Why Every CEO Needs a Coach

Matt, from being a founder and an operator, what led you to eventually become a CEO coach?

Matt: After selling my company Totality in 2003, I was always thinking about how I could have done things differently, perhaps build a better company, because even though the company did well financially, it was a complete mess organizationally. So I read Andy Grove’s book, High Output Management, and I read another book, and another book. I become extremely interested in the concept of helping others become better leaders to produce a better business. I remember someone mentioning that there was a growing crop of new entrepreneurs who didn’t make it into Y Combinator so they were looking for someone to work with. I agreed to coach them, and it turned out to be both fun and effective. So I kept going.

Steve, what is the biggest misconception about a CEO?

Steve: If at any point you think you have nothing left to learn, you're wrong. As a founder, you don't necessarily have the option to work for somebody who knows more than you. The closest thing you can do is to bring in somebody externally to show you. Sometimes I see people at the top forgetting that there's always more to learn.

Steve, when seeking out a coach, what were you looking for and how has he helped you as a founder?

Steve: The type of coach you want is somebody who knows your problems, but is adaptable and flexible enough to actually listen to what's going on and help you work to your own solution—not necessarily their solution. What I would watch out for is somebody who assumes that your problem is a problem they've already seen, and gives you a solution that isn't quite tailored to it. That said, any coaching is better than no coaching.

What I’ve found works best are coaches who were active executives and are able to teach me how to solve problems. I bring them a tactical problem and they'd give me a tactical solution. I also have a coach who is like a living business book and she teaches me processes, which has been really effective.

And then there's Matt. When we started working together, our process was very tactical, but over the years, our relationship and the mechanics of our process has evolved. The way he framed it to me was, "I'm going to be your manager, and I'm going to manage you as if I were your boss. What I would advise you to do is to manage your team the way I'm managing you.” The impact was immediate. I was less stressed and saw a significant difference in my productivity.

Now, Matt is helping me learn how to use the tactics to coach my team. When they bring me challenges, I think, “How would Matt coach this person?” The trickle-down effect is powerful and works its way through the whole company eventually.

How do you know if coaching is working for you?

Steve: Matt has actually taught me a lesson that I use to evaluate all meetings and people. It's binary, which is when this conversation or meeting is over, do I have more or less energy than I did when I went into it? That works for coaches, it works for employees, it works for friends. If you're leaving a coaching session and you haven't learned anything, and your energy levels are low, or you're dreading it going in, that would be the first sign. That's also true of people. That clarity of, am I looking forward to this or not? Did I get value out of it or not? If no, then it's time to make a change. 

Matt, how do you assess if the sessions are making a positive impact on the CEO? 

Matt: I use the same framework that Steve just mentioned. I only do things that give me energy. I continuously ask myself, “Am I feeling energized here right now?” If we're not creating value together, there is no reason to continue. I’m not here to waste anyone's time, it’s too valuable.

Can you walk me through an issue you both have worked on together? 

Steve: Sure, there are lots of great examples. One that sticks out in my mind was I was dealing with an employee that I loved, but they were not working out for the company. It has been creating tension in my mind and in the company for a while, and when I went to Matt for help the first session went horribly, but I learned so much. 

Matt and I role played having a conversation with this employee. It was a disaster. My pretend firing of this person was very uncomfortable. I got sued, I got cursed out, it was embarrassing. But in the end, what unlocked these types of “tough” conversations was actually the energy framing that Matt taught me. We usually go into these moments thinking, "This is going to be really hard and painful." That's just a self-fulfilling prophecy that will come true. People can smell your fear and they mirror your body language and your pheromones. If you're agitated, they'll be agitated. The second aspect is reframing the conversation: "This has nothing to do with our relationship. Let's call a spade a spade, we both know this isn't fun.”

Matt: This is a very common theme that comes up in anyone who has a team. There are always those who you have certain attachments to and when they don't perform, it causes a cycle of fear. You fear you will offend them and they could wreak havoc on the company, thus you fear the conversation, often to the point of not having it. Now you’re stuck in a death spiral. 

One of the fundamental bases of my coaching is that fear gives terrible advice because fear has a generally historically important purpose: “Watch out for the rattlesnake!” Fear creates a sense of caution to keep you alive, but in the modern world that translates into fear of having one's ego bruised. We all have experiences where we've tried to share feedback with someone, and it's just gone terribly. So an easy way to practice it is doing a role play. 

How do you help people break through the fear that they're experiencing?

Matt: One of the most common ways to approach a problem or an issue is to look at it through the lens of this is “something someone else caused.” You believe you’re a victim, just sitting there feeling like you are suffering for something you didn’t do. With this mindset you only see the solution that the person who caused it could do, but we don't have control over that person. It gives them all the power. 

One way to eliminate that sort of fear or anger-based thinking is to look internally and say, "Okay, what did I do to help create this situation?" It may feel like you didn't do anything. But really think about it. What did you do? In this situation, I coach people to walk through the steps, and usually, a lightbulb goes off. You have full control to unwind what you did to contribute, and that's usually where an elegant solution appears.

Steve, how to you incorporate what you work on with Matt into your day-to-day role?

Steve: There are two ways this works. One is actually driven by Matt, which is there's very little that we talk about that doesn't turn into an explicit action item for me. I don't get to wiggle out of any conversation and be like, "OK, that sounds good." It always ends with Matt saying, "What are you specifically going to do? And when are you going to do it?” It's pedantic, but it works. That's another mannerism I adopted with my team: Tell me what you're going to do. I want to watch you type it. We're holding each other accountable. This is how I internalize the mannerisms. You're told the lesson, but it doesn't really sink in until you can play it back. Another level is you don't really get it until you've taught it to somebody else. 

Matt, to what extent do you feel there's value also having a therapist in addition to having an executive coach?

Matt: Plenty of the folks that I coach have therapists and love them. I'm an advocate. You wouldn't say, "Because I have a head of marketing, I don't need a head of engineering." That would be crazy. So to say I have a coach and therefore I don't need a therapist would be the same thing.

Do you have a certain philosophy and approach on meetings? Have you changed the way you run meetings based on what you've learned?

Steve: We've completely redone one-on-one meetings, group meetings, and decisions based on Matt’s coaching. The core idea is less talking, more writing and being clear about what we're talking about. What the decisions are and people signing off on those decisions is now built-in behavior. 

Matt: Everything that I do and share, I didn't invent. Jeff Bezos luckily created this model of meetings and I simply read about it and started using it. That's another thing: just because you get a coach, don't make them your absolute source of learning. Branch out and read things on your own. 

Why does coaching seem to be exploding in popularity right now?

Steve: Because it works. It is one thing that requires the smallest amount of money and time that will dramatically change your company. If the CEO gets 10% better, the company's 10% better. If the CEO's twice as good, the company's twice as good. That will translate into valuation and other metrics you care about relatively quickly. We're just living through this era now where we are on stage talking about it, evangelizing it, and it picks up steam from there.