Bonus Episode: Kurt Wilkin Hates Business Books. So He Wrote One

Introduction:

This week, in a special bonus episode, Kurt Wilkin talks about how he helped build several businesses, including most recently a recruiting business called HireBetter, and explains why he hates most business books. It has to do with the attention deficit issues he, like many entrepreneurs, tends to experience. So when he decided to write a business book of his own, he kept it short, and he structured it so that you can find the parts that are most relevant to you and skip the rest. It’s called Who’s Your Mike? and it features chapters on the kinds of hiring and management challenges all entrepreneurs confront, including situations involving employees like Mike. Who exactly is this guy Mike? Oh, you know. He’s the incredibly loyal and hard-working employee who’s been with you from day one but who isn’t necessarily growing with the business. Says Kurt, “We all have, or have had, or will have a Mike.”

— Loren Feldman

Guests:

Kurt Wilkin is co-founder of HireBetter and author of Who’s Your Mike?

Producer:

Jess Thoubboron is founder of Blank Word Productions.

Full Episode Transcript:

Loren Feldman:
Welcome, Kurt Wilkin. Thanks so much for doing this. It’s great to talk to you.

Kurt Wilkin:
Hey, Loren, thanks so much for having me. I love what you guys are doing with 21 Hats and the podcast, the newsletter. Really a great resource for small business owners and entrepreneurs.

Loren Feldman:
I really appreciate that. Listen, in a moment, we’re going to talk about the book you’ve just written. It’s called Who’s Your Mike? We’re going to find out who exactly this Mike guy is and why we need to find him.

But first, you have a really impressive resume that has given you, I know from our previous conversations, great insight into the way lots and lots of privately owned businesses have been run. Let’s go through that resume real quick. You started I believe, as an accountant at EY. Is that right?

Kurt Wilkin:
I was there for four years and I loved the client service aspect and learning lots of different businesses. But I wasn’t a very good accountant.

Loren Feldman:
Why not? Too much of an entrepreneur?

Kurt Wilkin:
You know, I just love people more than I love numbers. And while the numbers interested me, and it was a great background, I just was way more interested in the relationships and the people involved.

Loren Feldman:
I bet it’s been of use to you, though, as an entrepreneur. Being familiar with the numbers probably has helped a lot, I would think.

Kurt Wilkin:
Absolutely, you definitely need to understand a profit and loss statement. You definitely need to understand how the numbers work. I didn’t want to make it my career. I wanted to use it as part of what I did, but not define who I was.

Loren Feldman:
So after that, I believe the first business you started was a fractional CFO business. Is that right?

Kurt Wilkin:
Not quite. Well, after there, I left to go work for a dotcom. But after the dotcom bubble burst, I started a business—

Loren Feldman:
What was the business, the dotcom?

Kurt Wilkin:
It was called eFanshop, and we sold licensed sports products on the internet, e-commerce. It was well before our time, and we got caught right in the middle of the crash in 2000.

Loren Feldman:
Interesting. What did you learn there?

Kurt Wilkin:
Wow, the biggest lesson I learned is when people want to give you money, as far as raising capital, don’t get greedy and try to raise your valuation because you feel like you’re in the driver’s seat. Take what money you can, because you never know when that next next check is gonna come.

Loren Feldman:
So what came after that?

Kurt Wilkin:
Well, when that went belly up, I had a young child and a new wife, and we had to make ends meet. So I started doing some consulting with old EY clients, and a friend, Jay Norris, connected me with one of his clients and made it into a nice project. And before you knew it, I had a burgeoning young business where I was helping companies prepare for their audit. And I thought it was a great business. I got pooh-poohed quite a bit as I was forming it, and we had some success.

Loren Feldman:
Why was it pooh-poohed? What was the concern?

Kurt Wilkin:
You know, the idea was: You’re going to go out in front of auditors and prepare the companies that they go to audit, prepare them to audit, to make their job easier. So you’re basically asking the company to pay twice—once for the preparation and once for the audit. But the auditors loved us because we got everything nice and pretty in a bow for them when the audit came out. So we were a lifesaver for them.

It was a solid business, but in all honesty, the Sarbanes-Oxley Act of 2002, which came out of the shambles that was Enron, which required all public companies to do an internal controls audit basically—that was what really catapulted our company from a nice idea to right place, right time.

Loren Feldman:
What was your target market: what size businesses?

Kurt Wilkin:
That was definitely in the middle market. I’ll say $20 to $200 million or so in revenue, which is really my comfort zone, which is where I’ve been my entire career working with companies who are big enough to be able to pay you and have complex enough problems—but not so big that they won’t listen to you.

Loren Feldman:
So after Sarbanes-Oxley, what happened?

Kurt Wilkin:
We grew that business to about $20 million in revenue over a relatively short period of five years. And we sold to a company—which is the fractional CFO firm you talked about—called Tatum CFO. When they acquired us, they changed their name to Tatum. Our company was called The Controller Group, which, if you know anything about accounting, a controller usually works and reports to the CFO.

We provided a leveraged consulting model for them, where when I say leveraged, meaning in a traditional consulting model, you have partners who bill a lot per hour, and then you have a lot of people underneath them who really do the bulk of the work. And so that’s what we did: a highly profitable, leveraged consulting model. Tatum CFO was a very flat organization. So really, no leverage whatsoever. So most of the money that was billed by the CFO partners stayed with the CFO partners, so the firm itself didn’t make much money. But we provided a profit for them, so that they could grow and really become a multinational firm.

Loren Feldman:
Why did you decide to sell?

Kurt Wilkin:
You know, I didn’t set out to sell—which I’m sure a lot of your listeners don’t necessarily set out to sell—but when they came to us in late 2005, we felt like it was a great opportunity to take their model that they built and their nationwide footprint, take our highly profitable market model, marry them together, and let’s go create a national firm out of it. So it was a really great opportunity to build something bigger. And we were able to take some chips off the table as well, which was very important, as I’m sure many of your listeners will appreciate.

Loren Feldman:
Everybody likes the sound of that.

Kurt Wilkin:
Well, look, I’m an entrepreneur. I get it. 95 or 99 percent of your wealth is typically tied up in the one asset, which is your business. And if anything goes wrong with the economy or Ukraine or you name it, all of a sudden, your house of cards, if you will, falls down. And I was fortunate enough to to be able to take some chips off the table and still try to grow something beyond what I had built prior. But I definitely understand the pressure when you’re an entrepreneur and 99 percent of your wealth is tied up in that one asset.

Loren Feldman:
So you stayed involved in the parent company after the sale?

Kurt Wilkin:
Yes, we grew our practice. We at least doubled it the next year or two, and then the ‘08, ‘09 banking crisis hit everybody, including us, so it was a tough go after that. So we were very fortunate to have sold when we sold.

Loren Feldman:
How did you come to start HireBetter?

Kurt Wilkin:
I actually bought it. After I left Tatum, I like to say I became “unemployable.” It is hard to go from being an entrepreneur to working for or working with a boss. I started with one of my former associates from Tatum, Melinda Owens. We started looking for companies to buy. We wanted to do something different, so I was really looking for something that was tech-enabled, maybe tech-focused in the—I called it “save-the-world” type of mindset. We called it Business Earth, which is marrying up the do-gooder, tree-hugger side of the left with the money-mongering capitalist pigs on the right to make the world a better place.

We looked at a couple of companies to buy, and I realized I wasn’t a tech person. So I retrenched and said, “What do I know? Well, I know people. I know business. I know that the recruiting industry is dastardly broken.” and about that time, I stumbled into the guy who founded HireBetter. He had built a nice, interesting little practice. It was different than most recruiters. And we decided, “You know what? Let’s buy this. And let’s make it what we want.” So we re-envisioned our little slice of the recruiting world.

Loren Feldman:
What was different about it that attracted you?

Kurt Wilkin:
Most recruiters in this lower-middle market are called “contingent recruiters.” That means they are paid contingent upon when they supply a body. There are so many misaligned incentives in that model. And I think the thing I liked about it was, it wasn’t a contingent model. It was an hourly-based model. So really, you paid for what you got.

Long story short, we’ve evolved that model quite a bit. So that’s why I call myself co-founder, because we’ve changed it so much. But I love the name. I actually have a trademark for the words “hire better.” So if you, Loren, decide you want to help people hire better, I can cease and desist your ass. [Laughter]

Loren Feldman:
That’s great. Do clients prefer the hourly model? I can imagine them thinking, “Yeah, I’d rather know exactly what this is going to cost and pay you a flat fee.”

Kurt Wilkin:
Yeah, we actually did evolve to that exactly. It was nice when you filled the role in 20 or 30 hours, and it cost a few grand. But if it took you 1,000 hours, and it’s $100,000, they didn’t like it so much. So we decided to get a more of a project-based billing structure.

Loren Feldman:
So obviously, I mean, all that experience adds up to a lot of insight into the way a lot of people have run businesses. And especially with HireBetter, you’ve had a front row seat on what’s come to be called “The Great Resignation.” I gather you consider The Great Resignation something of a myth. What do you mean by that?

Kurt Wilkin:
You know, it’s true that people are leaving their jobs. I think that if you really look back at the data, what the data would show you is that people have been leaving their jobs in increasing numbers over the last five or 10 years. And there was an anomaly in 2020, because of the pandemic. And it exacerbated, it kind of caught up, if you will, in ‘21 and ‘22, back to the same growth levels that were before people left in droves. The reality is people were leaving already, and now it’s just more pronounced because of the hiatus from 2020.

And the reason people are leaving is what a lot of folks have studied, and I think there’s perhaps still some disagreement. It’s not just for money. It’s usually for purpose, especially your younger generation folks who are beginning their careers or early in their careers. They realized they didn’t like the job they had, and they wanted to do something different. But even folks like you and me, Loren, we’re really realizing that life is freaking short. And the pandemic taught us that we have an opportunity to reinvent who we are.

Loren Feldman:
Do you put some of the blame for that on business owners who haven’t done enough to create cultures and environments where employees actually want to work?

Kurt Wilkin:
You know, I hate to use the word blame, but that’s what we’re really encouraging our clients and CEOs and entrepreneurs to do. You have to have more than just a paycheck. If you entice somebody with a paycheck, they may leave and join your opportunity. But if you don’t stand for anything else, they’re gonna leave. And so we’re actually seeing a lot of boomerangs: people who have left and then gone back to their previous jobs. So the encouragement I would provide to entrepreneurs is: Do the hard work to make your company stand for more than just a paycheck. And then make it a reality. Create your core values, but live your core values. Create your mission and vision, but live your mission and vision. We actually have a lot about that in this book. We have a chapter dedicated to building a great culture.

Loren Feldman:
You mentioned boomerang employees, some people going back after realizing that the grass really wasn’t greener. What do you think of that? Is hiring a boomerang employee a good idea?

Kurt Wilkin:
Personally—this is Kurt speaking—I love it, because they know what they left, and they left to go somewhere else because of some greener grass. But they came back because they appreciate what they left. And we’ve had it happen a couple of times. And I don’t want to name names, but typically I think those employees become more… loyal might not be the right word, but more dedicated, and some of your best team members.

Loren Feldman:
There are a lot of people who just absolutely refuse to even consider it. Have you had conversations with people like that?

Kurt Wilkin:
Who wouldn’t consider coming back, you mean?

Loren Feldman:
No, who wouldn’t consider taking an employee back?

Kurt Wilkin:
Oh, I mean, over the years, I’ve had those types of conversations, but nothing recently. Right now, most people are so desperate for people, that I think they’ll take what they can get. But I think they can be a good employee. You want to understand the reasons they left, and you want to make sure that they’re coming in with eyes wide open, and, “Here’s who we are,” and they’re not having some false expectations.

Loren Feldman:
How has all of this affected you at HireBetter? Have you experienced this kind of difficult period with people sometimes coming and going as well?

Kurt Wilkin:
I like to say, “We look very much like our clients.” We’re entrepreneurial-led, and entrepreneurs can be a pain in the ass, and I can be a pain in the ass. We’ve got a lot of the same challenges our clients have, including we hire some of the best people out there. And so when other firms are desperate for talent, they’ll come raiding us. And we had a period there in late ‘21 where we lost four or five people in a very quick time period. Some we didn’t mind losing, but some we definitely did, of course. And we’ve been hit just like everybody else. You lose your VP of sales to a CEO gig? It’s hard to argue for him [not] to take that opportunity.

Loren Feldman:
That’s not just about the money.

Kurt Wilkin:
Exactly, exactly. And I was very happy for him, and that’s what we want. I want people to be at HireBetter and leave for something really special.

Loren Feldman:
Did you change the way you do things? Did you react in any way?

Kurt Wilkin:
I would be lying if I said, “Oh, no, we’re just, ‘Stay the course, trust the process.’” You always feel like, “Oh shit, what’s happening,” right? So we’ve had to adjust just like our clients. What do we do? Do we increase compensation across the board? Do we double down on our values and who we are? We’ve done a little bit of both. We’ve definitely reassessed where we are compensation-wise because the comp studies you did six months ago are out of date the minute you print them.

Loren Feldman:
So let’s talk about your book. It’s called, Who’s Your Mike? And I have to say I really enjoyed reading it. You and I share some instincts, one of which is that I think neither one of us is a huge fan of business books in general. You wrote, “I hate most business books.” What is it you hate about most business books?

Kurt Wilkin:
There are a couple of things. The biggest one is, I think most business books—and I say most, not all—have a great nugget of value. And whoever wrote it says, “I’ve got to get this message out there. My nugget is this.” But that’s only 20 to 40 or 50 pages of a book, right? And unless you want to write a short story, like, “Who Moved My Cheese?” you need 200 pages to be able to sell a book. And so there’s a lot of stuff in there that you’ve read elsewhere, some rhetoric, some interesting stuff. It’s just fluff. And so I have a bunch of those books on my nightstand. The problem for me is, I’ve got ADD. And as an entrepreneur, I don’t know which 20 percent I’m supposed to read.

Loren Feldman:
Right. You’re not the only entrepreneur who feels that way.

Kurt Wilkin:
Exactly. So that’s part of it. The other part is, I think a lot of business books are sunshine and rainbows. You know, “My 12 steps to being a billionaire and having sex every day.” Or, “Follow my five steps, and you’ll be living on a beach like me.” And for me, I want to hear not just the stories that are successful for you. I call them the “glory stories.” I want to hear the “gory stories.” Tell me the shit that went wrong.

Loren Feldman:
Well, you wrote that in the book: “Don’t just give me glory stories. I want the gory stories, the messier the better. The bigger the shitshow, the more powerful the lesson.”

Kurt Wilkin:
Amen, brother.

Loren Feldman:
So what prompted you to write the book?

Kurt Wilkin:
So I wrote this blog article five or six years ago called, “Who’s Your Mike?” And I’ll get into Mike here in a second. When I tell that story to folks, the vigorous head nods, the, “Oh my gosh, I’ve got one of those guys.” The story resonated. And then over the last few years, I’ve been thinking, “Okay, what other consistent themes do I see with employees that you have at your entrepreneurial company?” and quite a few of them showed up in the book. There’s a few that didn’t quite make the book. I called it my “cutting room floor.” So there are some characters in the back that you can look up and see.

Loren Feldman:
We should say, this is how you organize the book. You kind of go character by character, each one sort of an employee archetype, offering explanations of what you’ve observed, as well as suggestions on how to deal with each situation.

Kurt Wilkin:
Exactly. My hope was that my stories that you can glean from the book would help you, the entrepreneur, with your own challenges. And then we call them “intermissions.” They’re basically some advice sections where we do a little Q&A: How can I assess my own situation? But the way we wrote it, Loren, and I mentioned it earlier, I tell the reader up front, “Look, you might only like 20 percent of this, but I’m gonna lay it out so you can tell which chapters apply to you. Just go read the five chapters that apply, and skip the other 12 chapters.”

Loren Feldman:
So tell us about Mike. Who’s Mike and why do you have a problem with him?

Kurt Wilkin:
Well, I’ll say first of all, my friends named Mike freaking hate me. [Laughter]

Loren Feldman:
I’m not surprised.

Kurt Wilkin:
Yeah, so here’s a quick story. So Mike was your fraternity brother in college, you guys were best buds, and you were thick as thieves in college. You think he might have taken three hours of accounting, but you don’t really know. But he’s a smart dude who’s got your back. When you started your business in your garage a few years later, Mike was right there with you nights and weekends, helping with all the administrative things that you either don’t like or just don’t know how to do—things like ordering office supplies, setting up your LLC, setting up your bank account. And so a couple of years later, you become a legit business, move out of your garage, and Mike quits his day job and becomes your accountant, still doing those back office administrative things.

But now he’s taught himself QuickBooks, and you trust him with your life. And so you reward his 100-hour weeks and his roll-up-your-sleeves, getting-stuff-done mentality with the controller title, and ultimately, the CFO title. But now you look up five years later, you’re doing $20 million in revenue. Mike hasn’t taken a vacation in those five years. He’s still working 100-hour weeks. He hasn’t built a team—either because he didn’t know how, or because he’s too cheap, or because he’s just in over his head. And he’s swimming. He’s trying to negotiate a $10 million line of credit with your bank. Maybe he’s trying to negotiate a $5 or $10 million merger agreement with your biggest competitor. He’s just so overwhelmed, but he’s so loyal he didn’t want to tell you. So the question is: Who’s your Mike? Every entrepreneur has got a Mike: Whether it’s finance and accounting, like this example. Maybe it’s sales, marketing, operations. We all have, or have had, or will have a Mike.

Loren Feldman:
Have you learned how to deal with the situation before it reaches the point where something really has to give? Is there a way to help Mike grow with the business?

Kurt Wilkin:
Absolutely. So in the intermissions, we ask a lot of questions, like, “What do I do with my Mike?” What this story says to me, it doesn’t mean Mike’s a bad guy or has to go. What it means is, Mike is not the right person in that senior leadership role in finance for your organization as you look to try to go from $20 to $40 million.

Loren Feldman:
But it doesn’t have to take until you get to $20 million, right? I mean, this can happen much earlier in the process.

Kurt Wilkin:
Absolutely. And so one of the challenges, when we’re entrepreneurs, is we look at things we can do to reward Mike for his work effort. One of the cheapest things we can give is a title. And so before long, Mike is your CFO, but he’s really a glorified accountant, at best. Maybe Mike’s just a great guy who we trust, but he sucks at accounting, like Kurt, right?

Loren Feldman:
And he’s been working those 100 hour weeks you mentioned. He’s your friend, he’s always been a friend. He’s been loyal. He’s maybe been the key person in building the business to where it is to this point. What do you do if there isn’t another role for him?

Kurt Wilkin:
First of all, I would say Mike may have a role. It doesn’t mean he has to go. Ask a few questions. Is Mike an asshole? Let’s get rid of him. He does not fit the organization. Is he humble enough to realize that he’s not the guy in that role going forward? Okay, now we’re starting to get somewhere. Is he coachable? Could he be mentored to be the future CFO? Maybe. Some people will do that. And some people might bring in a CFO coach, for example, to help him get there. The challenge with Mike in his existing role is you might still get to that $40 million or whatever that next level step is for you. But with Mike not having a coach or not having done this before, he’s going to learn a lot of lessons the hard way. And it’s just going to inhibit your growth.

Another thing you could do—and I’ve seen this in many cases and [it’s] an example in the book—maybe you put Mike back into an individual contributor role, like a controller or VP of finance, and bring in a CFO over him. And all along the way, you’re honest with him and telling him, “Here’s the situation. We need to go fast. We have a real market opportunity in front of us. I can’t afford to learn all these lessons the hard way, but I want you, Mike, to grow in your career, so that when we’re through this, you’re going to be a great CFO, whether it’s for us when we get to a certain point and we and we can do that, or for your next opportunity. I want you to grow as much as I want the company to grow.”

Loren Feldman:
How important is it to have an open conversation with Mike, when you first realize that this problem has arisen? Do you try to deal with it on your own? Or do you confront it head on?

Kurt Wilkin:
Well, I’m a fan of… and by the way, I’m not very good at this. I’m the best at avoiding some of those difficult conversations.

Loren Feldman:
Few people are very good at it.

Kurt Wilkin:
And I’ve tried to be very clear on this in the book: I make a shit ton of mistakes, and here’s just a few of them. With this one, I would really encourage you to have some open and honest dialogue with Mike and acknowledge, “Look, I realize we’re throwing a lot at you. You haven’t taken a vacation in five years. I see the efforts and what you’ve given up to make this happen.”

Loren Feldman:
By the way, if it’s a $20 million company, he probably should have taken a vacation during those five years. That was a mistake, too.

Kurt Wilkin:
That’s exactly right.

Loren Feldman:
On both ends. The owner should have insisted.

Kurt Wilkin:
Exactly. But have that open and honest conversation. Say, “Look, I’m doing this, learning all these things for the first time, and I’m making mistakes. I can’t afford to have everybody in the organization making the same mistakes along the way. I need to bring in some folks who have done this before.”

And CFO is usually a great opportunity to do that, where we can bring in somebody who’s grown a business from 20 to 40 and implemented all the systems you need in order to scale. And again, Mike might be a great individual contributor in accounting, or maybe he’s a great culture fit who could have some other role. But you just need to be careful not to move him around into a bunch of roles where he fails at all of them and just becomes a cancer in the organization.

Loren Feldman:
And it really depends on his personality. I mean, some people can accept a different role, and some people are humiliated by it, and it’s just not going to work.

Kurt Wilkin:
Exactly right.

Loren Feldman:
And in those situations, that means you have to have a really difficult conversation with somebody who you actually care about and who is a good person.

Kurt Wilkin:
I can’t tell you the number of times that yesterday’s hero, like Mike, who is in the foxhole with you making things happen, becomes tomorrow’s challenge or today’s challenge. And it’s just a reality of growing a business. And at some point, the leader might have to make a decision: What’s more important, my relationship with Mike, or the success of the business and all the other 100 employees that you might have?

Loren Feldman:
Having been through some of those conversations, have you learned anything? I mean, it’s never going to be easy. It’s never going to be fun. Is there any way to make it as pleasant as it can be to tell somebody that it’s over and it’s not going to work?

Kurt Wilkin:
Man, I don’t know that there’s any great way, Loren. I think being authentic and being honest is the best approach. I’ve made the mistake in the past of buying into the rhetoric of: You have a conversation. You need to have HR there and a lawyer and papers drawn up. And some of that might be true, but I’m sure not proud of myself from a couple of conversations I had when I was an employee at Tatum.

Loren Feldman:
All right, let’s talk about another type of employee. You have a chapter about Harry the Hustler? Tell us about Harry.

Kurt Wilkin:
Harry is another great example that you see in almost every entrepreneurial company. Harry is a sales guy—and by the way, not all these characters are guys. We have a mix. But Harry’s the sales guy. He knew your product inside and out, and he was the guy who really carried you in the early days while you were focusing on the product or maybe some other customers, but you counted on him to drive sales. And now you’re three, four, or five years down the road. And you realize, “Man, I’ve got to grow, and Harry’s one person. So I need to add several Harrys. I need more junior Harrys.”

But what you really need is to build a sales organization. And so when you come to that realization and say, “I need to build a sales process. And I need a sales leader.” And so what a lot of us do is we promote Harry, the great sales guy, into Harry, the now sales leader or sales manager. And those skills don’t always align. Harry might be very, very good at relationships and selling. But he’s not very good at vision, processes, managing. The last thing a real Harry wants to do is be looking over someone’s call reports to make sure they’re making the right calls every week. So it’s just a different skill-set. And so what happens many times is, Harry, the great salesperson, is now gone, because he’s in a management leadership role. But certainly thereafter, Harry’s probably gone from that role, too, because he sucks at it.

Loren Feldman:
Or because he misses being the lead sales guy?

Kurt Wilkin:
Very true. So he might leave your organization for another one, or you can perhaps talk him into coming back into that individual contributor role without him seeing it as a demotion, but more of a, “Here’s really where you’re a best fit.” Now, that’s the same thing as with Mike. It’s hard if he’s not humble and willing to have that conversation that maybe he’s not the sales leader.

Loren Feldman:
We’re talking about a salesperson here. Humble? [Laughter] I’m making light of it, but it’s a serious thing. I mean, I think salespeople are different from other employees oftentimes at many companies, and part of it is the way they’re compensated. They’re taught to think of themselves first. They’re rewarded for thinking of themselves first, in many cases. And maybe that’s part of the issue here?

Kurt Wilkin:
It is. I even have an example in the book where Harry, as a manager, might make more base compensation, but he might have less upside because he’s no longer in a true sales capacity. What some companies try to do is merge the two: “Harry, we’ll have you continue to ‘carry a bag’ or ‘carry a quota’ while you’re also leading,” but that’s just ripe for issues when a lead comes in. Does Harry keep the best ones because he’s greedy? Or because he wants to make sure they’re handled properly? It can be a mess.

Loren Feldman:
I’ve also heard situations where Harry is allowed to, or encouraged to, remain the lead sales person but is frustrated when someone else is brought in as a manager and isn’t comfortable reporting to that person.

Kurt Wilkin:
That’s also very true. What I’ve seen fail miserably is when someone brings in a sales leader without really having that conversation with Harry. So I think it still comes down to having an authentic conversation. I say in the book, “Trust, respect and communication. If you get those three things, you can do a lot.”

In fact, there’s an example in the book of a client of ours. One of the two founders is Harry. He is the great rainmaking, biz dev guy. When we envision with the client, this sales leader, he, of course, said, “That should be me.” And he tried it for a few months, and then we all had another sit-down session, and he said, “You know what? This is not me.” And we convinced him, and really, it was the right move: “Go be a great rainmaker with the key accounts and with the industry leaders and the stuff that you are so good at. We’re going to bring in a sales leader to work with you, kind of as your partner. You’re not going to report to him or her, but you’re going to work together and maybe coach some of his salespeople as they go.” It was really a great win-win. But it came down to that relationship that the two founders had to make that happen.

Loren Feldman:
Just as an aside, I’m curious, have you ever experienced a situation where salespeople are compensated on salary and not on commission?

Kurt Wilkin:
I have, and usually they don’t work.

Loren Feldman:
There are some people who swear by it.

Kurt Wilkin:
Let me just mention this, Loren. I think it’s important to note. A lot of the successes and challenges people have around people are with the people themselves. So the reason that might work is because you’ve got a very motivated person who has the innate skills and hardcore wiring to make it work. It’s not everybody across the board. So perhaps the failures and challenges I’ve seen in the past are because we simply have the wrong person in the role.

Loren Feldman:
One of the other things I like about this book is you’re not just describing situations. You’re offering some guidance on how to do certain things. You have a couple of sections that you refer to as intermissions. One is about how you assess your team. Tell us about that.

Kurt Wilkin:
This is really one of my favorite parts, and is really, I think, so critical to companies who are growing. We’ve worked with companies for so long who are so reactive in their hiring. “I have an empty seat. I need to fill it ASAP.” And that’s how the recruiting industry typically works.

What we learned is, sure, we need to move quickly, but we also really need to assess what we currently have. What do we need long-term? Let’s build a talent roadmap, as opposed to just knee-jerking. We like to ask our clients to envision where they’re going as an organization. It might just be something as simple as revenue. Use that $20 to $40 million number again. What are the key initiatives that are going to drive that growth? And then what does my team look like today? Do they have the ability to drive those initiatives? And the CFO who I’ve got today may not be my CFO in order to get to $40 million, just as one example.

And so we like to ask a few key questions of the people on that team that sounds super simple, but when you put them all together, it’s pretty powerful. The first one is: Knowing today what I know about my organization and where we’re going, would I enthusiastically rehire Mike, for example, in that role? Enthusiastically, like really, he’s the guy. That’s one question. The other question is: Does Mike have the ability and the tools and the resources to get us to the next level?

Loren Feldman:
I can imagine somebody confronting this and looking around the office and saying, “You know what? There are a lot of people here who I would not enthusiastically rehire.” Have you dealt with that situation? And what do you do?

Kurt Wilkin:
Yeah, I mean, that relates to Mike’s situation. What do I do with Mike?

Loren Feldman:
Well, what if it’s more than one?

Kurt Wilkin:
And most entrepreneurial companies, if you’ve really grown rapidly, you’re going to have more than one. What I like to do is build an org chart with no names. Hypothetical: I’m going to start over. Let’s get a whiteboard. Let’s figure out what our organization needs to look like. What are the skill-sets those people on that org chart need to have? And only then do we start thinking of names to put in boxes. Because if you think of names too quickly, too early in that process, you’re going to get very emotionally driven. And I’ve got to find a spot for Mike, for example, or for Loren, or for Kurt. And so no names and boxes allows us to be a little less emotionally driven.

My two other questions, by the way—as I said, simple but powerful—number one is: What if I had a team of Mikes? How strong would I be, if my entire team was nothing but Mikes? And some entrepreneurs are like, “I love Harry the Hustler, let’s go!” And some people are like, “Oh, crap, I would frickin’ panic.”

And then the other one is: What if Mike came into your office tomorrow morning and just quit on the spot? How would you feel? In some cases, you’re like, “Well, I’d be scared because I hate change.” And that’s a quick emotional reaction. But if you really dug down deep, how would you feel if that headache was gone? And many times, it’s, “Oh my God, that would suck for a few weeks. But it would be great in the long-term.”

Loren Feldman:
Your book goes through each of these situations, and there are many other types of employees that you deal with, types of situations. But then you also have another intermission about how you build a great culture. And it’s easy to get caught up in the day-to-day and just focus on these situations, employee by employee, situation by situation. There are some times when you need to step back, I think, and assess the entire culture and ask: What have you created here? And are there things that need to change? How do you mix those two thoughts?

Kurt Wilkin:
I think now is a perfect time to be having those discussions. Five years ago, I think a lot of talk around culture was the soft, gooey stuff, and, “We don’t need that here,” or, “Just give them a paycheck.” And the reality is that both the pandemic and this Great Resignation we talked about before have made it really table stakes. We need to have a great culture in order to not just attract somebody on the front-end, but to continue to attract them to stay with you.

Loren Feldman:
How do you get the word out? What’s the key step in establishing that culture with your existing workforce, but also with the people whom you’d like to hire?

Kurt Wilkin:
I think you’re gonna need some help. And maybe it’s an outside resource. Maybe it’s a new hire. Maybe it’s somebody internally, but somebody who understands the importance of a great culture that can help you make it a reality. And before you go and turn this over to your HR team, let me just warn you. In fact, one of my favorite chapters in the book is called “HR Rhoda.” And the opening quote is, “‘I hate HR.’ Source: every entrepreneur I’ve ever known.” [Laughter]

Loren Feldman:
Why do entrepreneurs hate HR?

Kurt Wilkin:
Well, the quick version is, the HR profession as a whole has really been brought up to be taskmasters to make sure that your payroll and benefits are right, which is absolutely paramount, and you’ve got to get it right or they get fired. But we, as entrepreneurs, know that’s important. But we really want this culture, this great place to work, this mission, vision, values—all the stuff we hear about that sounds so sexy. But the person who is your best taskmaster to do all the other stuff is not the right person, usually, to be your strategy partner on developing a great culture. So that’s just a word of warning.

But if you find the right person to help you and execute on the great culture, it’s going to start with some reading. There are better books than my book on pure culture building. And it could be as simple as: What do we stand for? What are we trying to build? And then keep asking yourself: Why are we doing this? Well, why are we doing that? And continue with almost a six-why concept from Toyota. But ultimately figure out: Why are we in business, and why do we matter? And that’s the basic premise, the basic core, of the core value work—the culture work.

Loren Feldman:
So you also include in this book an intriguing epilogue that raises the issue: What if you’re the problem? What if the entrepreneur is the problem? How do you think about that, Kurt?

Kurt Wilkin:
Well, this is from 11 years in the recruitment industry where we can deliver the best and brightest—that unicorn so to speak—that’s going to make your business sing. But if you are set in your ways, and you don’t want to be open to this new concept, or you don’t want to have someone helping you, or telling you what to do, or helping you build your business, oftentimes, the entrepreneur is the problem.

Loren Feldman:
Can’t fire him or her.

Kurt Wilkin:
Exactly. The reason it’s an epilogue is, initially when I started out the process of writing the book, I had about half and half: half chapters around the employee and half around the entrepreneur. We decided it was cleaner to do an employee book first. But oftentimes, we can bring the best and brightest to work with you, but if you’re so screwed up, and you’re so set in your entrepreneurial ways, they’re going to leave you. And it’s not because they didn’t work out. It’s because you’re a pain in the ass. And many entrepreneurs fit this mode.

Loren Feldman:
Have you had conversations with those kinds of entrepreneurs and tried to open their eyes? And does it ever work? Do they ever hear what you’re telling them?

Kurt Wilkin:
It has worked. And this is the same thing with your Mike. It comes down to your relationship with them, but also their humility. And if they’re so egotistical that their shit doesn’t stink, pardon my French, you’re not gonna be able to have a rational conversation with them about it. And we’ve had several of those.

But then there are others, like yourself, Loren. I like to think of myself and many others who I know who are like, “Thank you so much for putting the mirror in front of me. Now I can work on this.” I’ve heard things like this in the past from superiors, or maybe my employees, or maybe my wife, maybe my partner, whatever. And we can help them shine a light on it so they can get better and get stronger.

Loren Feldman:
All right. The book is called Who’s Your Mike? His business is called HireBetter. My thanks to Kurt Wilkin. Kurt, I really appreciate your taking the time. This has been a lot of fun.

Kurt Wilkin:
Man, Loren, I loved the discussion. And again, I love what you guys are doing with 21 Hats.

Loren Feldman:
I appreciate you saying that. Thanks so much.