Why Every CEO Needs a Coach

Lessons from Silicon Valley Coach Matt Mochary & CEO of Reddit Steve Huffman

Almost every serious athlete has a coach, often several for skill mastery, cross-training, and nutrition, and it is the norm for even Oscar-winning actors to hire acting coaches on set, so why has it taken so long for business leaders to get on board with executive coaching?

Executive coaching was previously reserved for the top slice of elite CEOs or global leaders who were facing challenges. But now as more public figures are raising awareness for the importance of self care, mental health, and their struggles to find a balance between work and home life, the idea of working with a professional coach has become more widely accepted, and accessible. And people are getting on board, since just 2015, the industry has spiked from $2.356 billion to more than $15 billion in 2019.

Our team at Emergence has seen incredible success working with various executive and leadership coaches over the years, and it is something we highly recommend to founders and entrepreneurs at any stage. Navigating the daily challenges of a starting and growing company is taxing mentally and physically, and having a neutral party to talk with and help instill exercises that can be used to handle various situations can create a night and day difference for someone. Coaching can have a significant impact on the rest of the business and team as well since culture starts with the leaders.

As part of our CEO Summit, we invited Matt Mochary, a well-respected and sought-after Silicon Valley CEO Coach (and author!), to speak to our audience about the impact of coaching, the various ways to approach it and his experiences with some of the Valley’s most successful executives. With him, Matt brought his client turned-good-friend, Steve Huffman, Founder + CEO of Reddit to share his first-hand experience going through Matt’s program and how it impacted his life and his entire approach to business.

Read on for the Q&A highlights and the full session video is available below.

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.