Dave Kerpen is a serial entrepreneur. He is the co-founder and co-CEO of Apprentice, which uses tailored social media campaigns to help companies reach a broader audience. He is also the New York Times Bestselling author of several books, including Likeable Social Media, The Art of People, and a new one on delegation, Get Over Yourself. Dave is also a world-renowned keynote speaker and has been featured in CNBC, NYT, and more.
Dave joined Robert Glazer on the Elevate Podcast to talk about the art of delegation, why leaders struggle to delegate, and how to overcome those challenges.
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Dave Kerpen On Mastering Delegation
Welcome To The Elevate Podcast
Welcome to the show. Our quote is from Craig Groeschel, “When you delegate tasks, you create followers. When you delegate authority, you create leaders.” My guest, David Kerpen, is a serial entrepreneur. He’s the Cofounder and Co-CEO of Apprentice, which uses tailored social media campaigns to help companies reach a broader audience.
He’s also the New York Times bestselling author of several books, including Likeable Social Media, The Art of People, and a new one on delegation we’ll talk about today, Get Over Yourself. David is also a world-renowned keynote speaker and has been featured on CNBC, New York Times, and more. David, welcome back to the show.
Thanks so much for having me. Good to see you.
We dug into your background on your first appearance on the show. I would encourage people to check that out way back in episode 97. Since then, you’ve dedicated yourself to this company Apprentice, where you’re co-CEO. Can you talk a little bit about how you make that co-CEO partnership work effectively? Normally, when I hear something like that, I’m like, “Uh-oh.”
I think it’s hard and actually, I have taken over as the sole CEO, but the idea behind it, which is actually part of what I wrote about in Get Over Yourself, was the company came from my mentee. It was an assistant of mine. I’ve always had college students working for me through my first several businesses. I had this college student assistant who worked for me for a couple of years while he was in school.
He came to me and said, “Dave, I think there’s a business model here connecting entrepreneurs and business leaders like you with college students like me.” I said, “Yeah, you’re right. Let’s start it.” We started Apprentice, a marketplace that connects college students and entrepreneurs a few years ago. Rob wanted to lead the company, but he was twenty years old. We became co-CEOs and it was challenging.
It was definitely challenging, but the idea was to divide up responsibilities. I was the CEO in my first company and my wife was the COO, but we were really partners. I used that model and all the lessons I had learned from all the screw-ups we had along the way with that company to apply to the co-CEO model. I will say that there were definitely some challenges and ultimately, it didn’t work, to be frank, to be honest. I think where it can work best is where responsibilities are clearly delineated and, therefore, accountability is also clearly delineated.
I have a couple of thoughts on this because there’s one leadership principle that I argue for a lot. That is being very wary of exceptions. When you do something over and over again, like playing the numbers, sometimes we get obsessed with the exceptions. I’d argue that Oprah Winfrey, Mark Zuckerberg, and Jeff Bezos are exceptions. Someone would say Slack is pointed to as the ultimate pivot company.
I’m like, “Yeah, but 10,000 other companies have tried to pivot and not turned into Slack.” It’s an interesting thing here in terms of like, one, I would say, “For one, I hear work, I hear 999 not work.” Sometimes, I think one should play the batting averages rather than try to be the exception, although the exceptions are often pretty good. I think, right, they’re inherent challenges when two people have the same roles. That’s one thing in common.
The other goes to what you were saying. I heard some thoughts these days, particularly around these global CEOs and just their 24/7 job, and it’s just not sustainable and there’s just burnout everywhere. It’s almost like, look, this job of the CEO as one component and doing everything in this world probably needs to change. I thought that was an interesting comment as well.
If I could go back and do it over again, I would have a similar model to the one I had with Likeable, which is CEO and COO. Ultimately, we moved into CEO Chairman, and I was the chairman, and now I’m CEO again. All of which is to say, I agree with you. Clearly delineated roles are key, which means, almost by definition, not two people having the same exact job title. Even if you divide up responsibilities really well, if you both have the title of CEO, there is a lack of clarity inherently in that.
Ultimately, different job titles are better. That being said, to your point about burnout, so much of what Get Over Yourself is about is limiting how much you do, delegating to others, and finding others to do other key work. The biggest pushback I’ve gotten is from CEOs who say, “I don’t have the money to hire other senior-level talent.”
You’re a president, like this is my thing on the title you give yourself. CEO is a chief executive officer. If you don’t have an executive team, then you’re not a CEO.
Right and to whom I say, especially to up-and-coming entrepreneurs, lifestyle entrepreneurs building EO-type million-dollar businesses, look, there are trade-offs here, but you can recruit another high-level talent to be your COO, CFO, or CMO. You might have to give up equity. You might have to bring in a partner instead. Many folks are hesitant to do that. If there’s no capital, you can either raise capital or dilute yourself and bring in a partner. Those are both options, though, and sometimes folks don’t see those options and they think they have no options.
The EOS traction model has this right. If you look throughout history at Disney or Apple or otherwise, great organizations have a visionary and an operator. There’s tension in those roles and they offset each other, but to what I said before, look, I’ve been an EO, a huge fan of EO, and been an EO member for years, but I did write an article. I do scoff at people when they have a million-dollar business and they’re chairman, founder, president, and CEO. Talk about getting over yourself. That’s just an ego. I think you should be president of your company until you have a leadership team that you are delegating.
In terms of the actual textbook definition of a chief executive officer, there was a forum that we put together, and this guy had a great business where he outsourced everything, which was probably a $10 million revenue business. A lot of that was passed through and his wife was on the executive team and all this stuff. I’m not judging your business, but in this forum and we were larger businesses and from a peer standpoint, the dynamics that people are dealing with around managing their executive team and you don’t have an executive team, It’s going to be very different.
I agree with you wholeheartedly. I think that as long as people understand what their goals are and have clarity again, I’m not here to say you need to build a large business or raise money. There’s no right or wrong. I wrote this book, Bob, because I’ve met countless entrepreneurs who are so remorseful about their inability to scale or the time they’ve lost with their family over the years that they never get back.
As long as you go in knowing what your priorities are, if your priorities are to build a million-dollar business or you could fill in that number with anything, fill in that blank with any number, and you are willing to sacrifice time with your family, that’s fine. Right now, with Apprentice, for example, I’ve hit the pause button.
I’m not looking to build a billion-dollar business right now because I want to spend every single day with my son at 3:00 when he gets off the bus. That’s really important to me. I’ve prioritized that time, even if it means scaling a little bit slower with my current business and that’s okay. The idea is let’s be honest with ourselves. Let’s be clear about our goals, and let’s be okay with sacrifices that we may need to make along the way.
Clear goals and honest self-reflection are key to success. Be clear on what you’re willing to sacrifice along the way.
What’s interesting is that it seems like the entrepreneurs who are more honest about what they’re good at and what they’re not good at do better. I just had Kendra Scott on this show and she was one of these EO people in the back of the room at the EMP program who became the billion-dollar business. It seemed like she was very good early on and like, “I suck at X, Y, Z. I need to get people to fill those roles. I know what I’m good at and I want to get out of the way.” I see so many people, again, they just can’t let go or control or otherwise and they’re just hurting themselves.
What the book is mostly about is not how to delegate because we basically all know.
It’s philosophical, not tactical.
The thing is the tactics easily come. There’s lots of tools, there’s lots of strategies. Those can come. Yes, of course, I have systems, etc, but what the first part of the book is about and what I think is absolutely the key issue is all the mental stuff. I identify four emotional detractors. I’m sure you could guess all of them, but the things that keep us from delegating are fear, trust, control, issues, and perfectionism issues. Those mental roadblocks, limiting beliefs, fears, and trust issues keep us from delegating. The ones that can get over those issues and bring on others and give other people a chance.
If you want to know the tactics, you can find plenty of tactics, but unless you’re actually committed. Let’s dive in. Delegation is one of my favorite topics. As someone who spent a lot of time in leadership, I think delegation and communication are the two biggest problems I see in leaders as they elevate. I would like to say to you that I think every entrepreneur has a horror story that forces them to accept delegation. I’m curious. What was your tipping point? Oftentimes, it’s a mental breakdown or a huge mistake or something like that.
We were pretty good at delegating from the start, but I would say the biggest thing was my wife and I started our first company, a marketing agency, and we started it thinking we were going to have a nice little lifestyle business and have time with our very young daughter, three-year-old at the time. All of a sudden, we started landing deals and all of a sudden, we didn’t have time for our kid. All of a sudden, we were spending all this time at work.
The very reason we started the company, flexibility, and freedom to be home with our kid was immediately thrown out the window. We were like, “Wait a minute. Do we try to build a big business here? Do we give up on this because it’s not working for our family life? No, maybe we can delegate. Maybe we can find other people to help do some of this work, which will, in turn, give us a break and let us stay at home. Who knows, maybe still build a business along the way.”
We hired college students because we couldn’t afford anyone else. That’s often a big issue with folks that are just starting out, and that is the affordability issue. Everyone’s like, “Dave, I want to delegate, but I can’t afford X, Y, Z. I can’t afford it.” We hired college students at very low rates and it worked. It really worked. I learned as I went in terms of delegating, being clear, checking up, and following up. Giving autonomy and all the things that are really important gave us that freedom with our kid and ultimately allowed us to build the business we wanted to build.
There are a couple of things I’ve seen with delegation. We’ll get into, I mean, you talked about fear and ability, inability to trust others and that’s really true, but there’s also this cycle of delegation that I’ve seen where people get totally overwhelmed with whatever they’re doing. They basically decide they have to delegate. They don’t understand that usually, delegation requires a little more work upfront. They just start giving all this stuff to people with no instruction and no understanding. Otherwise, they screw it up.
They take it all back and they go, “This is why I can’t trust anyone.” I’ve seen that cycle over and over again, and I realize, look, it’s actually more time. You need to do training, scripts, and all this stuff. It’s not an initial. You are so far past due at this point that it’s like you have to jump off the hamster wheel to fix the hamster wheel. That’s one. The other one is just expectations.
The 85% Rule In Delegation
This comes down to life, too. I have this rule of delegation called the 85%. It’s 85% how you would have wanted it and you didn’t do it. We’re all the best at everything. If our expectation is that people are going to do everything just like we do it, we are A, going to be disappointed, and B, we are going to stifle some independence and creativity and some thought process. When I’m trying to review with people, did you get it like 85% how you wanted it and you weren’t involved? That’s a win. If you’re going for a hundred, you’re always going to be disappointed.
Hiring The Right Person For Delegation
To your point, that cycle, I see that all the time as well, and folks have one bad experience with delegation, which is really caused by them, and it was their fault, and then they say, “I can’t do this.” You see, of course, that’s the self-fulfilling prophecy of the fear that they initially had. One thing I want to talk about is that I didn’t hear from you, that this is the single most important part of the delegation process. I’ve got a five Cs model, and that first C is choosing the right person to delegate the work to.
What so often happens is the person that gets the work assigned to them is the person that happens to be around. Not the best person to delegate the work to. Your husband or wife, your younger cousin who knows social media because she’s 20, your ex-person who built a website once that you’re going to give this website to. The reason that happens, Bob, is people feel that urgency and that rush, and then all of a sudden they need to get the work done immediately. Who’s the first person around? Who’s the closest person? Who’s the most accessible person? That is so rarely, if ever, the right answer for who should do the work.
When you’re doing that from a position of exhaustion rather than you’re more likely to make those portraits.
Exhaustion or desperation, you’re more likely to make a mistake. To your point about delegation being more work upfront and more time upfront, it is. The biggest piece of the time upfront is the choosing piece, is figuring out who should do the work. The good news is there are way more options than ever before. I’m just going to throw a few out there. There’s Upwork, there’s Fiverr, there are all these marketplaces, there are apprentices, there are interns, there are business partners, there are full-time hires, there are part-time hires.
There are so many options here. Scoping out what the project looks like, what the outcome is, what the ideal outcome looks like, and then figuring out who can do the work. Of course, the adage higher, slow, fire, fast is really key here. You might think you have to get this project done right away, but you have to take time to make sure the right person to whom you can delegate the work is the right one.
The outcome piece is key. Your biggest ally in this is recording video, recording you doing something, or trying to build up a training manual. Whenever anyone goes to Upwork or all of these sites, I’ve seen people get so mad. They’re like, I have three rules, I guess two rules, I think, that have helped in any outsourcing. One is whatever you’re doing, like, “I need you to do a collection of speaking events or this or that.”
First of all, design the template for how you want the information delivered. This is more task and then we can talk more leadership. Two is to fill in the first couple of records or provide the video, instruction, or whatever, how you wanted it done. I think three on an Upwork give that to three different people and give them $30 each or three and see which one produces the better outcome. The mistake is turning up the volume before you’ve made sure that the quality is right.
That gets into the trust issue, and folks can’t trust people, but then they jump in because they’re desperate. The equation for building trust is to start really small, create a win, and then expand from there. You don’t turn over the keys to your entire company to the first time you give somebody an assignment. Think that way. Let somebody build trust. To your point, it’s actually super affordable to let multiple people build trust with the first few assignments and let the winner emerge to the point of communicating clearly. That’s actually the second of the five Cs, communicating clearly. Communicating clearly the outcome.
Trust is built by starting small and creating wins. Let the best candidate emerge.
That’s what I was saying in the first three records. This is what good looks like. This is an example of what I’m looking for.
What I want to caution readers about here is that there is a temptation to get to micromanagement around the hows.
I was just going to say that.
Trust And Letting Go Of The How
When I’m talking about communicating clearly, it’s communicating clearly what the ideal outcomes look like, not precisely the way to get there because while that can occasionally work, people really value autonomy and freedom and the ability to get to the finish line the way they want to get there. If we’re entrepreneurs, if we’re leaders, do we really care exactly how they get there if they can get to 85% to 90% of the outcome that we want? Why? I don’t know why we would care, and yet sometimes people get stuck on the hows. It’s hard for me to understand how that happens, and I urge folks not to get stuck on the how.
I was going to say that and contradict myself because I think there’s some basic task administrative stuff that if you’re outsourcing, particularly on Upwork or otherwise, it’s good to be very specific about what you want. Similarly, I was going to say that doing that from a leadership management standpoint is exhausting. People need to understand what you’re trying to accomplish, why you’re trying to accomplish it, and what the outcome looks like. They want some creative latitude. Frankly, they might have a better idea or a better way to do it. If you’re trying to get everyone to think and do exactly like you, then you’re not really going to have a dynamic team in anywhere.
You mentioned that we think we’re the best at everything.
I joke around in my speeches. No one does it like I do.
We have this innate narcissism about that, but if we take a step back, there is pretty much nothing in the world that I’m the best at. It would be completely asinine to suggest otherwise. When I have something I want to be done, I might have a vision for what the ideal outcome looks like, but there’s basically a 0% chance that I know the best way to get to that outcome, zero. If I humble myself and realize that, then my goal isn’t to figure out how to get to the ideal outcome. It’s to figure out who is way better than I am at getting to that outcome and to recruit that person and to give the keys to that person and to trust that person slowly but clearly, carefully, and ultimately let that person achieve that outcome with me and for me.
Look, you touched on something there that’s interesting. I know one of the things talked about in the book, particularly entrepreneurs who’ve made a living betting on themselves. I think they tend to overestimate that they’re the best person for a different job. How particularly does the Marshall Goldsmith, what got you here won’t get you there? I assume it’s harder for entrepreneurs to quit on these things because they did the books and did them so carefully for five years. They never missed a bill or they never had a customer problem. That was when it was a $1 million business and now it’s a $10 billion business.
That’s right. Even if it worked then, it doesn’t necessarily mean that it was the best thing for the business then. It may have worked. We have a bias because this worked. I’ll just keep doing it, but it worked at what cost? At what cost to your personal life? At what cost to your spiritual life, etc.? This idea is that we need to be the ones doing the work. It’s just a misnomer. It’s funny. I actually got into an argument with my editor. I published with Ben Bella, which was awesome. Very entrepreneurial publisher and the CEO of Ben Bella worked personally with me on it, which was great, although slightly ironic because why wouldn’t he delegate to his team of editors on the book, but fine.
Glenn worked on the book. Glenn’s brilliant. Actually, he published Traction. That was their biggest book. He’s done all of Gino Wickman’s books. He does the first read of the book and he comes back. In the book, I say that the CEO should do three things and three things alone, vision and strategy for the company, hire the right people in the right seats, and make sure there’s enough money and access to capital and resources to get the job done. Everything else should be delegated.
The strategy, culture, and whether is there enough gas in the tank.
He pushes back. He goes, “Dave, what if you’re really good at something? What if you really like doing something like you love marketing? You’re really good at marketing. Shouldn’t you be doing marketing?” I said, “No, actually, I disagree with that.”You can do something that you’re really good at and you really enjoy. If you have so much passion about marketing or coding or fill in the blank any discipline within the business, of course, you can do it, but there’s a downside there.
The team that you’re hopefully hiring to do it might feel disempowered by you doing it. They might feel micromanaged by you doing it. They might feel like they don’t have real autonomy because you are doing it. you might be giving up other things from your personal life because you’re so passionate about marketing that you’ve got to do the marketing. It’s nice for me to be able to sit in on marketing meetings occasionally because I love marketing, but I don’t need to be the guy driving that just because I’m good at it.
Also, if you want to be the marketing person, then you might need someone to be the CEO or run the company. I mean, that’s also an option. If that’s really your passion and you want to sit in the marketing seat, then maybe your passion is not the other stuff.
That’s right, which is okay.
We’ve seen some founders, particularly sales, that they should be the chief revenue officer because all they’re really doing is selling.
That’s right. Self-awareness is such an important part of leadership, and in all my books, self-awareness again is key here. Understanding what you really want to do. Understanding what your limitations are. Understanding what you are good at versus not, and challenging yourself with that. That’s really, really important and valuable.
I want to push back on one of your things in that list because, and I guess the list is multivariate, but hiring, because I’ve actually seen this go both ways. I was pretty adamant as we scaled the business. One of our core values was to own it and it was like, “Look, I’m responsible for hiring the people on my team, but you’re having me interview these people for your team.” I’m like, “Dave seems like a nice guy, and I had a good meeting with him, but I’m not responsible for digging in and figuring out if he could do the work or not.”
I actually felt like it became an impediment because they’re like, “Bob likes her.” I’m like, “I like a lot of people.” I actually thought it was the opposite and that I should be responsible for my executive team, but delegating hiring, I was more interested in the hiring system in the organization that produced readable results because I see some entrepreneurs. They’re a hundred deep and they’re two hundred. They’re interviewing every person in the company. I don’t think that’s scalable at all.
No. To be clear, that is not the model.
It’s a good example of both sides of the coin.
The right people in the right seats for your team. We’ve been talking about CEOs, but there are lots of managers at bigger companies who struggle with delegation, too, and I think the book can be very helpful. you can apply those three things, strategy and vision for your team, hiring and rights people, right people, and right seats for your team and then making sure your team has enough resources. You have the budget and headcount that you need to get the job done. To your point, that’s micromanaging. If you’re part of the hiring process for somebody else’s direct reports, there’s a problem there. You haven’t really delegated and given the freedom to your executive team or whoever your team is, the way that it would be ideal.
There’s a saying in the EOS system, that lead managers are held accountable. Anyone who is a leader or a manager in an organization is a mistake the companies make. One of their top responsibilities has to be how they lead, manage, and hire their team. Push that on them to see if they do a good job. Great managers hire well, they fire well, and they coach up or out well. If you’re taking that away from them, then I don’t know how you can judge them as a leader or develop them as a leader. As you said, each leader needs to build their own team, and then it’s responsible for helping that person build their own team and not interfering with them.
The model, hopefully, cascades across the whole organization, starting with the CEO, but every single leader is responsible for those three things and those three things alone. Strategy and vision for the team or department: hiring the right people for the right seats and making sure the team or department has enough access to the capital and resources to get the job done. That’s it. That should theoretically be able to cascade across the whole organization, whether the organization is 10 or 10,000 in terms of employee count.
I know one of the things that you’ve said that you prioritize in talent is coachability. I would assume that coachability and delegatability go hand in hand. How do you assess that? How do you assess coachability in your experience or your own interviews in a short window?
I think coachability is so, so important. Frankly, undervalued and underrated typically. I typically assign a project, get a first draft, give some feedback and check the second draft. That’s really the ultimate way I can test coachability, and if I can’t do that for whatever reason, I give feedback on something in the past and ask people to reflect on their mistakes and their own growth.
My favorite interview question, it’s perhaps a little bit intense, but it’s, “What’s the biggest mistake of your life and what did you learn from it?” That throws people into a loop sometimes because they’re not used to such an intense question, but ultimately, I’m looking for the vulnerability to admit first. You’d be shocked, Bob, how many people say, “I don’t think I’ve really made too many serious mistakes.”
You have to leave some space.
The second, of course, and even more important or equally important, is what they learned from that mistake. Were they able to coach themselves on growth from there? I think those are the two ways that I look at coachability. once they’re hired, of course, you quickly learn. This is why hire slow, fire fast. You do quickly learn if you miss the mark. If I missed the mark on hiring and they’re not as coachable as I thought, that’s going to be a problem.
Coachability is key. It’s not about perfection, but how someone learns from mistakes and grows.
I need to recognize that quickly and then coach them out, probably because maybe I missed the mark, and that happens a lot. Unfortunately, I know there are a lot of hiring systems out there. I think that ultimately, once they’re on, we really understand the extent to which the person that we’ve hired is an A player and the right person for the job.
I’ve gotten some pushback in the past when I say this, but again, I play the numbers. I think with things that you do over and over again. We have way too many people who glorify exceptions. If you tell me something has a 90% fail rate, I’m just not going to do it, even though 1 out of 10 is going to work. In the long run, I’m going to be 90% right. What I have seen consistently now in hiring a thing over a twenty-year career of places that I think put some work into hiring and put some work into training is that if the first couple of weeks are a disaster, it’s almost impossible to get out of that tailspin.
There’s actually a fair amount of data around this Dan Pink and timing and on bad starts, but the pushback is always you’re not looking at your culpability or your training, or did you train this person well or other. I’m like, all of those things, I understand those, but generally, in our business over the last twenty years, our acceleration partners. We were hiring about 80% to 90% of the same thing. Account managers in client service for marketing.
We’d hire 4 or 5 at a time. Four would come in and crush it, and one would just struggle from day one. The problem is when they struggle, they get a trust deficit pretty quickly. They’re swimming underwater. It’s like we all know the end. We can put a lot of work into this, but we’re going to put a lot of work and double down our trading and put, and we know where this is going to end in six months.
Then they’re going to have a 6-month thing, which is the worst, versus going to them after 3 weeks and being like, “We made a mistake. We did something wrong.” Oftentimes, maybe the candidate tries to mirror the core values or whatever when they’re not actually them because they like the job. Wouldn’t it be better if we pretend this job never existed and take a mulligan? The worst is a six-month thing. There’s pushback. You’re not being fair otherwise but my data is 99 out of 100 on this one doesn’t start well, not recoverable.
First of all, you say the worst is the six-month thing. Bob, I have talked to entrepreneurs in EEO who have had people working for them for six years who aren’t the right person and the right job. Six months isn’t the worst-case scenario.
Worst case for the candidate. I actually think I was saying that the worst case to have a job for only six months. It looks really bad on your resume, versus you could just disappear and say, “I left that job and no one could even know that you took this job.”
I see. It depends on how it’s communicated at the start. My point is that this tailspin continues and continues and sometimes I’ve seen it continue for years and years. We have this cognitive dissonance that keeps us from admitting we screwed up or we didn’t do something right. We must fix this. This person must be right. Maybe we’ll move them to a different seat. Maybe we’ll pay them more. Maybe we’ll train them better over and over and over again. Months and years go by sometimes when this could be avoided to your point much, much earlier.
I did this for a little while. I became a bit more of a cheapskate and I stopped doing this. For a while, I was doing what the late great Tony Hsieh did, which was offering folks. He actually paid $3,000. He offered up to $3,000 to employees who wanted to quit and realized within six months that they weren’t fit and they quit the organization. It was a really interesting experiment. I thought it because it weeded people out who weren’t players much more smoothly and frankly more gracefully because they got some money. At least they got some cash out of the deal to help move them to the next spot.
That’s the biggest thing that I coach folks on who are struggling with firing people. You’re not doing them any favors by keeping them in a position where they are not benefiting you. You’re setting them up to fail. You’re actually stealing time away from their career that they could be moving to a better fit for themselves where they will be an A player somewhere else. You think you’re doing them a favor by giving them chance after chance and changing and training and comp. You’re not. The sooner you realize that letting them go is actually helping them. They might not realize it at the time. No one loves being fired.
They’re not going to love it, I agree.
You are not doing people a favor by keeping them in a gig where they are not and can’t become A players. You’re not. You have to give people the freedom to find what’s best for them.
We are an organization that believes in people and developing people and training or otherwise, but we were struggling with some of these things and people were doubling down and, like you say, cognitive dissonance and what you’ll do to not admit that you made a mistake or we just know in my gut like this isn’t going to work. We hired 6 of you and you went through the same training and 5 are killing it and one is a constant struggle and now no one trusts them and now they’re working twice as hard. They’re in a tailspin. What this mentor said to me was, “Never train anyone to get them to average.”
That was some of the best advice that he’s like, “Use your training and your resources to make your best people better.” If you’re saying, “We thought we hired Dave and we hired him because we thought he could do this on day one, he’s way behind that, we’re out of deficits. Now we’re pouring training money in to get him to where we thought he was when we hired him, and that’s just a lose-lose proposition.” From that day, I always adopted that mantra like, “Are we training Dave because we think he’s a superstar and he could be one, or are we pouring resources into Dave to just try to get him to be the person we thought we hired?” That’s a lose-lose value proposition.
I will use another analogy as a big poker player. Of course, no one to hold them, no one to fold them. The secret to winning poker, in my experience, over several years of playing poker pretty regularly now, is folding a lot of hands. You have to fold a lot of hands. That’s hard for a lot of people to fold hands. They want to stay in. They want, “What if I hit this next card? What if I hit this?” The key to winning poker is folding more. The key to managing and hiring employees is folding more, letting people go faster.
Annie Duke is actually on the show, and her new book, Quit, which is basically on this topic, like walk away from losing hands. That’s the key to winning and that’s a big part of the book.
That’s right, awesome. I gave you a free sneak preview of Annie Duke, very exciting. I’ll have read that one.
Perfect, so this book’s a little bit of a pivot for you. You’ve written a lot about likeability and marketing, people skills, and networking. How did this topic become a book for you?
We built this company called Apprentice and we are connecting all these entrepreneurs and small business owners with a level of college talent that works on marketing, biz dev operations, data and analytics, and a bunch of different projects for our customers. I realized, Bob, that the number one reason that our clients were failing and saying, “This isn’t working for us. We need to stop,” wasn’t because of our talent. It was because of their struggles with delegating key tasks and projects to our talent.
I very selfishly wrote this book to help our clients, to help our customers, and hopefully to help many, many more small business owners, entrepreneurs, and business leaders delegate better. After a couple of decades of working in businesses where I have a lot of exposure to other small businesses, as well as being an EO and YPO, where I have lots of exposure to other entrepreneurs and business owners, I think the delegation is probably the single biggest issue that I have seen folks struggle with.
I wanted to help our customers, entrepreneurs, and business leaders. They know they need the help, but so many things are getting in the way that they don’t necessarily prioritize delegation. Years and years go by. We’ve talked about the business aspects of this, but for me, the stakes are so high because we only live once. You talked about exceptions. Chances are very few of your readers are going to build billion-dollar companies.
If they do, it’s all because of the show, and tell your friends.
That’s for sure. We’re all a much higher percentage of us are going to have children. What percentage of people on their deathbed said, “I wish I had built a bigger company. I wish I had worked more hours.” It’s negligible. It’s less than 1%. Do you know what percentage of people on their deathbeds say, “I wish I had spent more time with friends and family, I wish I had had more time to pursue my passions, I wish I had more time to travel, fill in the blank?”
Over 50%. Why would we live our lives in a way where we’re going to end up with these regrets when we can’t control living our lives in a way where, through delegation, we can have our time back? We can have our freedom back. We can do those things. We can spend that time that we never get back with our children or hobbies or our passions, the things that really drive us and move us. I know there are some people reading that are thinking, “My passion is my business.”
That’s okay, I get it. Just make sure that 10 or 20 years from now, you’re not going to look back and say, “I wish I had spent more time doing blank.” If you are, then now is the time to start putting the wheels in motion to delegate some work or bring on partners if you don’t have people to delegate high-level executive work to so that you don’t have those regrets.
The ghosts of Christmas future when they come for you.
That’s why I wrote the book and I do think the stakes are high here because you’re not going to be able to scale a business without delegating, but you’re really not going to be able to spend the time doing what’s important to you without delegating.
As you said, there are plenty of tactics and there are tactics in this book, but if you don’t get over the psychological pieces, the tactics aren’t relevant and you won’t even get there. I just don’t see how you can be a leader without learning how to delegate if that’s the goal.
Getting better at it. The thing is the older I get, the more experienced I get, and the more I realize how little I know and how much I have to learn. There are so much learning opportunities out there. Why wouldn’t I learn to be a better delegator, to be a better leader? I want to take any opportunity that I can to learn, which is why, of course, your show is so valuable to so many people.
I’m going to tweak the last question for you because it’s usually about a personal or professional mistake you made that you learned from. What’s a delegation mistake that you made, either personally or professionally that you learned the most from either where you did delegate or I guess you should have delegated?
Delegating Without Enough Coaching
I have a problem that fewer people have, but I think it’s still important and worth talking about in tackling. I sometimes go too far in empowering others and delegating without enough coaching and check-ins, and I’ve worked in the book on the importance of those coaching and check-ins. I think that to be quite blunt and vulnerable with Apprentice, it’s funny because you are open with the co-CEO thing, and I’m going to say my biggest mistake was really over-empowering and over-delegating to my partner at Apprentice. The kid was just 21 years old, super bright, and super driven, but he needed more. I should have given him more.
Delegate, don’t abdicate. Empower others but provide the coaching and check-ins needed for success.
More resources, more check-ins, more tools, more support for the role that I put him in and I feel just horrible because I was fine, the company was fine, but I gave him too much too soon without enough support and it’s really important. I want to get everyone to get over their fears and trust issues and give people work, but we have to do it. We have to give them the support along with it. If we don’t, then nobody wins. In this case, it was not a great outcome for the person, and I feel horrible about it.
Those are real case studies to learn from. I appreciate you sharing that with everyone. Dave, where can people get the book and learn more about Apprentice, your work, and all things Dave?
Thanks. First and foremost, I’ve been doing office hours. I probably mentioned this last time I was on the show, but I do free office hours on Thursday afternoons for anyone who wants to meet with me. I’ve now met with 836 people over the years. You go to ScheduleDave.com to book pro bono free office hours with me. If anyone wants to chat with me on a Thursday afternoon, ChooseApprentice.com is an apprentice for anyone who wants a level of college talent.
The book’s available, of course, in bookstores everywhere and on Amazon and all that fun stuff. I’m on social media. One of my core values is personal responsiveness. Anyone that reaches out to me on social, I do typically try to respond to everyone. Feel free to reach out and I’ll either give you that link for that free office hours if you missed it here or hopefully connect with you. If I can be helpful to any of your readers, I’d be delighted.
First of all, I love that core value of personal responsiveness, and then showing how you do it shows actual alignment. Thanks for coming back on the show. I love this topic of delegation. I’m thrilled that you wrote a book about it and we could dive in here and hopefully, people who are leading and managing have a few takeaways that they can go back in their professional or personal lives and implement.
Thank you so much for having me. It’s great to see you again.
To all our readers, thanks for tuning in to the show. If you enjoyed the episode, make sure to follow the show to be notified about new episodes. Also, if you like what you read, I’d really appreciate it if you could leave a quick rating or review, as it’s the single best way to discover the show. Thanks again for your support. Until next time.
Important Links
- David Kerpen
- Apprentice
- Likeable Social Media
- The Art of People
- Get Over Yourself
- Episode 97 – Past Episode
- Kendra Scott – Past Episode
- Traction
- Annie Duke – Past Episode
- Quit
- ScheduleDave.com
