seem as consequential without the future ahead of it.

Eric Zimmer
Yeah. And, I mean, and, frankly, that moment came about because of lots and lots of little small moments before that where I did make attempts to change, right? All of those were important, too. And we tend to think of, when we go to change something, we tend to think of just the action piece of it, and the action piece is part of it.

But if you look at models in behavior science around change, you recognize, and the most famous one is called the stages of change model, right, where you go through pre-contemplation, then you you’re going through contemplation, you’re thinking, “Should I make this change? Is it worth it?”

Then you’re doing planning before you actually even get to the activity. And so this book is really trying to show all of those mechanisms and how we can get better at both making change. That’s the first half of the book. And then the second half of the book is, “How do we get better at working with the sort of changes that life just tends to throw our way that we don’t really like?”

Pete Mockaitis
Understood. Yeah. Okay. Well, then, lay it on us, in terms of when we want to make changes, how do we do it better? And can you keep illustrating it with real changes made?

Eric Zimmer
Sure. I mean, let’s just pick something like you want to get an exercise routine. The way most people do it is they, one day, wake up and they go, “All right, I’m going to get in better shape.”

Now, oftentimes, this is just a vague idea for a while, right? Maybe you go to the gym occasionally, you take a walk occasionally, but nothing’s really happening. So I would say, you know, we’re kind of in the contemplation stage there, right? We’re thinking about it.

We might be taking certain things that we’re doing, but we’re not really making progress. And so the first thing is the book walks through it, is to sort of accept and understand the little by little approach. Then what we need to figure out is like, “Why are we changing? Like, what is it that we’re changing? And why does it matter?”

Because we really do need to be motivated to do it and understand why it’s important to us. How does it tie into the things that are most important to us in life? And then from there, I have a method in the book called the SPAR method, where we go through and we plan the change out. We get very, very specific.

And we can go into that in more detail if you would like. And then the next piece is we learn to navigate the moments that are difficult. So if I do the the work right in the planning phase, I kind of get pushed to what I call a choice point.

It’s the moment where you basically say, “Oh, yeah, I am going to get on the bike,” or, “I’m going to continue to lay here on the couch.” And so the next skill we need to learn is we need to learn how to negotiate those choice points.

Because if we go the direction we don’t want to go, we end up on the couch when the best part of us wants to be on the bike, then it’s because we were feeling or thinking something, or saying something to ourselves at that moment, that we didn’t know how to work through. And so then we can look at those moments and find our way and work through them.

And that’s the basic process of setting up a new positive change. And we can go into any more detail on any aspects of that, but that’s the framework broadly.

Pete Mockaitis
Well, yeah, let’s hear it. Let’s work through the S-P-A-R there.

Eric Zimmer
Yeah, so the S stands for specificity. When we’re trying to do a new behavior, we need to be really specific about what we’re doing.

“What’s the exercise? When am I doing it? How am I doing it? Where am I doing it?” All that specificity is important because ambiguity is really often our enemy. Because what happens is we’re trying to figure out what to do and do it at the same time.

The best example I can give you is that, like, in my day-to-day work, I get off a call and I have an hour and a half window. And now I’m sitting there, I’m going, “Well, what should I work on? Well, I could work on this, and I could work on that. But you know, I should walk. I haven’t really moved much at all today. And, you know, oh, I could check this score.”

And we end up burning a lot of that time because we don’t know, specifically, what we’re doing. I know I do much better when I’m like, “Oh, that hour and a half between the call with Pete and my next conversation, that hour and a half is going towards interview prep for the two interviews I need to do on Wednesday,” right? So specificity is always our friend in the beginning. Ambiguity is our enemy.

P stands for prompts. It’s basically we get reminded to do the thing. Now that sounds sort of silly, but it’s not. Like, I’ve been doing this thing where I’m trying to take a walk about every 30 minutes for five minutes. It doesn’t always work. You and I are going to talk for 45 minutes. I’m not going to get up in the middle of it.

But if I don’t remind myself to do it, I just don’t do it. If it’s the morning, and I’m on the couch, and at a certain point, I need to go get on the exercise bike, and at that moment, I’m doing what I like to do in the morning oftentimes, which is read Substack. So there I am reading Substack.

If I don’t have an alarm that tells me it’s time to get up and go do it, I’ll often go right by it. And then I’ll suddenly be like, “Oh, I only have 15 minutes to do it now. Why bother?” So prompts are important. Alignment is about setting up our environment to support us in what we’re trying to do.

So the simplest example of that in my life is, if you could see over my shoulder, I’ve got two guitars there, and they are sitting out on stands. I play my guitar probably 75% more often when it’s on the stand versus in the case laying right there, which makes me feel like, “Well, what kind of dumb animal am I? Like it takes five seconds to open a guitar case.”

But friction, you said it before we started, thinking about friction, right? If I want to make something easier, if I want to do more of something, I want to make it easier to do. How can I set up my environment, alignment? And a key part of our environment also is other people.

So what kind of support do I have? Who’s helping me? Who am I sharing this with? Who might help me be accountable to this? And then finally the R is for resilience, which is where we step back and we go, “Okay, what could go wrong with this plan?” So if I’m walking a client through this, we go through all that, and then I’ll say, “All right, now let’s find the flaws in what we’ve planned.”

You can’t plan for everything. But if I’ve got a client who is trying to finish a novel, and the plan is to write for an hour after the kids get on the school bus, the thing we have to talk about is, “What happens when they don’t get on the school bus?” because that’s inevitable. That is going to happen.

Now the answer might be, “If the kids are home sick, that’s just a day I don’t write. Okay.” But it might be like, “Oh, here’s what I’m going to do. I’m going to go in the room where the kids are, and I’m not going to get any actual real writing done but I’ll use that as research time.” We just have a plan. And so that’s SPAR: specificity, prompts, alignment, resilience.

Pete Mockaitis
Okay. I’m thinking about the specificity part, and I think you’ve nailed it in terms of, “Oh, hey, I got some ‘free time’ in between my calendared obligations with other humans.” And there’s a question there, like, “What should I do?”

And, in a way, the answer is infinite in terms of there’s billions of things you could do, and maybe dozens of things that would be useful to your general goals and values and priorities. So how do we land at that kind of clarity like, “Ah, of course, I’m preparing for interviews,” or, “Of course, I’m writing this book,” or, “I’m getting on the exercise bike”?

Eric Zimmer
Well, I mean, I have a section in the book where we kind of start by talking about like, “What do we value? Like, what’s most important to us?” And I have a bunch of different exercises for doing that. And then there is a process of translating that value into action, right?

And so I can’t give any advice that says, like, “Here is exactly how you always figure out what the most important thing is.” As professionals say, in a career, that’s part of what we get paid to do. We get paid to look at all the stuff that has to get done, which is always more than can get done. And we’re paid to decide which of those things is going to add the most value.

But the more often we ask that question, the better, right? The more often we ask that question, the better choices we make. Whereas, a lot of times, we just run into the default. So if I’m not planning well, what will happen to me is I’ll get off the call, and I’ll look at my task list.

And what ends up usually happening is whatever is easiest to do, right? And I call this separating decision from action. I want to decide. And then, at a different time, I want to act. And what I want is the the wisest version of myself deciding what’s important to do this week. There’s no shortcut for that, right?

There’s no shortcut for spending the time to go, like you said, “Of all the things I could do, what matters here?” And then deciding that those are the things that are going to happen, and then trying to stick to it. So there’s not a simple answer to that.

But starting, you know, Stephen Covey, in his famous book, The 7 Habits of Highly Effective People, said, “Begin with the end in mind,” right? Like, “Where am I going and why? What matters to me? What’s important to me?”

Pete Mockaitis
Okay. So do you have any thoughts for separating what you “should do” from what is, in fact, truly, deeply, resonantly aligned with your deepest value-ness?

Eric Zimmer
Yeah, I mean, values are hard to figure out. They really are. It’s hard work, because two things happen, right? One is we’re very often just presented a giant list of values to pick from, and you agree with nearly all of them, right?

Like, you look at it, you’re like, “Well, I value, yeah, I value truth, I value honesty. Sure, I value freedom, and I value responsibility, and I value…” right? I mean, okay, great. I don’t know how to figure that out, right? It’s just a giant list.

The other reason values work is really difficult is that, often, as you start to determine what you really do value, you start seeing the gap between what you value and what you do, and that’s uncomfortable, but it’s good medicine, right? It’s the kind of medicine that tastes bad going down, but is really good for you because that’s the only way we end up with a life that feels meaningful to us, is to take the time to figure it out.

So I’ll give you one quick one that’s from the book that people could do. And it’s called pick a guide. And it basically says, “Find somebody that you admire, and write down what is it about them that you admire. Why do you admire them? What are the traits about that person that you value?” And that’ll tell you something about what’s important to you. Because you’ve put this person here as somebody that you admire, “Why? Why do I admire them?”  So that’s a very simple one.

Like I said, there’s a bunch of others, and my recommendation is just to do a variety of different values exercises, like, you know, do one today and do another tomorrow, and then one next week. And, ideally, then we start to triangulate in on what is most important to us.

Now there’s an important thing to know, though, which is that in that chapter I talk about two types of conflicts, right? One is values versus desires. And values are the thing, you know, the way I define a value is it’s the thing that the best part of me has decided is worth wanting.

Desires are the things you just want. So we have values-versus-desire conflict all the time. It’s kind of the way I frame it is, “What do I want most?” a value, versus, “What do I want now?” a desire. And those are very difficult sometimes, but you can work through those.

The harder type of conflict is the values-to-values conflict, when you value two things. If you have a family and a career that you value, you are familiar with this values conflict all the time. We call it work-life balance, right? And we want it to balance so we don’t have to keep having it tug us in different directions.

But the reality is that I don’t think, that ever goes away. It doesn’t ever go away. But for me, when I recognize that and I can say, “Oh, look, this value is conflicting with this value,” and I can name the stakes. It doesn’t necessarily mean I know exactly what to do.

But I can relax a little bit because I go, “Oh, this is just totally normal that I’m going to feel this pull.” And then I can think about, “Well, okay, how can I work with these?” And I think of it less in my life these days as like this tension and pull, and more as sort of a dance.

You know, it’s a little bit more of a dance between these different values. So, yes, that’s my not-short answer.

Pete Mockaitis
Oh, well, thank you. That’s good. Well, then in the universe of prompts, alignment, and resilience, do you have any favorite examples or tips and tricks, do’s and don’ts for doing this well?

Because, I mean, I think, in many ways, prompt it’s like, “Okay, I could set a timer on my phone. That’s handy.” I’d love to hear what are some cool, creative, clever approaches to these bits?

Eric Zimmer
Well, prompts can be lots of different things. The obvious one is a time-based prompt. If something goes off on my phone at a certain time and it tells me to do X, Y, or Z. And these are really important. It’s basically how we organize most of our lives, right, “Oh, it’s time to go to that meeting,” “It’s time to eat dinner,” “It’s time to go to bed,” right? So that’s one type of prompt.

But there are also some others. And another is like a preceding-event prompt, right, “I do this, then I do that.” So an example of this is I will spend five minutes meditating after I take the dogs for a walk. You take the dogs for a walk, ideally, every day. It’s something that consistently happens. You just bolt something onto it.

That’s a really good one. I think the term, one of the terms in behavior science that is used for this sometimes is habit stacking. You’re stacking one on top of the other. You need to make sure that what you’re stacking it on is something that actually happens consistently. So we’ve got that kind of prompt.

We can have a location-based prompt. We can be like, “Every time I come to a red light…” Now, again, you’re not going to be like, “Every time I come to a red light, it’s time to get on my bike,” right? But it could be, if you’re trying to change a way of thinking, like you’ve got a thought pattern, “You know, every time I come to the red light, I could just reinforce the thoughts that I want to have.”

“Every time I come to a red light, I will just spend two minutes thinking about, like, what’s actually going well in my life.” So those location-based prompts are also really valuable. So that’s a couple different tips on prompts.

Pete Mockaitis
Okay. And then with regard to alignment, environmental setups, we got the guitar example, which is delightful. Any other good moves you’ve seen there?

Eric Zimmer
Well, I think there’s a basic principle we just want to keep in mind. And it’s if we want to do more of something, make it easier. And you want to do less of it, make it harder. So it’s the classic, you know, if you don’t want to eat junk food, don’t have it in the house.

Now, DoorDash and Uber Eats and Delivery and all that has really made that one harder. But if I have to, if it’s just open the fridge and there the thing is, versus I maybe have to get in the car, or I have to spend the time getting on an app, I mean, you just want to have friction, right?

Pete Mockaitis
Yeah.

Eric Zimmer
And so that’s the basic idea. And you just want to get creative, like, “What can I do to make this easier? Oh, I can, if I have trouble getting out the door in the morning, I could have all my gym clothes set out and right by the door. I could set the coffee to automatically brew 10 minutes before I get up.” I mean, we could just do things to ease us along.

And again, oftentimes, we think of these, and we go, “That’s so obvious, it doesn’t matter.” But there’s the guitar case example, right? And again, like I said, when I think about that, I’m like, “That is stupid. Why can’t I just open a guitar case? That’s dumb.” But it’s unquestionable that I do it more when it’s sitting there.

Pete Mockaitis
Yes. And, likewise, with junk food in terms of if it’s there, I mean, I will eat it, even though I don’t want to. Yeah.

Eric Zimmer
Yeah, 100%. Yeah. Try not to. Just make it harder. You know, I had a client for a while who was dealing with some issues with pornography, and it just wasn’t what he wanted to do.

And so we started, and we were like, “You know what, let’s have you log out of your computer before you go to bed.” Well, that wasn’t enough friction. “Oh, let’s have you power the computer off.” Not enough friction.

Where we ended up was, “Let’s have you put your computer in your car before you go to bed.” That was enough friction. It gave him enough time to think, “Do I want to do this?” And that is really valuable in that way.

Here’s an example of an environmental setup. So my digital tick, such as I have one, is checking my email too often. There’s just no need to check my email as often as I sometimes will. So, for me, what I have is a little app on my phone, in that when I click my email app, this other app pops up, and it says, it makes me take a deep breath, and then asks me, “Do you want to do it?”

Very often, my answer to that is no. I just was doing it automatically. So by introducing that little bit of environmental change, a little bit of friction, I go, “No, I don’t want to do it,” because it’s given me a moment to contemplate.

Pete Mockaitis
Yeah, that’s great. And then with regard to people, I mean, they can do that as well. Like, I’ve had a friend say to me, “Hey, if you see me in this shared office space, playing XBOX for more than 20 minutes, say, ‘Hey, looks like you’ve been playing for more than 20 minutes.’”

And he’s like, “Oh, yeah, you’re right.” And then he immediately shut it off. It’s like, “Oh.” Like, that’s all it took was enough of a prompt in terms of, like, “Oh, yeah, you’re right. I kind of totally zoned out. Now I’m zoned back in. So thank you, and we’re done now.”

Eric Zimmer
Yeah, find a friend to meet you at the gym. Find a friend to take a walk with you. Those are all people prompts. And many of us may know a person prompt that’s just no good for us, also. The minute we see so and so, you know, we know we’re going to get in trouble that night.

Pete Mockaitis
Yeah. Understood. Okay. Well, now, let’s talk about these choice points, where the rubber meets the road, the battle. Yeah, there’s a thing and the time comes to do the thing, and, by golly, you just don’t want to. What do you do with that?

Eric Zimmer
Yeah, so again, I want to stress the first part of this, the structural, the planning, the why I’m doing it, like, we need to do that. If we don’t do it, we will lose at choice points far more often than we win.

So we want to stack the deck. That’s one thing almost all behavioral scientists would agree on. It’s, like, don’t rely on self-control more than you have to. And self-control is the kind of thing that we need when it’s that moment.

So the good news about being at a choice point is that we don’t have to analyze our whole life for why we’re not doing something. We analyze that moment. And in the book, I have something I call the six saboteurs of self-control.

But what I really did is I thought about, like, “What are the common things that are going on inside someone at the moment that they make the choice that the best part of them wishes they hadn’t?” You know, I just discussed one, which is like the autopilot, “I’m not even choosing, it just happens automatically. I have my phone in my hand and I don’t even know how it happened.” “Oh, I wasn’t even thinking, and the next thing you know, I’m eating a Twinkie,” right?

Another one is, and I had this a lot with writing the book, it’s around self doubt. Like, I really didn’t think, I really doubted my ability to write a good book. I mean, deep doubt. It brought up self-doubt I haven’t had in a long, long time.

And so what I would find is, it’s time to write, and I don’t want to. There’s resistance. And if I would examine, “Okay, what’s going on in that moment?” what I would realize, it’s some form of there’s just this underlying like, “You’re not any good at this. It’s not going to go well. What’s the point? None of this is going to…You’re not good enough to write a book.”

And so, in that moment, I don’t have to solve self-doubt, because you can’t in a lot of cases. All I have to do is turn it down enough to allow me to do the action. So I might say something to myself, like, “Well, do you know that you can’t write a good book?”

And the answer is, “Well, no, of course, I don’t know that.” Even my most pessimistic self is like, “Well, we don’t know.” And sometimes I just go, “Okay, well, do you believe if you sit down and write that you’ll get better at it and you’ll have a better chance of writing a good book?” And I’ll go, “Yeah, I think so.” And that would be enough, right?

I don’t have to suddenly believe that I am the next John Steinbeck in order to do it. I can’t tell myself, “You’re an amazing writer,” because I don’t believe it. But I find what I can say to myself that gets me to do the action.

So, there’s another one which is like emotional escapism, right? Like, for whatever reason, when I get close to doing this thing, I just feel yucky inside. Okay, well, how can I work with that? You know, how can I say, “Okay, well, what am I actually feeling? Oh, what I’m feeling is, oh, I’m actually tired.”

Okay. Well, how would I talk to myself if I’m tired? I might say, “Well, you know what, it’s always hard getting started. Just get started, see what happens, you know, and let’s check in five minutes down the road.” Enough to get me started.

So a lot of times, in those moments, it’s just we’ve got to find out what to say to ourselves, how we coach ourselves to go in the direction we want. And most people have the experience of, very often, once you start something, it gets easier to do. It’s that initial friction.

I’ve been watching this show about space, and every time I see a rocket launch, I think about this. I’m like, that’s sometimes what it feels like to start something, right? You see, and you’re like, “They use so much energy to get the thing out of the atmosphere. Once it’s free of the gravity of the earth, it tends to go on its own.”

We’re often the same way, “I’ve got to get out of the gravity of the moment that’s pulling me down. If I can start, then I go.”

Pete Mockaitis
Yes. You know, I’ve coaxed myself successfully a number of times in terms of, “Oh, that just feels too hard.” But sometimes even five minutes feels like too big of a commitment. And so it’s like, “You know what? I’m going to do one minute. I will do one minute, and then we’ll see what happens.” And that’s enough.

Eric Zimmer
I use that trick far more than I think I should. I’m like, “Oh, I’ve hosted a podcast about this stuff for 12 years. I’ve coached hundreds of people around the world. I’ve written a book on this. Surely I don’t need to do that.” Well, yes, I do, right, because it works.

You know, my one is I keep talking about the Peloton bike because it’s just a consistent thing, right? It’s a big part of my workout routine, and I face resistance in the morning. So I’ll just be like, “Just go put on your bike shoes.” By the time I’m in there, off the couch, I’ve escaped the gravitational pull of my couch. And now, I can take the next step, and I can take the next step.

I use that so often. And it’s another example of the little by little principle, right? One idea is that you try and make a small change. The other is that you take a big change and you just try and bite off the littlest part of it to start.

Pete Mockaitis
Very good. Okay, so we’ve got six saboteurs. We’ve got three. Let’s hear some more.

Eric Zimmer
Let’s see. We’ve got the insignificance trap. This isn’t where I so much doubt that I can do it. I doubt that it matters. This is where I’m not connecting the dots of little bit by little bit, a little becomes a lot. My favorite story of this is I had someone I was good friends with, and she was an alcoholic addict also.

And she tells this story, and she’s totally serious. She’s like, “My landlord would come to me, and say, ‘You haven’t paid the rent again, and yet here you are on the porch drinking a six-pack. Why can’t you take that money and put it towards the rent?’”

And she would say, “You dummy. Like, I can’t pay rent for the cost of a six-pack.” Like, she could not connect the dots in her mind that if she didn’t do that every day, she would have a whole lot more money. It just didn’t add up.

And so that’s often the way we are also. It’s like, “Well, what does this one time matter? It’s not going to go anywhere.” I think finances, people fall into this. I know I have. Like, I’ve made the mistake that we all caution every young person against, which is start early – saving. Well, I didn’t.

So what happens is, let’s play that forward 15 years, and my brain starts going, “Well, I didn’t really start early enough. And so what I’m able to put away now, like, I’m not going to be able to get where I need to get. So I don’t do it,” right, which just then perpetuates the same problem. So that’s a really big one. We have to kind of convince ourselves that the little things we do, do, indeed, add up to something more.

Pete Mockaitis
You know, I like that a lot in the world of finance because I’m thinking about, when I look at a recurring monthly expense, like a subscription or something, it’s like, “Oh, it’s whatever, it’s five bucks a month, you know, whatever.”

And so I just now habitually rephrase that to, “It’s $600 per decade. So a decade from now, would I rather have 600 bucks that has, hopefully, been invested and growing? Or would I rather have that subscription?”

Eric Zimmer

Exactly. And then the other thing that’s really helpful for me, also, is sometimes that works. Other times, I have to say like, “What else could you do with that money?” That’s always a really helpful one. Like, “Oh, I’m spending $200 a month on this business system that does X, Y, or Z. Oh, I could take that $200, and I could put it into ads for the podcast. Oh, well, that might be even more valuable.”

So that’s another one for me is always recognizing, like, “What am I trading it? What’s the actual trade here?”

Pete Mockaitis

Sure thing. And the other saboteurs?

Eric Zimmer
Another is that we physically just don’t feel good. And this one is, part of it is the response, part of the response goes back to planning, right? Like, the thing, you know, it’s the most obvious thing in the world, but most people don’t obviously think of it.

If you’re going to do something in the morning, you actually have to start that process the night before. Because if you don’t go to bed until 2:00 in the morning, your odds of doing something at 6:00 are very low, right? So we could say that this tiredness is partially planning.

We have a phrase in recovery, “Don’t allow yourself to get too hungry, angry, lonely, or tired,” because that will manifest for you as wanting to drink. And so I think we can look at this same thing. Like, “What is going on here? Am I too hungry? Well, do I need to eat?”

Sometimes we just need to take care of the physical stuff that’s going on. Or, again, back to tired, “How do I learn to talk to myself through tired?” And, for me, that is usually a version of it’s always hardest at the beginning. Once you get going, you’re going to feel better, you’re going to be more into it, you’re going to get energy from doing it. And so I talk myself through that physical state.

Pete Mockaitis
Okay. And then the last one?

Eric Zimmer
Oh, yes, a classic one. I gave it the clever name out of the short-sighted stumble. But, basically, it is the incredibly human tendency that says that, “I value what’s happening right now way over something that’s in the future.” Researchers call this delay discounting.

We’re just not good at it as people. We’re not good at going, “Oh, well, you know, I want this little thing right now, but what I really want is this.” So the short-sighted stumble, there’s two ways to work with that.

The first, for me, is to ask myself that question, “What do I want most versus what do I want now?” It puts it in time. That works for me a lot, because I go, “Well, what I want most actually is to be healthy. What I want now is to eat the ice cream.”

The other tool for this is another thing I learned early in recovery. We called it playing the tape all the way through. And it meant that, for a lot of us, we just think about the first scene. So if I go back to myself and drug addiction, what I’m playing through is how good it would feel to get high, or how bad I feel right now, and how that would help that.

But I got to keep going because what’s going to happen after that? “Oh, well, about five minutes after that, what’s going to happen is that all the shame and the fear are going to come rushing in. And then I’m going to want to get high even more because how do I cope with shame and fear? It’s by getting high.”

“Oh, and how do I have the money to do that? Oh, I got to go steal something. Oh, you know, well, you’re looking at 50 years in prison already.” I play it all the way through. And so we can do this with so many different things.

Imagine you’ve got an issue where you scroll too long on Instagram in the morning, you end up being late for work. It’s one thing to think, “I should get off Instagram.” You know, you may have that thought vaguely. It’s another thing to pause and go, “Okay, what’s going to happen next? Oh, well, I’m going to end up in 15 minutes, frantically rushing out the door, saying to myself, ‘Why do you always do this?’”

“Then I’m going to get in the car and I’m going to hate everybody on the road for going too slow. Then I’m going to get to work and I’m going to have to do that sort of awkward shuffle past my boss’ office, hoping they don’t see me. And then I’m going to sit there and wonder all morning, like, ‘Did I screw up again? Am I jeopardizing my career?’”

When I think through that and I see it and I feel it, that’s a lot more visceral than “I should probably stop doing this.” So that is the short-sighted stumble.

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

Eric Zimmer

I think the only thing I’ll say about the book, also, is that the second half of the book is really about dealing with the sort of changes that happen to us, and really about some of the ways that our mental attitudes shape our response to both change we’re trying to make and change that happens to us. So, in some ways, it’s kind of two books in one.

Pete Mockaitis
Well, is there any kind of critical guiding light or mantra about that second piece you’d like to share?

Eric Zimmer
Yeah, I think that it’s that we are – we’ve heard this before, I’m sure you’ve heard people say it – we are meaning-making machines. Meaning, we always are constructing meaning out of the facts of what happens.

We don’t see that. We just think the way we see it is the way it is, but learning to be able to question that is really valuable. And there’s just three quick questions we can ask ourselves, right? The first is, “What am I making this mean?” It just recognizes that we are, indeed, constructing a meaning.

And then, “What else could it mean?” And then the final one is, like, “Which of those two is most useful?” So if I have a day where I’m writing, and it goes really badly, at the end of the day, I could say to myself, “See, I knew you couldn’t write a book. You’re not a good writer. This is never going to work,” etc.

I could also say, “You know what? You just had a bad day. Everybody has bad days. You didn’t sleep well last night.” So that’s the “What else could it mean?” Which meaning is more useful? Well, the one that says, “You had a bad day. Try again tomorrow,” is far more useful.

It’s not necessarily even more true because the future is not written at that moment. It’s not that one of those is true and the other isn’t, but one of them is decidedly more useful than the other.

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

Eric Zimmer
It’s a line from a song, and the song is called “My Mind’s Got a Mind of Its Own.” It’s by Jimmie Dale Gilmore. And I love that phrase, “My mind’s got a mind of its own,” because it points to this fact that we do want multiple different things. We are motivationally complex creatures. And I just think it’s a clever way of making that obvious.

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

Eric Zimmer
My favorite is probably the Rat Park experiments.

Pete Mockaitis
All right.

Eric Zimmer
It’s basically, you know, there were a bunch of studies done that showed that if you give a rat heroin or cocaine, and it’s a rat in a cage, it will take those drugs till it dies, which tells us the basic idea is how terrible those drugs are. And this is really the way it was used, particularly, in the ‘80s, the war on drugs.

But there was a researcher named Bruce Alexander, who asked a question, he said, “Well, what if the problem isn’t the drugs, but it’s the cage?” And so he, basically, constructed what he called Rat Park, which was like paradise for rats, you know, lots of other rats to hang out with, lots of room to run around, fun things to do.

And what he found was that most of the rats, not all of them, but most of the rats moved away from a constant heroin-cocaine addiction to a normal life. Now some remain addicts, just like there’s addicts in every population. But it really pointed to the important role that our environment plays in what we do.

Pete Mockaitis
Yeah. And a favorite book?

Eric Zimmer
My favorite book is, it’s called The Brothers K, not The Brothers Karamazorov, which is the Russian novel by Dostoevsky. It’s called The Brothers K, and it’s by an American writer called David James Duncan, and it is a fiction book, and it’s a family saga epic. And it’s still my favorite novel, you know, 30 years after I read it, probably.

Pete Mockaitis
Okay. And a favorite tool?

Eric Zimmer
My favorite tool is that little app I shared on my phone that allows me to sort of cause myself to pause before I do something.

Pete Mockaitis
And what is it called?

Eric Zimmer
ClearSpace.

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

Eric Zimmer
“A little bit of something is better than a lot of nothing.”

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

Eric Zimmer
OneYouFeed.net. That’s O-N-E-Y-O-U-F-E-E-D.net. You can find the book, the podcast, our weekly newsletter, all things related to what we do.

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

Eric Zimmer
Keep thinking about what really matters. Keep thinking about what adds the most value. Can I share a quick story on that?

Pete Mockaitis

Oh, yeah.

Eric Zimmer
Okay. So when I started the podcast, I was leading really large software projects, you know, $150, $200 million software projects. And I, all of a sudden, had this side job that I wanted to give all my time to. And so I had this real challenge because, I mean, my professional career was really, really demanding.

And what I found out was something really interesting, is that the more time I spent thinking about, like, “What really matters in this project being successful? What really matters in this software release? What really matters?”

And I was doing that because I wanted to spend more time doing this other thing. I got better at what I did. I was spending less time doing it, and yet I got better at it, you know? And it was because I was so focused on, “What is the most important thing here?”

We do so many things every day that don’t actually really make that much difference. And by being ruthlessly focused on what did, I became better at my job while freeing up time to do something else.

Pete Mockaitis
All right. Eric, thank you.

Eric Zimmer
Thank you so much, Pete. It’s wonderful to see you and talk to you again.

2024 GREATS: 935: The Five Steps to Winning Every Week with Demir Bentley

By | Podcasts | No Comments

Demir Bentley reveals the five simple steps to successfully plan and execute vastly more satisfying and productive weeks.

You’ll Learn:

  1. Why nobody really plans their week—and how to fix it
  2. The master key to getting ahead of your to-do list
  3. How to transform your calendar into a power tool  

About Demir

Demir Bentley is an executive productivity coach, co-founder of Lifehack Method and WSJ Bestselling author of Winning The Week: How To Plan A Successful Week, Every Week.

He teaches hard-hitting efficiency techniques and proven accountability strategies that have helped clients generate millions in revenue while saving thousands of hours.

In the past eight years, he’s helped more than 70,000 professionals, including executives from Facebook, Google, Uber and PepsiCo, to prevent burnout and create more freedom in their lives.

Resources Mentioned

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  • CleanMyMac. Use the promo code BEAWESOME for 10% off on any CleanMyMac subscription plan.
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Demir Bentley Interview Transcript

Pete Mockaitis

Demir, welcome.

Demir Bentley

Good to see you, Pete.

Pete Mockaitis

I am so excited to learn all about Winning the Week and your flavor of productive goodness. And I think I’d like to start with your origin story.

Demir Bentley

Like a comic book.

Pete Mockaitis

Yes, very much, maybe as a radioactive spider but, in your case…

Demir Bentley

It’s close.

Pete Mockaitis

…you’re working at Wall Street, not loving it so much. Take us into the scene.

Demir Bentley

Like a lot of people, I learned to perform for love when I was really young, and I don’t want to get too deep, but I think a lot of people just realized that they just get a little bit more love and attention if they can get those A’s, and if they can exceed. And so, I figured out young, I was like, “Oh, I can do this stuff. I can perform. I can get grades. I can write papers. I can produce things.” And so, I became one of those insecure overachievers who’s really developed a strong juicy core of, “I’m only valuable by what I can do and what I can produce.”

So, obviously, I ended up on Wall Street because that’s where all of the insecure overachievers, the most insecure overachievers go when they really want to prove to themselves that they are somebody. And I really was that “If I can make it here, I can make it anywhere” dreamer. I really felt, “If I could hack it in finance, then maybe that deep hole inside of me would finally truly be filled and I would be somebody.

No, I jest a little bit, but, seriously, there was that juicy core of, “I’ve got to make it in finance.” And I did, I got to a really high level of finance but I did it by working 80 to 100 hours. And my secret sort of sin, or my secret, like, hidden behind-the-scenes was that I was actually really massively unproductive. I just masked that lack of productivity with brute force work and just the deep guilt and shame that kept me coming back to the trough.

And so, I remember thinking, there was an episode where I remember thinking that I was so proud that my boss had come in on the weekend and had seen me there all alone, there was nobody else on the floor, and I was just there. And right after that weekend, he called me, and he said, “You know, this is actually not a good thing. Everybody else can get their work done in 40-50 hours, and you seem to be needing 80 to 90 hours of work to produce what other people are producing in 40-50 hours.”

So, that was my big wakeup call of, like, “Oh, I’ve been wearing this like a badge of pride, like a badge of honor,” the busy badge, I call it. I’ve been awarding myself the busy badge, thinking that I’m just inherently, intrinsically more valuable than other people because I have this ability and this desire to outwork everybody else and come in on nights and weekends, and just realizing that, “Actually, other people saw that as sad and pathetic.”

That didn’t stop me. I wish I could’ve said that that was the moment when I stopped but, actually, I had a health implosion. I was overweight, I was overstressed, I wasn’t sleeping, and I got, like, a mystery illness. After much testing and three surgeries, I was diagnosed with something called salary man sudden death syndrome. It’s not very common in the United States but it’s extremely common in Asia where, otherwise, healthy young person dies from extreme overworking.

And so, although there was no definitive, “You’ve got this condition,” there was a general recognition among my three doctors that if I kept working this hard, I would probably, at some point in the future, die, and that I needed to immediately cut my hours down to 40 hours a week. Now, mind you, I’m doing everything I can to keep my head above water, working 80-100 hours a week, and they’re telling me, “As of next week, you need to bring it down to 40 hours a week.”

And so, that weekend, I talk about a lot in our book, that weekend was this like crisis moment. I felt like my whole world was crashing in. I thought I was going to have to quit my work or I’d certainly get fired. It just felt like there’s just no way that it’s going to happen.

And, yet, there was a series of events that happened over the course of that weekend. I walked in next week, I worked 40 hours, I got everything done in 40 hours, and that was the beginning of this sort of rebirth, this, like, religious awakening that I had, realizing that I suck at this productivity thing, and I realized that so much more was possible. And that was the beginning of my journey in my personal productivity work, and also the beginning of my journey as, ultimately, which is hilariously becoming a productivity coach for other people and showing other people how to have that same transition.

Pete Mockaitis

Wow, this is powerful. You have a chat about productivity, you don’t think it’s going to be life or death but, for you, it literally was.

Demir Bentley

It actually was.

Pete Mockaitis

“Become more productive or die or lose your job.” Like, high stakes stuff. So, I want to dig deep for a moment. You mentioned deep shame there. What were you ashamed of?

Demir Bentley

So, like many people who are unproductive, I’m a very emotional worker. And emotional worker isn’t defined by crying in the corner. That’s not what I’m talking about. Emotional workers are the kind of people that, if they’re feeling it, they can show up in two incredible acts of productivity, incredible feats of productivity, but they can also have incredibly long periods where they can’t motivate themselves, and they’re not feeling it. And in those periods, they can barely bring themselves to lift a pencil. And in those moments, they just feel incredible self-lacerating shame and unworthiness. And they know and think that somebody is going to find them out.

Pete Mockaitis

Well, Demir, lay it on us the way. What were the initial steps you took when you were in the I-can’t-lift-a-pencil mode? And, ultimately, how did you survive by doubling your output per hour, I guess, like cutting your hours in half?

Demir Bentley

The funny thing is what really solved my first tranche of the problem was something that everybody thinks that they know that they should be doing. And I’m going to come back to the word “thinks that they know.” And it’s just planning your week. The problem with this is there’s nothing more dangerous than somebody who thinks that they know something because, then, they approach it with zero curiosity, zero sense that they have anything to learn or anything that they might be doing wrong, and way too much confidence.

And so, we actually ran a survey of 5,000 people, and the survey was only people who manage between five and 50 people, so managers, people who are already very successful, earning a lot. We asked them, “What are the top five things that you can do to be highly productive?” And almost everybody in the top three put, somewhere in the top three put planning their week. So, duh, that’s a duh moment. Almost everybody knows it. Out of 5,000 people, it is common knowledge that you should plan your week.

Then we followed up with the same 5,000 respondents. We said, “Have you planned the last, the four out of the last four weeks?” And out of 5,000 people who had said very confidently, these were people who manage between five and 50 people, making over $100,000, out of those people who confidently said, “Yes, you have to plan your week,” less than 1% of the people had planned their week in the last four weeks.

So, there’s something odd about planning your week. It is something we all know that we should be doing, and less than 1% of us have a consistent practice in doing it. That kicked us off on a sort of curious exploration around why that is. But let me just say, coming back to my story, that borne out of sheer desperation, I looked at my calendar and I did what I call the first planning session of my life, the first real planning session where I took all 40 hours, and I took every task that I needed to get done, and I allocated it a spot in that 40 hours.

And every single 30-minute increment had to fight for its life to be on my calendar. That was the very first real planning session I had. And, lo, and behold, it went from spinning my wheels at 80 hours a week to actually getting everything done 40 hours a week. And so, I will say that my rebirth, my sort of aha moment came a lot earlier than the framework that I built around it. I think I spent a lot of years trying to understand, “What happened to me? What went right? What was the difference? What changed?”

When I finally got that through the course of my coaching, I was able to sort of boil it down into the winning-week method. And now we have a framework where we can explain to people. But, at the time I realized that it was just me being desperate. And in my desperation, I realized “I’ve only got so much time. I need to be excellent with that time.”

Pete Mockaitis

Okay. And so then, you were putting individual tasks onto specific pieces of time, like, “Thursday 4:00 p.m., I answer my emails,” or whatever the thing is. So, it went there, scheduled, appointment style.

Demir Bentley

It’s called calendarization. It’s the idea that you take all of your tasks and actually put it on the calendar. And most people stop short of this. I almost say it, like, calendarization is when Pinocchio becomes a real boy, that’s the magic moment. If you’ve done all of your planning, meaning you’ve reviewed your calendar, and looked at your priorities, and looked at your task list, but you do not take your task and put them in a specific slot in the calendar, what’s happened is you’ve done all of the necessary work but Pinocchio cannot become a real boy now.

It is when you take your tasks and put them on your calendar that you truly become a plan because, now you’re actually allocating. By stopping short, we stay in the realm of wishful thinking. Wishful thinking is sort of we’ve got all of the things that I want to do over here in this bucket, and I’ve got my available time in this bucket, and I’m just sort of vaguely in a wishful thinking way, hoping that by the end of the week they’ll match up.

But by not actualizing them, by not marrying those two markets together, then we never really meet base reality. And this is where a lot of people’s plans fail, and that’s why a lot of people say, “Oh, planning doesn’t work for me,” and that’s why a lot of people stop planning after initial tentative events to plan. It’s because, the truth is, is that the way most people plan doesn’t result in a holy-crap moment where they just kill it in their week, and so they stop doing it because they didn’t feel that magic, they didn’t feel the lift.

You know, the moment in the Tesla when somebody hits the accelerator, and your face sort of gets plastered to the back, and you go, “Oh, that’s power.” That’s what you want to feel in a productivity technique when you try it, to be like, “Oh, this works.”

Pete Mockaitis

I love that, the planning gives you a holy-crap moment, like, “Whoa, this works.” And I feel that way about most interventions that I assess. It’s like, “Hey, is that supplement doing anything for you?” “Well, I mean, I think it might potentially be making a little bit of a difference.” More and more, I don’t really want to mess with much of that in my life. It’s like I want to be like, “Holy schmokes, I feel the difference with fish oil and saffron.” And the rest, I’m like, “Meh, maybe.”

And so, that’s that. Likewise, I think it was Taylor Jacobson, shoutout to Taylor, over at Focusmate.com, which is awesome, who put us in touch, and that’s how I felt about that tool, which is online accountability partners on demand. Very cool. It’s like, “Holy crap, this is making it happen. Wow!” And there’s no maybe squinting about it.

And you’re telling me we can have that experience from the act of planning our week, and if we haven’t felt it, we ain’t been doing it right. Is that fair to say, Demir?

Demir Bentley

Absolutely. People say, “How do you know you’re in love?” It’s like, you know because it hits you like a sledgehammer. “How do I know that my planning worked?” You know because it hits you like a sledgehammer. You have no doubt in your mind that that week, out of 100,000 variations of that week, different alternate realities, imagine 100,000 different realities of the last past week where there were 100,000 versions of you playing out the same scenario, you can look at yourself in the mirror, and say, “That was the best that I could’ve done. In any alternate reality, this one was the best that I could’ve done. I met my challenges with as much resourcefulness and willpower and ingenuity and leverage as I possibly could,” and you just know it.

Pete Mockaitis

Love it. I love it. All right. Well, Demir, lay it on us, calendarization is important. How do we pull this off? How do we, in fact, win the week?

Demir Bentley

So, I’m just going to start with just a tiny bit of setup, which is that a lot of people assume, and I think I totally understand why they would, that if you’re doing a technique right, that it’s going to feel good. Let me just start by foregrounding this that when you’re doing planning right, there is a base amount of fear, anxiety, and stress that is just table stakes.

If you’re doing any planning, and you’re feeling fear, stress, anxiety, you’re doing it right because the essence of planning is pulling forward all of the unmade decisions, worries, potential things that could go wrong in the next seven or 30 days, and you’re pulling that into a 30-minute moment. How do you think that 30 minutes is going to feel? Not amazing.

So, first, let’s let go when we’re going into planning, this idea that it needs to feel good, or that, “I’m doing it wrong if I’m feeling fear, stress, or anxiety.” No, that is the tradeoff. You’re taking a slap in the face on Friday instead of a punch in the teeth on Wednesday.

Pete Mockaitis

Okay, Demir, it’s not going to be one of those Instagram-worthy situations where I’ve got my latte and my multicolored Post-Its, and I’m crafting a beautiful visual of what’s going to happen in my week or month. That’s not what it’s like?

Demir Bentley

So, what we did was we condensed it down into five simple steps. So, step one, actually, I’ll get a little clever. In our book, we talk about step zero. The reason we called it step zero, not to annoy people, is because you only have to do this step once and you’ll never have to do it again. And that is create an environment for your planning that is a reward in and of itself.

My wife and I, we go to a little brunch place, a little like French café experience. It’s like our date. Call us a nerd if you want because we probably deserve it, but this is like our date afternoon. We have babysitting, we go down to this French café, we spend 30 minutes planning, and then we’ll spend the rest of the time, two and a half hours, just connecting because there’s no better way to connect with your spouse than to get resolution on the unresolved things in your relationship.

So, step zero, do this once, you’ll never have to do it again.

On Friday night, go to a wine bar. Saturday morning, go to a café. Create an environment for your planning that you actually look forward to, that’s a reward in and of itself, and that will have help tamp down on that avoidance that people get around planning because you’ll think to yourself, “Oh, this is a treat. I’m making it a treat for myself.” Okay, that’s step zero.

Step one, and this is something you do every single week, learn a lesson from the past week, five minutes. Take five minutes, don’t learn five lessons, not 500 lessons, just skim the cherry right off the top of the cake, “If I had to find one lesson that I could derive from the past week, something that I did really well, something that I didn’t do well, what would that be?” And fold that into the next week, “How can I apply that in the next week?”

This is what we call a learning loop, and this is how people get better, whether it comes to flying an airplane, or playing sports, or playing music. They all have positive learning loops built into their practice where they’re not just practicing, they’re doing what we call positive intentional practice, where they’re focused on, “What did I do well?” or, “What did I do wrong? And how can I use that to get better?” And just five minutes, that’s it. Not 50, not two hours.

Take five minutes and just observe to yourself, one thing you did right that you want to keep doing, that you should do more this week; one thing that you did wrong that you should maybe correct and learn from this week, and then move on, and roll that into your planning. And that might sound small but do that 100 times, 200 times, and, all of a sudden, you’re getting 1% better in an accumulated sort of exponential way.

Pete Mockaitis

And so, the learning could be anything from, “Hey, when I worked in the morning, I felt very energized. Maybe I should try that again.” Like, that kind of a thing?

Demir Bentley

Perfect.

Pete Mockaitis

So, that’s our first step. What’s number two?

Demir Bentley

Step two, choose a leveraged priority, because the number one mistake people make is they’ll either choose too many priorities, which is an oxymoron because the word priority literally means the one thing above all other things. So, when somebody says to you, “I have five priorities.” It’s like you’re misunderstanding what the word priority means. Priority means the order: one, two, three, four, five. So, people tend to conflate multiple priorities instead of having one. Or, they choose a priority that has no leverage in it.

So, I just want to talk about that for a moment. When we choose something that has no leverage, it means that we have to expend a lot of effort to do that thing but it is no easier to do it the next time that we do it. And when we apply leverage to something, we’re doing it in such a way that every time we come back to do that thing, we have made it at least 1% easier to do it the next time, sometimes 50%, sometimes 80%.

And so, leverage is just walking through your world in such a way as you can say, “How do I choose a priority such that the thing that I do this week does not just benefit me this week but it makes every week in the future easier?” This comes from the book The ONE Thing by Gary Keller and Jay Papasan.

Pete Mockaitis
I was going to say, that rings a bell.

Demir Bentley

Yeah, shoutout to Gary Keller and Jay Papasan. I’ve read that book 12 times. It’s a productivity bible for me. If you haven’t read it, and you’re out there listening, it’s a must read.

Pete Mockaitis

It is amazing. Jay has been on the show, and it’s one of my all-time faves.

Demir Bentley

It’s the ultimate. So, ultimately, it’s really just about as you’re going through your planning, let’s choose a leveraged priority for the week, because, ultimately, you don’t have to be perfect. I know this sounds crazy, people think, “I can only be great at productivity if I’m perfect.” No, if you are in there doing things with leverage every single week, everybody else is going linear and you’re going exponential.

And all it takes, and I’ve seen those with clients again and again and again, is when I get them doing that for six weeks, there’s something magic that happens between week four and week six, where the cumulative effect of four weeks of doing something that makes the future easy, by the time they get to week four, five, or six, they start seeing that loop coming back around, and start saying, “Wow, there’s something different about my life now. Things are feeling easier.”

Pete Mockaitis

And can you give us a couple examples of the sorts of things that have reverberating echoing effects for many weeks to come?

Demir Bentley

Yes, so it could be really anything but I’ll just give you a stupid example. So, when we first had our first kid, I had one of those overly-fancy coffee machines where it took, like, 30 minutes to make a cup of coffee, but now we have a newborn, and I just realized, “This is crazy. It’s taking me 30 minutes to make a cup of coffee. If I make two cups of coffee a day, that’s effectively an hour a day that I’m losing to simply getting caffeine into my system.”

So, I basically said, like, “No matter how much I love this coffee, it’s not worth an hour of my day.” I went ahead and created the simplest coffee station. I consolidated everything down. That whole moment, that aha moment, took me 15 minutes. Now, today, it takes me 10 minutes from the moment I walk into the kitchen, to the moment I walk out, it’s 10 minutes to make a cup of coffee. So, what does that mean?

Pete Mockaitis

Well, now, Demir, if I may. What are we talking? Are we talking about a drip? Are we talking about an AeroPress? How was this done?

Demir Bentley

It’s just a button. Slide the thing in.

Pete Mockaitis

Coffee maker button?

Demir Bentley

Like a Nespresso.

Pete Mockaitis

All right, a Nespresso machine.

Demir Bentley

An espresso, slide in the pod, hit the button. There’s a little time for warmup, I’ve got the coffee foamer, and it’s just 10 minutes, in and out, and I’ve got a delicious-tasting coffee that’s 90% as good as the one I made in half an hour but it comes out in 10 minutes or less. And I’m talking about I could really, if I was rushing to it in five or seven minutes, but I’m being generous saying it was 10.

So, think about this in terms of leverage. I did something once that cost me 15 minutes to do in terms of setup. Then every single day now, instead of spending an hour, I’m spending 20 minutes. That means there’s 40 minutes a day, ad infinitum, that I get back into my life.

Pete Mockaitis
Okay. Cool. All right. So, we have steps one and two. What’s three?

Demir Bentley

So, three is interrogate your calendar. Have you ever heard the term review your calendar? “Oh, do a calendar review.” I find that to be so gutless and passive. Review, like, “Oh, okay, I glanced at it, right?” The truth is your calendar is a slippery bastard. There’s so much in there that could screw you up but it doesn’t jump out at you, and say, “Hey, give me a watchout for this, a watchout for this.” It’s there but it’s just sort of buried.

So, I like to think about your calendar, you need to put on the witness stand, and, like one of those procedural shows, or a witness in a movie, you got to sweat your calendar. You got to get in there. You got to hit it from the left, hit it from the right, try to trick it, try to catch it. And so, a lot of people will do a passive calendar review and there are still a lot of landmines hidden in their calendar. It could be that meeting that got rescheduled from noon to 9:00 and you just missed it, but now it’s going to blow you up next week, you’re going to forget it, it’s going to make you look bad.

It could be that you volunteer to take your kids and drive your kids and their friends to a volleyball game, but you forgot about it, you didn’t put in your calendar, another landmine. And when these landmines blow up, it costs us huge amounts of stress and anxiety, you lose social credibility and capital, and you end paying a higher price in terms of your cognitive energy and your actual time to try to fix it in the moment. That’s what I call a landmine.

So, you need to get into your calendar and sweat out those landmines. You need to pour it out and really find them. And the reason why is you need a calendar that you trust more than your instinct. To me, when I look at my calendar now, a lot of people will say, “Well, Demir, you’re supposed to be here next week.” I’m like, “I don’t think so.” And they’ll say, “Your calendar says so.” And I’ll say, “Then you’re absolutely right,” because that’s the kind of effort and attention I give to my calendar. I want my calendar to be the single source of truth in my life when it comes to my time availability and my time supply.

Pete Mockaitis

Okay. Noted.

Pete Mockaitis

So, when we interrogate it, we’re really looking at each thing and ensuring that it’s true, that it’s accurate, it belongs there, and it’s worth the time that you have put for it to be there. That’s what you mean by interrogate?

Demir Bentley

Yeah, I have a series of like nine questions, “What should be there that isn’t? What’s there that shouldn’t be?” because a lot of times people will decide they’re not going to go to that party but they don’t get it off their calendar. It’s like, “Get it off your calendar.” If it’s not actually going to happen, get it off. They also forget the things around the calendar appointment, like if you’re going to go to the dentist, you need to get out the door, get prepared, drive, anticipate traffic. Then you need to get back.

So, typically, people’s calendar is more of a sketch of their time supply than it is a detailed accounting of exactly where their time is going to need to get allocated. I’m not saying there’s no place for blanks in your calendar. In fact, that’s where we’re going to go next when we actually look at our task list, that’s our time demands. So, once we do this, you should end with a calendar that still has some open spots but you feel very confident, “These are the hard-edge commitments that I have in my calendar, and here’s the time that I have available.” This is what I call your time supply.

If you’re running a basic business, if you don’t have a really good sense of supply and demand, like, “How much inventory do I have to sell this week?” If you don’t know how much inventory, you’re liable to oversell your inventory, which is what people do all the time with their time. They commit to too many things and think that they’ve got more time to get thing done, which means they overcommit to doing to many things, which means that they’re either going to have to work nights or weekends to get it all done, or they’re going to suffer a loss of credibility when they invariably have to come back to people, and say, “I’m sorry, I can’t do that for you.”

Pete Mockaitis

Understood.

Demir Bentley

Got it. So, time supply and time demand. So, we just took care of time supply. Go over to the demands. Where do your time-demands live? Look at your task list. And that was weird, like when I call your calendar your time supply, and I call your task list time demands, people have to sort of scratch their head, and be like, “Oh, yeah, I guess I’ve never really thought about it that way.”

Your calendar is not just your calendar. It is a tool to help you understand your supply of time, and your task list is really there to help you understand the demands on your time. These are the bids for your time. And the problem is you don’t have enough supply to meet all the demand. So, what you’re really doing when you’re going with your task list is you’re saying, “What are the best highest quality bids?”

So, if I was selling truffles, I used this example in my book, if you’re selling truffles, there’s always fewer truffles in the world than there are demand for truffles. There’s only the small finite supply. And so, this is really elaborate system for allocating truffles in a way where the highest bidder always gets the truffle. And so, that’s what we need to see our time as, as this highly perishable, incredibly finite thing that needs to go only to the highest bidder. And if you don’t send it to the highest bidder, what’s happening is you’re leaving money on the table and under-utilizing that precious resource.

So, we go to your task list for five minutes, and what I really want you to do is the same thing that you did on your calendar, get rid of the stupid stuff. Come on now. Let’s get rid of all that stuff that you know doesn’t really need to happen. Let’s identify that really high-value leveraged stuff. Let’s get into places where something might be urgent but not important, and let’s start to put it in an order where it’s going from the order of most leverage to least leverage, or at least most urgent to least urgent so that we can really understand and look at that top 20% which is our highest-value bids for our time.

I’ll say one more thing here, if I can plug it in. The nature of the modern world is that you will never, from now on to the day that you die, ever finish the weekend that we can get everything done that you planned for the week. I defy you to have a week, because human nature is that, even if you had one week where you got it all done, next week you would increase the amount that you thought you could get done, and you would, thereby, get back into the cycle.

We are greedy and lusty for life. We want more. We want to do more. We want to live more. We want to be more. It’s great. There’s nothing wrong with it, but you need to understand that the definition of winning your week is not that everything got done this week. The definition of winning your week is that, “I did the right things at the right time in the order of leverage and the right level of completion.” That, my friends, is what David Allen calls the martial art of getting things done.

Let me say it one more time because I said it really quick. It’s doing the right thing at the right time to the right level of completion with the right degree of leverage. If you can get those things right, you can look back and say to that bottom 80% of your task list that didn’t get done, “I’m fine with that. I can live with it because I know I did the right things in the right order to the right level of completion.”

Pete Mockaitis

Beautiful. And the next step?

Demir Bentley

Yeah, and that’s the final step, which is marry the two together. You’ve got this beautiful market, you’ve got time supply, you’ve got time demands, but if you don’t actually marry them together on your calendar, you’ve stopped before Pinocchio becomes a real boy. So, the idea now is to take that top 20% on your task list and actually take it over onto your calendar and give everything a specific time that you’re going to do it. Does that mean it’s written in stone, like the tablets from Moses of old, and God Himself cannot change it? No, it’s just an initial sketch of a plan.

But here’s what happens, and here’s what’s so beautiful. When you start pulling things over, I don’t have one client who will not come back to me after pulling things over and calendarizing, and saying, “Wow, I really don’t have as much time as I thought I had.” But we tend to live in this world of wishful thinking, and there’s nothing that will banish wishful thinking around your calendar and around your capabilities quicker than actually saying, like, “How much of this will fit?” Right?

My grandma used to have a saying, a very religious woman, very pious, so this is the only cussing she ever did, she said, “It’s like 10 pounds of shit in a five-pound bag.” She had this analogy, “That’s like 10 pounds of shit in a five-pound bag.” And what I thought was funny of that was this idea that it’s just you’re trying to put more in here than can possibly fit, and it’s just exploding out. And this is the case with a lot of people’s week, is that by not marrying the two together, they have this idea that they’re going to fit more in than they can. And what ends up happening is that they got a lot of you-know-what sitting all over the place.

Pete Mockaitis

Yeah, that’s graphic, and it makes the point because you are. You’re going to have a big old mess on your hands and it will be…and something is going to get hurt. Maybe it’s your credibility, maybe it’s your sleep, maybe it is your patience with your loved ones. Something is going to get damaged when you have too much stuff that just doesn’t fit with your time supply available.

Demir Bentley

We’re in a crisis right now of commitment debt. This is something people don’t think about. We know about financial debt. We know about the crisis of financial where people are borrowing against their credit card, they’re not really living within their means, but it’s happening so slowly and so insidiously that it’s just building and building, and for a while they’re robbing Peter to pay Paul, and everything is fine, until it’s not fine.

And we’re actually experiencing the same thing with commitment debt, meaning every week for 10 years, we’re just overcommitting a little bit, and we’re just taking what we didn’t do this week, and we’re trying to push it into next week, and we’re robbing Peter to pay Paul, and we’re shifting things around and trying to, oh, apologize here and come up late with some miraculous productivity here.

But you run that for a decade or two decades and there’s a point at which you can’t rob Peter to pay Paul anymore, the whole Ponzi scheme comes falling down, and you realize, “I am way overcommitted,” and that comes from not being clearly anchored in living within your means. And it’s not just that you can live within your means financially, you can live within your means from a commitment perspective, “Am I actually making commitments that I have enough or more than enough time to satisfy?” And I would tell you most of my clients come to me and they’re in severe amounts of commitment debt.

Pete Mockaitis

Okay. Understood. And what’s our next step?

Demir Bentley

Yeah, that’s it. You allocate time supply to time demand, and you meet those two together. Now you’ve got a plan for the week that actually matches base reality. And I can tell you, do that the first week, you’re going to experience something different. And it’s not because there’s anything so amazing or magical about our coaching. It’s just because you’ve covered every single important base.

You have looked at your time supply, you’ve looked at your time demand, you’ve understood where your leveraged priority is, so you have what I call the holy trinity of planning your week. Look at your time supply, your time demand, and your priorities. You’ve covered off on each of those bases, that is better than 99.9% of people do. Most people don’t plan the week at all. The people who do plan the week, they’ll do maybe one of those of three, two of those three. It’s incredibly rare that you’ll see somebody do all three of those and make sure that it fits into the allocated time in the calendar.

The funny thing is it feels magical when you do it. It feels like one of those aha moments where it becomes advanced common sense where once you do it, you’re like, “Well, I can’t really unthink this, I can’t really unlearn this because it has to be like this. It just makes sense.” But then you look back, and say, “Yeah, well, it can’t have made that much sense because I wasn’t doing it for years.” So, it’s just a simple way to cover off on every base.

When most people can actually just plan their week correctly in the right way, they’re going to see that they’re winning more weeks.

And just like investing, you don’t have to win on every investment. You just have to win more investments than you lose to make money. Well, you don’t have to win every week. You just have to win more than you lose with leverage to see yourself in a much better position next year than you are this year.

Pete Mockaitis

And winning, so we do the planning, what is winning, just like executing most of the plan, or how do we define winning?

Demir Bentley

Well, that’s why I defined the leveraged priority. To me, winning is if I can achieve my leveraged priority, I have won for the week, and most of the time, I can do that by Tuesday. So, if I can do something every single week that has leverage on it, I’ve won because I’ve done something this week that makes next week and every week thereafter easier.

Now, that’s probably 5% of my time. Five percent of my working hours is my leveraged priority, not even close to the majority. Again, perfection not needed, not required here. You don’t need to spend 50% of your time working on a leveraged priority. If you could just allocate 5% of your working hours to do something that has a little bit of leverage in it, that means that you’re planting a seed every single week that’s going to benefit all the weeks thereafter.

So, that, to me, is the definition of winning. If I can get my leveraged priority done every week, I’ve won. And then, thereafter, I’m just scoring extra credit bonus points.

To win the week is not, “I’ve got everything done.” Win the week is, “I’ve got the big thing done and I made the biggest possible dent I could in the rest.”

Pete Mockaitis

Beautiful. Demir, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Demir Bentley

I would just say that I wrote the book Winning the Week because I think that we need to be more humane in our conception of how we treat ourselves in the productivity world. There’s a strong undercurrent right now of, like, “Be more disciplined. Be more excellent. Get up at 4:00. Do all of the things. Do the perfect habits. Do everything right. Don’t lose a day.”

And I just feel like that doesn’t match up with the thousands and thousands and thousands of clients I’ve had. Human beings have good days, we have bad days. It’s a mix. Every day in every week, we’re sort of meeting ourselves at a different level. Sometimes we wake up, we’ve got more energy, more desire to do something. Sometimes a little bit less.

The thing I love about playing the game in a week-long increment is you can have a bad day or two and still win the week. And this is sort of the message I want to get out to people. You can feel that you got your butt kicked five days out of the week, and yet still look back and look at what you did that week, and realize that you won the week.

So, I don’t want people trying to connect themselves to this idea that, “I need to be perfect every day. I need to crush it every day.” Actually, no, you can get your butt kicked five days out of the week. And if you did it with the right level of intention, and you chose the right leveraged points, you can actually look back on a week that you really felt like took you to the cleaners, and realize that you won the week.

Pete Mockaitis

Fantastic. Well, now can you tell us a favorite quote, something you find inspiring?

Demir Bentley

We came up with The ONE Thing when we were talking earlier. I think that book is a productivity bible. There are so many quotes and amazing things from that book. So, although I don’t have a quote, I’ll put in everything in the book The ONE Thing. That book is just amazing.

Pete Mockaitis

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

Demir Bentley

I think the best one, his name is Czechoslovakian. It’s so hard. It’s Czecemensky or Zemensky or something like that.

Pete Mockaitis

Mihaly Csikszentmihalyi?

Demir Bentley

There we go. Thank you, yeah. He did a study that, basically, said, it proved that when we walk away from a task that’s incomplete, our brain continues trying to problem-solve around it, unless, and this was the important part of the study that really intrigued me, unless you actually gave yourself a breadcrumb trail to come back to it. So, that when we actually terminated something midway, meaning we hadn’t completed it, if we actually created a specific plan for when we were going to come back to it, and what we were going to do when we came back to it, they found that your brain actually didn’t spin around it.

I think the reason I love that so much is because the truth is that we still have to live as human beings in the midst of our productivity journey. There’s always going to be moments where you’re deep in the middle of something, you’re knee-deep in it, and you need to step away, whether that’s the weekend where we all have to step away every five days, or whether it’s a crisis in your personal life and you need to step away from something.

I think there’s something so beautiful about being able to sort of recognize, “If I don’t give myself a specific time and plan when I’m going to come back to this, I’m going to be spinning on it and burning a lot of cognitive energy that’s going to keep me from enjoying my weekend, that’s going to keep me from being present in this moment where I need to be present. But if I actually just say, ‘This is the plan, and this is where I’m coming back to it,’ I can actually put it down and know that my brain isn’t burning and losing cognitive energy as I’m facing this thing that I need to face in my personal life.”

Pete Mockaitis

All right. And a favorite tool?

Demir Bentley

I think my favorite tool is Asana. And the reason my favorite tool is Asana, or choose your flavor, it could be Monday.com, is because I think it represents a paradigm shift in how we think about productivity and communication, and that’s a different podcast. But I think Asana is more than a technology. I think it’s a paradigm shift.

Pete Mockaitis

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

Demir Bentley

I say all the time, I say perfection not required.

Pete Mockaitis

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

Demir Bentley

Yeah, check us out at WinningTheWeek.com or you can check us out at LifeHackMethod.com. That points to over our different socials, and we’re everywhere. We’re on Insta, and we’re on YouTube. It’s got some cool trainings. So, if you want to sample a little of the goods, we’ve got a lot of free trainings on YouTube and different places you can check us out.

Pete Mockaitis

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

Demir Bentley

Yeah, I’ll just say do less than you think. Just like working out, people think, “I got to get in the gym. I’ve got to become this warrior. I’m going to lose all this weight.” And, really, what you should be doing is getting out and getting up to 10,000 steps. The difference between 7,000 steps and 10,000 steps is huge when it comes to your health. And the difference between planning your week for 30 minutes versus not is tremendous in your productivity.

So, stop trying to be a weekend warrior, and get in there, and be Rambo, and just blow the competition away, and start thinking about really, really small things that can have huge disproportion effects for your productivity.

Pete Mockaitis

Fantastic. Demir, this is awesome. I wish you much winning of many weeks.

Demir Bentley

Thank you so much. It’s a pleasure, man.

935: The Five Steps to Winning Every Week with Demir Bentley

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Demir Bentley reveals the five simple steps to successfully plan and execute vastly more satisfying and productive weeks.

You’ll Learn:

  1. Why nobody really plans their week—and how to fix it
  2. The master key to getting ahead of your to-do list
  3. How to transform your calendar into a power tool  

About Demir

Demir Bentley is an executive productivity coach, co-founder of Lifehack Method and WSJ Bestselling author of Winning The Week: How To Plan A Successful Week, Every Week.

He teaches hard-hitting efficiency techniques and proven accountability strategies that have helped clients generate millions in revenue while saving thousands of hours.

In the past eight years, he’s helped more than 70,000 professionals, including executives from Facebook, Google, Uber and PepsiCo, to prevent burnout and create more freedom in their lives.

Resources Mentioned

Demir Bentley Interview Transcript

Pete Mockaitis

Demir, welcome.

Demir Bentley

Good to see you, Pete.

Pete Mockaitis

I am so excited to learn all about Winning the Week and your flavor of productive goodness. And I think I’d like to start with your origin story.

Demir Bentley

Like a comic book.

Pete Mockaitis

Yes, very much, maybe as a radioactive spider but, in your case…

Demir Bentley

It’s close.

Pete Mockaitis

…you’re working at Wall Street, not loving it so much. Take us into the scene.

Demir Bentley

Like a lot of people, I learned to perform for love when I was really young, and I don’t want to get too deep, but I think a lot of people just realized that they just get a little bit more love and attention if they can get those A’s, and if they can exceed. And so, I figured out young, I was like, “Oh, I can do this stuff. I can perform. I can get grades. I can write papers. I can produce things.” And so, I became one of those insecure overachievers who’s really developed a strong juicy core of, “I’m only valuable by what I can do and what I can produce.”

So, obviously, I ended up on Wall Street because that’s where all of the insecure overachievers, the most insecure overachievers go when they really want to prove to themselves that they are somebody. And I really was that “If I can make it here, I can make it anywhere” dreamer. I really felt, “If I could hack it in finance, then maybe that deep hole inside of me would finally truly be filled and I would be somebody.

No, I jest a little bit, but, seriously, there was that juicy core of, “I’ve got to make it in finance.” And I did, I got to a really high level of finance but I did it by working 80 to 100 hours. And my secret sort of sin, or my secret, like, hidden behind-the-scenes was that I was actually really massively unproductive. I just masked that lack of productivity with brute force work and just the deep guilt and shame that kept me coming back to the trough.

And so, I remember thinking, there was an episode where I remember thinking that I was so proud that my boss had come in on the weekend and had seen me there all alone, there was nobody else on the floor, and I was just there. And right after that weekend, he called me, and he said, “You know, this is actually not a good thing. Everybody else can get their work done in 40-50 hours, and you seem to be needing 80 to 90 hours of work to produce what other people are producing in 40-50 hours.”

So, that was my big wakeup call of, like, “Oh, I’ve been wearing this like a badge of pride, like a badge of honor,” the busy badge, I call it. I’ve been awarding myself the busy badge, thinking that I’m just inherently, intrinsically more valuable than other people because I have this ability and this desire to outwork everybody else and come in on nights and weekends, and just realizing that, “Actually, other people saw that as sad and pathetic.”

That didn’t stop me. I wish I could’ve said that that was the moment when I stopped but, actually, I had a health implosion. I was overweight, I was overstressed, I wasn’t sleeping, and I got, like, a mystery illness. After much testing and three surgeries, I was diagnosed with something called salary man sudden death syndrome. It’s not very common in the United States but it’s extremely common in Asia where, otherwise, healthy young person dies from extreme overworking.

And so, although there was no definitive, “You’ve got this condition,” there was a general recognition among my three doctors that if I kept working this hard, I would probably, at some point in the future, die, and that I needed to immediately cut my hours down to 40 hours a week. Now, mind you, I’m doing everything I can to keep my head above water, working 80-100 hours a week, and they’re telling me, “As of next week, you need to bring it down to 40 hours a week.”

And so, that weekend, I talk about a lot in our book, that weekend was this like crisis moment. I felt like my whole world was crashing in. I thought I was going to have to quit my work or I’d certainly get fired. It just felt like there’s just no way that it’s going to happen.

And, yet, there was a series of events that happened over the course of that weekend. I walked in next week, I worked 40 hours, I got everything done in 40 hours, and that was the beginning of this sort of rebirth, this, like, religious awakening that I had, realizing that I suck at this productivity thing, and I realized that so much more was possible. And that was the beginning of my journey in my personal productivity work, and also the beginning of my journey as, ultimately, which is hilariously becoming a productivity coach for other people and showing other people how to have that same transition.

Pete Mockaitis

Wow, this is powerful. You have a chat about productivity, you don’t think it’s going to be life or death but, for you, it literally was.

Demir Bentley

It actually was.

Pete Mockaitis

“Become more productive or die or lose your job.” Like, high stakes stuff. So, I want to dig deep for a moment. You mentioned deep shame there. What were you ashamed of?

Demir Bentley

So, like many people who are unproductive, I’m a very emotional worker. And emotional worker isn’t defined by crying in the corner. That’s not what I’m talking about. Emotional workers are the kind of people that, if they’re feeling it, they can show up in two incredible acts of productivity, incredible feats of productivity, but they can also have incredibly long periods where they can’t motivate themselves, and they’re not feeling it. And in those periods, they can barely bring themselves to lift a pencil. And in those moments, they just feel incredible self-lacerating shame and unworthiness. And they know and think that somebody is going to find them out.

Pete Mockaitis

Well, Demir, lay it on us the way. What were the initial steps you took when you were in the I-can’t-lift-a-pencil mode? And, ultimately, how did you survive by doubling your output per hour, I guess, like cutting your hours in half?

Demir Bentley

The funny thing is what really solved my first tranche of the problem was something that everybody thinks that they know that they should be doing. And I’m going to come back to the word “thinks that they know.” And it’s just planning your week. The problem with this is there’s nothing more dangerous than somebody who thinks that they know something because, then, they approach it with zero curiosity, zero sense that they have anything to learn or anything that they might be doing wrong, and way too much confidence.

And so, we actually ran a survey of 5,000 people, and the survey was only people who manage between five and 50 people, so managers, people who are already very successful, earning a lot. We asked them, “What are the top five things that you can do to be highly productive?” And almost everybody in the top three put, somewhere in the top three put planning their week. So, duh, that’s a duh moment. Almost everybody knows it. Out of 5,000 people, it is common knowledge that you should plan your week.

Then we followed up with the same 5,000 respondents. We said, “Have you planned the last, the four out of the last four weeks?” And out of 5,000 people who had said very confidently, these were people who manage between five and 50 people, making over $100,000, out of those people who confidently said, “Yes, you have to plan your week,” less than 1% of the people had planned their week in the last four weeks.

So, there’s something odd about planning your week. It is something we all know that we should be doing, and less than 1% of us have a consistent practice in doing it. That kicked us off on a sort of curious exploration around why that is. But let me just say, coming back to my story, that borne out of sheer desperation, I looked at my calendar and I did what I call the first planning session of my life, the first real planning session where I took all 40 hours, and I took every task that I needed to get done, and I allocated it a spot in that 40 hours.

And every single 30-minute increment had to fight for its life to be on my calendar. That was the very first real planning session I had. And, lo, and behold, it went from spinning my wheels at 80 hours a week to actually getting everything done 40 hours a week. And so, I will say that my rebirth, my sort of aha moment came a lot earlier than the framework that I built around it. I think I spent a lot of years trying to understand, “What happened to me? What went right? What was the difference? What changed?”

When I finally got that through the course of my coaching, I was able to sort of boil it down into the winning-week method. And now we have a framework where we can explain to people. But, at the time I realized that it was just me being desperate. And in my desperation, I realized “I’ve only got so much time. I need to be excellent with that time.”

Pete Mockaitis

Okay. And so then, you were putting individual tasks onto specific pieces of time, like, “Thursday 4:00 p.m., I answer my emails,” or whatever the thing is. So, it went there, scheduled, appointment style.

Demir Bentley

It’s called calendarization. It’s the idea that you take all of your tasks and actually put it on the calendar. And most people stop short of this. I almost say it, like, calendarization is when Pinocchio becomes a real boy, that’s the magic moment. If you’ve done all of your planning, meaning you’ve reviewed your calendar, and looked at your priorities, and looked at your task list, but you do not take your task and put them in a specific slot in the calendar, what’s happened is you’ve done all of the necessary work but Pinocchio cannot become a real boy now.

It is when you take your tasks and put them on your calendar that you truly become a plan because, now you’re actually allocating. By stopping short, we stay in the realm of wishful thinking. Wishful thinking is sort of we’ve got all of the things that I want to do over here in this bucket, and I’ve got my available time in this bucket, and I’m just sort of vaguely in a wishful thinking way, hoping that by the end of the week they’ll match up.

But by not actualizing them, by not marrying those two markets together, then we never really meet base reality. And this is where a lot of people’s plans fail, and that’s why a lot of people say, “Oh, planning doesn’t work for me,” and that’s why a lot of people stop planning after initial tentative events to plan. It’s because, the truth is, is that the way most people plan doesn’t result in a holy-crap moment where they just kill it in their week, and so they stop doing it because they didn’t feel that magic, they didn’t feel the lift.

You know, the moment in the Tesla when somebody hits the accelerator, and your face sort of gets plastered to the back, and you go, “Oh, that’s power.” That’s what you want to feel in a productivity technique when you try it, to be like, “Oh, this works.”

Pete Mockaitis

I love that, the planning gives you a holy-crap moment, like, “Whoa, this works.” And I feel that way about most interventions that I assess. It’s like, “Hey, is that supplement doing anything for you?” “Well, I mean, I think it might potentially be making a little bit of a difference.” More and more, I don’t really want to mess with much of that in my life. It’s like I want to be like, “Holy schmokes, I feel the difference with fish oil and saffron.” And the rest, I’m like, “Meh, maybe.”

And so, that’s that. Likewise, I think it was Taylor Jacobson, shoutout to Taylor, over at Focusmate.com, which is awesome, who put us in touch, and that’s how I felt about that tool, which is online accountability partners on demand. Very cool. It’s like, “Holy crap, this is making it happen. Wow!” And there’s no maybe squinting about it.

And you’re telling me we can have that experience from the act of planning our week, and if we haven’t felt it, we ain’t been doing it right. Is that fair to say, Demir?

Demir Bentley

Absolutely. People say, “How do you know you’re in love?” It’s like, you know because it hits you like a sledgehammer. “How do I know that my planning worked?” You know because it hits you like a sledgehammer. You have no doubt in your mind that that week, out of 100,000 variations of that week, different alternate realities, imagine 100,000 different realities of the last past week where there were 100,000 versions of you playing out the same scenario, you can look at yourself in the mirror, and say, “That was the best that I could’ve done. In any alternate reality, this one was the best that I could’ve done. I met my challenges with as much resourcefulness and willpower and ingenuity and leverage as I possibly could,” and you just know it.

Pete Mockaitis

Love it. I love it. All right. Well, Demir, lay it on us, calendarization is important. How do we pull this off? How do we, in fact, win the week?

Demir Bentley

So, I’m just going to start with just a tiny bit of setup, which is that a lot of people assume, and I think I totally understand why they would, that if you’re doing a technique right, that it’s going to feel good. Let me just start by foregrounding this that when you’re doing planning right, there is a base amount of fear, anxiety, and stress that is just table stakes.

If you’re doing any planning, and you’re feeling fear, stress, anxiety, you’re doing it right because the essence of planning is pulling forward all of the unmade decisions, worries, potential things that could go wrong in the next seven or 30 days, and you’re pulling that into a 30-minute moment. How do you think that 30 minutes is going to feel? Not amazing.

So, first, let’s let go when we’re going into planning, this idea that it needs to feel good, or that, “I’m doing it wrong if I’m feeling fear, stress, or anxiety.” No, that is the tradeoff. You’re taking a slap in the face on Friday instead of a punch in the teeth on Wednesday.

Pete Mockaitis

Okay, Demir, it’s not going to be one of those Instagram-worthy situations where I’ve got my latte and my multicolored Post-Its, and I’m crafting a beautiful visual of what’s going to happen in my week or month. That’s not what it’s like?

Demir Bentley

So, what we did was we condensed it down into five simple steps. So, step one, actually, I’ll get a little clever. In our book, we talk about step zero. The reason we called it step zero, not to annoy people, is because you only have to do this step once and you’ll never have to do it again. And that is create an environment for your planning that is a reward in and of itself.

My wife and I, we go to a little brunch place, a little like French café experience. It’s like our date. Call us a nerd if you want because we probably deserve it, but this is like our date afternoon. We have babysitting, we go down to this French café, we spend 30 minutes planning, and then we’ll spend the rest of the time, two and a half hours, just connecting because there’s no better way to connect with your spouse than to get resolution on the unresolved things in your relationship.

So, step zero, do this once, you’ll never have to do it again.

On Friday night, go to a wine bar. Saturday morning, go to a café. Create an environment for your planning that you actually look forward to, that’s a reward in and of itself, and that will have help tamp down on that avoidance that people get around planning because you’ll think to yourself, “Oh, this is a treat. I’m making it a treat for myself.” Okay, that’s step zero.

Step one, and this is something you do every single week, learn a lesson from the past week, five minutes. Take five minutes, don’t learn five lessons, not 500 lessons, just skim the cherry right off the top of the cake, “If I had to find one lesson that I could derive from the past week, something that I did really well, something that I didn’t do well, what would that be?” And fold that into the next week, “How can I apply that in the next week?”

This is what we call a learning loop, and this is how people get better, whether it comes to flying an airplane, or playing sports, or playing music. They all have positive learning loops built into their practice where they’re not just practicing, they’re doing what we call positive intentional practice, where they’re focused on, “What did I do well?” or, “What did I do wrong? And how can I use that to get better?” And just five minutes, that’s it. Not 50, not two hours.

Take five minutes and just observe to yourself, one thing you did right that you want to keep doing, that you should do more this week; one thing that you did wrong that you should maybe correct and learn from this week, and then move on, and roll that into your planning. And that might sound small but do that 100 times, 200 times, and, all of a sudden, you’re getting 1% better in an accumulated sort of exponential way.

Pete Mockaitis

And so, the learning could be anything from, “Hey, when I worked in the morning, I felt very energized. Maybe I should try that again.” Like, that kind of a thing?

Demir Bentley

Perfect.

Pete Mockaitis

So, that’s our first step. What’s number two?

Demir Bentley

Step two, choose a leveraged priority, because the number one mistake people make is they’ll either choose too many priorities, which is an oxymoron because the word priority literally means the one thing above all other things. So, when somebody says to you, “I have five priorities.” It’s like you’re misunderstanding what the word priority means. Priority means the order: one, two, three, four, five. So, people tend to conflate multiple priorities instead of having one. Or, they choose a priority that has no leverage in it.

So, I just want to talk about that for a moment. When we choose something that has no leverage, it means that we have to expend a lot of effort to do that thing but it is no easier to do it the next time that we do it. And when we apply leverage to something, we’re doing it in such a way that every time we come back to do that thing, we have made it at least 1% easier to do it the next time, sometimes 50%, sometimes 80%.

And so, leverage is just walking through your world in such a way as you can say, “How do I choose a priority such that the thing that I do this week does not just benefit me this week but it makes every week in the future easier?” This comes from the book The ONE Thing by Gary Keller and Jay Papasan.

Pete Mockaitis
I was going to say, that rings a bell.

Demir Bentley

Yeah, shoutout to Gary Keller and Jay Papasan. I’ve read that book 12 times. It’s a productivity bible for me. If you haven’t read it, and you’re out there listening, it’s a must read.

Pete Mockaitis

It is amazing. Jay has been on the show, and it’s one of my all-time faves.

Demir Bentley

It’s the ultimate. So, ultimately, it’s really just about as you’re going through your planning, let’s choose a leveraged priority for the week, because, ultimately, you don’t have to be perfect. I know this sounds crazy, people think, “I can only be great at productivity if I’m perfect.” No, if you are in there doing things with leverage every single week, everybody else is going linear and you’re going exponential.

And all it takes, and I’ve seen those with clients again and again and again, is when I get them doing that for six weeks, there’s something magic that happens between week four and week six, where the cumulative effect of four weeks of doing something that makes the future easy, by the time they get to week four, five, or six, they start seeing that loop coming back around, and start saying, “Wow, there’s something different about my life now. Things are feeling easier.”

Pete Mockaitis

And can you give us a couple examples of the sorts of things that have reverberating echoing effects for many weeks to come?

Demir Bentley

Yes, so it could be really anything but I’ll just give you a stupid example. So, when we first had our first kid, I had one of those overly-fancy coffee machines where it took, like, 30 minutes to make a cup of coffee, but now we have a newborn, and I just realized, “This is crazy. It’s taking me 30 minutes to make a cup of coffee. If I make two cups of coffee a day, that’s effectively an hour a day that I’m losing to simply getting caffeine into my system.”

So, I basically said, like, “No matter how much I love this coffee, it’s not worth an hour of my day.” I went ahead and created the simplest coffee station. I consolidated everything down. That whole moment, that aha moment, took me 15 minutes. Now, today, it takes me 10 minutes from the moment I walk into the kitchen, to the moment I walk out, it’s 10 minutes to make a cup of coffee. So, what does that mean?

Pete Mockaitis

Well, now, Demir, if I may. What are we talking? Are we talking about a drip? Are we talking about an AeroPress? How was this done?

Demir Bentley

It’s just a button. Slide the thing in.

Pete Mockaitis

Coffee maker button?

Demir Bentley

Like a Nespresso.

Pete Mockaitis

All right, a Nespresso machine.

Demir Bentley

An espresso, slide in the pod, hit the button. There’s a little time for warmup, I’ve got the coffee foamer, and it’s just 10 minutes, in and out, and I’ve got a delicious-tasting coffee that’s 90% as good as the one I made in half an hour but it comes out in 10 minutes or less. And I’m talking about I could really, if I was rushing to it in five or seven minutes, but I’m being generous saying it was 10.

So, think about this in terms of leverage. I did something once that cost me 15 minutes to do in terms of setup. Then every single day now, instead of spending an hour, I’m spending 20 minutes. That means there’s 40 minutes a day, ad infinitum, that I get back into my life.

Pete Mockaitis
Okay. Cool. All right. So, we have steps one and two. What’s three?

Demir Bentley

So, three is interrogate your calendar. Have you ever heard the term review your calendar? “Oh, do a calendar review.” I find that to be so gutless and passive. Review, like, “Oh, okay, I glanced at it, right?” The truth is your calendar is a slippery bastard. There’s so much in there that could screw you up but it doesn’t jump out at you, and say, “Hey, give me a watchout for this, a watchout for this.” It’s there but it’s just sort of buried.

So, I like to think about your calendar, you need to put on the witness stand, and, like one of those procedural shows, or a witness in a movie, you got to sweat your calendar. You got to get in there. You got to hit it from the left, hit it from the right, try to trick it, try to catch it. And so, a lot of people will do a passive calendar review and there are still a lot of landmines hidden in their calendar. It could be that meeting that got rescheduled from noon to 9:00 and you just missed it, but now it’s going to blow you up next week, you’re going to forget it, it’s going to make you look bad.

It could be that you volunteer to take your kids and drive your kids and their friends to a volleyball game, but you forgot about it, you didn’t put in your calendar, another landmine. And when these landmines blow up, it costs us huge amounts of stress and anxiety, you lose social credibility and capital, and you end paying a higher price in terms of your cognitive energy and your actual time to try to fix it in the moment. That’s what I call a landmine.

So, you need to get into your calendar and sweat out those landmines. You need to pour it out and really find them. And the reason why is you need a calendar that you trust more than your instinct. To me, when I look at my calendar now, a lot of people will say, “Well, Demir, you’re supposed to be here next week.” I’m like, “I don’t think so.” And they’ll say, “Your calendar says so.” And I’ll say, “Then you’re absolutely right,” because that’s the kind of effort and attention I give to my calendar. I want my calendar to be the single source of truth in my life when it comes to my time availability and my time supply.

Pete Mockaitis

Okay. Noted.

Pete Mockaitis

So, when we interrogate it, we’re really looking at each thing and ensuring that it’s true, that it’s accurate, it belongs there, and it’s worth the time that you have put for it to be there. That’s what you mean by interrogate?

Demir Bentley

Yeah, I have a series of like nine questions, “What should be there that isn’t? What’s there that shouldn’t be?” because a lot of times people will decide they’re not going to go to that party but they don’t get it off their calendar. It’s like, “Get it off your calendar.” If it’s not actually going to happen, get it off. They also forget the things around the calendar appointment, like if you’re going to go to the dentist, you need to get out the door, get prepared, drive, anticipate traffic. Then you need to get back.

So, typically, people’s calendar is more of a sketch of their time supply than it is a detailed accounting of exactly where their time is going to need to get allocated. I’m not saying there’s no place for blanks in your calendar. In fact, that’s where we’re going to go next when we actually look at our task list, that’s our time demands. So, once we do this, you should end with a calendar that still has some open spots but you feel very confident, “These are the hard-edge commitments that I have in my calendar, and here’s the time that I have available.” This is what I call your time supply.

If you’re running a basic business, if you don’t have a really good sense of supply and demand, like, “How much inventory do I have to sell this week?” If you don’t know how much inventory, you’re liable to oversell your inventory, which is what people do all the time with their time. They commit to too many things and think that they’ve got more time to get thing done, which means they overcommit to doing to many things, which means that they’re either going to have to work nights or weekends to get it all done, or they’re going to suffer a loss of credibility when they invariably have to come back to people, and say, “I’m sorry, I can’t do that for you.”

Pete Mockaitis

Understood.

Demir Bentley

Got it. So, time supply and time demand. So, we just took care of time supply. Go over to the demands. Where do your time-demands live? Look at your task list. And that was weird, like when I call your calendar your time supply, and I call your task list time demands, people have to sort of scratch their head, and be like, “Oh, yeah, I guess I’ve never really thought about it that way.”

Your calendar is not just your calendar. It is a tool to help you understand your supply of time, and your task list is really there to help you understand the demands on your time. These are the bids for your time. And the problem is you don’t have enough supply to meet all the demand. So, what you’re really doing when you’re going with your task list is you’re saying, “What are the best highest quality bids?”

So, if I was selling truffles, I used this example in my book, if you’re selling truffles, there’s always fewer truffles in the world than there are demand for truffles. There’s only the small finite supply. And so, this is really elaborate system for allocating truffles in a way where the highest bidder always gets the truffle. And so, that’s what we need to see our time as, as this highly perishable, incredibly finite thing that needs to go only to the highest bidder. And if you don’t send it to the highest bidder, what’s happening is you’re leaving money on the table and under-utilizing that precious resource.

So, we go to your task list for five minutes, and what I really want you to do is the same thing that you did on your calendar, get rid of the stupid stuff. Come on now. Let’s get rid of all that stuff that you know doesn’t really need to happen. Let’s identify that really high-value leveraged stuff. Let’s get into places where something might be urgent but not important, and let’s start to put it in an order where it’s going from the order of most leverage to least leverage, or at least most urgent to least urgent so that we can really understand and look at that top 20% which is our highest-value bids for our time.

I’ll say one more thing here, if I can plug it in. The nature of the modern world is that you will never, from now on to the day that you die, ever finish the weekend that we can get everything done that you planned for the week. I defy you to have a week, because human nature is that, even if you had one week where you got it all done, next week you would increase the amount that you thought you could get done, and you would, thereby, get back into the cycle.

We are greedy and lusty for life. We want more. We want to do more. We want to live more. We want to be more. It’s great. There’s nothing wrong with it, but you need to understand that the definition of winning your week is not that everything got done this week. The definition of winning your week is that, “I did the right things at the right time in the order of leverage and the right level of completion.” That, my friends, is what David Allen calls the martial art of getting things done.

Let me say it one more time because I said it really quick. It’s doing the right thing at the right time to the right level of completion with the right degree of leverage. If you can get those things right, you can look back and say to that bottom 80% of your task list that didn’t get done, “I’m fine with that. I can live with it because I know I did the right things in the right order to the right level of completion.”

Pete Mockaitis

Beautiful. And the next step?

Demir Bentley

Yeah, and that’s the final step, which is marry the two together. You’ve got this beautiful market, you’ve got time supply, you’ve got time demands, but if you don’t actually marry them together on your calendar, you’ve stopped before Pinocchio becomes a real boy. So, the idea now is to take that top 20% on your task list and actually take it over onto your calendar and give everything a specific time that you’re going to do it. Does that mean it’s written in stone, like the tablets from Moses of old, and God Himself cannot change it? No, it’s just an initial sketch of a plan.

But here’s what happens, and here’s what’s so beautiful. When you start pulling things over, I don’t have one client who will not come back to me after pulling things over and calendarizing, and saying, “Wow, I really don’t have as much time as I thought I had.” But we tend to live in this world of wishful thinking, and there’s nothing that will banish wishful thinking around your calendar and around your capabilities quicker than actually saying, like, “How much of this will fit?” Right?

My grandma used to have a saying, a very religious woman, very pious, so this is the only cussing she ever did, she said, “It’s like 10 pounds of shit in a five-pound bag.” She had this analogy, “That’s like 10 pounds of shit in a five-pound bag.” And what I thought was funny of that was this idea that it’s just you’re trying to put more in here than can possibly fit, and it’s just exploding out. And this is the case with a lot of people’s week, is that by not marrying the two together, they have this idea that they’re going to fit more in than they can. And what ends up happening is that they got a lot of you-know-what sitting all over the place.

Pete Mockaitis

Yeah, that’s graphic, and it makes the point because you are. You’re going to have a big old mess on your hands and it will be…and something is going to get hurt. Maybe it’s your credibility, maybe it’s your sleep, maybe it is your patience with your loved ones. Something is going to get damaged when you have too much stuff that just doesn’t fit with your time supply available.

Demir Bentley

We’re in a crisis right now of commitment debt. This is something people don’t think about. We know about financial debt. We know about the crisis of financial where people are borrowing against their credit card, they’re not really living within their means, but it’s happening so slowly and so insidiously that it’s just building and building, and for a while they’re robbing Peter to pay Paul, and everything is fine, until it’s not fine.

And we’re actually experiencing the same thing with commitment debt, meaning every week for 10 years, we’re just overcommitting a little bit, and we’re just taking what we didn’t do this week, and we’re trying to push it into next week, and we’re robbing Peter to pay Paul, and we’re shifting things around and trying to, oh, apologize here and come up late with some miraculous productivity here.

But you run that for a decade or two decades and there’s a point at which you can’t rob Peter to pay Paul anymore, the whole Ponzi scheme comes falling down, and you realize, “I am way overcommitted,” and that comes from not being clearly anchored in living within your means. And it’s not just that you can live within your means financially, you can live within your means from a commitment perspective, “Am I actually making commitments that I have enough or more than enough time to satisfy?” And I would tell you most of my clients come to me and they’re in severe amounts of commitment debt.

Pete Mockaitis

Okay. Understood. And what’s our next step?

Demir Bentley

Yeah, that’s it. You allocate time supply to time demand, and you meet those two together. Now you’ve got a plan for the week that actually matches base reality. And I can tell you, do that the first week, you’re going to experience something different. And it’s not because there’s anything so amazing or magical about our coaching. It’s just because you’ve covered every single important base.

You have looked at your time supply, you’ve looked at your time demand, you’ve understood where your leveraged priority is, so you have what I call the holy trinity of planning your week. Look at your time supply, your time demand, and your priorities. You’ve covered off on each of those bases, that is better than 99.9% of people do. Most people don’t plan the week at all. The people who do plan the week, they’ll do maybe one of those of three, two of those three. It’s incredibly rare that you’ll see somebody do all three of those and make sure that it fits into the allocated time in the calendar.

The funny thing is it feels magical when you do it. It feels like one of those aha moments where it becomes advanced common sense where once you do it, you’re like, “Well, I can’t really unthink this, I can’t really unlearn this because it has to be like this. It just makes sense.” But then you look back, and say, “Yeah, well, it can’t have made that much sense because I wasn’t doing it for years.” So, it’s just a simple way to cover off on every base.

When most people can actually just plan their week correctly in the right way, they’re going to see that they’re winning more weeks.

And just like investing, you don’t have to win on every investment. You just have to win more investments than you lose to make money. Well, you don’t have to win every week. You just have to win more than you lose with leverage to see yourself in a much better position next year than you are this year.

Pete Mockaitis

And winning, so we do the planning, what is winning, just like executing most of the plan, or how do we define winning?

Demir Bentley

Well, that’s why I defined the leveraged priority. To me, winning is if I can achieve my leveraged priority, I have won for the week, and most of the time, I can do that by Tuesday. So, if I can do something every single week that has leverage on it, I’ve won because I’ve done something this week that makes next week and every week thereafter easier.

Now, that’s probably 5% of my time. Five percent of my working hours is my leveraged priority, not even close to the majority. Again, perfection not needed, not required here. You don’t need to spend 50% of your time working on a leveraged priority. If you could just allocate 5% of your working hours to do something that has a little bit of leverage in it, that means that you’re planting a seed every single week that’s going to benefit all the weeks thereafter.

So, that, to me, is the definition of winning. If I can get my leveraged priority done every week, I’ve won. And then, thereafter, I’m just scoring extra credit bonus points.

To win the week is not, “I’ve got everything done.” Win the week is, “I’ve got the big thing done and I made the biggest possible dent I could in the rest.”

Pete Mockaitis

Beautiful. Demir, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Demir Bentley

I would just say that I wrote the book Winning the Week because I think that we need to be more humane in our conception of how we treat ourselves in the productivity world. There’s a strong undercurrent right now of, like, “Be more disciplined. Be more excellent. Get up at 4:00. Do all of the things. Do the perfect habits. Do everything right. Don’t lose a day.”

And I just feel like that doesn’t match up with the thousands and thousands and thousands of clients I’ve had. Human beings have good days, we have bad days. It’s a mix. Every day in every week, we’re sort of meeting ourselves at a different level. Sometimes we wake up, we’ve got more energy, more desire to do something. Sometimes a little bit less.

The thing I love about playing the game in a week-long increment is you can have a bad day or two and still win the week. And this is sort of the message I want to get out to people. You can feel that you got your butt kicked five days out of the week, and yet still look back and look at what you did that week, and realize that you won the week.

So, I don’t want people trying to connect themselves to this idea that, “I need to be perfect every day. I need to crush it every day.” Actually, no, you can get your butt kicked five days out of the week. And if you did it with the right level of intention, and you chose the right leveraged points, you can actually look back on a week that you really felt like took you to the cleaners, and realize that you won the week.

Pete Mockaitis

Fantastic. Well, now can you tell us a favorite quote, something you find inspiring?

Demir Bentley

We came up with The ONE Thing when we were talking earlier. I think that book is a productivity bible. There are so many quotes and amazing things from that book. So, although I don’t have a quote, I’ll put in everything in the book The ONE Thing. That book is just amazing.

Pete Mockaitis

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

Demir Bentley

I think the best one, his name is Czechoslovakian. It’s so hard. It’s Czecemensky or Zemensky or something like that.

Pete Mockaitis

Mihaly Csikszentmihalyi?

Demir Bentley

There we go. Thank you, yeah. He did a study that, basically, said, it proved that when we walk away from a task that’s incomplete, our brain continues trying to problem-solve around it, unless, and this was the important part of the study that really intrigued me, unless you actually gave yourself a breadcrumb trail to come back to it. So, that when we actually terminated something midway, meaning we hadn’t completed it, if we actually created a specific plan for when we were going to come back to it, and what we were going to do when we came back to it, they found that your brain actually didn’t spin around it.

I think the reason I love that so much is because the truth is that we still have to live as human beings in the midst of our productivity journey. There’s always going to be moments where you’re deep in the middle of something, you’re knee-deep in it, and you need to step away, whether that’s the weekend where we all have to step away every five days, or whether it’s a crisis in your personal life and you need to step away from something.

I think there’s something so beautiful about being able to sort of recognize, “If I don’t give myself a specific time and plan when I’m going to come back to this, I’m going to be spinning on it and burning a lot of cognitive energy that’s going to keep me from enjoying my weekend, that’s going to keep me from being present in this moment where I need to be present. But if I actually just say, ‘This is the plan, and this is where I’m coming back to it,’ I can actually put it down and know that my brain isn’t burning and losing cognitive energy as I’m facing this thing that I need to face in my personal life.”

Pete Mockaitis

All right. And a favorite tool?

Demir Bentley

I think my favorite tool is Asana. And the reason my favorite tool is Asana, or choose your flavor, it could be Monday.com, is because I think it represents a paradigm shift in how we think about productivity and communication, and that’s a different podcast. But I think Asana is more than a technology. I think it’s a paradigm shift.

Pete Mockaitis

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

Demir Bentley

I say all the time, I say perfection not required.

Pete Mockaitis

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

Demir Bentley

Yeah, check us out at WinningTheWeek.com or you can check us out at LifeHackMethod.com. That points to over our different socials, and we’re everywhere. We’re on Insta, and we’re on YouTube. It’s got some cool trainings. So, if you want to sample a little of the goods, we’ve got a lot of free trainings on YouTube and different places you can check us out.

Pete Mockaitis

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

Demir Bentley

Yeah, I’ll just say do less than you think. Just like working out, people think, “I got to get in the gym. I’ve got to become this warrior. I’m going to lose all this weight.” And, really, what you should be doing is getting out and getting up to 10,000 steps. The difference between 7,000 steps and 10,000 steps is huge when it comes to your health. And the difference between planning your week for 30 minutes versus not is tremendous in your productivity.

So, stop trying to be a weekend warrior, and get in there, and be Rambo, and just blow the competition away, and start thinking about really, really small things that can have huge disproportion effects for your productivity.

Pete Mockaitis

Fantastic. Demir, this is awesome. I wish you much winning of many weeks.

Demir Bentley

Thank you so much. It’s a pleasure, man.

929: Ending Overwhelm by Delegating Masterfully with Kelli Thompson

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Kelli Thompson reveals how to beat the cycle of overwhelm through smarter delegation.

You’ll Learn:

  1. Why you seem less capable when you don’t delegate
  2. The four mindsets that hinder effective delegation
  3. How to ensure others don’t screw up delegated tasks 

About Kelli

Kelli Thompson is a women’s leadership coach and speaker who helps women advance to the rooms where decisions are made. She has coached and trained thousands of women to trust themselves, lead with more confidence, and create a career they love. She is the founder of the Clarity & Confidence Women’s Leadership Program, and a Stevie Award winner for Women in Business—Coach of the Year. She is the author of the critically acclaimed book, Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck.

Resources Mentioned

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Kelli Thompson Interview Transcript

Pete Mockaitis

Kelli, welcome back.

Kelli Thompson

Oh, I’m so excited to talk to you again.

Pete Mockaitis

Me, too. Well, you’ve been talking a lot about shifting from a doer to a leader lately. Tell us, why, of all the topics you could research you’ve chosen this one?

Kelli Thompson

Yeah. Well, I think the things that we need most in our lives, what we’re most guilty of, sometimes become our most common topics. I mean, I don’t know, tell me where I’m wrong. But I just found myself always, and I don’t think I’m alone in this, Pete, in corporate America, I think a lot of times we promote the best doers. And I remember seeing this not only as a leader, I remember experiencing this myself, I remember I experienced this as an HR person. I think we say, “Okay, Pete is the best we have at producing these widgets. He’s amazing. He’s so fast. We should make him a manager.”

And so, I think sometimes what happens in this, we promote this person and we think this magic transformation is going to happen overnight, that tonight you’re going to bed, and tomorrow you’re going to wake up, and go, “Ooh, my new title, my new salary, I’m going to be comfortable delegating, coaching, having hard conversations, and really stop doing all the doing,” when I think, we don’t realize how payoff we get from doing.

Doing feels good. You can check a box. You get a gold star. We were raised our entire lives doing, “Oh, we’re so fast at this,” “You’re so quick,” etc. and it just feels good. And I think, even as a parent, I really have struggled with this, asking myself, “How much am I doing for my child?” So, I don’t think this has leadership implications or work implications. I think, as parents, we see this, too. We see somebody do something that that’s not how we would do it. They do it slower than us. It’s, like, really painful for us to watch. And so, we jump in and we do.

And even now, running my own business, it’s been really hard for me to let go of all the doing. But the problem is my business can’t grow if I’m doing all the doing. And so, I’ve had to hire a lot of help in the last 18 months, and so this topic has never been more important to me, or more relevant to me, in raising a teenager who’s gone off to college, but then also really learning the hard work of letting someone else take care of things for you and do it in their own way.

Pete Mockaitis

That’s really resonant. And as I’m thinking about my kids who are four and six, and then one super young, but it’s like they are capable of cleaning, and yet it is so much harder to ask them 20 times, sometimes literally 20 times, to pick up sort of maybe three key items. It might require 20 requests because they get distracted and they have imaginative play fun, which is adorable, and I sort of hate to put a kabash on that too much but sometimes it’s just not that quick.

And so, it’s like if I actually want the place clean fast, doing it myself is so much faster and less aggravating than asking many, many, many times, as opposed to asking them repeatedly. And so, yes, I could see from an emotional payoff perspective there’s a wide array of tasks in the world of work that would probably feel a whole lot better to just do yourself than to delegate and coach and to feedback-refine through other people to get done.

Kelli Thompson

Absolutely. And you really hit on something important because these are the things that I hear with leaders today, especially folks who are moving into kind of that first jump of leadership. So, they’re moving into team lead, maybe a manager, senior manager, director, is they say things, like, “Kelli, I don’t have time to delegate. I don’t have time to explain this to anyone.” They might say things like, “Kelli, I can’t delegate because people just make too many high-impact mistakes. I have company coming, and so we cannot make any mistakes in this presentation.”

The other thing that I hear a lot is when leaders say, and I remember feeling this, too, and even as a parent, “It makes me feel guilty. I feel guilty that I am delegating this.” It’s almost like I feel like I’m shirking work. But one of the things that I like to remind folks and offer them to consider is that people will make mistakes, expect them. Yes, it is normal to feel all sorts of uncomfortable feelings when you’re delegating because society has told us that our worth oftentimes is tied to our productivity, and, yes, people don’t do things the way that we would do them, and, yes, it can take some time.

But those things are going to be exacerbated when you are delegating and you’re waiting to delegate when the stakes are too high. So, I just want to talk about the overwhelm cycle. So, like, what tends to happen is, let’s just say, we are working on a project, we get more projects put on our plate, and we want to say to all the things because maybe we are in this belief that, “If I say yes to everything, I look capable and confident.” Well, then we get overwhelmed.

And so then, we delegate sometimes out of panic. Even as parents, right, it’s like we hoard and we hoard and we hoard, and, “Oh, my gosh, company is coming in an hour, and I’m delegating out of panic.” And so, when we delegate out of panic, lots of times we’re delegating when the stakes are way too high, when mistakes can’t be made, when it will take a long time to explain something to someone because the project that you’re trying to delegate is just huge.

And so, what happens is the stakes are high, we’re panicked, we delegate, and people make mistakes. Of course, they make mistakes because that’s what we do the first time we try something. And then when people make mistakes, as leaders and as parents, we get frustrated that people make mistakes, and we say, “See, I can’t delegate. I have to take this back. I have to jump in and fix it.” And so, we jump in, and we fix it, and tell ourselves a story, “See, I can’t delegate because nobody can do things as good as I can,” and the whole overwhelm cycle starts again.

So, one of the things I’d offer leaders and parents is to start delegating while the stakes are low. So, I can think of a time where I delegated out a presentation that needed to go to senior leadership, way, way, way too high of stakes because the people made mistakes. They didn’t put the slides together the way I would’ve done it. And so, what did I do? I took it back. And so, I had to learn to say, “Wait a minute. You don’t delegate out a whole presentation. You delegate out one slide. One slide that perhaps the person has expertise or experience in, and you coach them on the delivery of that one slide.”

And we should just hope that people make mistakes because if you’re delegating when the stakes are low, there’s low impact. In fact, those mistakes can be used for learning. When there’s a mistake in that single slide, we can have a coaching moment about it, we can start to talk about it, we can start to talk about delivery and presentation and those sorts of things.

And so, my challenge for you is to really think about, “How can I start to delegate when the stakes are low?” And if you are panicked about someone making a mistake, mistakes are still too high, let’s cut in half. Because here’s the thing, we’ve all learned through making mistakes, and that uncomfortable learning and growth moment, and I think lots of times we feel guilty that we’re dumping or shirking work when, in fact, the opposite is true.

And Gallup research shows us that one of the number-one things that keeps people engaged is the ability to learn and grow on the job. And so, if you’re hoarding all that work, you are not allowing people to learn and grow. And so, how can we create those safe spaces for people to learn and grow, and that’s what’s very low-stakes delegation, so that they can build their rep and confidence? So, when the stakes are high, we’ve got some reps under our belt.

Pete Mockaitis

Well, Kelli, can you tell me, really, what’s at stake for someone who’s an emerging leader who has done a smidge of delegating and coaching, and it’s like, “Nah, this isn’t working so well for me,” so they haven’t really embraced it, and they are continuing to do a lot, maybe 80% plus of what they were doing before? They started taking on the leadership responsibilities as well. Like, just how bad is it to keep on rolling that way if it’s comfortable, and you know you’re awesome at your job?

Kelli Thompson

Yeah, honestly, that, I think is the biggest hurdle is you are, you got promoted because you are awesome at your job. And so, when you get promoted into leadership, guess what? Because you’re awesome at your job you get more projects because they hope that you continue to be awesome at your job. But now, you not only have doing responsibilities, especially if you’re a working manager, but now you also have to hold team meetings, coach your team, develop your team, think strategically, plan for the future.

And so, what I see happen sometimes, and I think what the consequences are of this, is these leaders keep saying yes to these things. And then they often get told, “Well, you’re not being strategic.” “Well, because I haven’t left any time to be strategic because I’m still doing all of the doing.” The other thing that I see happen is burnout. More than ever with my own clients, lots of times they’re coming to me because they are so burnt out.

And when we do a little bit of a calendar audit, one of the things that we see is they are still holding onto and attending meetings that their team members are in. They should’ve stopped attending that meeting six months ago. They’re still hanging on to work projects that are no longer a development opportunity for them. They still just keep doing them because it feels good and they get the rewards and the accolades but they’re exhausted because they’re still doing all the doing, they’re still saying yes to all the things, and they haven’t delegated down.

The real impact, though, and where I see this, especially with the clients that I coach, because they’re coming to me wanting to accelerate in the organization but, unfortunately, it becomes really hard to accelerate in the organization when you continue to hang on to old projects. So, let me just kind of give you an example of what happens. So, they hang on to projects because they are the expert in what they do. And lots of times, that first promotion into leadership, we are managing people in which we have also done the work.

And so, you know what that means, it’s so easy to jump in and do and help and all the things, but as you promote, want to get promoted into leadership, guess what’s going to happen? You are going to start to inherit teams in which you have never done the work. And we see that with senior leaders all the time. They manage teams in which they’ve never done the work. And so, lots of times there’s a crisis of confidence that happens because, before, they got all their confidence and leadership expertise because they knew the work. But now they’re managing teams in which they don’t know the work.

And so, they have to learn how to lead in a whole different way, and that’s why delegation becomes so important. One, because you’re going to need to learn how to expand your leadership team to coaching people in which you’ve never done the work, so you can’t do anymore, but now your job is to coach, to motivate, to inspire, and you can’t do that if you are still hanging on to all those pieces of work that you know how to do, and you can jump in and do it better, faster. It becomes a real kind of skill and confidence crisis as people want to accelerate in the organization. And lots of times, it can really keep them stuck if they’re unwilling to start to delegate when those stakes are low, and test and trust people.

Pete Mockaitis

Kelli, that’s powerful and what a compelling case there. So, when you’re doing the stuff that you need not to be doing, you’re going to burn out, you’re not developing. It might feel good in the moment but developing also feels really good. So, you can just trade it for another source of work pleasure if you’re doing the stuff that is development-y instead of not development-y. And then, ultimately, you’re going to capped in terms of your career progression. It’s like, “Oh, I guess you just don’t have the capability to lead folks doing work that you have not done before because you’re not sort of inching in that direction.”

Okay. So, I’m also curious, could you tell us a hopeful story of someone who was struggling with these very common sorts of challenges and then did some things differently and saw some cool results?

Kelli Thompson

Yeah, so I’ll just throw myself under the bus here. So, I remember early on in my career, I went to my leader, and I said, “Hey, I want to develop my executive presentation skills.” I was that leader who was managing a team that I hadn’t done the work but I had gotten a few other teams, and so I’m thinking big picture, “I want to develop these presentation skills so I can continue to accelerate,” all the things.

And my leader, she was awesome, she goes, “Oh, that sounds great.” She goes, “You know what, all those slides that I have you prepare that I present to the C-suite every month for the month review, I’m gonnahave you come and you just present them.” And I’m like, “Oh, yeah, that sounds great.”

So, I go ahead and I prepare my slides, like I’ve always done, and we go to the top floor of our building, and I’m meeting with the CEO of the company, my boss, my boss’ boss, I think the CFO was there too, and I start presenting, and so far, so good. They’re asking me questions; I know the answers.

Well, what I didn’t know was she had prepped them ahead of time to let them know that I wanted this development opportunity, and I did not know this at the time. But they started to have a little fun with me, I think, and they started to ask me questions that, quite frankly, I didn’t know the answers to. Now, these questions were next-level questions that the senior leaders should be able to know and answer about sales, and revenues, and ratios, and all that sort of stuff.

Pete Mockaitis

“Kelli, how is this going to drive long-term scaleable synergies and keep going on?”

Kelli Thompson
Yeah, it was like that. And so, if you’ve ever been in a meeting like that, like let’s just pause and picture. Like, I’m stammering, my neck is red, I’m pitting out, I’m feeling like a complete idiot. It is so uncomfortable. But I know we’ve all been in meetings like that. And I don’t know who it’s worse for, the person, like me that’s sitting and stammering, or my boss, who is watching the train wreck go down in action.

And I think all of us watching the train wreck, and I know I’ve done this as a leader, have jumped in, interjected, saved the day, answered the questions, but she didn’t. She just sat there silently and gave me space to struggle through and answer the questions. She only answered questions when they were directed at her directly.

And so, the meeting finished, and we get in the elevator and we ride all 40 flights down, and she looked at me, and she said, “So, how do you think that went?” And I’m like, “Oh, my God, it went terrible,” and all the things. She goes, “You know what, Kelli, I prepped them a little bit. They were having a little fun at the end.” She goes, “But those questions are things that you’re going to have to learn how to answer.”

So, she goes, “I have a question for you. Who do you know that always seems to present well in front of senior leadership with those types of high-level questions?” And I actually named off a few people who I really admired. She said, “Great. I want you to go to them, and I want you to find out how they prep. And I want you to incorporate some of those methods so that you can do this again next month when I ask you to do it again.” And I was, like, “Oh, my gosh.”

So, I think we learn a couple of things from that. One, had my manager jumped in to save me, all I would’ve learned was that I only need to prep to a certain amount because, at any point, if this gets too uncomfortable for me or her, she’ll jump in and save. And so, when we do that to people, I know I’ve done that to people, they’re like, “Eh, I only got to do about this much. My manager will come in and take the rest,” and that really limits someone’s development and their learning because we never allow people that uncomfortable space for growth. So, one, she did not jump in and save me.

Number two, she did not tell me what to do. She just said, “How do you think that went? How do you want it to go? Who else do you know that does this well?” Well, she gave me my problem back, she’s like, “You go talk to them, you go figure out new ways, and then let me know how you’re going to present differently the next time.”

And so, she really let me own that discomfort and that struggle. And while it didn’t feel good, she still provided a lot of empathy, “Hey, we’ve all done this the first time. This is totally normal. They were testing you a little bit, so you can relax. You didn’t kill your career.” There’s lots of empathy and compassion but there was also this, “Hey, you have a new problem to solve, and how are you going to go about that for your own personal development?”

Pete Mockaitis

Oh, that’s beautiful. Thank you, Kelli. Well, now can you share with us what are perhaps the mindsets we need to adopt in order to pull this off effectively? And I think the answer to that is mistakes is to be expected, but you have more.

Kelli Thompson

There is. And so, maybe you can ask yourself these questions. I have found in my own life and in all of the hundreds of clients that I’ve worked with, there are four mindsets that keep us saying yes instead of saying no. And when I say, say yes, it’s doing all the doing, saying yes to all the things. Mindset number one is kind of a capability mindset. It’s this belief that, “Oh, if I don’t say yes, people are going to think I’m not capable.”

Then there’s sometimes a people-pleasing mindset, and it’s this, “Oh, gosh, if I don’t say yes, people are really going to be disappointed in me. They’re going to be really unhappy.” We say yes to keep people happy. Then there’s mindset number three. These are our responsible-caretaker mindset folks, where they’re like, “I have to say yes so that I look responsible and people know that I support them.” And then the fourth mindset that I often see is of, like, a perfectionist mindset, “I have to say yes so that I look perfect, and then I’m going to stall and stall and stall in this until it is perfect.”

And so, I think, sometimes, just by recognizing what’s happening in that moment can bring a little bit of self-aware so you can pause, in that way when your leader comes to you, and says, “Hey, can you take on this massive project?” or when you think about continuing to do the things instead of delegating, it’s like, “Wait a minute. Why am I hanging onto this project? Why do I feel that I’m the only one that can do this?”

I know for me, personally, capability mindset was a big thing, “If I delegate this and I delegate all this work, people are going to think I’m not capable, and that’s going to show up in my performance review, and my manager is going to be upset, and then I’m going to get fired,” we go down the whole spiral. So, maybe just really think about what is that mindset that keeps you saying yes, and then ask yourself, “Could the opposite actually be just as true?”

I know one of the things that I learned in my own life, and I know my clients have learned, is that sometimes when I say yes to too much, people actually start to question my capability. Why? Because I’ve said yes to too much. My quality suffers. I turn stuff in late. I don’t get back to people when I promised them. And so, now all my fears of looking incapable have come true.

And so, I think that would be the first place that I would really start is just to go, and we’re going to be like, “Why am I keeping this? Why am I taking this on? Why am I saying yes when I should be delegating and coaching others?” And so, something to take a look at.

Pete Mockaitis

That’s powerful. And it’s funny, when you said when you say yes too much, people’s perception of your capability declines. And where I thought you were going to go with is if there’s a restaurant that has everything in the buffet, like, “Oh, we got pizza, and French fries, and, oh, burgers, and sushi, and Lomi,” it’s like, “Hmm, yeah, I don’t know if you’re actually capable of making all these items well. I actually sort of have less faith in this restaurant as being able to do that.”

So, is that also a phenomenon that happens in the human work perception of each other’s skills domain? I imagine it would. What’s your experience?

Kelli Thompson

Oh, absolutely. So, I often call this rust-out. It’s a type of burnout. And so, you’re right. What can happen? “Because I’m people-pleasing, or I want people to see that I’m capable and responsible so I’m going to say yes to all the things. And now, all of a sudden, I’m running a project, and I’m quasi-managing a sales ops team, and, oh, yeah, why don’t you add in a little bit of training team to that or HR,” right? You have all of these things on the buffet. So, you’re just very mediocre at all of them.

And one of the things that I’ve noticed, and I even notice this for me, personally, especially in running my business because you kind of have to do the buffet of all the things, is those create a ton of energy leaks because my hunch is, and I work on this with my clients, there’s something that probably just totally ignites your energy.

Same with you, Pete, right? You probably do a podcast because you geek out, and it’s exciting, and people know you for it, and every time you come, you’re like, “Yes, this is going to be so fun. We’re going to have a great conversation.” That’s the type of energy that you want to bring into your work because it builds your brand as a leader, is you become known for something.

And so, when you start saying yes to all of these things that are outside your genius zone, at least in my own experience, I face a lot of what I call energy leaks. I was spending my time and energy on things that absolutely drained my energy. And that sort of energy drain creates rust-out. And I call rust-out as not using your talents. You feel rusty, you feel tired, and it’s actually a type of burnout.

And so, I love that you brought up this restaurant that offers too many things on the menu because they’re not known for anything, they’re not doing that one thing that they can do in their genius zone and offer excellently so they become known all over town as the place to go for that thing. And I don’t think leaders are any different. I think it’s so important to find that genius zone. What is it that you’ve been put on this Earth to do? Where do you make the biggest impact for your organization, drive their most revenue, save the most money? And how do you delegate everything that isn’t that?

Because my hunch is, if you’re doing work that’s not in your genius zone, you are robbing the people around you and below you of doing work in their genius zone. I can’t work in a pivot table. But you know what, I’ve got somebody on my team that excel in pivot tables, and numbers is their genius zone. Why would I rob them of that and do it in a mediocre way that just burns me out at the end of the day?

Pete Mockaitis

That is beautiful. And it’s so true in terms of, I think, we can all think of tasks that, really, we’re fired up to do, and tasks that we really, really, really dread doing, and then afterwards we just feel not great.

I also like what you had to say with regards to when you delegate, mistakes are to be expected. And this brings me back to one of my favorite conversations, Episode 528 with Aaron Levy, is that we have an expectation of iteration on certain things, and other things we don’t, and that’s really intriguing. It’s that if you look at that where you have it.

And it’s funny, I’ve been working with a composer to redo the music here – Shoutout to Breakmaster Cylinder – and it’s been really cool how we’ve been going through a lot of iterations, and I don’t mind. I actually really appreciate Breakmaster Cylinder for going through that with me, I appreciate that patience, they’re like, “Hey, here’s the eighth version. Tell me what you think about these things.”

And yet there are other times in which if it doesn’t come back perfect the first time, I’m really annoyed and irritated, and so I’m like, “What’s that about?” I think it has more to do with me than the person who is sending me something. And I think that’s just an intriguing area to explore within our own psyches, is, “Where do we expect mistakes and iterations? And where do we not? And why? And is it fair?” Can you help us sift through a little bit of this mess, Kelli?

Kelli Thompson

Yeah. So, I learned this lesson the hard way, as all hard things are learned. First, when I switched jobs, when I switched careers, and switched industries. And the second time I learned it was when I launched my own business. And so, I remember switching, I moved from banking and I went into, like, a healthcare tech startup.

And in my first 90 days, and I see this a lot with my clients, too, I think there’s this expectation, like, “I’m going to go in, and I’m going to knock their socks off, and I’m going to do all the things and achieve all the results in 90 days or less,” and it doesn’t happen that way. And, in fact, a lot of times you kind of push people the wrong way. People are like, “Gosh, who’s this person coming in and pushing their agenda?”

I had to learn a different way. I had to learn that, actually, your first 90 days should be about learning, “How much can you learn? How much can you ask? How curious can you be?” And when I was working for that tech startup, I had a gift that I didn’t I was going to give me a reading The Lean Startup.

Pete Mockaitis

So good. Eric Ries. Shoutout in the show notes. Link it.

Kelli Thompson

It’s so good. And if you don’t have time to read it, just watch the YouTube summary. You’re going to get everything you need. When I started my own business, I totally had a, “If I’m going to launch this, it better give me all the results I want.” But, thank goodness, I had read that book because I had to change my mindset, that when we try something, when we test something, when we delegate something, our goal should not be results. Our goal should not always be revenue, or perfection, or excellence. Our goal should be learning.

Because if we can go in with that curious, iterative, experimenter’s mindset, Pete, it’s the only reason I’m still in business five years from today, and I haven’t totally burnt myself out, or had unrealistic expectations. But it’s just way more fun. It is just so much more fun to be, like, “I’m going to just test this and just see what happens, see how the world responds to it.” Like, when your only job is curiosity and learning, it is so much more fun. It is so much more freeing.

Like, I know so many people who beat themselves up and it does, it causes depression, burnout when they launch something, and they expect it’s going to be perfect on that first iteration. Like, what a pressure to put yourself under as a leader, and what pressure to put people under us. So, I just find, personally, it is way more fun, and it is so much easier to be a leader for the long game, or be in a business like mine for the long game, when you are just thinking about iterating, and testing, and learning, and just seeing what the world gives back to you.

Pete Mockaitis

It’s so true. And I recently did a keynote speech to a bunch of creators, and it was really fun. And I sort of shared, “Hey, here’s ten of my creations, from books to podcast, to whatever, and you’re going to vote in advance. Was it a hit or was it a dud? And then I will tell you afterwards, and then what lessons I learned.” And so, it’s kind of a fun format we did.

And it was intriguing that, as I took this stroll through memory lane, the majority of the things I created were a dud, particularly the first time around, and then I took some iteration, or you scrap it, like you learn something. And one of the biggest lessons learned is just about sort of validating a concept before you build it. There’s some more Lean Startup action for you.

But what was really cool, some of the audience – shoutout to Jonathan Blevins – said, “You know, this was so encouraging because I’m embarking on this thing, and I put all this pressure on myself, like, this really has to succeed, it really has to succeed. But, no, it could fail and that can be fine.” And it really can.

And so, I loved what you said, in that world of delegating, is you want to give people those opportunities where they can fail and it can be fine because you’ve got some buffer in the deadline, you got a review step before it reaches the super CEO, or the clients who have a huge account with you, or whatever. Like, one way or another, it’s okay to fail, and, in fact, it might even be enjoyable, in so far as you come up with some new learnings and insights and aha-s along the way.

Can you give us some more practical tactical approaches for setting up that kind of safe delegating environmental vibe?

Kelli Thompson

Yeah. So, let me do it from two sides here. Side number one, I just want to continue to reiterate, delegate when the stakes are low. Okay, so let me give you an example from my own life. I didn’t go out and write my book, Closing the Confidence Gap, because it was the first time I’d ever talked about those concepts. Like, “No, we’re not going to go and put that out in a book.”

That book came from years of conversations, curiosity, asking questions, talking to people, and, quite frankly, putting information out. Like, I love sharing content on LinkedIn. I think it’s fun. It’s a good place to iterate and test, “I’m going to share this idea and see if people react to it.” And you know what, the more kind of people engage and react, I’m like, “Okay, I might be onto something. I can expand this and grow it.”

And sometimes, I’ll put stuff out and it is a dud. And so then, I have to ask myself, “Okay, was it tone? Was it too much? Was it too long? Is this idea not resonating right?” It’s really like a lab. And so, I wrote the book through lots and lots and lots of iteration and testing in low-stakes environments. Like, LinkedIn is a low-stakes environment to test ideas. But then we refine those ideas with people and with audiences, and I might share them with a small group, and then it gets into a book.

So, I want you to think about that at work, how we are constantly testing low-stakes environment where we can learn and it feels fun to learn, but I want to flip this and I want to put it also from the person who’s, like, “But, Kelli, I am not a manager. I’m awesome at my job. And because I’m awesome at my job, guess what, everybody wants me to do all the things.”

I want to share with you a tactic that actually my business manager did to me just about a month ago, because, as leaders, I just want to normalize, sometimes we get really excited about things. We read things, and we’re like, “Oh, I’m going to have my team work on this right away,” and we forget everything that we delegated to them the last three months.

So, that was me. I got all jazzed about an idea. I think it was some sort of competitive analysis, and I emailed my business manager, I said, “Hey, Kristen, I just thought about this, and we should do this this week.” And she so beautifully said, “Kelli, here are the three priorities that you gave me in the last month to work on for the business. Would you like me to stop one of these priorities so that you can focus on this one that you came up with today?” And, of course, she was very nice, she was very tactical, and I laughed, I was like, “Well, she’s read my book, and she used my technique on me.”

Because I think, sometimes, we forget, as leaders, what we’ve told people, what people are working on that maybe we forgot to tell them to stop doing, we’re like, “Oh, I forgot to tell them that’s not a priority anymore.” So, I think if you’re an individual contributor who’s awesome at your job, and you don’t want to be burnt out, just have a very intelligent conversation with your leader, and say, “I love that idea. Here’s the three things I’m working on this week because you said they were a priority, and they’re due by the 15th of the month. Is this still the case? Is this still a priority? Or, would you want me to pull one of these off the list so that I can put that one on?”

Like, let’s just have a priorities conversation because, that way, we’re not getting overworked, we’re not getting overloaded. And for somebody who has no one to delegate to, I think it’s a good way to manage up some of those delegation opportunities.

Pete Mockaitis

Beautiful. And tell me, when you’re engaged in some of the coaching, the follow-up, the accountability, the hard conversations, do you have any top do’s or don’ts or favorite scripts you like to use in the course of these conversations?

Kelli Thompson

I like to think of the four P’s. So, when you’re delegating something, talk about the purpose, “Why are we doing this? Why am I asking you to do this? Like, what is the bigger picture?” The second thing that I want folks to focus on is the second P, which is people, “Who is involved?” And when you think about people, “Who are the decision-makers? Who needs to be consulted in your work? And who just needs to be informed?”

And so, that’s a really good conversation to have when you’re delegating something because, then, you can say, “Who is the decision-maker here? Is it you, Pete? Or, is it still me? Do you still need to bring things to me? Or, are you capable of making all the decisions about this project? Who do you need to consult? What stakeholders do you need to talk to before you move forward on any progress? And then when you made these decisions, or you’re doing this work, who do you need to keep informed?”

The third thing is the process. So, I think this is a good conversation to have to say, “Okay, here is where, perhaps, you need to follow some standardized processes.” I used to work in banking, so there were just some rules we had to follow, like, “Hey, here are some rules you have to follow here to get this done, but here’s where you can have leeway.” I think it’s great. Instead of just saying, “Hey, do whatever you want.” I think that can cause a lot of panic in folks. So, let’s communicate what processes or systems do we need to follow here but where you can have a little bit of creativity.

And then the last P is performance. I see people miss this one all the time. I struggle with this one. But be specific about what great outcomes look like, meaning, “What does success look like in this project? Are there ratios we’re trying to achieve? Is there a certain revenue number we’re trying to achieve? Is it a certain number of signups, or money saved, or risks reduced?” Whatever that is, but be specific so that you can communicate to this person.

And I think about, like in my own team, when I’m talking, my business manager helped me implement a customer relationship management system. And so, when I delegated that to her, I said, “We will know we have been successful in choosing the right system because it will do, A, B, and C.” Like, be clear about that so that people aren’t just assuming that they know what the results look like, but we actually have a conversation about what looks like success.

Pete Mockaitis

That’s lovely. Well, Kelli, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Kelli Thompson

I would say, in terms of delegations, I think sometimes, we do, we feel it’s hard. We feel uncomfortable Sometimes we feel guilty. It’s hard sometimes watching other people struggle. It truly is because it evokes feelings in them and in us because sitting in discomfort is not something that we, as humans, enjoy.

But I would really just encourage you just to pause one moment longer. When you’re watching somebody struggle, when you’re watching your child try to clean the living room or use the vacuum, before you jump in, can you pause just one moment longer to allow them to work through that discomfort because that’s where all the learning happens?

Pete Mockaitis

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

Kelli Thompson

Because I love to play the long game. I’ve been really reciting this quote back to myself, which is, “Consistency isn’t sexy but it works. Just showing up every day, playing the long game keeps you from burning out.”

Pete Mockaitis

And a favorite study or experiment or bit of research?

Kelli Thompson

So, every year, I love the McKinsey and LeanIn Women in the Workplace Report. It comes out every year, usually November-ish of every year. And the one I’ve especially been focusing on is this, is that first promotion that happens. And so, what they find is that the talent pipeline breaks down because, for every 100 men that are promoted, 87 women are promoted. And as those job roles continue to accelerate in the organization to the C-suite, it gets less and less and less and less.

Pete Mockaitis

Okay. And a favorite book?

Kelli Thompson

My favorite fiction book I read in the last year was Lessons in Chemistry by Bonnie Garmus. It is fiction but it does read like nonfiction when it talks about, again, women’s role in the workplace in which it takes place. But the book I waited way too long to read was, Never Split the Difference by Chriss Voss.

Pete Mockaitis
Oh, yeah, we had him on the show.

Kelli Thompson

Yes. And so, I won’t give too many spoilers but I will say that that is not a negotiation book. It is an emotional intelligence and empathy book, and I highly recommend all leaders read it.

Pete Mockaitis

And how about a favorite tool, something you use to be awesome at your job?

Kelli Thompson

I don’t know what I’d do without Calendly. It makes everything so easy, so much less back-and-forth.

Pete Mockaitis

And a favorite habit?

Kelli Thompson

My favorite habit is to lift weights almost every morning.

Pete Mockaitis

And is there a key nugget you share, something that really connects and resonates with folks; they quote it back to you often?

Kelli Thompson

“Confidence is a side effect of taking action.” I think, all too often, we wait until we feel confident to take action, but it’s after we take the action that we actually feel the confidence.

Pete Mockaitis

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

Kelli Thompson

You can go to my website, www.KelliRaeThompson.com. I’m Kelli with an I, and then R-A-E. The two places I hang out on social are LinkedIn. So, find me at Kelli Thompson, or Instagram @kelliraethompson.

Pete Mockaitis

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

Kelli Thompson
I would say find that one thing, one tiny thing, even if it you don’t manage people, I bet you can do it in your personal life. What’s one low-stakes item that is draining your energy that you can delegate, either to your children, to an outside company, or to somebody on your team?

Pete Mockaitis

Beautiful. Well, thank you, Kelli. I wish you many successful delegations.

Kelli Thompson

Awesome. Thank you.