Just Ask: Leadership Through Questions with Serial Entrepreneur Gary Cohen

Brent Peterson (00:01.682)
Welcome to this episode of Uncharted Entrepreneurship, where it is, I'm gonna start again, all right. Sorry, all right, here we go, one more time. Welcome to this episode of Uncharted Entrepreneurship sponsored by EO Minnesota and the EO Rally coming up May 8th, 2025. Today I have Gary Cohen. is a business entrepreneurial coach and CEO coach. Gary, go ahead, do an introduction for yourself. Tell us your day-to-day role and one of your passions in life.

Gary Cohen (00:29.966)
Sure, well, I am a serial entrepreneur. I started right out of college and grew a business with a business partner to 2200 people in the Minnesota area and took it public. then coaching found me. It just hooked me and I have not looked back. It's been 20, I think we're going to 21 years of coaching CEOs and presidents of fast growth companies who are really good and just want to get better.

Brent Peterson (01:01.01)
That's awesome. So Gary, before we do get started, you have been voluntold, I guess. You volunteered to be part of the Free Joke Project. We'll leave it at that. I'm gonna tell you, right? All you have to do is give me a rating eight through 13. So here we go. A caveman and a bear walk into a bar. The bartender says, okay, what's your story? Caveman replies, bear with me.

Gary Cohen (01:11.968)
As long as I don't have to tell the joke, we're good.

Gary Cohen (01:32.782)
8 to 13, I'll give it a solid 10. Solid 10.

Brent Peterson (01:37.938)
All right, that's perfect. Thanks. You we do some creative editing and you know, you'll see how the ratings turn out. All right, so Gary, tell us a little bit about your past and how you got started and tell us, yeah, let's start there.

Gary Cohen (01:43.946)
Yeah, exactly.

Gary Cohen (01:55.16)
Yeah, well, three people found me. It was interesting. So I was working on my book, Just Ask Leadership, which was published by McGraw-Hill in 09. And it had nothing to do with my profession, even though it has everything to do with my profession today. And it's called Just Ask Leadership, and it's about how do you get leaders to use questions to lead from.

While I was working on this people sought me out to coach them and I thought that's interesting. I don't coach and I did have a reputation of coaching employees so That is how I got started in this coaching world and now there's 17 of us coaching people through co2 coaching and The the passion for me is seeing how you can accelerate people Who are already really good at what they do?

And like my business partner, Rick Diamond and I, we hired John Coons, who used to be president of Dun & Bradstreet to be our coach. And I think he was our coach for seven years, made more money than we did in our first few years. And it was well worth it. It was absolutely well worth it. It got us to avoid a lot of problems that we would have had without him and see things that we couldn't have seen. So opportunities and

It's fun to be in that role today with folks.

Brent Peterson (03:26.354)
Tell us a little bit about the idea of asking questions and maybe we could frame it up with a lot of entrepreneurs think they already know all the answers and maybe they don't ask the questions. Is that one of the reasons that maybe they don't ask so many questions?

Gary Cohen (03:41.966)
Sometimes it's that, and like for us it wasn't. Like the personal story would be that my business partner Rick and I, we asked a lot of questions, but they were all about learning something we knew nothing about. We went into the call center business, we knew nothing about it. And so what we found was we were asking questions, but it was more about informing ourselves so that we could make better decisions. But as you grow, you start to realize.

that if you become the fountain of all knowledge, you're going to stop growing. You become the bottleneck. And so it's at a certain point we realized we better start asking the questions of them for them. So how do you get them to do it? And that kind of took a while, but it came. But what was so interesting is when I was working on the book, I interviewed a hundred plus leaders.

hour plus interviews, some were three, four hours, all transcribed. And what was interesting is only two of them and local kind of heroes in Minnesota, one was the dad, David McLaughlin, and the son, Bill McLaughlin. Bill ran SelectComfort, right? And then went on to Orbis. And dad was the youngest CEO of the time at Toro. And both of them,

were very deliberate to change their questioning style and saw how that worked. Everyone else, including people like Mike Harper, who grew Canagra to, what was it, $20 billion, and started, I think, at $500 million. General Jack Chain, four-star general, ran the Air Force. Just incredible people, but they all stumbled upon it.

that somewhere in their career they realized they could not be the fountain of knowledge and they had to switch it and make it into action. Like, how do you think you're going to go about solving this? Right? Something like that. As opposed to what do we need to know about this problem so I can solve this for you.

Brent Peterson (05:53.958)
Yeah, that's, mean, that's such a good point. And I suppose too, if you do ask that question of somebody, how are you going to go about solving this? And they look at you saying, well, you're here to help me solve it. You're here to solve it for me. You know that maybe they're not the right leader, right?

Gary Cohen (06:07.722)
or they've been too nurtured. I'm working on a new book, and in this book, we're talking about accountability. And one of the things we learn is, just to your point, which is if you're answering their question and giving them the decision, likely you've taught them to be the way they're being, or you hired them knowing that they're that way.

And what's really hard and we see it in our coaching work with clients is getting both the leader to give up that sense of, know the answer and I'm going to tell you the decision. I remember going through, I was in Vistage and we had somebody come in and he says, you know, the number one thing about leadership and everybody gives their answer and he says, you're all wrong. It's about making good decisions. And I'm like, he really doesn't know what good leadership is about.

Right. And I think it was then that I was just so clear that as a leader, you really have to learn to get other people to provide the answers and put them on the personal risk side of getting it wrong. Right. It's not that you don't ask questions to help them become better informed. You just don't give them the answer or the nod or the look or any of that, because all of that will say to them,

my boss is with me on this. And it's, you want to support them. You want to do all those things, but you do not want to say, yes, I agree. Give them the nod. and there are certainly times when you're betting the company, you're going to be the decider, but I'm talking about all those times in which that leader doesn't need to decide. They can take the risk with this employee to learn just as they had learned. what is the right way to do this thing?

Brent Peterson (08:05.606)
Yeah, and I think in our green room, you talked a little bit about accountability and how I can see how that that leads into not being accountable because your boss told you something to do. Suddenly you're not accountable for that decision. Your boss is accountable. Is that kind of where you're going?

Gary Cohen (08:21.282)
That's exactly right. And there's two sides to that coin of this permission seeking and permission giving. both sides are, there's a codependency there, right, with it. And the thing about it is when somebody gets permission, the high isn't as high. It's like, I just did what my boss agreed with me to do, right? Or,

the accountability doesn't feel as onerous. Like, I'm not gonna stay up all night because, you know, my boss was in on this too, so I don't have to solve this. I'm not in this alone. I'm gonna count on my boss to rescue me. And the idea is to stop that, to stop it, because it really slows down your growth of your business. I remember one month I asked our...

chief operating officer, how many promotions we had, we had 87 promotions that month. Right? So think about it, if we had decided to bottleneck this thing, right? With us being, we'd have to approve those, we'd have to know job description. I mean, there's just too much, right? As you scale, you have to let go more and more. And people also have to accept a reduction in their scope, which is really hard for them.

You know, to say, you know, I know you were senior vice president of everything, and now you're going to be senior vice president of this thing. And somebody else is going to be over here doing the other thing. And it's hard for everybody and it's necessary.

Brent Peterson (09:49.777)
Yarrid.

Brent Peterson (10:05.852)
Do you find it's very common for a small business that's growing to have employees that say, I wear a lot of hats and they really embrace that wearing a lot of hats. But if you think about it, the more that they're doing, the less they're doing well on any one thing.

Gary Cohen (10:21.986)
Yeah, it's, think it's almost essential. If you, if you're not building it with funds or excess funds to not have that. And it is a riot. It is a hoot. Like for people who are skilled that way, fast learners, right? Do anything, figure it out, learn it. And to the entrepreneur, they're just loving it. Okay. And at a certain point.

that love has to stop. And it's really sometimes impossible for that person, which is just sad because they were there at the beginning, usually, and to have to see them go if they cannot dislodge themselves from that style of leading. And absolutely essential. Who was the, I forget is the author, Zero to One? Really good for the Zero to One.

starting point. But getting anywhere as you start merging on past that, you really need experts in those given areas. And entrepreneurs as they start to see this, they go, my God, I didn't even know this could be done that well. Right?

Brent Peterson (11:38.454)
There's a degree of empathy that a boss needs to have. And I think sometimes it happens that they are, if a decision was made that didn't work out and somebody went and did it on their own, then they come down very hard on them, which just discourages you from making more decisions. What do you say to the boss, the owner, when they're enabling their team to do those things, how do you get them to not?

Gary Cohen (11:57.88)
Yeah.

Brent Peterson (12:07.686)
berate somebody who's done something that was done in good, you know, good conscience, let's say.

Gary Cohen (12:13.006)
I love the question. It's a great question. And there's a number of things. One is to ask the boss, have you ever had, it depends on the size of the company. I'm thinking a little larger, but I'll make it smaller. Have you ever made a hundred thousand dollar mistake? And they laugh and they go, just one, you know, all the time. Right. And then I say, how do you react to it? Oh, I get so mad at myself. Yep. And then what?

Well, I get over it, how long does it take? A day or two, and then I just move on. Okay, so when an employee does it, why is that different? What's the number? like 10,000. so at $10,000 you'll move on in a day or two, but for you it's 100,000. What is that difference, right? And it's like helping them see that they're attached.

to the scale of the problem, but the scale of the problem has to do with the scale of the business, right? And that they themselves, if they were unforgiving about 10,000 or 50,000 with an employee, shouldn't they be unforgiving to themselves, right? Now, it would be a different thing if they said, this employee repeatedly does that, right? Different story.

But that's usually not the case, especially if you build the ownership feeling in the employee, they're already suffering from that. So I'm with you on the empathy and kindness, and it's a hard thing. It's not an impossible thing to teach, and we do. It's just a hard thing. And people to scale need to see that the business is not who they are.

And part of the attachment is they saw that money that the employee mistake or error or whatever it was.

Gary Cohen (14:21.504)
was not attached to that human or to them as the entrepreneur because the business lost it, they didn't lose it. But so many entrepreneurs so tightly connect those two and they don't see it in themselves. So helping them chase that one down and understand that attachment that they have with the business. It also helped their relationships at home because it's often the same thing that they bring home.

is they're bringing home that attachment with them, as opposed to leaving it and then having a real relationship at home.

Brent Peterson (14:57.978)
What kind of advice then would you give to a entrepreneur to help them understand how they ask questions of their employees and how to get their employees to ask questions? do you get that? Where's a starting point for that?

Gary Cohen (15:12.12)
First understanding that whether you're, it doesn't matter who you are, you'd rather be asked. I mean, I've done the research, I've talked to thousands and thousands of people, had them vote on this, and every single time, everybody less about 3 % of an audience says they'd rather be asked than told. So the first thing is to accept that almost,

all of your employees, including you as the boss, would rather be asked than be told, right? And you start talking about what does it feel like when you've been told? What was it like when your parents told you what to do or a teacher or a coach? How did you react to it? And it's usually the same thing. You know, I didn't like it. I didn't care for it. So why do you think that the idea behind asking your employees questions needs any more explanation than that?

that you already know internally, you know from people around you, you can do your own survey and you'll find that they'd rather be asked what to do. Now, remember, you gotta listen too. And you talked about empathy. Empathetic listening is critical to this process, right? Because you wanna actively listen and hear what the other person said so that they know you're listening.

That builds trust and we all know that this psychological safety is so important if we're gonna get our employees to really put themselves out there for us.

Brent Peterson (16:46.862)
Is that a trait, the not listening? I think that's probably, is that one of the biggest problems that maybe an entrepreneur has is just not listening? Maybe if they even ask the questions, but they don't listen. okay, I think you're right. I think you're right.

Gary Cohen (16:58.638)
Can explain that to humanity? Can we explain that to you, right? Yeah, I don't think it's close to entrepreneurs. I think entrepreneurs sometimes get so captivated by a vision, which is beautiful because to make something out of nothing is, I think, just exquisite. And it takes kind of a sense of determination and rigor.

and passion to do that, even when it's against all their other traits, because often we find that entrepreneurs have a higher degree of ADD, I call it ADD, some people ADHD, which makes them want to be in all sorts of different things and keep changing things. And to think about having to move this focus forward and do the same thing repeatedly over and over.

until it gets traction, right? And it's astounding, the will of people to do that. And sometimes they get frustrated from the fact of how much it takes and they feel like people don't understand how hard it is. And because of that,

then it turns into a bit of bitterness or edge with employees. They don't understand me. Yeah, but they're not going to win. It's not their idea. I mean, there's so many reasons why, you know, it's hard to get them engaged. So how do we get them engaged? Ask them.

Brent Peterson (18:39.942)
Yeah, I'd like to kind of close out with that last part. And I think that a lot of leaders struggle with communicating their internal thoughts and getting it out to the team. And also I can say that personally, I really struggle with thinking that my subordinate knew, knows what I know, and that if they don't do it, I'm really frustrated that they didn't do it, right? I think that that's a great way.

place for every entrepreneur to start with and I think you kind of keyed in on it there that they don't always know and that asking those questions and listening is a good way to understand and help them understand. Would you agree with that?

Gary Cohen (19:22.668)
I would agree with that. I think what I learned in having a coach from our second year in business with Rick is that there is so much to learn, right? And there's so much to learn about ourselves and we need that reflective time. I also found that having a place to talk about these things beyond your board or your financing and your employees, even if you feel like they're my best friends.

and they should feel that way, especially in the small stage. And it's not the right place to air new ideas out because the right coach will get you to narrow that focus, not bring up the idea that you have that's killing you because that will help you realize you have enough ideas. Just stick with it.

Brent Peterson (20:12.454)
Yeah, yeah, my, think I need a car. need my wife of 32 years will say the exact same thing that she's sometimes overwhelmed by the amount of things that come out of my mouth and she, she needs to just turn off for a little bit. And I suppose that happens to any, any visionary that would have, have lots of, have lots of those things.

Gary Cohen (20:34.286)
My number two at my company from years ago, when I'd leave her office, she'd write it on the board, the thing. She wouldn't act on it. She'd wait three times for me to come back, what's happening with this, what's happening, and she'd put a little mark. I never noticed. And it was years later, she told me, that this was her strategy of just slowing the pipeline of ideas down.

And I congratulate her. said that was a brilliant strategy because she knew that if I had come and returned on the idea, then I was in.

Brent Peterson (21:12.624)
Yeah, that's such a great point. Gary, as I close out, I give everybody an opportunity to do a shameless plug on anything they'd like. What would you like to plug today?

Gary Cohen (21:23.266)
I'd like to plug our coaching. We are all operators turn coaches. We are not kind of the whole psychological thing. We do that, but that comes second to us. We love helping people scale their business and being that sounding board for them. And that's what we do best at CO2 coaching.

Brent Peterson (21:45.808)
And how do they get a hold of you?

Gary Cohen (21:47.598)
CO2coaching.com is the easiest way. Garybcowen.com I think will get them to me. I'm easy to find on the web.

Brent Peterson (21:57.458)
That's awesome. Gary Cohen is executive coach, managing partner at CO2 Coaching. Thank you so much for being here today.

Gary Cohen (22:04.428)
You're welcome. Thanks for having me, Brent.

Brent Peterson (22:08.242)
Alright.