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957: How to Push Past Discomfort and Expand Your Comfort Zone with Dr. Marc Schoen

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Dr. Marc Schoen discusses the critical role discomfort plays in our lives—and offers powerful techniques for getting better at managing it.

You’ll Learn:

  1. Why we need more—not less—discomfort
  2. Everyday techniques to build your discomfort tolerance 
  3. The 45-second trick that helps you handle stress better 

About Marc

Dr. Marc Schoen is an Assistant Clinical Professor at UCLA’s Geffen School of Medicine where he specializes in Boosting Performance and Decision Making Under Pressure and Mind-Body Medicine. He works extensively with elite athletes, professional and college, as well as, executives and UCLA medical students in strengthening their ability to thrive under pressure, and in competitive and uncomfortable conditions. His method of Discomfort Training and Pilates for the Brain builds hardiness and resilience, by rewiring the fear region of the brain which is responsible for Performance Under Pressure.

Resources Mentioned

Dr. Marc Schoen Interview Transcript

Pete Mockaitis

Marc, welcome!

Marc Schoen

Yes, very fun to be here.

Pete Mockaitis

I’m so excited to dig into your wisdom. I have listened to your book, Your Survival Instinct Is Killing You: Retrain Your Brain to Conquer Fear and Build Resilience twice, partially because I think your voice is so soothing. I guess that’s the hypnotist in you. But I would love to kick us off by hearing what’s a particularly striking, surprising, counterintuitive discovery you’ve made about us humans and how we perform best in your many years of working in mind-body medicine?

Marc Schoen

The biggest discovery, I would say, is that I was trained to believe that performance really had to do with controlling pressure or discomfort. And what I found is that, in reality, that’s not really what it is. It’s that we all should be feeling some amount of discomfort. And it’s not the discomfort alone that impairs performance. It’s that it’s our reaction to discomfort. And I have a great two studies on that, if that’s okay to elaborate on.

One was a great study done right around the start of the Afghanistan War, where they took two groups of people, the general infantry and the Special Forces, and they subjected them to a very intense, grueling workout. And the hypothesis was, is that the general infantry would show much higher signs of stress in the body, while the Special Forces would show very little stress.

Well, what they found out is that the Special Forces actually had a higher stress response than the general infantry, but the difference was they were able to parlay that stress response into productive action and, therefore, bring down the stress response, while the general infantry continued to hover in that higher level.

And that really is something that I have seen in several studies that I’ve done, whereas we can train people to manage discomfort and pressure better. But it doesn’t mean they will report that they’re not stressed, but their physiological response shows that they are managing the stress far superior than those who do not receive that kind of training.

Pete Mockaitis

That’s beautiful. Well, I think we could all use a little bit more of that. Did you say there were two studies?

Marc Schoen

Yeah, that was my main study on it, and then the second study was the Afghanistan study. That was not mine. That was someone else’s study.

So, two studies. The Afghanistan study, and the second study was mine, my own. And that was one where I had people who, in their everyday life, come in, report just the stress levels they’re having at work, and every day took blood measures of them, then trained a group into managing the discomfort and the pressure better, and their blood measures, which were cytokine measures, called Interleukin-6 and tumor necrosis factor, those people that received that kind of training had a far reduced inflammatory response, but they still reported being stressed.

Pete Mockaitis

Okay. Well, we’re going to dig deep into what training consists of but, first, maybe let’s hear the big picture in terms of the big message behind your book Your Survival Instinct Is Killing You: Retrain Your Brain to Conquer Fear and Build Resilience. What’s the core thesis here?

Marc Schoen

The core point of it has to do with discomfort. And I think of it this way, is that here we are in this advanced technological society, and it’s done a great job of really limiting our discomfort in our lives. But the paradox of it all is that, even though we have less discomfort, theoretically, we’ve become far more sensitive to being uncomfortable. So, the premise of the book is, “Okay, how do we learn to manage discomfort without precipitating the fear response, like the fight or flight response?”

Pete Mockaitis

And that is a powerful message and question, and so rich and apt, I think, for our time. I’ve also enjoyed Michael Easter’s book, The Comfort Crisis, which explores some of these bits as well. You’ve got a fun word you use frequently in the book. Can you tell us the definition of agitants? What is that? And tell us a little bit of the story for how it is we’ve come to find ourselves here in this place with greater comforts and yet less resilience to discomforts?

Marc Schoen

Yes, I call it the comfort zone dilemma, is that we all strive to be in our comfort zone. And no doubt, it feels good to be in the comfort zone, to be a non-stressed organism, but the downside is, if we take refuge in this comfort zone, what we end up doing is that actually shrinking our comfort zone because we become more and more uncomfortable with the idea of getting out of it. It’s the effect is a lot today.

I see so much of this today, is that, as this shrunken comfort zone happens, we get many more mental symptoms, particularly phobias: fear of getting on the freeway, fear of flying, fear of closed places, or fear of heights. And so, we want to be challenging our comfort zone. If we just fall back into it, we are setting ourselves up for poor performance and many mental symptoms.

Pete Mockaitis

Okay. And so, what is the concept of agitants?

Marc Schoen

So, agitants comes from the word agitation. And I’m very interested in, as our body gets more and more agitated, or has agitants in it, is that we cause a certain sort of high bar, I think of it, and the more agitants we have that exceeds the high bar, the more we are likely to impair performance and have psychological, physical symptoms. But if we can keep our agitants below that high bar, we tend to perform well and have no symptoms. But the key point of this is not the absence of agitants, but rather the well-management of agitants.

Pete Mockaitis

And so, is agitants the same as stress and agitation? Or what is the distinction or the core of this concept?

Marc Schoen

Well, I think of it more as a warming up of the body, heating it up. So, like, we all are theoretically around 98.6 is our basal temperature, and we do okay if we get into the low 99s, we may feel a tiny bit off. But once we start overheating and getting above 100, then our performance is very much affected. So, I like agitants more as a continuum, rather than thinking of we’re stressed or not stressed.

Pete Mockaitis

Okay, certainly. And so then, and for a given stressor, we may very well experience a different internal agitants response, like whether something gets us really steamed and furious, or a little bit like, “Ah, it’s kind of annoying, but I’ll shrug it off.”

Marc Schoen

Yeah, I just find it better to refer to that because of that continuum, rather than that you either have it or don’t have it.

Pete Mockaitis

All right. Well, can you walk us through the history, the chronology, the narrative of how we found ourselves in this place with lots of comfort, and yet a shrinking comfort zone? And you suggest it’s not just the smartphone but this journey starts much earlier.

Marc Schoen

I really think it starts as prehistoric humans, where humans learned to have an instinct to avoid being uncomfortable because the brain is pretty black and white about this. So, if we start feeling discomfort, then the brain starts experiencing a threat. So, in the early days, obviously, that threat was not enough food, or cold, or a mountain lion, or someone throwing a spear at us.

So, we learn real quickly to become sensitive to any impending discomfort and threat. And those humans that were capable of being able to respond effectively to that, live a whole bunch longer than those who are more tight-beat folks that were, “Oh, I’ll be fine,” and they just didn’t live long enough to propagate. And so, we’re a product of worriers and people that are constantly concerned that something bad will happen.

So, it’s natural that we would evolve more and more as a society to want to limit our discomfort because it just feels so much better. But that’s the ultimate trap, is that by continuing to pursue this path of greater comfort, which has really come significantly with technological advance, we’re losing that discomfort muscle so it atrophies, so we’re less capable of responding to the world.

And here’s, like, I think a wonderful example of this. We are in a world with tremendous amounts of psychological resources. And to help people do well and manage resilience and become hardy, but yet with all of that, and all of these technological advances, we have more mental illness than ever, and our troops are more likely to die from their own hands than they are from enemy fire. So, what’s happened is that we, as a society, have become less hardy, more fearful, and so that’s what’s happened to us.

Pete Mockaitis

Ooh, that’s tricky. And you say that in many ways that the march of technological progress has contributed to that, whether it’s microwaves and fast foods and convenient packaged foods, it’s like we don’t have to sit in even hunger or discomfort for long at all.

Marc Schoen

So true. And look how quickly we can create perfection by just tweaking things on the computer, making ourselves look better, sound better, or edit our responses. And not to mention, this was sort of what you alluded to is the issue of delayed gratification. We don’t have to wait long, do we, for gratification anymore? So, we don’t get uncomfortable in the same way we did in earlier times.

Pete Mockaitis

Well, bringing this to careers, in particular, could you tell us a story of how this scenario we find ourselves in, with a relatively tiny comfort zone, has been harmful to someone’s career, and what they did to turn it around and the cool results they saw on the other side of that training?

Marc Schoen

One great example was, some years ago I was sent a fellow that wanted to be drafted into the NBA. He was a senior year at the university, so he knew this is a make it or break it year.

And so, while he was playing during the year, he was never, by the way, historically a very good free throw maker. He’s always like around 60%, but now here he is in this last season, and many of the games being nationally televised, is that he’d get to the free throw line and freeze. He would push the ball rather than just be relaxed, and then his percentage went from 66% or 68% into the high 30s. So, he was having lots of pressure, and then of course freezing under the pressure.

So, I would go to Pauley Pavilion where he would play, and every time he got to the free throw line, the crowd would go, “Oh, no.” You just hear this large moan of 15,000 to 17,000 people. So, I had him come in, and I asked him questions, “What is your memory?” And this is so important for the bigger question that you’re asking, “What’s your memory of being under pressure?” And his memory was oral reports in school, and getting up to do an oral report and being nervous and shaking, and then the kids teasing him about his inability to talk.

So, now, years later, he goes to the free throw line, it’s like going up there for an oral report, and then when the whole crowd starts moaning, it pushes that old button and he freezes up. So, that’s a good example. So, what the solution was is that we couldn’t stop the pressure that he was feeling. Didn’t want to. What we wanted to do to make it so that the pressure, which is uncomfortable, no longer pushed the fear response.

Pete Mockaitis

And how does one make it such that that occurs?

Marc Schoen

It is possible to create a physical, emotional state in the brain that neutralizes the fear region of the brain, as many of you their listeners know is the amygdala part of the brain. So, what we do is put someone under pressure, when they’re uncomfortable, create this physical state in the brain. Hypnosis is the big way I do it, and it will block the fear response. So, now we’re having someone be uncomfortable, and learned that no fear is associated with it, and that’s how it stops.

Pete Mockaitis

Okay, cool.

Marc Schoen

Neuro-conditioning.

Pete Mockaitis

Neuro-conditioning. Hypnosis. Okay. And you said you had another story.

Marc Schoen

Another story is more directly related to business. I see a lot of folks that are young entrepreneurs, and have come up with a fabulous concept, made a lot of money, and venture capitalists come in to give them more funding for their company. And it was their idea, their intuitions, their hard work that created the success, but now you have the venture capital people, working with someone that’s a lot younger, and the entrepreneurs can get very intimidated by these people with their mathematical models, being older, putting pressure on them, second guessing their decisions.

And so, what happens is they start getting frozen up inside, starts second-guessing themselves, start losing confidence, start basically bowing to the pressure, which isn’t necessarily good because the venture capitalists aren’t the ones that created it, nor the ones that made the money. And so, we get this, again, this dilemma where we have pressure, uncomfortableness, pushing the fear response. And what is the fear response mostly is the area of rejection.

You think about it, when it comes to performance, if you look at “What is the issue?” It’s usually rejection, judgment, worry what other people might think, what they might say. When I asked my medical students, “What’s your biggest fear?” And these are super bright medical students at UCLA, “What’s your biggest fear?” Of saying something and embarrassing themselves.

And so, we get this with these young entrepreneurs and they buckle under that pressure. So, what I do is, again, create the pressure but make it so it does not push the fear response, so they can respond accordingly, express their opinion, stand up for what they believe.

Pete Mockaitis

And in your book, you mentioned that it’s very possible to feel two emotions at the same time. You’d say, “I feel stressed, worried, concerned, anxious, and also I’m safe.” Could you talk about that principle?

Marc Schoen

Yes. And that goes to that early concept of being able to create an emotional, physical state in the brain that blocks the fear, but yet, you can have them feel pressure. So, we have a neutral state or a safe state induced by this type of hypnosis, I like to call it hypno-meditation, and the real-world stress, and I also alluded to that study I gave you, is that, yeah, the people did report plenty of stress in their lives, but physically there was no trace of it. It’s an interesting dynamic. I call it duality, is my term for it.

Pete Mockaitis

All right. So, hypnosis is one way that we can get there. You also lay out 15 strategies to stay cool, calm, and collected. Could you share with us maybe your top three favorites for professionals that do a whole lot for folks, and yet are pretty easy, a big bang for the buck or ROI?

Marc Schoen

Yes, so the overarching goal is not to banish discomfort. The goal is to make it so discomfort does not experience as a threat and, therefore, push the fear response. Okay, so then that’s the goal of any exercise that we want to do. I have a lot of different ones that push the button, that make us uncomfortable, because it again pushes that button of rejection, or being judged, or being embarrassed and so on.

One thing that I’ve done to help train myself in this area was to ask people for favors, and that’s an uncomfortable thing. And the exercise I did was, and remember the goal wasn’t to get the favor granted, the goal was dealing with the uncomfortableness of asking for the favor. So, I would go around and ask people for $100. And, of course, virtually everyone would say no.

Pete Mockaitis

Virtually.

Marc Schoen

I actually had one person say yes.

Pete Mockaitis

Alright.

Marc Schoen

Of course I gave it back, but that’s really uncomfortable for me to ask that, and then justify it, or for people just to say, essentially, “Screw you,” or just ignore me, or walk away. That’s uncomfortable. But I wanted to give myself practice in that, and that’s a great tool.

Now, there’s different degrees of pushing this button. One is you could put yourself out there. Let’s say you’re uncomfortable about dancing in front of other people. You could go take dance lessons. Let’s say you’ve always wanted to sing, but you have a terrible voice. Well, you could take some voice lessons. Or, very simple, it’s so easy for us to just take the same way to drive to work or use our Google Maps. What if we were to try to navigate our way without the help of that? Again, the overarching goal is to feel uncomfortable and learn we can manage it and not get a fear reaction.

Another great way is to approach someone that you think is important or very attractive, and introduce yourself. All of these things really push that button. And so, the goal is to be uncomfortable, but still be able to do it.

Pete Mockaitis

And so, if we are in the midst of it, feeling super uncomfortable, and we’re not sure if we can do it, and we are maybe feeling the fear response getting pushed, what do we do? Do we do some breathing? Or what’s your pro tip to pulling it off?

Marc Schoen

Yeah, I have a breath technique. That’s what I call it. It’s on my website. It’s a free download, and it’s a way that you can really expediently knock down your heartbeat and blood pressure. It really just takes 45 seconds to create a result. So, you can use this as a preface to doing any of these exercises, and all we want to do, we just bring it down below that high bar that I talked about so we’re not so overheated, and then move forward with the task.

Pete Mockaitis

Well, Marc, that sounds like 45 seconds well spent. Could you give us a demo on this breath technique?

Marc Schoen

Yeah, it really is something I developed back in, like, 1983 in a biofeedback room at Cedars-Sinai when I wasn’t allowed to do hypnosis on the medical units so I had to find a way that would rapidly relax people. So, I hooked myself up with all these electrodes and then later ran other people through it, borrowed from here, borrowed from there, took from here to make something really quick.

And what I found is that an inhale through the nose, just a medium inhale, not having to be a big diaphragmatic breath, just medium. I’ll make a sound, but you wouldn’t make the sound. Kind of like this, about that amount. We pause for a second, and then have a pattern of four exhales. But the key part of it is to have no inhale between the exhales.

So, it looks and sounds like this, and the sound of the exhales is important. Here’s the inhale. Hold it for a second or so. Start of the exhales. And the last one, we just release the remaining air, and then we repeat that four times. And it’s remarkable, if you’re measuring someone’s blood pressure or heartbeat, how pronounced of an effect that can have.

Pete Mockaitis

All right. So then, these exhales, it’s like a shh sound, like we’re calming, like telling a child to “Hush up now. Shh.”

Marc Schoen

Exactly. Yeah.

Pete Mockaitis

And then there’s a pause between the shushes. And so, it’s about a medium level of inhale, not like a huge maximum.

Marc Schoen

Through the nose.

Pete Mockaitis

Through the nose. And then is the exhale there then, are we aiming to get mostly out, all of our breath out, or like completely evacuated, or just mostly evacuated, or does it really not matter?

Marc Schoen

Yeah, most of it, but we don’t want to deplete ourselves that we’re gasping for air. So, just a medium amount like that.

Pete Mockaitis

And then do we pause after the fourth exhale before the next inhale?

Marc Schoen

Yeah, a comfortable space between. And as you do this, cycles, you slow it down, so you’re pausing more between the exhales. Oh, and what I learned back in the ‘80s about this is that it’s not the inhale that relaxes us, it’s the power of the exhale.

Pete Mockaitis

That’s cool. That’s cool. All right. So, we’ve got that breathing. And tell me, when it comes to perhaps physical interventions, whether it’s cardiovascular exercises, or resistance strength exercises, or getting in cold water, or walking with a weighted backpack, are there any kind of physical fitness-y things that go a long way in improving our discomfort tolerance?

Marc Schoen

Well, it’s best for us to think about these kinds of techniques that I’m talking about, is that we have both discomfort, physical discomfort and emotional discomfort. And so, it is very important to work on our ability to tolerate both of them, and they both affect each other. So, obviously, if we’re physically less capable, then we’re going to be more emotionally uncomfortable, and vice versa.

So, the more emotionally uncomfortable we are, the less we tolerate physical discomfort. So, it makes sense to work on both. Now, here’s what I like to do, is to challenge myself physically. For example, when I used to run quite a bit, I would run, but meditate on the ability to stay calm and keep my heartbeat at a certain level. Or, when I take a sauna and have the temperature like 175, is to see how long I can keep my body cool from sweating. So, there’s that kind of interplay that we can do.

Pete Mockaitis

That’s great. Well, let’s talk about hypnosis for a moment before we wrap up. And so then, for those unfamiliar with hypnosis, could you maybe first share with us some of the best data or studies suggesting that hypnosis is a real thing that’s useful beyond our stage amusements?

Marc Schoen

Yes, it used to be that we thought hypnosis only changed people’s perceptions, and so it’s just sort of like a surface charge with a battery, that you can charge it a little, but it doesn’t seep into the true fabric of what it is. But as we’ve had more advances, we can truly measure the impact of what it does, and we see that it has a cellular impact and a biochemical impact. I even did one of those studies to show that we can use hypnosis to block the inflammatory response in the body, and that’s by measuring cells.

So, now hypnosis can be seen as having both a psychological and a physical effect. I like it because it’s like the difference between a Scud missile and a Patriot missile. It is precise, direct, and much quicker than going in more globally.

Pete Mockaitis

Okay. Well, for folks who are jazzed about that as a tool for being more awesome at their jobs, I mean, I guess we could schedule a session with a professional like yourself. Or, how can we get a taste of this benefits hypnosis might have to offer us?

Marc Schoen

I would like to offer your listeners a free download where it’s a hypnotic set of suggestions, all geared for job performance based on this whole concept of discomfort, threat, fear, and being able to manage discomfort without threat.

Pete Mockaitis

Oh, thank you. That sounds beautiful. We appreciate that. We’ll make sure to link that in the show notes, etc. Okay, so we got that going for us. And then you mentioned the notion of the precision, like targeting anything. I’ve seen a whole boatload of different hypnosis pieces on YouTube for any number of things. What are your thoughts on those? My guess is that the quality and effectiveness vary. Is there any danger in just trying those out? Or, what are you thinking about these?

Marc Schoen

I certainly wouldn’t try someone’s work that isn’t credentialed and has significant training in it. And so, it should be a mental health professional that’s done it for a while because it’s very powerful and mishandled can create some bad results. So, be careful, selective, as to who you allow to do it. And again, most hypnosis can be seen as just trying to deal with changing people’s thoughts only, and just like cognitive behavioral therapy, it certainly can work.

But, if a lot of our behavior is influenced by fear, then it makes far more sense to deal with that part of the brain where it is centered in this limbic part of the brain. So, I like to use hypnosis to go directly at those limbic areas, such as the fear center, such as the pleasure center, the sleep center, and so on. And so, you can use hypnosis in a superficial way, or you can use it in a much more profound way, because to me, if we don’t deal directly with the fear response, no matter what we tell ourselves consciously, it’s just not going to hold.

Pete Mockaitis

All right. And maybe, I’d love to get your…we’ll do your hot takes. I saw a YouTube video where they quickly said underrated, overrated for all sorts of, like, health and fitness interventions. So, let me get your hot takes here, the good doctor, Marc Schoen in the house. Hypnosis for, if I would like, I’m just going to put out some scenarios and say, could hypnosis be useful for this? Maybe say yes, no, or a little would be the three options if I may. We’ll say, “I crave cigarettes, and I’d like to crave them less.” Is hypnosis useful for that?

Marc Schoen

A little.

Pete Mockaitis

Okay. “I get scared when I’m asking for referrals or feedback, and I’d like to feel less scared”?

Marc Schoen

Very positive. Good.

Pete Mockaitis

Okay. “I’d like to sleep longer and better with less interruption.”

Marc Schoen

Good.

Pete Mockaitis

“I would like to stop eating as many cookies, candies, sweets, and diet more disciplined-ly.”

Marc Schoen

A little.

Pete Mockaitis

“I would like to be more assertive in telling my team my expectations for them and how they can improve.”

Marc Schoen

Good.

Pete Mockaitis

All right. Anything else I should have mentioned, Marc?

Marc Schoen

Well, no, you did a great job. And you noticed where I said just a little tend to be those things which are more addictive in nature, that hypnosis is just a medium, it’s a single, it’s not a triple or a home run for addictions.

Pete Mockaitis

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

Marc Schoen

The thing I say is just a summary statement, is that in reality, what a lot of people say, “What doesn’t kill me, strengthens me.” It’s really more this, “It’s not the adversity that makes us stronger. It really is our effective management of adversity that makes us stronger and more resilient.” That is the key part of this.

Pete Mockaitis

Well, that’s good. Thank you. “I often find myself procrastinating and putting off the hard, uncomfortable things, and doing easier tasks like email.”

Marc Schoen

That’s a mixed one. That’s why I have to say a little, but possibly good. It depends what’s the source of the procrastination. A lot of people just come into the world wired as a procrastinator, and those folks, you can slightly modify it. There are groups of people that are procrastinators that’s totally out of fear.

Pete Mockaitis

Okay.

Marc Schoen

That can be modified that way.

Pete Mockaitis

And how about, “I find myself I just get so distracted. I sit down to do a thing and then I find myself around the news or social media or shopping minutes later.”

Marc Schoen

Not necessarily a good one either. Just a little bit of an effect.

Pete Mockaitis

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

Marc Schoen

One I always like was something that Lance Armstrong had said when he was the Olympic athlete. It’s something along the lines like, “Pain is temporary, but quitting is forever.” That was a good one.

And there’s an old time one, God knows if I’m saying it correctly, it was something along the lines, you know, that we really want to judge someone based on the stage or position in life, but rather judge someone on the obstacles they have overcome. I like that one. I don’t know who said that but…

Pete Mockaitis

And a favorite book?

Marc Schoen

I love this book called The Untethered Soul.

Pete Mockaitis

All right. And a favorite habit?

Marc Schoen

I do self-hypnosis meditation once to two times a day. That is such an incredible way to keep our body in the zone. Because as we get older, it would seem like it shouldn’t be this, but as we get older, it takes more work to stay in that zone.

Pete Mockaitis

And I’m curious, within that self-hypnosis, are there a couple key messages or suggestions that you think really hit home and bring a lot of the result?

Marc Schoen

If I had to say a core feeling is a belief, but it’s a feeling, is that when I’ve looked over my life, I have not had an absence of bad or tough things happen, but I’ve been very fortunate, that ultimately, it all resolves favorably with a few exceptions here and there. So, what I get to is a place of trust and faith and confidence, that no matter how tough something is, I will ultimately have the resources to manage it effectively. So, I’m just going to trust and let this feeling of total openness, non-tightness, safety, lightness be the prevailing dominant feeling I’m going to feel in my body. That’s what it is.

Pete Mockaitis

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

Marc Schoen

It really is this notion that we have talked about that I can be uncomfortable, I can feel pressure, and nothing bad will happen to me. There’s no danger. And that I can persevere and succeed and that, ultimately, most people will say, my ability to hang in that place of fire is where the greatest results happen.

Pete Mockaitis

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

Marc Schoen

I would have folks feel free to look at my website. It’s my name, Marc Schoen, M-A-R-C S-C-H-O-E-N.com. You can find out more about me. I will have the downloads that I’ve referenced already there under the product section. But it’ll give you an overview of my work.

Pete Mockaitis

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

Marc Schoen

I would really, really encourage people to challenge their discomfort zones, to push against that key thing I’ve said about rejection and judgment. And even though our tendency is to want to limit our losses, some people call that the negativity bias, often the probabilities of success are actually higher than the probabilities of failure. And so, so I would recommend really pushing that, and being uncomfortable, going in there and just challenging, “I can hang in here, persevere and succeed.”

Pete Mockaitis

Beautiful. Well, Marc, this is a great time. Thank you. And I wish you the very best.

Marc Schoen

Many thanks. Enjoyed being here.

956: How to Delegate Anything with Dave Kerpen

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Dave Kerpen shows how to get over delegation hangups to tackle your top life priorities and prevent burnout.

You’ll Learn:

  1. How to get over yourself and finally begin delegating
  2. How to become a master delegator in 5 steps
  3. A simple rule to prevent embarrassment when delegating and automating

About Dave

Dave Kerpen is a serial entrepreneur, New York Times bestselling author, and global keynote speaker. He is the co-founder and co-CEO of Apprentice, a platform connecting entrepreneurs with top college students, and is the author of several bestselling books, including The Art of People, Likeable Social Media, and Likeable Business.

He is a popular contributor to Inc.com and a LinkedIn Influencer, and has been featured in many media outlets, including the New York Times, the TODAY show, CBS Early Show, BBC, Financial Times, and more. Additionally, Kerpen is the executive chairman of The Nursing Beat and the cofounder and CEO of Remembering Live. He was previously the founder and chairman of Likeable Local, and was the cofounder and CEO of Likeable Media, which was sold to 10Pearls in April 2021.

Resources Mentioned

Dave Kerpen Interview Transcript

Pete Mockaitis
Dave, welcome.

Dave Kerpen
Thank you so much for having me.

Pete Mockaitis
Well, I’m excited to get into your wisdom about delegation. And I’d love it if you could kick us off with maybe one of your most surprising and fascinating discoveries about us humans and delegation.

Dave Kerpen
Well, the most surprising thing is that the secret to delegating is much less about how to do it and much more about getting over yourself up here, getting through your brain, and dealing with the fear and the distrust issues and the perfectionism issues that are likely holding you back.

Pete Mockaitis
All right. Well, succinctly stated right off the get-go, Dave. Thank you. Appreciate it. All right. So, that’s the scoop. So, that’s funny, if people think I’m having trouble delegating, they may very well say, “I need a model. I need some steps. I need an acronym. I need a mnemonic.” And, Dave, you’re saying, “No, what you probably need first is to get over yourself because you’ve got some emotional stuff that’s hindering this whole process.”

Dave Kerpen
Yeah. And, look, my book has the steps and the acronyms and the models, and I love acronyms. I’m all for models, I’m all for systems and tools, but too many people do it to try a system or tool for anything, but certainly, in this case, for delegation, it doesn’t work, and then they say, “Forget it, this doesn’t work.” And the real answer is, “Let’s do the work on ourselves and deal with the issues, the limiting beliefs, the challenge, the fears that are holding us back.”

And then my model might work well but there’s a lot of other models right, or this software might work well but there’s 15 other software that might work well as well. And it’s less about choosing the software and more about getting the mindset right to be able to delegate.

Pete Mockaitis
I hear that. And so, so maybe if folks are so not over themselves, and they don’t even think it’s possible, Dave, can you paint a picture of hope, maybe share some data or a story?

Dave Kerpen
So, first, I’ll paint a picture of a sadder story and then I’ll tell my story, which, hopefully, is a little less sad. Scott came to me, names have all been changed to protect the guilty, but Scott was a long-time real estate entrepreneur, worked for himself, essentially, but built a nice little practice with having a couple people work for him over the years, made a lot, a lot of money, came to me years and years into his career, sort of mentoring me.

He said, “You know, I made a lot of money over the years. My son just turned 21, and I missed his growing up. I missed basketball games. I missed parent-teacher conferences. I missed an awful lot because I was so focused on building my business. And if I could go back, maybe I wouldn’t care so much about building my business because, yeah, it made me lots of money, but I will never get that time back with my son.” And that story struck me.

So, as I was doing the research for my book, I looked at deathbed research, and researched on what deathbed regrets people had. And perhaps this won’t surprise you at all, but, as you might guess, Pete, a very, very small percentage, under 1% of people regret not working enough hours. People almost always, over 50% of people, on the other hand, regret, when they’re asked for deathbed regrets, regret not having more time with friends and family, not having more time to pursue their passions, not having more time to pursue travel and other key hobbies.

We all get the same amount of time and we only get one shot at it in this lifetime. And the reason I wrote this book is that, sure delegation will make you a more productive employee, delegation will make you a more productive leader, delegation will make you a more successful entrepreneur depending on what it is that you do, but I think the stakes are much higher than that. I think delegation is the single biggest key to unlocking success and happiness in life.

And I will share that there’s many, many things that I’m not good at, but one thing that I’ve been fortunate, you know, the sort of happier story is that I pick up my son from the school bus every day, and shut off my phone, and for those three hours after school, I’m helping him with his homework, and we’re playing baseball, we’re having to catch, playing basketball. I’m getting that all-important family time, that all-important parenting time, that’s my priority.

If you’re listening, that might not be your priority, but then you might want to climb Mount Everest, or you might want to work out three hours a day, or you might want to find the love of your life. Delegation is the biggest tool that allows us to have the freedom to pursue our number one, two, and three priorities in life. And so, for me, that’s something I’m proud of, and I wrote this book to help share that with others.

Pete Mockaitis
All right. Beautiful. So, delegation unlocks all kinds of good possibilities for us. The hangup is that we are stuck believing that, “I don’t trust them. They won’t do it as good as I can. Only I am capable of doing this,” any number of these beliefs, mindsets, etc.

So, Dave, help us out, if we are in that place, like, “Okay, Dave, that sounds really awesome. Maybe you’ve managed to find some great people, but I mean, I’ve got a team of knuckleheads or I’ve been burnt before in terms of trying to delegate, and it didn’t go so well. So, what do I do?”

Dave Kerpen
Well, I mentioned before, maybe you try a tool and it doesn’t work, and then you sort of give up. I think a lot of people delegate poorly and choose poorly the person to delegate to. And when we get into my system, an acronym, and I do believe in such things, like I said, the number one and the most important aspect in the beginning is who you choose. And they choose the wrong person, they choose the person that’s there, the most convenient, cheapest, lots of reasons, but they choose the wrong person. And then, of course, it’s going to fail if you choose the wrong person.

But you got to keep trying until you get it right because the solution can’t be that you do everything. You’ll burn out. You’ll be miserable. You won’t have all that time. So, let’s attack one of those myths that you shared, Pete, “You’re the best person for the job.” Let’s really think about this. If we think about this rationally for a minute, there’s 7 billion people. I said I’m good at delegating. I’m pretty good at marketing, there are so many things I’m not good at.

And for me to think that I am the best person for any given task, virtually anything, let’s say anything actually, because honestly, there’s lots and lots of people that are way better at any possible thing that I could do. It’s frankly narcissistic and somewhat ridiculous of me to really try to convince myself that I am the best person for the job. I am very, very rarely the best person for the job. I might be the only person that knows precisely what’s in my head for how to do something, but I might also be wrong about the best way to do something. In fact, I’m probably wrong about the best way to do something.

Chances are there’s people out there that could get to the finish line much, much better than I can. So, if that’s, in fact, true, then the next challenge that I have is, “Okay, how can I choose the right person and then explain what that finish line looks like in a really clear, concise way that allows that person to be mutually aligned with me on precisely what the outcome looks like?” And then the trust issue comes up, “How can I…?”

This is hard, I get how hard this is, you know, I’ve been there, I’ve managed a lot, I’ve coached a lot of people here that have a tough time trusting others, but there has to be some level of trust that somebody else is going to get, it’s going to make their way to the finish line, and they’re probably not going to do it the same way I would. In fact, it’s very rare that they would do it the same way I would, but they might do it differently, and they might do it better than I would. And if they can get to the finish line, if they can get even to 80% of the finish line the way I would have done it, but allow me the time to do other things and not worry about it, well, then I have won.

Pete Mockaitis
Inspiring, yes. I like the winning and that’s cool. Let’s stay with the myths for a little bit longer. I’m with you. Okay, fair enough, Dave, 7 billion people alive on this Earth. Maybe I am. Maybe I am one in a million. Well, there’s 7,000 people that are as good or better than I am at that thing. So, okay, fair enough.

But in terms of realistically speaking, can I find that person? Will they be available? Can I afford them? In terms of the practical realities, are we thinking that, in fact, it is still the case that I could find someone who will do a thing better than me, even if I’m awesome at that thing, given these real-world constraints?

Dave Kerpen
Well, let me answer that in two ways. First is maybe they won’t do it better than you, but this is where most of us, to one extent or another, are perfectionists, so we have an idea about what we want something to be, and perhaps better than us is not necessary, and perhaps the same as us is not necessary. That’s where I got to that 80-85%. If they can get to 80-85% of what we would want, but relieve us of all the stress and the work and the agita of getting there, then I see that as a good outcome.

The other thing I want to address is this issue of, “How do I find this person, this mythological person? I can’t afford it. I don’t have the resources. I don’t have the money, etc.” That may be the case, but more often than not, when people come to me with this, and I challenge them on it, we get to the heart of it, and it seems like they’re making excuses because they’re afraid or distrustful or maybe truly ignorant.

In this day and age, when I can personally go on Fiverr and hire somebody for $5 to design a flyer for me, or if I’m really looking for high level…so, that’s on the one end, on the basic task, right? And then on the higher end, folks come to me, and say, “Well, I can’t find a CMO. I can’t afford a CMO.”

And to them I say, “Maybe you can’t afford it, maybe you don’t have the cash, but then maybe if you’re an entrepreneur, you can share equity and find a partner here. Find a partner. Much better to have a smaller piece of a bigger pie and find a partner, or a partner or two or three.” I think there are always creative solutions to find folks to delegate. You could be listening to the show, Pete, and you could be an entry-level employee.

If you have a set of tasks, and you’re responsible for getting those tasks done, and you think of a more creative way to get them done than you doing it, like, for instance, hiring somebody on Upwork and Fiverr for X dollars, and you vet the process and manage the process, and you pitch your boss on the business case for getting the job done that way versus you doing data entry, or whatever that tedious work is all day long, I can’t predict what the boss will say.

But I know that if somebody came to me and gave me a good business case for managing something differently and better than I had thought of in the first place, I’d say, “Great, go for it.” So, a lot of the time, it’s a matter of creatively thinking through better ways to divvy up the work than maybe we’re thinking. Maybe we’re too stuck in the box of having to get the work done ourselves.

Pete Mockaitis
Okay. So, we’ve busted one myth. Could you bust another or help us with a general thinking, doing approach for getting over ourselves?

Dave Kerpen
So, Pete, I think the number one thing that holds us back, and the reason Get Over Yourself is really as high as the dual meaning of get over yourself to delegate work, but also get over the mindset issues that get in your way is fear. I think that a lot of us, at all ages and all levels of seniority at companies, have fear of failure, have fear of not getting things right, have fear that other folks won’t get the job done as well as we would, have fear that, maybe if we’re off with our kids or golfing or doing something else, that we’re not doing our job right, even if the work gets done.

There are all these fears that we have, and, ultimately fear, of course, is false evidence appearing real. Fear holds us back. All fear holds us back. And so, in my model, in my vision, in my dream, and in my scenario, and what I try to do, is feel the fear because I’m afraid. I’m afraid of screwing up on your podcast right now. I’m afraid about being valuable for your listeners. I’m afraid of not delivering. But I understand that fear, and then I proceed and act anyway. That’s literally the definition of courage.

And so, instead of, like, trying to push the fear away, when we embrace it and tackle it head on, and say, “It’s okay to be afraid that this person is going to screw up. It’s okay to be afraid that we’re going to lose our jobs. It’s okay to be afraid that we’re going to lose our clients.” And, in the face of that fear, I’m going to take an action and figure out how to best delegate this work so that I don’t lose my mind, so that I don’t burn out, so that I get this job done in a better way than maybe I would have otherwise. And that’s the courage that it takes to get over ourselves in that manner.

Pete Mockaitis
All right. I dig it. Thank you. So, yeah, let’s talk about the model in terms of how, in fact, do we determine what we ought to delegate, and then do so effectively?

Dave Kerpen
So, we’ve got two acronyms. You mentioned the acronyms earlier, and while I said that acronyms are great, I said, “We got to deal with the mindset issues first.” So, we’ve dealt with the mindset issues. We’re through it. We’re having the courage to act. And now what do we actually do and what do we actually delegate?

And so, the model is there’s three things that we should be doing as leaders, managers, individuals with jobs. Those three things have to do with the overall vision and strategy of the goals here. If we’re in a position to hire people, making sure that we have the right people in the right seats, the hiring process, and the resources issue.

Now, resource is a tricky one. If you’re the CEO, yeah, it’s your job to make sure there’s money in the bank. If you manage an apartment, it’s your job to manage up and make sure to your boss that you have the headcount and the resources to get the job done. And if you are managing projects but not people, it is absolutely your job to make sure that you, personally, have the bandwidth and resources, and that, again, you manage up your boss, to say, “This is what I will need to get the job done.” And if that includes an extra $100 to manage a Fiverr project, well, then you’ve got to advocate for that.

So, those three things, strategy and vision, hiring the right people in the right seats, and access to resources and capital to get the job done. After those three things, my belief is that you can delegate nearly all, if not all of the rest. And so, the SHARE model is strategy, hiring, access to capital, and then remind ourselves that, if there’s anything else, we can, E, empower somebody else to do the job.

Pete Mockaitis
All right.

Dave Kerpen
Then we move into the 5Cs model of delegation. The first, and probably most important C, is choosing the right person or resource to delegate to. Again, we may think, listening right now, because I’ve done a bunch of podcasts that I already know, and I’ve done a lot of coaching of people, and I’ve heard all of the complaints, all the excuses already, “I don’t have the resources. I don’t have the money. I don’t have the budget.”

So, let me share that when we’re thinking about choosing the right person, it is not just a full-time employee that you could delegate this work to. It could be an intern, it could be an apprentice, it could be a contractor on Upwork or Fiverr, it could be a virtual assistant, it could be a vendor, a consultant, there are a partner, there are numerous types of folks that you could delegate the work to.

And the biggest mistake folks do is jumping immediately to hiring the wrong person, maybe just the person that’s the closest in proximity, the person that works down the hall from them, the person that is their peer, the person that, “Oh, my goodness, my first company was in the social media space.” Do you know how many people hired their 21-year-old niece or nephew to run social media for their company because they happened to be the 21-year-old?

Pete Mockaitis
“You use Instagram.”

Dave Kerpen
“You’ve been on it. You’ve been on TikTok. You have a TikTok account, don’t you? Make some videos for me.” So, this first big mistake is choosing the wrong person. And if there’s anything that should be the bottleneck – nothing really should be a bottleneck – but if there’s anything that it’s worth taking the most time on, it’s that first piece of choosing the person to delegate to.

The next C is communicating clearly what the intended outcome is. And, note, what I’m talking about is not every step. There are some folks out there that, whether I say it or not, they’re going to micromanage, they’re going to do the standard operating procedures, they’re going to do detailed instructions on precisely how to get to the finish line.

And if that’s really important to you, I’m not here to say you can’t do that, but in my experience when hiring people, folks like autonomy. They like to be able to get to the finish line in their own way, zigzag a little bit, learn a little bit, have some freedom. People aren’t robots. They don’t want to just, like, input in, output out. They don’t want to be robots.

Exception might be GPT and actually delegating to robots. We can get to that in a little while. But when we’re managing people, what I would say is, the key thing here with this C is to communicate clearly the intended outcome, what does success really look like, paint that picture, and then, ideally, empower them to get there the way that they see fit.

The next C is coaching them to success. Way too many people see themselves as managers. Nobody likes managers. Managers are bosses. Managers are in your face. Managers are not there to support you. They’re there to boss you around. Coaches, on the other hand, which is I strongly urge you all to use the word coach instead of manager. Coaches, anyone that’s played sports as a kid has had the experience of having a coach, hopefully, a good coach, somebody that cheers them on, teaches them along the way, supports them when they have challenges. So, by all means, coach your person on to success.

The fourth C is check in on the regular. I personally like weekly 15-minute check-ins, just where I’m there to say, “Any challenges? How can I help you reach your goals, etc.?” And then the final C, which is often also forgotten, is congratulate them. When you get to the finish line, please, by all means, like, celebrate success. Celebrate success together and then, of course, move on to the next project. So, that’s, in a nutshell, the SHARE model for what to delegate, and the 5Cs model for how to delegate when possible.

Pete Mockaitis
Oh, I like that a lot. And, Dave, I’d love it if you could make this come alive for me with an example that I’ve heard is quite tricky. I was chatting with someone who is just excellent at sales, in terms of when he’s having those conversations with a prospect, they are just listening wonderfully, asking great questions, building rapport, being super honest and creative, like, “Hey, these are the solutions we got. This might work for you. This probably won’t. This is what I would try instead, such that it generates referrals and business and great close rates, all sorts of lovely things.”

And yet, the challenge is there’s a whole lot of other responsibilities in the universe of making sales happen beyond talking to a prospect in terms of managing the lists, and the outbounds, and the marketing, and the vetting of the potential prospect, etc. And so, we’ve had some conversations, like, “Boy, it should be great if there’s a way that we could delegate all of that, such that you just had appointment after appointment after appointment, and doing what you’re amazing at, and doing less of what sort of sucks your energy, and is not perhaps the highest and best use of your time. That’d be really cool.”

And he said, “Yes, that would be really cool, but in practice I’ve never actually seen a master salesperson do that effectively because people come in, prospects come in, you want to be quick and responsive to them, like, all the time, before the demo or the meeting, and then have the follow-ups, but the follow-ups are best coming from you and not someone else, because they’re like, ‘Wait, who’s this other person? Am I going to talk to this person? I want to talk to the main salesperson, and not the secondary assistant to the salesperson.’”

And so, these are the sorts of hang-ups that have made this tricky. So, Dave, I’m just going to lay that on you, and say, here’s the trickiest delegation question I’ve bumped into, how do we crack it?

Dave Kerpen
Well, Pete, it’s as if we planned this, and God is my witness, we did not. But the story that I will share is actually precisely the same role, and I didn’t write about this in the book, but perhaps I should have. A very impressive young man, Sam, who was a salesperson for me, who, very similar to what you said, was an excellent salesperson, not so excellent, as frankly probably many salespeople are, not so excellent at the pre-work, the post-work, the putting it into the CRM, all of that administrative stuff.

And he said to me, “Dave, can I have a budget for an assistant?” And I said, “No. So, here’s what I’m going to do. You take the chats. You prove the business model. You hire the assistant out of your commissions. And if it works, I’ll make the budget for you.” I wanted him invested in making it work. And, lo and behold, he took money out of his own commission check to fund an assistant to do all of that, to delegate all of that stuff to. And this is a rare case because in corporate America, you’re not funding a headcount out of your own pocket, right? That’s pretty insane.

But in this small business entrepreneurial environment, he pitched me. I said, “Here’s the deal. You want to do this? Go ahead.” And guess what? It worked, and I created the budget for sales support, for admin support because he was able to prove that there was a business value in delegating all that other stuff, that frankly was not the best use of his time, to somebody else. So, it’s absolutely doable. It is doable.

Pete Mockaitis
Okay, so it is doable, and that’s encouraging. Could you share with us a little bit of the particulars, some of the nitty-gritty for how this vexing delegation problem can actually be cracked in the nuts and bolts?

Dave Kerpen
I mean, he chose, he interviewed a bunch of people. We’ll walk you through with the five C’s model. So, he interviewed a bunch of people. He knew what he was looking for. And for him, while the tasks were important, the fit, the cultural fit, the somebody that he could reach out to and really bounce things off of was probably even more important. So, I’m not him, but as I understand, he interviewed maybe seven or eight people, hired somebody.

Hired AJ. Gave AJ very clear directions over the types of prospects that he wanted him to reach out to. AJ did the prospecting. AJ did the outreach. There were some missteps along the way. People are going to make mistakes, that’s okay, as long as you coach them. So, Sam coached him, “You know, actually, I’d like more prospects like this,” and he did just that.

He adjusted along the way, getting him better prospects. They showed up for the call. Sam did his work. He closed them up, passed them back to AJ, who followed up to do the contracts and do the follow-ups and do all of that administrative work, getting them in the CRMs and doing the contracts and all that stuff. And, ultimately, both people did their jobs. And Sam made a lot more money for himself, and for me, for the company, by delegating that work and see him coaching his assistant through the steps that he needed done.

Pete Mockaitis
Okay. And not to get too much into the weeds here.

Dave Kerpen
Yeah, no, weeds.

Pete Mockaitis
When AJ was reaching out, AJ is reaching out, as AJ in his name and his email to the people, and he’s saying to the prospects, “Oh, let me have you speak with Sam.” And there’s a handoff? Or is AJ stealth being Sam?

Dave Kerpen
No, no, there’s a handoff. I think that authenticity is important. And so, I’m all for delegating, clearly, many, many things, but if you get a LinkedIn message from me, it’s from me. And I might have an assistant, my apprentices are going to write all the messages, they might draft all the messages, they might select all, using whatever criteria, they’ll do all the work in figuring out who to send messages to. But I like to click send. I do think it’s important, at the end of the day, for authenticity of we are who we say we are.

Pete Mockaitis
And I agree. And what’s really funny is, in this particular delegation scenario, and I guess this is a tricky nuance I’m glad we’re discussing, it’s funny because, well, so, Dave, I get a lot of inbound pitches. People want to be on the podcast, and that’s cool. What a great place to be. What a blessing. But what’s really funny is it’s clear that either there are, I don’t know, PR firms or software or automations or something happening, where someone says, “Oh, hey, Peter, I think we could really make a great podcast, blah, blah, blah, blah, blah,”

And I say, “Yes, I agree. In fact, we did make a great podcast four months ago. It was memorable to me. I’m sorry if you’ve already forgotten it.” And I’m just teasing them because I know what’s happening, and they’re like, “Oh, Pete, I’m so sorry. Oh!” you know. Or, I’d be like, “Hey, Justin, I’m getting this message from you, but it feels as though we don’t have a relationship and we haven’t seen each other in person numerous times, and we certainly have.” And he’s like, “Oh, yeah, sorry!”

And so that happens, and I don’t hold it against them, like, “You’re dead to me for this faux pas.” But it does diminish a little bit. It’s not a good feeling, and it could actually, in fact, be more devastating if, in fact, they’re like, “Hey, what the heck, man? We’ve had a long-standing business relationship, and maybe actually things are tense right now in our business relationship, and I’m getting an automated message from ‘you’ that isn’t really from you.” That might be enough to push it over the edge.

I think there’s a lot to it, whether it’s a human or a robot or an automation, that the way you’ve said it is, it’s like, you’re the person who clicks send, because then you can be like, “No, wait a minute, not that person. I’m already friends with that person. They don’t get a message like this.”

Dave Kerpen
That’s right. That’s right. And as much as I think that there are lots and lots of opportunity for delegation to tools and use of software tools when we don’t have, you know, I talk about resources to delegate, sometimes we don’t have individuals, or we don’t think we have individuals to delegate to. There are a lot of great tools to manage a lot of tasks. But when it comes to communication with people, I do think authenticity is an issue.

It’s funny. I told the story in my very first book, now 12 years ago, about I was friends with a State Senator on Facebook and I got a chat, a live chat from him asking me for a donation. And I was like, “Huh? I donated. I feel like I donated recently.” And he replied, “I know but I really need a little bit more.” And something was amiss, so I said, “Wait, this is my State…” I’ll protect the guilty here. I said, “This is my State Senator, X and X name, right?” Pause. And I said, “Please respond.” “Actually, this is an intern. I’m managing the account.”

Like you said, sometimes the stakes are higher than other times. I mean, if I really wanted to blow that person up for using interns to pretend to be them, to ask for money, I mean, it’s a really bad look, I think. So, I think we have to be very cautious about how much we, I’ll say how much we automate, and how much we automate about that final step in the process.

Pete Mockaitis
Certainly. And I’ve heard that said as a general rule of thumb for AI, like, “Have a human in the process so it doesn’t do dumb things, like automatically deny everybody’s health insurance claims.” Like, whoopsie daisy, you know, or a number of the embarrassments that people have managed to get themselves into when they use AI without the human oversight touch.

Dave Kerpen
Yeah, I love, love, love large language models like ChatGPT for drafts, first drafts of articles, of emails, of marketing plans. I mean, there is massive, massive value in the work that a large language model can provide and produce, given the right input. So, the work becomes less about what to produce and more about the inputs, the prompts that you give the models.

But all of that is really wonderful, again, for a first draft, and then I urge you, as a human, to take that first draft and check it over, first of all, like literally, for some obvious ones. We’ve heard some of the horror stories there. But then work with it, use it as a starting point, because what a great starting point. Sometimes folks have come to me super overwhelmed.

Actually, I just had a woman that I invested in say, “I need a marketing plan. I don’t know even where to start.” And I said, “Here’s where to start. Go to ChatGPT, put in your goals, put in your budget, put in your target audience, and ask for a draft of a marketing plan.” She did it, and it produced a six-page marketing plan for her to consider. Now that’s a great first draft, but it took 10 minutes. And years ago, or without me, without that idea, she might have taken 10 hours to come up with that initial starting point.

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

Dave Kerpen
I want to give the listeners credit. Sometimes I take for granted that some of this stuff is easy because I’ve been doing it for a while, but I want to recognize that it’s hard. It’s hard to shift the mindset. It’s hard to change. It’s hard to let go of stuff that you’re used to owning and controlling and doing the work on. I want to really take a moment to recognize that and appreciate that. If you’re listening and you’re thinking, “Well, he’s full of S-H, and in the real world, this is hard.”

I hear you and I get it. It is hard stuff and it is worth doing the work on, is my pitch. It’s worth muddling through and challenging oneself, and becoming more self-aware about the limiting beliefs and challenge and fears that are holding us back from delegating more, and the constraints that we think we have that maybe we don’t have as badly as we might think, and then doing the work. And there’s a brighter side on the other side of the rainbow, it really is. It gets easier.

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

Dave Kerpen
Sure. My favorite quote is from Seth Godin, who writes, “How dare you settle for less when the world’s made it so easy to be remarkable?” I think so many of us go through life like not being as intentional as we could be, and not doing the work to really stand out, and be amazing. And I think, like Seth says, it’s not that hard to be amazing. Go for it.

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

Dave Kerpen
Probably Adam Grant’s research. He’s probably my favorite author and I love his research. I’ll go back to his initial research from his first book, Give and Take, that talked about givers, takers, and matchers, and the value of becoming a giver and giving freely. It’s a little tricky to talk about this on a podcast because I get that I’m giving information, but it’s more of a matching situation. I’m expecting to get book promotion. I’m getting that and I’m grateful for it.

But that first book of his that I read really moved me, if I wasn’t a giver already, to become a giver to the extent possible, and the research shows that it pays. It’s ironic because we need to give without the expectation of getting something back, but when we do that, it just comes back to us tenfold in the long run.

Pete Mockaitis
All right. And can you share a favorite tool something that helps you be awesome at your job?

Dave Kerpen
There’s so many that I could talk about, but I want to say that the free, simplest set of tools is Google Suite. Yeah, Google Sheets, Google Docs, and Google Slides. Those three I use nearly every day, and for next to nothing I’m able to do a lot of cool stuff. So, thank you, Google.

Pete Mockaitis
All right. And a favorite habit?

Dave Kerpen
Walking. Walking gets the blood flowing and is a healthy habit. I chuckled because I have a whole bunch of habits that maybe aren’t enjoyable, maybe not as healthy as walking.

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?

Dave Kerpen
With the context of delegation in mind, it’s probably “Hire slow, fire fast.”

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

Dave Kerpen
I would say, first and foremost, I have pro bono office hours. I’ve met with 838 people over the last 10 years on Thursday afternoons. So, anyone that wants to chat with me, get some free coaching, absolutely no strings attached, I never charge for coaching ever, go to ScheduleDave.com, and you can book some free time with me on a Thursday afternoon. Of course, the book Get Over Yourself, and all my books are available on Amazon and bookstores everywhere. And if you’re looking for really awesome college-level talent, ChooseApprentice.com is our website.

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

Dave Kerpen
Feel the fear. Life is scary. Be courageous. Think of what you can get off of your plate and challenge yourself to say no, say no to more, and then figure out how you can take those no’s and get that work done in one way or the other, either delegating to humans, delegating to ChatGPT, getting that work off your plate so that you can say yes to more, not necessarily at your job, but more of your priorities in your life and with your family.

Pete Mockaitis
Lovely. Dave, this is powerful stuff. Thank you. I wish you many more successful delegations.

Dave Kerpen
Thank you so much for having me, Pete. It’s great to connect.

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.

825: The Six Steps of Masterful Delegation with Aaron Schmookler

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Aaron Schmookler shares practical, hard-won wisdom on how to delegate wisely to minimize time, and frustration.

You’ll Learn:

  1. How to get over the resistance to delegate
  2. What you need to do before delegating anything 
  3. The simple trick to ensuring follow through 

 

About Aaron

For nearly 30 years, Aaron has helped people find their intrinsic motivation, their capacity to collaborate, and the fulfillment that comes from harnessing their creativity. As the co-founder and CEO of The Yes Works, he specializes in supporting business leaders who believe that people are their greatest asset to create environments that bring out their best. 

Aaron and The Yes Works serve clients across the country and across industries including Microsoft, MOD Pizza, DiscoverOrg, Burkhart Dental Supply, SOG Knives, 9th Gear, and Textainer to make work good for people and people good for work. 

Resources Mentioned

Aaron Schmookler Interview Transcript

Pete Mockaitis
Aaron, welcome back to How to be Awesome at Your Job.

Aaron Schmookler
Thank you for having me, Pete. It’s exciting to be talking to you again.

Pete Mockaitis
Well, I’m excited too. And I was taking a gander at our last conversation. Fun fact, in the transcript of Episode 497, the phrase “Tell me more about that” appeared 13 times.

Aaron Schmookler
Oh, fun that you counted.

Pete Mockaitis
Well, I could just do Control-F find. It’s funny because I think we’re both such fanatical fans of the phrase and how useful it is for a variety of purposes. And, listeners, I recommend you check that out. It may transform your lexicon forever. But I’d love to hear, over the last three years, have there been any interesting stories or discoveries or saves of that day that have emerged with you trying out our favorite phrase?

Aaron Schmookler
Boy, I’m sure that there have been countless times that that has come up. I had already experienced the time when somebody called me a jerk or some other less kind, less family-friendly term, and I said something to the effect of, “Well, clearly, I’ve rubbed you the wrong way. Tell me more about that.” And that turned the relationship around.

Since then, I’m sure it’s helped with the health of my marriage and with my daughter. I’m sure, also, that it’s helped with my business partners and with my clients. It’s such a natural and consistent part of my lexicon now that I don’t think that I have the dramatic stories that I might’ve had when I first started to employ that phrase as a tool.

Pete Mockaitis
Yeah, I hear you. Well, it has continued to serve me well also, particularly when I just need a beat to think, to orient, to, “What the heck is going on right now?” as well as, “I genuinely don’t understand what you said,” and it’s much more friendly than, like, “What the heck are you blathering on about now?”

Aaron Schmookler
“What? That doesn’t make any sense,” is what I’m often tempted to say.

Pete Mockaitis
Okay. Well, good to know. So, now, I’d love to chat with you about delegation. You sent me a beautiful proposal. Thank you for that. And I thought that’s exactly something that we should talk about, so let’s do it. Can you kick us off with any particularly surprising or fascinating or extra counterintuitive discoveries you’ve made about delegation in your 30 years of working with different folks?

Aaron Schmookler
Well, I’ll skip to the end and say I love the book Who Not How. And I’m trying now to remember the name of the author, but “Who Not How,” the premise or the thesis of the book is, essentially, “Stop trying to figure out how to do it. Somebody already knows and they can do it better than you. So, figure out who should be doing this instead of how you are going to do it.”

Pete Mockaitis
I love that so much that I was frantically Googling in the background. It is Dan Sullivan. I believe that’s the strategic coach Dan Sullivan.

Aaron Schmookler
That’s the guy, yeah. Thank you.

Pete Mockaitis
Who’s got a wealth of goodies that I’ve enjoyed.
Who Not How
, I think that really holds true. And I am astounded at how people can often do things so much better than me. Maybe I shouldn’t be astounded. I should just expect that by now, having learned it so many times. Where I thought, I’ve got a rental property in Chicago, and I thought, “Okay, I’ve checked out the BiggerPockets podcast, okay, I’ve got a little bit of sensibility associated with finding a bargain and renting it out and making it look okay.”

And then I get a property manager who just, like, ran circles around me in terms of, “Oh, yeah. Well, that’s actually a two-car garage so you just got to paint a really good line in there.” I was like, “Oh, but it’s kind of tight.” He’s like, “Welcome to every parking space in Chicago. Also, here’s how we can make them pay for their own water.” It’s like, “Whoa, you should be doing this and not me.”

Aaron Schmookler
One of the things that’s coming to the top of my mind as you’re sharing that story, as a counterintuitive truth about delegation, when I’m training managers to delegate effectively, one of the questions that I ask them in kind of preparing before we got to the “What are our six-step model looks like?” is I ask them, “What holds you back from delegating?”

And, very often, I get responses like, “I don’t want to give people things that I wouldn’t want to do. I don’t want to just push the scut work off onto somebody else.” And the remarkable truth is all the stuff that I hate doing, somebody else loves.

Pete Mockaitis
It is remarkable and true. Hence, a remarkable truth.

Aaron Schmookler
Right. I thank God every day for inventing accountants, for example.

Pete Mockaitis
Oh, yes. You’re speaking my language, and I love accountants too. I hope I haven’t been harsh on them just because I dislike doing accounting work so much, but if it’s in the realm of bookkeeping or compliance-y things, today, we had to find a title for a car in order to renew a thing, I was like, “What? Is a paper I was supposed to have received in a mail and then held on to for a year? That’s really pushing my capability.”

Aaron Schmookler
As my friend Dave would say, “I resemble that remark.”

Pete Mockaitis
All right, so that’s cool. So, it’s who not how, and Dan Sullivan wrote a great book called just that, which is nifty. And some things we sure dislike doing, other people love doing. That’s cool and a blessing. So, then lay it on us, is there, maybe, a particularly inspiring story to tee this up and get us going, “Oh, yeah, I’m fired up to delegate”? Maybe there’s someone who’s overwhelmed and transformed their effectiveness and their stress levels with delegation. No pressure, Aaron.

Aaron Schmookler
I’ll tell a story from my own history. I don’t know if we talked before, Pete, about the fact that I come from a theater background, and my primary training there was as a director, but on the way, I was also a technical director. And one of the things that the technical director is responsible for is, at the end of the show, the very night that the last audience sees the show, as soon as the audience is out the door and those doors are closed, at that very moment begins what’s called strike and they start tearing down the set.

A lot of it goes, ridiculous amounts of the set goes into the trash, all the lights are removed, those that aren’t part of the regular repertory in the theater. And the technical director’s job at strike is, essentially, to make sure that it goes and that it goes off without a hitch. And the first time that I ever led strike, I remember standing on the stage, I’ve got my tools in my hands, I’m spending a fair amount of time working on the materials myself, and pointing and telling people, “Okay, go do this,” and giving them a single task to do, and people would be flocking to me.

I, eventually, had to put my tools down, and it was just so much work for me to try to direct 23, or something like that, people to go and do this task and then this task, and then this task, and then this task. I was so exhausted at the end of that night that I might as well have done the strike myself in order to have gotten that exhausted, and it wasn’t very effective. And we were there much longer than we should’ve been, and we made much less progress than we should’ve been.

So, I called up the last tech director that I remembered working for and really enjoyed, and I said, “What did I do wrong? What do I need to do better?” And he said, “Okay. Well, tell me about what you did.” So, I told him the story of the night, he said, “You are assigning things task by task. And then he said, “You got to break things down into objectives, what’s the result that you want to see, and put somebody in charge of that result.”

“And when somebody comes to you and says, ‘What do I do next?’ you say, ‘Go join Mary over there,’ or, ‘Go join John over there. He’s got this project and he’ll put you to work.’” And so, by delegating objectives, I was able to create mini-teams of my team. And the next time, we got more done than we had anticipated. We got out earlier than we had anticipated.

And so, just that one shift from delegating or assigning tasks, and this is a distinction that I was expecting to talk to you about by the end of our conversation, this distinction between assigning tasks and delegating end results, delegating outcomes, was tremendously powerful for me in an instant.

Pete Mockaitis
I love it, and it really does resonate. I am thinking about events. When you talked about striking the stage, like, “Oh, I did some theater stuff back in the day.” And some events, like putting on these, it was called HOBY, Hugh O’Brien Youth Leadership, sophomore leadership seminars for high school students, as well as my wedding. Like, one of my favorite things to do was carve out zones of responsibility for people.

And sometimes, I even like to make up new names. It’s like, “Okay, Michelle, you’re fantastic and I’m going to trust you to be the person who answers all of the guests’ questions that they would like answered when me and my bride would rather not be tied to our phones on our wedding day.”

Aaron Schmookler
There you go.

Pete Mockaitis
Because I’ve been on both sides of that equation in terms of, “Oh, I’ve got some questions but it’s not quite clear. Like, where do I go? What do I do? Can I do this at the wedding? I don’t want to bother the bride and groom but I kind of like to know.” And so, I was like, “Michelle, you are the director of guest experience. That’s your role. And we’re letting all the guests know, ‘If you have any questions, you call Michelle.” And so, that was really cool.

And for HOBY, we got someone who’s talented with design things but she didn’t want to be in charge of the whole programming thing, so we said, “You are the artistic director. If there’s any sort of color or logo or design or image that goes on a T-shirt or a booklet or a nametag or a door decoration, you are the master of that.” And she’s like, “Oh, sweet.” I knew it was fun for both of us because it decimates ambiguity, it was like, “Oh, that’s me.” It’s like, “Oh, lights? You say lights, Aaron, that’s me.” “Oh, did you say the huge backdrop? Oh, that’s me.” And you get to feel good when you own that thing.

Aaron Schmookler
That’s right. That’s right. And I’ve created an event recently that we called “I’m not participating in this recession.” And it was an event for C-suite folks to come to. I had a CEO, who had been the CEO of SOG Knives, to come because he had taken his company through some recessions. And one of the things that he shared with our attendees was that he likes to make people the CEO of their realm within his company because it just creates so much leverage for him to be able to say, “You handle this.”

And one of the things that I advise, when people are contemplating, “Can I delegate this?” is that if somebody can do a job up to 75% as well as you can, 75% is a good marker to say to them, “You, go take care of this.” Because if you can delegate to three people 75% of what you could accomplish, well, the leverage of all that multiplicity is tremendous.

Aaron Schmookler
Seventy-five percent of three things is much better than 100% of one.

Pete Mockaitis
Yeah, I dig that. And I think it’s really useful to note, “The thing that you’re delegating, is it super crazy mission-critical?” Like, there are very few things in this world, although there are some, in which if you do it a hair better, the rewards are huge. I’m thinking about maybe direct-response copywriting. I’m thinking about Google search engine optimization. I’m thinking about Olympic swimming. Hundredth of a second, like, gold versus nothing.

Aaron Schmookler
Yes, that’s correct.

Pete Mockaitis
But almost everything else is, “You can do this 75% as well? Well, then have at it, and away we go.”

Aaron Schmookler
Especially within our companies, part of the time and effort that we put in our companies is on the core competency of our company, “This is what we do. This is what we do different from other people. This is what we do better than other people. This is what you have come to us for. Everything else in our company is not that.”

Pete Mockaitis
That’s right. Bookkeeping, you didn’t come here. Or, invoicing. Yeah, that’s good. All right. Well, lovely concepts. Now, you actually have a pretty precise five or six, depending on how we’re counting, steps for effective delegation. Can you walk us through these?

Aaron Schmookler
Sure. And you’ve hinted at the idea that this is a six-step model with five steps, in a way, because step zero, I’m considering step zero because, though this is the first step in delegating, it is just you, all by yourself, getting yourself ready to go and do the delegation. And there are some questions for you to answer before you go and do that.

One, “What is the desired outcome? What do you want? What is the end state that you need to have accomplished?” In the military, they call this commander’s intent, “What’s the commander’s intent?” It sounds simple but it’s often very hard, and one way to get there is to think about, “Why do I want this done?” That will help you to conceive what is the end result look like.

So, then when you’ve got your end result mapped out, you also need to answer the question, “When do I need to have this result in hand? And, therefore, what’s a decent margin for failing?” So, if I’m going to delegate something to you, Pete, that I need on Friday by 3:00, if I asked you to deliver it to me by Friday at 3:00, I’ve set us both up to be in real trouble. Better that I should ask you for it by Thursday at noon so that we’ve got time to look it over, make some adjustments, figure out that we’ve got problems, resolve them before I need the thing.

The next question to ask yourself, and we’re still in step zero, is, “Who will be served by taking on this responsibility? And who is able to serve the purpose?” That’s kind of a two-part question. So, who is the right person because they’re going to be served by this? Maybe they really enjoy this kind of work. Or, when I have somebody working for me, I ask them, “Where do you want your career to end up? Where do you want your career to be a year, five years down the line? Okay, what skills and talents are you going to need to get there? Oh, well, this project is going to serve you developing that. So, that is a good reason to give this to you, also, because you’re going to be capable of serving the purpose.”

And then the last question to ask yourself, but still in prep, is, “What are they going to need to succeed? What’s the information that they’re going to need? What resources are they going to need?” And do not skip this one, “What authority, what decision-making authority are they going to need in order to succeed?” That’s step zero before you even begin to delegate, preparing yourself to be ready.

Pete Mockaitis
Okay. And then, I’m wondering, for those who have a hard time letting go, delegating, they might say, “Well, nobody is sufficiently qualified or able to handle this.” How do we respond to that?

Aaron Schmookler
Two things. One is, “Are you sure?” We talked already about that 75% rule. If somebody is going to be able to deliver 75%, then maybe it’s time to reassess what nobody looks like. The second thought that I have is Dennis Bakke wrote a book called Joy at Work in which he suggests that you push decision-making down. And in delegating, he says, “You can set parameters. Without withdrawing the authority to make decisions, you can set parameters.”

So, if I delegate to you, Pete, and I think you don’t have the judgment yet, I might say, “I want you to talk to Betty and Bob about everything that you’re considering before you make the decision. At the end of the day, the decision is yours, and I want you to have the benefit of their insights before you make the final decision.” So, that’s another way of cranking up people’s capability while leaving their decision-making authority intact.

And I’ve actually thought of a third thing to share, which is, “If they can’t do the whole thing, what parts of it can they do? What parts of it can you delegate and then maybe you retain the rest?”

Pete Mockaitis
That’s good. All right. I like that notion of the parameters. So, one of it could be, “If it’s you get the input from these people, another one could be if it’s over X thousand dollars or whatever, then you check in with me,” or, “If it’s concerning super client A, B, or C, I want to know about it. If it’s any dozens of other clients, have at it.”

Cool. So, we’ve got the parameters, so it’s not a sort of 100% carte blanche, “It’s all yours,” but rather, “Okay, here’s a slice of it,” and it may very well still be the vast majority, which is cool. All right, so that’s step zero. What’s our step one?

Aaron Schmookler
Step one, and this one is a little bit counterintuitive, is to ask somebody, to give them something to do without giving them any details. And this is counterintuitive on a couple of levels. When we’re training managers, some people push back on the idea that they should ask anybody anything instead of just simply telling them, “Hey, here’s what you’re going to do.”

And then the other reason that they push back is they say, “What do you mean with no details?” So, here’s what I mean, “Hey, Pete, can I get your help with something?” “Pete, may I give you a project?”

Pete Mockaitis
It’s so funny, like, when you asked me that, you’ve galvanized my attention but maybe in an anxious kind of a way, it’s like, “Ahh, what do you have in mind exactly, Aaron?” And maybe…

Aaron Schmookler
So, the maybe is important because the maybe is correct, and we’ll get to that in a moment. The galvanizing your attention is the biggest part of this. One is I’m treating with respect by asking for permission. And then I can’t count the number of times, somebody will poke their head into my office and simply start to ask me questions, and my attention is on whatever I’m doing, and I have no idea what they’ve said, it goes in one ear and out the other.

And with my attention deficit disorder, and I’m very much like this, and even neurotypical people are like this as well, we all need a basket to put things in. So, when you say, “Can I get your help with something? Can I give you a project? Can I give you a new responsibility?” I now have a basket to put all of the details that you’re going to give me in and create order for my brain, and that’s going to serve everybody.

And with respect to the anxiety that I’ve created, largely that’s because you and I don’t have a relationship where we’re doing this, where you know what’s going to come next. So, one of the things that I recommend to any manager or anybody who’s in a position to be delegating is to tell people in advance, “Hey, when I delegate to you, here’s what it’s going to look like. I’m going to go through these six steps.”

“And what this step I’m going to do before I even get to you, then I’m going to come and I’m going to ask you, ‘Can I get your help with something?’ I’m going to ask you, ‘Can I give you a new responsibility?’” And no is a perfectly good answer, and here are the other steps that I’m going to go through so that that anxiety is alleviated in advance by your knowing, “Okay, this is just step one in a five-step process.”

Pete Mockaitis
Certainly. And then I think you say no is the acceptable answer to, “Can I get your help with something?” I guess, also, maybe any number of context-sharing things, like, “Well, I feel wildly overwhelmed by this crazy important task that’s due in two hours, but what did you have in mind?”

Aaron Schmookler
Right. And if you tell me you have a crazy important task that’s due in two hours, I’m going to say, either, “Thank you for telling me, Pete, you’re not the right person,” or, “Oh, well, this is not pressing. Why don’t I come to you three hours from now to give you a chance to get that turned in and catch your breath?”

Pete Mockaitis
That’s good.

Aaron Schmookler
So, that takes us to step two, which is now we’re going to lay out the details of who does what by when, what is it that I’m asking you for. And there’s another podcast called Manager Tools, and one of the things that they suggest at this point in any delegation is that instead of delegating the task be done, delegate the reporting that it is done.

And I think that is just a brilliant insight to say, instead of, “Hey, Pete, will you do this?” to say, “Hey, Pete, please tell me by 3:00 p.m. on Thursday that this is complete,” or, “Please send me an email with the file of this report by 3:00 p.m. on Thursday.” So, you’re delegating the reporting because if I don’t know it’s done, it has no value to me.

So, delegate the reporting, “Tell me as soon as this is complete. Here’s the outcome I’m looking for,” the manager’s intent, what is the end state, rather than all of the meticulous details, “Here’s the deadline and here are some resources, here are some considerations, here’s the authority that you have.” When I say consideration, that might be you might be tempted. If I’m asking you to rent us a truck, I might say, “The last time we went to U-Hall, we had these problems, so consider looking at Penske and Budget before you go talking to U-Hall.” So, that’s step two, is to lay out what it is that I’m asking for.

Pete Mockaitis
All right. So you’re elaborating, so who does what, by when, to what standard, for what reason, with what resources. Can you elaborate a little bit on the standard? Like, how can we go about unpacking and delineating what is good optimal acceptable versus what is not?

Aaron Schmookler
So, you’re going to want to ask yourself the question of, “What do I need to see?” So, the standard for a truck might include it needs those rails on the wall that you can latch things to. The standard might include the budget. The standard might include the size of the truck. If I’m asking you to create a report, the standard might include margins for error.

Or, if I’m asking you to design something, the standard might be, “I want this to look opulent.” What are the ways that you can describe what it should look like, what it should feel like, what it should be like? And what are the questions that you’re going to be asking when you assess its success?

Aaron Schmookler
In other words, how do we know if you’ve succeeded at the end? Are there no grammatical errors? Are there no spelling errors? Does that matter? And perfectionism, when we talk about perfectionism, perfectionism is somebody insisting that they go beyond the standard, which wastes time, effort, and peace of mind.

Pete Mockaitis
Yeah, okay. Cool. Well, now, can you share with us the step three, negotiate?

Aaron Schmookler
Yeah. So, step three, as you said, is to negotiate, “I asked you if I could give you something. You said yes. And you said yes sight unseen, or maybe you said it depends, so you don’t know what…you didn’t know until now what I was asking for.” So, at this point, the negotiation includes asking the questions, “Okay, now that you know what I’m asking for, Pete, are you still in? Does this still work for you? Do you have what you need?”

“I’ve told you about these resources, I’ve told you about that authority, I’ve given you these tools. Is there anything else that you need that I haven’t thought of? Do you need help? Do you need people? People are some of the resources that you might need. And if you’re tempted to say no, and/or if you’re not sure how to meet the rest of your obligations, then we may be reallocating your other priorities and your other responsibilities.”

“I don’t have time to do that because I’ve got this.” “Oh, well, let’s delay the deadline on that,” or, “Okay, let me take back this thing that I was trying to delegate to you because, clearly, this isn’t going to fit on your plate,” or, “Let’s take this other thing off your plate and give it to somebody else so that you have the bandwidth to handle this.” So, the negotiation is, “Okay, what will it take to make this work if, in fact, it does?”

Pete Mockaitis
Okay. And then step four?
Aaron Schmookler
So, step four is to keep in touch, and this is very often an overlooked step because people say, “Okay, go do this. I’ll see you at the end.” Tools for this include if you’re a manager having weekly one-on-ones where you’re checking in with your direct report, or the weekly one-on-one is focused on your relationship in general where you keep touch, “How is this going?”

Or, if this is a longer-term project, you set, “Here’s the final deadline,” that there are benchmarks along the way, “Here’s how we know we’re on track. This is going to be accomplished three weeks away from the deadline,” “This is going to be accomplished four weeks away from the deadline,” “This is going to be accomplished five weeks away from the deadline.” So, you’re keeping touch of, “Are we on track at each of those benchmark locations?” And you’re checking in on the standards at those times as well.

So, you create a channel for reporting and keep in touch at least weekly, at least briefly. So, that’s step four, is to make sure that you’re keeping in touch.

Pete Mockaitis
At least weekly, that’s handy. And then you mentioned that fine is not a status report in terms of, “Hey, how are things going?” “Fine.” What more precisely are we looking to hear when we’re keeping in touch?

Aaron Schmookler
Here’s where the benchmarks come in, “Oh, well, I’m two days behind on this benchmark,” or, “I’m two days ahead. I’ve reached this benchmark even though it’s not actually due until two days from now.” So, that’s one thing. Or, a status report is, “We’re on track and, in terms of we’ve hit all the benchmarks, up until now. And there’s an obstacle emerging that I didn’t anticipate. Let’s talk about how I might get around this obstacle. Can I have your insight?” Or, “I’m going to need a $100 or $1,000 to level this obstacle that’s come up.” “The price of lumber has changed.”

Pete Mockaitis
Okay. And then step five, debrief?

Aaron Schmookler
Step five is after the fact. So, arguably, this isn’t part of a delegation model. It’s part of a checking in, and I think it needs to be there because I don’t consider it complete until we’ve learned what there is to learn from the process that we just went through, “What worked and what didn’t? What worked in terms of how our communication went? What worked in terms of my execution of what you delegated to me? What worked in terms of did our standard actually meet the need?”

“I delivered this entirely on standard. This is exactly what we designed and it still didn’t solve the problem that this project was intended to solve. So, what needs to change?” So, a few questions to ask here, “What do we need to keep? What do we need to stop, to just get rid of this entirely? This was completely extraneous. What do we need to add? What wasn’t there that needs to be there? And what do we need to adjust? We got the blue one, it was the wrong blue. Or, we got these but, instead of five, we need seven.”

So, what do we need to keep, what do we need to stop, what do we need to add, what do we need to adjust. And that takes us, Pete, through six steps if you include step zero to prepare yourself for the delegation.

Pete Mockaitis
Okay. And then maybe zooming out or cutting across all these steps, what are some of the top things that make all the difference for preventing disasters, disappointments, oopsies, and stressful moments?

Aaron Schmookler
So, I’ll start with perhaps the answer that people are going to like the least. I remember when I took my first advanced level biology class in college was a genetics class. And I sat down for the first exam, and I looked at the cover sheet of the exam, and what it said was, “This is one test in one class, in one part of your schooling, which is just one part of your life. Your performance on this exam, while it may be important right now, is not critical to the outcome of your life, so don’t fret.” That was the cover page of this exam.

And then I opened up the exam, and the first question was, “For ten points, what color is a Golden Retriever? Hint: Look at its name.” So, that story is intended, Pete, to illustrate that part of how you can prevent disasters is by chilling out, both because the things that you’re thinking of as disasters are probably not as disastrous as you think they are, and because fearing disaster makes disaster more likely. And so, one illustration that I love about this, I used to be a hang glider pilot.

Pete Mockaitis
Oh, cool.

Aaron Schmookler
And when you land a hand glider, generally, you’re looking for a big open field to land the hang glider in. And what happens more often than you would imagine is that there’s a big open field with one tree in the middle, and the hang glider pilot hits the tree in the middle. There’s lots of open space, and the hang glider pilot flies right into the tree.

And the reason is that in the fear and anxiety of not wanting to hit the tree, the pilot looks at the tree. And your brain is designed to take you where you’re looking. Millions of years of evolution have made our brains direct where we go to where we’re looking. So, if you’re looking for a disaster, you are much more likely to steer into it. Look instead for the clear open field, and you think, “Open field. Open field. Okay, there’s the tree, that’s where I don’t want to go,” and then you spend the bulk of your time and attention on, “Here’s where I do want to go. Here’s where I do want to go.”

Another part of the answer to your question, Pete, is to consider those benchmarks, and to really not get lazy about checking in with those benchmarks, and assessing along the way, as part of your keep in touch step, “Do these benchmarks still make sense or do they need to be reassessed? Are we still on target to meet the deadline? Are we still on standard? Are we getting further and further? If we start to fall behind, are we getting further and further behind, or are we finding that, over time, we’re catching up?” So, those are a few of the thoughts that I have about that question.

[39:21]

Pete Mockaitis
All right. And then when it comes to micromanaging, I think folks don’t like being micromanaged, and, on the flipside, managers are scared to be micromanaging. How do we make sure we strike this balance appropriately?

Aaron Schmookler
Micromanaging is about backseat driving. It’s about checking in so regularly that people can’t get into a flow. Micromanaging is about making decisions that other people could make. It is not about the frequency of your check-in, provided you’re allowing people to accomplish stuff and get into a flow state before your next check-in. People are so afraid of micromanaging in my experience. The tyranny of micromanagement is the fear of micromanaging far more often than the tyranny of micromanagement is actual micromanagement.

Pete Mockaitis
Okay. Well, so that’s reassuring and comforting. So, then any maybe pro tips or indicators, like, “Oh, you might be getting close to that line”?

Aaron Schmookler
Of micromanagement?

Pete Mockaitis
Yeah.

Aaron Schmookler
If you are tempted to take back the project that you’ve given to somebody, think twice. Taking back the delegation is often a piece of micromanagement. If you are trying to get marginal improvement by changing the decisions that they have made, you’re very likely micromanaging. And it’s important to think about… micromanagers are very often, what they’re trying to do is risk management, “I don’t want this to go badly. I want this to go as well as it possibly could. I want the outcome to be 100%.”

The risk there, the risk that you actually attain is demoralizing people, is losing the leverage that you have as somebody who can delegate, to get more than one thing done at a time. And so, if you are wasting human capital, if you are wasting people’s potential and fulfillment in pursuit of marginal accomplishment, you are a micromanager. It’s time to rethink your priorities.

Pete Mockaitis
Okay. Well, now, Aaron, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Aaron Schmookler
I’m glad you brought up micromanagement because that probably would’ve been how I would’ve answered that question. I think I’m ready for favorite things.

Pete Mockaitis
Let’s do it. Could you share a favorite quote, something you find inspiring?

Aaron Schmookler
This quote is often attributed to Goethe and it, evidently, is not his, and it’s not known where it came from. So, it is, “Whatever you can do or dream you can, begin it. Boldness has genius, power, and magic in it.”

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

Aaron Schmookler
there’s an experiment around something called enclothed cognition.

Pete Mockaitis
Oh, yeah.

Aaron Schmookler
And enclothed cognition is, essentially, enclothed, meaning the clothes that you are wearing, cognition, meaning thought. And so, this experiment took people and put them in a smock, like a painter’s smock, and asked them to do accounting work, like work on a spreadsheet, the kind of stuff that you and I were talking about we don’t really like.

And wearing a smock, they were worse than if they were just wearing their normal clothes at doing that task. And wearing a lab coat, they were better than they were at doing that task than if they were just wearing their normal street clothes. And by contrast, if they were asked to do something creative, like create a painting, then they were better wearing the smock than they were in their normal street clothes. And if you put them in a lab coat, they were worse at being creative and original and interesting in creating their art than they were…worse in a lab coat than they were in their street clothes. Fascinating.

Pete Mockaitis
Okay. And a favorite book?

Aaron Schmookler
Today, I’m going to name Never Split the Difference by Chris Voss. A very compelling book about negotiation.

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

Aaron Schmookler
I love Calendly. I’m not that great at tracking administrative details, so being able to give somebody either a link to go and book time on my calendar, or Calendly gives you this one-off meeting thing where I can tell you, “Here are a bunch of times. Click one and you’ll appear instantly on my calendar.” Very, very useful for me.

Pete Mockaitis
All right. And a favorite habit?

Aaron Schmookler
“One more” is my favorite habit right now. There’s a lot to do in my life, as there is in all or our lives. And I might go to the sink that’s maybe full of the day’s dishes and start to wash the dishes and start to be tempted to go, “I’m feeling hungry. I want to go dirty another dish.” And I just say, “One more.” And one more will often get me all the way through all the dishes, or all the phone calls that I need to make, or any of those things. So, I have a habit right now of saying, “One more,” when I start to feel like, “I’ve got to move on from this.”

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

Aaron Schmookler
I’ve mentioned some of the manager training that we’ve been doing lately, and this is something that hits all managers, I think, where they live. I’ve had CEOs audibly kind of get hit, they sound like they’ve just been punched in the stomach when I say, “If there’s no consequence for consistently missing a job requirement, then that thing is not actually a job requirement. It’s something that you’ve put on your wish list and it’s a resentment-builder.”

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

Aaron Schmookler
You can find me on LinkedIn. I’m the only Aaron Schmookler on LinkedIn. And you can find me on all the work that we’re doing at TheYesWorks.com.

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

Aaron Schmookler
Yeah, I’ll stay in keeping with the theme of the day – delegate. Go delegate. Are you not good at it? Delegate it. Are you not interested in it? Delegate it. You don’t have time? Delegate it. Delegate it. Go delegate. There’s almost nobody that I know who delegates too much, but there are lots of people that I know who delegate too little. Myself included, by the way.

Pete Mockaitis
All right. Aaron, this has been a treat. I wish much luck and fun in all your delegations.

Aaron Schmookler
Well, thank you. Likewise, right back at you.

594: Achieving More by Embracing Your Productivity Style with Carson Tate

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Carson Tate says: "There's no one-size-fits-all approach to productivity."

Carson Tate discusses the four productivity styles—and how to pick the best tools and practices that best suit you.

You’ll Learn:

  1. How to pick the right system for your productivity style
  2. The top tools for keeping your inbox under control
  3. How to work in harmony with opposing productivity styles

About Carson

Carson is the founder and Managing Partner of Working Simply. She is the author of Work Simply: Embracing the Power of Your Personal Productivity Style. Her views have been included in top-tier business media including Bloomberg Businessweek, Business Insider, CBS Money Watch, Fast Company, Forbes, Harvard Business Review blog, The New York Times, USA Today, Working Mother and more.

Prior to starting Working Simply, Carson worked in Human Resources and sales functions with Fortune 200 firms. Carson holds a BA in psychology from Washington and Lee University, a Masters in Organization Development, and a Coaching Certificate from the McColl School of Business at Queens University.

Resources mentioned in the show:

Thank you Sponsors!

Carson Tate Interview Transcript

Pete Mockaitis
Carson, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Carson Tate
Thanks, Pete. I’m glad to be with you today.

Pete Mockaitis
Well, I’m glad to be with you and to get into some of the mess that is our lives and productivity and such. But I understand you also love the mess of mud runs and more. What’s the story here?

Carson Tate
Yes. So, a couple of my girlfriends and I got bored a few years ago with just regular road races and we decided to branch out, and it is some of the most fun that we have, and we are literally cleaning mud out of our ears for days afterwards, and obstacles, and you push yourself, but it’s great fun.

Pete Mockaitis
Cool. Let’s see, I’m familiar with the Tough Mudder. What are the other big names in mud running?

Carson Tate
So, the Tough Mudder is the one that we’ve done. And there’s also, in North Carolina, a couple of just very small local races as well.

Pete Mockaitis
Okay. Cool. Well, that’s some fun background. I want to get your view here, so you’ve done a lot of work about work, researching people and productivity, and kind of what makes us tick. What would you say is maybe the most surprising and fascinating discovery you’ve made about people and productivity from all of your explorations?

Carson Tate
If we really want to be productive, you’ve got to align your tools and your strategies to how you think and process.

So, what often happens is people try a new app and it doesn’t work for them, and then they think they’re not capable of getting organized or there’s something wrong with them. No, it’s just the tool that doesn’t work for you. So, it’s about aligning your tools to how you think and process, and then really creating a custom toolkit.

Pete Mockaitis
Okay. Well, so in your world, you defined four different productivity styles. And I’d love it if you could, call me a skeptic or what the word is, but I’d love to hear a little bit about the underlying research in that. I guess for like with the Enneagram, for example, I’m like, “Who says there’s nine types? How do we know there’s nine? Why are there not eight or 12? Why are they not like 34 like the Strengths?” So, can you lay it on us, how do we come up with four?

Carson Tate
Absolutely. So, first of all, my graduate research looked at cognitive thinking styles, so this is different than personality. This is literally how you think and process information. And so, I looked at the research, neuroscience and research, into how we think. And so, the concept of left brain and right brain, it’s not technically accurate but that’s easy classification, and then started digging into an instrument called Hermann Brain Dominance Inventory that looks at thinking style, and realized that that’s a great instrument, and there’s a gap, and that that instrument does not tell you how your thinking style informs how you work. And by how you work, I mean how you think about time, how you structure your day, whether you like to take notes or not, what your inbox looks like, and whether or not you like file folders.

So, using what I understood around our thinking styles, I developed first-tier assessment in grad school and then tested it out, and realized that there really are topologies, there are four different styles that broadly characterized these thinking styles. So, one is prioritizer, analytical, linear, fact-based. These are the folks that like spreadsheets and data and details. Then planners, organized, sequential, detailed. These are the folks that have never met a checklist they didn’t like. These are the project planners. Arrangers, these are your intuitive, kinesthetic, relational folks. They do their work with and  through people. They like colorful pens, they’re visual. And then visualizers, these are your big-picture strategic thinkers. They are the ones that are pushing the envelope, “Why not?” They don’t like structure. They think in big, broad concepts.

So, first iteration, tested it, had to refine the topology. Tested it again. And now we’re on an iteration, this is our third iteration. We’ve had over 2.5 million people take it and validating the results.

Pete Mockaitis
Wait. What’s the number again?

Carson Tate
Two and a half million.

Pete Mockaitis
All right. Good work. Cool.

Carson Tate
So, it’s working. It’s definitely working. And, Pete, I think what is helpful about it, like any of these assessments, and I hear you on what’s the science behind it. Fundamentally, it’s just an awareness tool. So, if you’re my client, I’m coaching  you, and I can help you see how your thinking is informing why you do not want to schedule your day in 15-minute increments in a way that would better help you optimize your time, that is what’s going to lead to your productivity. So, that awareness. So, it’s just an awareness too. It’s just access into how you think.

Pete Mockaitis
Well, yeah, I would love it if you could sort of make that come alive for us here in terms of if you could maybe share a story of maybe someone who was doing something and it wasn’t working for him, and then they made a discovery about this, and then they saw some cool results from there.

Carson Tate
Yeah, absolutely. So, I was working with a client, we’ll call him Bill, he worked in the nonprofit sector, and Bill, very tech savvy, Bill had probably tried every app that’s out there, every to-do app, and he would stick to it for like a week or so, he’s so excited, and then the wheels fall off, and he’d be crazy it’s not working out. He could never find an email. He’d taken plenty of email management classes, he was late on all of his projects. And so, when I met with him, the first thing I realized was that he was a visualizer, really big-picture thinker. So, an app that was very linear and very designed for really discrete details, it went counter to how he thought about things.

He thought about things in terms of ideas, so this was how he was going to solve the waste management issue, like these big concepts. So, what I’d asked him to do was try mind-mapping software so he could anchor the central concept, and then from it, pull out things that needed to happen around it. So, making these really graphical charts he could see. And the second thing we did was we removed every single folder that he had in his inbox because out of sight was out of mind. He’d get an email and then he’d file it away in the to-do folder, but he’d forget about it because he was visual.

So, we turned his inbox into a visual to-do list by changing the subject line of his email messages to his next action steps so he could see them. They never went away. He could search them and see them. And then we reconfigured his calendar. So, these tight little very structured meeting, meeting, meeting didn’t work for him. So, we started thinking about his work in terms of theme days. So, Monday’s theme for him was admin, so all of the internal work, the internal meetings, the one on one’s. Tuesday, he was out in the field, he did some work out in the field inspecting job sites. Wednesdays was back in the office. Thursday was another field day, so he could kind of group and organize things based on themes.

So, fits and starts. Three weeks later, I checked in with him, and he’s still on those early stages of trying to get it to work, but what had happened is that his manager noticed that he was arriving on time to meetings, and that he’d actually turned in two things early. He was so proud of him, super proud of him. Fast forward six months later, he’s hitting all of his marks, he’s up for a promotion, and he actually had started working on a book that he was talking about for his nonprofit that he had setup because he created the mental space and the time space to also start to pursue some of his personal passions because he got work dialed in.

Pete Mockaitis
Well, there’s a lot in there. And it’s funny because I’ve heard about how grand mind mapping is, and I haven’t really had much cool results with it, part of it is like my writing is hard to read and it gets kind of crunched. I could try the big piece of paper. So, yeah, I haven’t personally had a mind-mapping session that knocked my socks off in terms of, “Wow, that’s so cool. I’m glad I did that.”

And, yet, when you first mentioned the prioritizer, I am in so all about finding sort of the 80/20 high-leverage thing that does it. And I do have a spreadsheet that estimates the profit generated per hour invested of various business initiatives and then that gets me fired up, like, ‘Holy smokes, that one is worth ten times what that one is worth.” So, as you laid this out, it makes a lot of sense how, hey, mind mapping is game-changing for some but, for me, it hasn’t been resonant yet.

Carson Tate
Right, because it’s not quantifiable for you. So, as a prioritizer, you need to quantify your efforts. So, we either quantify in terms of minutes, we quantify in terms dollars, we quantify it in terms of emails processed in minutes, number of items checked off, how quickly you achieved an objective, how many minutes were shaved off of a meeting. So, that is speaking your productivity language. But for Ben, he doesn’t care. That doesn’t motivate him. He doesn’t care about that. He’s more concepts, “What’s next? And how do we build a system for him?” And he actually used a whiteboard, and then there’s also a software called MindJet that you can do mind mapping on the computer.

Pete Mockaitis
Yeah. Well, okay, since you opened up that door, I can’t resist. Let’s hear the tools because it can be tempting to play tools all day long, but if we can have just a couple of minutes. So, MindJet is cool for mind-mapping individualizers. Is there any other sort software or tools you recommend for each of the other three?

Carson Tate
So, I like Trello for planners, and arrangers can use it a little bit. Evernote is great for arrangers and for visualizers because they have blank pages. And prioritizers, you can use Todoist, you can use Things, and there are a host of them that are designed for prioritizers.

Pete Mockaitis
Well, it’s funny, I think that I love OmniFocus and just a spreadsheet most often because I can see those numbers.

Carson Tate
Right.
I would say that you’re definitely onto something but it really doesn’t matter what the tool is as long as it works for you. So, Excel, a great tool for you, but it might not have the flash or the name recognition, but it works for you. So, part of the push and the struggle on productivity is, can you stand on the ground of, “Hey, you know what, I use a legal pad. It works for me”?

Pete Mockaitis
Right. Understood. Okay. Cool. And then I guess I’m also thinking that, I guess, in some ways, different projects and different outputs that you’re shooting for sort of seem to align more readily to different folks. I guess I’m thinking if I’m trying to say, “Hey, manufacturing plant manager, I need you to optimize our outputs and shave off all the time associated with cranking out the widgets,” going on a visualizer style, or maybe just my bias as a prioritizer, but it doesn’t quite seem like that’s ideal but maybe all roads lead to Rome or something. Like, there’s multiple paths that will end up doing the same thing. What’s your take on that?

Carson Tate
All roads lead to Rome, and each of these styles has a strength. So, if we’ve got to optimize throughput on a manufacturing line, I’m going to strongly encourage that we have a prioritizer to think about that. If we need to redesign the line, then I’m going to suggest we have a visualizer to think about a new approach. And if it’s about, “Do we have a team that’s highly functioning on this line?” I’m going to ask the arranger to do that work.

Pete Mockaitis
Okay. Well, so then I suppose, tell us, how does one learn what their style is?

Carson Tate
So, we have the assessments on our website WorkingSimply.com, you can go and take it on the website. Then we also have multiple articles on our blogs that talk about these styles and questions you can ask to help you determine your productivity style.

Pete Mockaitis
Okay. And so then, can you tell us, once we are aware of our productivity style, I guess what are some of the sort of top do’s and don’ts that we should keep in mind? Either things that are sort of universally applicable to all or the particulars, “Hey, prioritizers probably do this and don’t do that.”

Carson Tate
Yes. So, universal, I have two universals across the board for all four styles. One is the concept which, I think, Pete, you are 100% in alignment with, which is time is a commodity. And so, we talk about it with our coaching clients and our training clients that time is non-renewable resource, “We all have the same 168 hours in a week. How do you choose to invest it for your highest ROI?” So, that’s across the board best practice, “Can you make that paradigm shift to being as intentional and as thoughtful about your time spent as you are your money spent?” What you’ve done with your spreadsheet is you’ve quantified time. You know what an hour of your time is worth and you make your decisions based on that.

The second universal principle is around inboxes, and we believe that your inbox is the best personal assistant you’ve ever had.

Pete Mockaitis
Do you mean email inbox or…?

Carson Tate
Your email inbox, yes. And so, to use all of the technology tools that are available in your platform, to automate as much as possible of your email management.

Pete Mockaitis
Don’t even know we’re going to go here. Let’s go there now.

Carson Tate
You want to dig into email? Let’s talk email. Let’s talk inboxes.

Pete Mockaitis
So, there’s the tools. I mean, hey, I love my email tools. I like Superhuman to fly through them, and I like SaneBox to filter. I guess, what are the other tools, and what are the other just sort of approaches in terms of what you’re doing in there, kind of regardless of the software you got?

Carson Tate
So, regardless of the software, we suggest a process we call the email agility process. You read it. You decide what it is. Does it require action by you? If action is required by you, you do it, not channeling Nike. You just do it if you do it under five minutes. Delegate it if you can, if you don’t have the knowledge and authority. Don’t have the knowledge and authority, you delegate it or you convert it to a task. So, convert them to task in Gmail, Outlook, you can send it to Evernote, but you are making that decision around the action step because what we don’t want to do is re-read the email. And if no action is required, you delete it or you file it. And then the final step is to contain and think thoughtfully about how you want to store and retrieve your messages.

Pete Mockaitis
Well, yeah, how do I arrive with that decision, the containing?

Carson Tate
The containing, yes. And this goes back though, Pete, the containing piece is where it becomes really personal. So, for you as a prioritizer, it’s going to look different than my example Ben, the visualizer. So, he doesn’t use folders. His containment method is everything lives in there, and he uses search functions. It works great for him. You probably have some folders, yeah, or nothing in your inbox.

Pete Mockaitis
It depends on what day you catch me.

Carson Tate
Yes.

Pete Mockaitis
Yes, search is the primary way I pull one up although I do have the labels and the archiving. Okay. And so then, you say it’s the best personal assistant we have in the sense that it’s kind of like bringing to our attention that which we need to deal with or…

Carson Tate
Right. So, I’ll take Outlook, for example. So, in Outlook, you can use a function called conditional formatting. It’s very similar to labels in Gmail. And we can set it up so every time Pete emails me, that email comes in in bright red. So, what I’m doing is I’m telling my assistant, “Flag Pete. Turn him this color.” And when you come in my inbox, I now have a visual prioritization. I’ll read red first, then blue, then I’ll deal with the black ones. So, my assistant, I’ve told my assistant what to do, and then my assistant does it over and over again with no input from me, saving me that step of getting in and prioritizing every time.

And so, it’s thinking through if you always file this email, well, write a rule. Don’t do it. Have the technology do it for you. Another example we use with all of our clients, a lot of the emails that we send, and I can imagine for you, a lot of these are the same thing, “So, here’s the logon, here’s the link, here’s what you need to do as a guest on my show.” You’re written it. It’s a template. Well, save it as a template in your email program so that you can just use it over and over again, just like you would a Word doc or an Excel doc. So, we want to eliminate rework and automate using the tools as much as possible.

Pete Mockaitis
Okay. Thank you. Well, so then when we got the productivity style of your own self, and then you’re interacting with others, how do you play that game? Because I imagine some people are pretty kind of chill, “Hey, man, however you want to do it. Just get it done by this time according to these principles.” And others are going to pretty precise, it’s like, “Hey, I need you to do…” I’m thinking about podcast sponsorship now, “I need you to do an air check, and you download reporting at this time. And I’m on this platform and this system.” So, yeah, I imagine that can create either harmony or irritation when these things come together. How do we navigate that?

Carson Tate
You’re exactly right. So, harmony when you’re working with someone who has the same style as you or similar style. So, Pete, if I was a prioritizer, and you and I are paired up on a project, we end up speaking quite the same language. We’re focused on the outcome. We want the data. We want to be quick. We want to be efficient. So, it’s very easy for us to work together. We’re pretty aligned. We get it done.

But if you were working with an arranger who’s focused on the people and wants to get everyone’s opinion about what the objective is, that’s going to be pretty frustrating for you. Very frustrating. And for the arranger, they’re going to be frustrated because you just want to get to work, and they don’t feel like they’ve built the team and aligned around the team. The planner, detailed, organized, who wants to put together your project plan, when they work with a visualizer, the visualizer doesn’t like structure, they don’t want a project plan, they don’t want details, so that’s going to create a pretty predictable clash. So, when you work with someone like you, easy.

When we talk about going cross-quadrants, so prioritizer to arranger, that’s the most significant difference, the biggest clash. Planner to visualizer, going that way, other very significant clash. It’s just going to be harder to work together.

Pete Mockaitis
Okay. And so, acknowledging that’s going to be harder, what do you do about it?

Carson Tate
What do you about it? So, first, you got to communicate. So, each of these four productivity styles has a central question they want answered. So, you as a prioritizer, you want the what, “What’s the goal? What’s the objective? What’s the data?” The planner, how, “How have you done it before? How do you want to do it? How do we need to produce this deliverable?” The folks on the process, the how. The arranger’s focus is on the who, “Who’s on the team? Whos’ involved? Who are the stakeholders?” And the visualizer is asking those big-picture questions, “Why not? Why are we thinking about this? Why does this matter? How does this connect to strategy?”

And so, if I’m a planner working with a visualizer, I need to be thinking about and answering those why questions, talking about strategy, talking about big picture, creating opportunities for innovation. And, vice versa, if the visualizer is working with a planner, they need to be comfortable talking about the how and the details and being willing to work through a sequential process with them.

Pete Mockaitis
Okay. Yeah, understood. And you also had a note associated with a master task list, an acronym, TASK. Can you unpack this for us?

Carson Tate
Sure. So, I’ll give you the why behind it and then we’ll unpack it. So, the why is because our brains are terrible at to-do lists, right? I mean, how often have you sat on your desk, like, “Oh, I forgot to do this on the way into my office.” Well, we all have this happen. So, the master task list creates one central repository to capture all of your commitments, both personal and professional, in one place. So, the T in task stands for think, and this is when we ask our clients basically do a brain dump, get it all out of your head everything you need to do.

The second step is the A, is the action because a lot of the stuff in our heads will be a project. So, for example, clean out the garage. Well, you’re not going to do that. That’s a big project. So, what we have to do is determine the next action step. Well, the first action step would be maybe to measure the wall. If you want to hang something up, we got to measure to figure out how many hooks so that I can start to create some organization.

And then the S is just sort. So, once you’ve done your brain dump and you’ve need to determine next-action steps, we have to create a list that’s actually manageable and that you can get in and out of. So, the sort is just a grouping or a classification of like items. So, it might be podcast prep, it might be calls, it might be research, it could be a project name, but you group all of those action items under that category. And then the last one is you keep one and only one list. So, we don’t have a list in this app, a list in your pocket, a list on your refrigerator. You’ve got just one master list.

Pete Mockaitis
Okay. And since you mentioned multiple lists and multiple places, I’m thinking about sort of the paper versus digital part of this all. How does that sync up to, do you find that some of the four styles prefer one versus the other? Or is it just sort of that’s a whole another dimension there, prioritizers who love paper, and visualizers who love computers, and it’s all over the place?

Carson Tate
it’s all over the place, absolutely, with an asterisk. So, all over the place. We have folks in each category that like paper or tech. The asterisk would be the arrangers. They tend to be kinesthetic, so they have very nice writing utensils. You will see them touch and feel objects. They’re very visual dashboards. They are more likely to use paper than the other four styles.

Pete Mockaitis
Okay. Well, tell us, Carson, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Carson Tate
Just excited I’ve got a new book coming out, October 6, called Own It, Love it, Make it Work: How to Turn Any Job into Your Dream Job. So, it is the roadmap if you do not enjoy your job or you want to enjoy your job even more. This is the tool to help you get there.

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

Carson Tate
I’m going to say, “Just do it.”

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

Carson Tate
My graduate research on cognitive thinking styles was my favorite research project I’ve ever done.

Pete Mockaitis
And a favorite book?

Carson Tate
The Awakening by Kate Chopin.

Pete Mockaitis
And you’ve mentioned a few of them, but how about a favorite tool?

Carson Tate
Paper.

Pete Mockaitis
All right. And with a paper, how specifically do you use it in a way that’s great for you?

Carson Tate
Yes. So, I actually have a paper to-do list because I have a little notebook I’ve created and leaves with me wherever I go.

Pete Mockaitis
All right. And a favorite habit?

Carson Tate
Early morning meditation.

Pete Mockaitis
And is there a particular nugget you share that really seems to connect, it resonates with folks, and they quote it back to you frequently?

Carson Tate
There’s no one-size-fits-all approach to productivity. You must personalize it based on how you think and process information.

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

Carson Tate
WorkingSimply.com or on LinkedIn, Carson Tate.

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

Carson Tate
Yes. Figure out how you think and process information, and then align your productivity tools to support you.

Pete Mockaitis
All right. Carson, this has been a treat. I wish you lots of luck and fun in your productive adventures.

Carson Tate
Thank you, Pete. I appreciate it. Thanks.