Finding the Right CEO Coach with Jerry Colonna

INTRODUCTION: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend Jerry Colonna. Jerry is the founder of Reboot, which is one of the, if not the, premier leadership consulting and coaching firms in the world. Before that, Jerry had a storied career as one of the earliest VCs and investors in Internet 1. 0, as a publisher in the media world before that. And Jerry, it's great to see you. Thank you for being here.

Jerry Colonna: Thanks for having me, Matt. It's really a delight to be with you.

Matt Blumberg: So I have a question for you about coaching, and I want to kind of turn the camera around on this question. So we advise CEOs, as you know, and we help them find coaches. And they're always asking us like, " Hey, when I'm interviewing a prospective coach, what am I asking them?" And they need to know that. They need to come in with some questions. But my question to you is, when you are talking to a prospective client, you must be doing your own evaluation of whether or not you would be a good fit. Because in my experience, picking the right CEO coach is a lot about fit. So when you are being interviewed by a potential client, what are the things you are looking for and how are you thinking about that evaluation as to whether or not you'd be a good fit as a coach?

Jerry Colonna: Yeah. Well, I think this kind of question lends itself to sort of trying to break it down into two or three items, but the truth is it's really one thing, and that then breaks down into different items. The one thing that I'm looking for, the one thing that I think is critically important for a successful coaching engagement generally, is the willingness of the focus person to do the work. Now, we think we're willing to do the work, but the truth is, too many people try to use coaching as a bypass to doing the work. And they focus on, tell me how to do the job, help me perform better, rather than, what do you mean I actually have to be a better leader? So long way to answer to your question.

Matt Blumberg: It's kind of like going to the doctor and having them tell you to lose weight and not wanting to go to the gym, right?

Jerry Colonna: Or eat well.

Matt Blumberg: Right.

Jerry Colonna: "I don't understand. Can't you just give me a pill?" And unfortunately, there are pills for that now, but yes.

Matt Blumberg: And how effective are you at screening for that?

Jerry Colonna: Pretty effective at this point. I mean, I've been doing this for about 20 years. And I'll tell you a funny story. I remember, maybe about 15 years ago, there was this one CEO who's just desperate to work with me. And finally he was like, " Well, what do you charge? What do you charge?" And it's like, I gave him a number and he said, " Well, I'll pay you three times that." And I said, " And you're never gonna be...." Because that's exactly the wrong attitude. I'd rather actually charge less and be with someone who wants to roll up their sleeves and grow than somehow get some brand name person who's so interested in. I don't care about logos, I don't care. I don't care about that.

Matt Blumberg: So that's a great example of a marker of like, no, thank you. What's a great example? Maybe this is a good one to end on. What's the marker of, yeah, this CEO, she's going to lean in.

Jerry Colonna: I could give you all sorts of complicated things, but I'll tell you what my colleagues would say about me. If they cry. If they cry in that initial conversation. I am a sucker.

Matt Blumberg: If you get them to cry during the initial interview before you've even engaged, that's incredible.

Jerry Colonna: In the first 10 minutes, Dude. I'm lost.

Matt Blumberg: Jerry Colonna from Reboot. Thank you for being here.

Jerry Colonna: Oh, thanks for having me, Matt. Take care.