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How to get the most out of working with a CEO Mentor or CEO Coach

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

In previous posts (here, and here), I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement.

Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience.

Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work with a CEO Coach by doing a DEEP 360. Not one that’s a bland anonymous survey instrument, but one that involves the Coach doing 15-20 in-depth interviews with a wide range of people from team to Board to others in the organization to people you’ve worked with outside the organization, including some non-professional contacts. Let the Coach really learn about you from others. The reason for this is that, although you may have an area of development that you want to focus on (like I did when I met Marc), you may actually need help in other areas a lot more acutely.

In general, I’d say these are a few good rules of thumb for getting the most out of your Coach or Mentor relationship and sessions of work together:

Do your homework. If you have an assignment to read an article, take a survey, or just write something up, either do it or cancel the next meeting or it will be a waste of everyone’s time

  • Be present. Step away from your desk. Turn off email. Silence your phone. These are some of the most valuable times for your own personal development and growth, and they are few and far between when you get to be a CEO. Treasure them
  • Bring your whole self. Even if your coach is a full 5 on the Shrink-to-Management Consultant scale I mentioned above, people are people, and you’re no exception. You have a bad day at home – it will show through at work and it will impact your Coach conversations (maybe less so your Mentor ones). Don’t ignore it. Mention it up front
  • Don’t bullshit. You know when you’re wrong about something or have made a mistake. You may or may not be great about admitting it publicly, or even admitting it to yourself. ADMIT IT TO YOUR COACH. Otherwise, why bother having one?
  • Encourage primary data collection. The biggest place I’ve seen coaching relationships fail is when the Coach or Mentor only has access to a single point of information about what’s happening in the organization – you. Even if you’re not in full-on 360 mode, encourage your Coach or Mentor to spend time with others in the organization or on your board here and there and have a direct line of communication with them. If they don’t and all they’re working off is your perspective on situations, their output will be severely limited or subject to their own conjecture. Especially if you can’t get the prior bullet point right (garbage in, garbage out!)
  • Make it your agenda even if it means changing on the fly. You may be working on an analysis of your team’s Myers-Briggs profile with your Coach - and that’s the topic of your next meeting - but right before the meeting, you learn that one of your CXOs is resigning. Change the agenda. It’s ok. It’s your time, make it work for you
  • Learn to fish. At the end of the day, a good CEO Coach should offer you ways of thinking about things, ways of being, ways of learning in your organization, processes to give you the ability to do some elements of this by yourself - not just answering questions for you. Sports trainers are useful for an athlete’s entire career to push them harder in workouts, but they also teach athletes how to work out on their own
  • Reality check the advice. Make sure to test the strategies that Coaches or Mentors are giving you against your organization. All strategies won’t work in all organizations. These conversations should offer a variety of strategies – you can pick one or pick none and do something totally different. The value isn’t in being told what to do, it is in going through the process of deciding what to do for YOUR organization with some expert inputs and reflections on other experiences
  • Close the loop. I’ve written before about how to solicit feedback as a CEO. To make sure your coaching work is effective, be sure to include feedback loops with your key stakeholders (team and board) on the things you’re working on with your CEO Coach

It’s worth the money. CEO Coaches can be really expensive. Like really, really expensive. $500-1,500/hour expensive. CEO Mentors can be free and informal, but sometimes they charge as well or ask for advisor equity grants. Even if you have a thin balance sheet, don’t be shy about adding the expense, and you shouldn’t pay for this personally. Adding 10-20% to the cost of your compensation will potentially make you twice as effective a CEO. If your board doesn’t support the expense…well, then you may have a different problem.

There’s a lot written publicly about this topic. Jason Lemkin at SaaStr has a particularly good post that really puts a fine point on it. And the coaching team at Beyond CEO Coaching a new boutique coaching firm specializing in coaching black CEOs, writes in “Who are you not to be great?”, “You can play it safe and reduce your risks and likely the rewards, or you can go big. We at Beyond CEO Coaching want to help you to go big.”

By the way, this entire framework applies to non-CEOs as well. Every professional would benefit from having a Coach and a Mentor in their life, even if those aren’t paid consultants but more senior colleagues or members of the company’s People Team. Sometimes a Mentor and a Coach are one and the same…sometimes they are not.

Thanks to a large number of Bolster members I know personally who are CEO Coaches and Mentors for reviewing these posts – Chad Dickerson, Bob Cramer, Tim Porthouse, Marc Maltz, Lynne Waldera, Dave Karnstedt, and Mariquita Blumberg.

-Matt Blumberg, May 20, 2021