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How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic).

In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coaches who are right for you. First, you need to find candidates. Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this. Those trusted sources could be your VC or independent board members, friends, fellow CEOs – or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them.

Selecting a CEO Mentor is literally like selecting a teacher but at a vocational school, not at a research university. You want to select someone who has done something several times or for several years; done it really well; documented it in some organized way (at least mentally); and can articulate what they did, why, what worked and what didn’t, and help you apply it to your situation. Do you want to be taught how to be an electrician by someone with a PhD in Electrical Engineering, or by someone who has been a master electrician for 20 years? Fit matters mostly around values. It’s hard to get advice from someone whose values are quite different, as their experiences and their metrics for what did and didn’t work won’t apply well to yours. Fit is a lot less around personality, although you have to be able to get along and communicate with the person at a basic level. Find someone with the right experience set that you can learn from RIGHT NOW. Or at least this year. Maybe the person is the right mentor next year, maybe not. Depends on what you need. For example, if you’re running a $10mm revenue DTC company, find someone who has scaled a company in the DTC or adjacent eCommerce space to at least $25-50mm.

Although I’ve been very international in getting mentoring as a CEO over the years, I’ve never hired a formal CEO Mentor. Several people, from my dad to my independent directors to the members of my CEO Forum have played that role for me at different times over the years. Knowing what I know now, I’m working with CEO Mentors who have experience with talent marketplaces at different scale, since this is a new industry for me.

Selecting a CEO Coach is different. I got lucky in my selection of a CEO Coach almost 20 years ago. My board member, Fred Wilson, told me I needed to work with one. I naively rolled my eyes and said ok, he introduced me to Marc Maltz, I told Marc something like “I need a coach because clearly I need to learn how to manage my board better,” and for some reason, he decided to take the assignment. I got lucky because Marc ended up being exactly the right coach for me, going on 20 years now, but I didn’t know that at the time.

Selecting a CEO Coach is all about who you “click with” personality wise, and what you need in order to be pushed to grow developmentally. CEO Coaches come on a spectrum ranging from what I would call “Quasi-Psychiatrist” on one end, to “Quasi-Management Consultant” on the other end. The former can be incredibly helpful – just note that you will find yourself talking about your thoughts, feelings, and family of origin a fair bit as a means of uncovering problems and solutions. The latter can be helpful as well – just note that you will find yourself talking about business strategy and having someone hold up the proverbial mirror so you can see you the way other people see you as the CEO, quite a bit. There is no right or wrong universal answer here to what makes someone the right choice for you. For me, if one end of the spectrum is a 1 and the other is a 5, I prefer working with people who are in the 3-4 range.

Therapy and coaching are different, though. A good CEO Coach who is a 1 will refer clients to therapy if they see the need. While coaching can “feel” therapeutic, and actually may be therapeutic, it is not a replacement for therapy. The differences between the 1s and the 5s are not just style differences but also really what you want the content of the coaching to be. A 1 is going to help you discover and drive to your leadership style. A 5 is going to help you align those decisions to how you actually act, what approaches you bring to the organization and how you address challenges. Some CEO Coaches can move back and forth between all of these, but knowing where you sit with your needs relative to the coach’s natural style when you pick a coach is critical.

I know CEOs who have shown tremendous growth as humans and leaders with Coaches who are 1s and Coaches who are 5s. A good CEO Coach is someone you can work with literally forever.

I always encourage CEOs to interview multiple Coaches and specifically ask them what their coaching process is like and what their coaching philosophy is. How do they typically start engagements. How structured or unstructured are they in their work? Check references and ask some of their other CEO clients what it’s been like to work with them. This is all true to a much lesser extent with Mentors. In both cases, you should probably do a test session or two before signing up for a longer-term engagement. You wouldn’t buy a car without taking it for a test drive. This is an even more consequential decision.

And in both cases, there should be no ego in the process. You should never feel like you’re being sold by a CEO Coach or CEO Mentor. And they shouldn’t feel hurt by you picking someone else, either. Alignment and chemistry are so critical – there is no way to have that with every person, and the good professionals in this industry should know that.

The bottom line is that hiring a CEO Mentor is low risk. If it’s not working out, you stop engaging. Hiring a CEO Coach is a longer-term decision, and it’s worth having couple of sessions with a coach before making the commitment.

Next post in the series coming soon: How to get the most out of working with a CEO Mentor or CEO Coach.

- Matt Blumberg, March 31, 2021