Interview: Secrets of a CEO Coach

Brian Grey shares advice for startup CEOs

As we discussed in “It’s Lonely at the Top,” being a CEO of a startup can be a lonely existence. To expand on this topic, our scribe-in-residence, Russ Rizzo, sat down with executive coach Brian Grey to discuss his advice for startup CEOs. Grey serves as CEO of Remind, a leading communication platform in education. Before his current role, he spent two years coaching startup CEOs. He shares his secrets to coaching success.

Russ: What are you doing now?

Brian: I’m currently a CEO, so I’m back in that chair here at Remind. For the two years between this CEO role and my previous CEO role (at Bleacher Report), I focused on being a CEO coach or advisor. I still do some coaching, but it’s not my main focus.

Russ: What should founders or want-to-be founders know about mentorship and coaching and why it’s important?

Brian: Let’s start with some definitions. Mentors, coaches, advisors—people conflate these terms. The work I’ve done cuts across formal definitions of them all. The way I define my role: It’s the one person a CEO can confide in, at any time, around any topic, for any reason. Sometimes I advise, which can be synonymous with “mentor.” I tell a CEO how I dealt with a specific issue in the past, and I can be a little prescriptive. I might say, “You might consider doing this versus that.” Other times I coach, which is more about helping the CEO get to an answer on their own. I help them develop the muscles of decision-making. It’s oftentimes a Socratic approach. I ask a lot of questions. This allows the CEO to come up with ideas that we can shape together.

I tend to switch between using “coach” and “advisor”—though there are nuances. You could say, “How do I do blank” or “I don’t know how to do blank.” These are the kinds of things you might not ask a board member or an investor, and it’s good to have someone to share that vulnerability with. Sometimes CEOs think this is a role their partner or spouse can play. I tell them, “Listen, I love my wife and we’re great partners on a lot of things; but I learned pretty early on that if I tried to unload ‘CEO stuff’ on her, I’d more likely get a, ‘Hey, that sounds rough, but can you shoot over to Whole Foods and pick up a few things we need?’” I encourage people to find that person—or maybe it’s a group of people—that you can go anywhere with when you really need it.

It’s especially important when the outcomes aren’t all up and to the right—when you’re not “crushing it” and unicorn status isn’t six months away. This is the trajectory of the vast majority of startups. They’re evolving towards becoming viable businesses. That’s one surprising area, particularly for the CEOs themselves—the value they get having a person in their corner who they can go anywhere with when things are going well and, probably more importantly, when facing challenges and when things aren’t as clear.

Russ: Ash and Mike recently wrote a blog post advocating for CEOs to find coaches and mentors because of the lonely nature of the job. Why is the CEO role so lonely?

Brian: If you think about the CEO role, it can be a pretty lonely job. You spend a lot of time in your own head. You’re processing things as they come at you from different directions. You have a board, investors, an executive team and a team of employees. A lot of cognitive load builds up as you context switch from one interaction to the next. With a coach or advisor at your side, you can feel comfortable saying anything; you can let your guard down without being concerned that you’ll be judged or evaluated on the spot. A lot of times the CEO doesn’t appreciate how cathartic or releasing it is to have someone at their side who they can really confide in. Sometimes they don’t really know the value of the leverage they get until they begin working with somebody.

CEOs tend to be Type A; they push hard. They’ve likely had a track record of success for most of their career. And yet, in the CEO role there’s a lot of exogenous variables, including serendipity, that can determine a company’s fate. There’s pretty nuanced psychology involved with helping a CEO separate their actions and hard work from the company’s ultimate outcome, which isn’t entirely in their control. Given the lonely nature of this role, the ability to do that is critical. 

Particularly in early-stage startups, there’s not a lot of predictability. A lot of ambiguous stuff happens that you can’t control, and you have to react. You have to bob and weave. It’s another layer of complexity that adds to the cognitive load for them. CEOs can feel extra lonely because there’s nothing that they can really look at and say, “OK, if I do A, then B and then C, all will be good.” The human brain is not great at dealing with that level of ambiguity.

Russ: What types of things do you work on with your clients?

Brian: There are two sides of the same coin. Sometimes a CEO wants to find a coach to help with the “people stuff,” the soft skills. And other times CEOs say, “I want someone who’s been there and done it and has been in this seat.” You can find a coach who maybe has a psychology background, maybe a professional coach who can go deep and get theoretical on some of those people elements. But they’re likely not to be someone who’s ever been a CEO or necessarily run anything. So they’re not going to check that second box. Alternatively, you can find someone who’s “been there and done that.” But oftentimes CEOs don’t exude a lot of people-centered empathy.

The reality is the CEO job’s intertwined with various strands of those two elements. There are the people skills and what I would call the Xs and Os of running a company.

Russ: What topics come up the most in your coaching?

Brian: We tend to talk about the same five topics. The first is generally something around capital formation or fundraising strategy—making sure the company can get funded to get to the next milestone. The second area is the long-term vision and strategic path—where the company can go with the capital raised so far and the plan for where it will go with additional capital. The other three topics are always: people, people, people. That’s one area that consistently comes up, especially with first-time CEOs.

“What should I be spending my time on?” is a common question among first-time CEOs, especially ones transitioning from a focused area like product or engineering. They realize, “Hey, now I’ve got to cut across this whole organization—all of the departments and groups and my executive team.” I coach CEOs to create a framework they can lean on that brings everything together and gives them clarity that allows them to answer that question—What should I be spending my time on?—on their own.

I encourage every CEO to construct a framework that ties everything together and guides how they lead the company. At any given point, they can check in and ask themselves: “Am I spending my time in the most high-impact areas for the company?”

I talk about five Ps: Plan, Product, People, Promotion and P&L. If you look at all of those, they all center around the people one. I always put people in the center; the other pieces flow through the people part. You can’t build a plan without people; you can’t execute on that plan without people. That starts with your vision and values and then gets into things like goals, strategies and actions. You can’t execute on that if people aren’t team-minded or collaborative across groups. If your product is a central part of executing on your plan, then everybody’s got to buy into what the product strategy is—not just your head of product or engineering team but also the go-to-market team and operations folks.

Russ: How does the process work?

Brian: It starts with the CEO feeling like working with a coach or advisor would be valuable for them. If it’s pushed on them, it’s less likely to evolve into a meaningful relationship.

Next, I encourage CEOs to meet with a few different coaches to get a feel for who will be the best fit. A lot of times it comes down to the relationship: Does the relationship feel like an authentic one, not a transnational one? Do I feel this is someone who will be there for me when I need to have an important conversation about something critical for the company and when there’s no clear path ahead? From there, it’s creating a bit of structure and meeting consistently.

Russ: Are there misconceptions about coaching?

Brian: I think the biggest misconception or hangup about coaching is that it somehow shows a sign of weakness or lack of competence in the CEO if they work with a coach. Was Michael Jordan less of a player because he had Phil Jackson? Are Serena Williams’ accomplishments less spectacular because she’s had a coach throughout her career? The answer is no. Coaching and advising helps bring out the best capabilities and strengths in an individual, whether it’s an athlete or a startup company CEO.

Another misperception is CEOs might think that working with a coach/advisor is going to be a big time commitment and create a bunch of new work. I say to CEOs: “You have enough overhead. I’m here to create leverage for you and do it in a way that doesn’t create additional overhead.” If they want to create the agenda and work off of a framework, great. But they don’t have to. A lot of times something pops up, and a CEO is thinking, “Who can I unpack this with? Who can I bounce it off of in real time?”

Russ: What strategies do you recommend to make the best use of a coach or advisor?

Brian: First, create and build out a framework that anchors the engagement. It should be defined and driven by the CEO—something that helps the CEO both lead and operate effectively. It’s something the CEO and coach can return to each session to see what progress has been made and where more work or attention should be applied. Whether it’s the five Ps or anything that the CEO constructs and feels connected to because they designed it. Sometimes they may not even go to the framework. Maybe they go down another path and then bring it at the end of the session to see where it fits or how it impacts the framing. It needs to be flexible and malleable.

The second important strategy is commitment and consistency. Agree on a timeframe. It could be six months; it could two years. The benefit comes over time. It’s not like you sit down for your first session and a light from above shines and you hear a chorus of angels. It’s a practice. It takes going through things together and getting in the muck. It’s a couple steps forward, a half step back type of thing. Also, agree on rules of engagement. I get calls the day before a board meeting or when some emergency happens, and I’m fine with it. Be sure you agree on those sorts of parameters.

Russ: What are some of the more surprising areas you’ve covered in your coaching and advising?

Brian: When the trust is secured between a CEO and a coach, the CEO might share stuff going on in their personal life. It’s an additional cognitive load they’re carrying that is impacting their performance, whether consciously or subconsciously. Coaches who aren’t trained psychologists need to know when it’s time for a CEO to meet with a professional counselor. This can often come up around parenting, when a founder becomes a parent or children reach new stages in life. 

Russ: Do you have a coach?

Brian: I do. I use a system engineered uniquely for me. I call it coach-by-committee. There are a few individuals I’ve known for a long time who I chat with on a rotational basis, either weekly or biweekly. Part of our conversation will ultimately turn to a CEO-coach conversation. They’ve either been CEOs themselves or are currently in those roles. I know I can skip back and forth easily in our conversations. I wouldn’t say this approach is suitable for everyone.

I suspect that CEOs who don’t have a coach right now, maybe without even knowing it, are trying to unpack stuff locked in their heads through conversations with friends or former colleagues they trust. That could be working. For a first-time CEO or one without a lot of operational experience, I would definitely recommend they seek out a coach or advisor. When it’s done right, it can be a high-leverage addition.