I think about this topic a lot because I know how lonely the startup CEO job can be.
Being a CEO isn’t easy at any stage, but the job is vastly different if you’re running a public company (which I’ve never done) versus if you’re leading a venture backed startup that’s somewhere between zero and exit (which I have done).
Typically, the startup CEO profile looks like one of the following personas:
Founder from a functional area of expertise (i.e. product development, engineering, etc.) who has to learn how to build a company working with functions they aren’t expert in and with investors they have sold on a big vision. This CEO may take the company all the way to exit or may hand off along the way to a CEO who fits the profile below.
Experienced operator (who may or may not also be a first time CEO) brought in by the board to help a company navigate from some level of product / service usage (and likely some “issues” that need to be navigated) to an exit, which statistically speaking will most likely be an acquisition.
Given the complexity of the CEO job—and the reality that nobody gets a Bachelor’s degree in “Being a CEO”—it’s pretty common these days that folks (i.e. board members) will at some point recommend that the startup CEO work with a “CEO coach” who can help them navigate the twists and turns inherent in leading an early stage company.
So if you’re a startup CEO what questions might you ask to answer the “CEO coach” question?
Here are 5 questions that can help you sort it out:
1) “Do I even want or need a CEO coach?”
Are there topics or questions you want to talk with someone about in a confidential manner, and do you have a sight line on what those topics and questions might be? I’ve met with many CEOs who felt they didn’t need a CEO coach, or perhaps weren’t “there yet” in understanding what a coach could help them with. Don’t sign up for a coach because someone told you to get one. Only lean into finding a CEO coach when you feel drawn to the idea of being able to talk about “things” with someone who’s 100% there for you, and you alone.
2) “Who can I talk to about anything?”
This might be the best way to identify not only whether you should work with a coach, but who the right coach might be. Let’s face it, startup CEOs can’t (and literally don’t) talk to their co-founder(s), members of their executive team, their board members, their partner, or even their best friends about everything they are wrestling with at any given moment. (Well, they probably could tell their partner everything, but that’s likely not a great dynamic if you’re hoping to build a healthy long-term relationship). When you need to talk to someone other than that little voice in your own head, you might be ready to find a CEO coach.
3) “Do I really think I can talk to my board members about everything?”
Part of what makes being a CEO so difficult is the collective opinion everyone around you has about how you’re doing the job. No matter how confident a startup CEO appears to those around them, they’re not actually that confident everything’s going to work out. Here’s the reality: the group you’ll spend the most time managing your confidence in front of is the group whose job it is to hire and fire you…your board. And this dynamic is more pronounced in an early stage company where your board members are primarily (or exclusively) your investors. What you need is an “independent independent”. More on this concept later.
4) “Do I think one of my independent board members can be my coach?”
Sorry, but even if you add your mom to the board as an independent director, she has a fiduciary responsibility to all shareholders, including the preferred equity holding shareholders like her fellow investor board members. So if you end up telling your independent director (aka your mom) over dinner something like “I don’t know how to [insert one of the many things you don’t know how to do as a startup CEO]”, all that’s going to do is make mom think “Hmmm…maybe my kid isn’t cut out to be the CEO of this company.” See above: what you need is an “independent independent”. Again, more on this concept shortly.
5) “Do I have to pick between a ‘been there, done that’ former CEO as my coach or someone with a graduate degree in psychology who can ‘help me develop my leadership skills’?”
This is a false choice. First, plenty of former CEOs who have been through what you’re dealing with can—and often do so very effectively—provide great insights around the “soft skills” that some CEOs feel can only come from a “psychologist”-type coach. Second, if you can’t find the right coach who can do both, then select a CEO coach who can address topics you want the most help with right now. That’s either someone who you can ask something like “how did you think about how much of your series B to invest in the core business versus new initiatives?” or it’s someone who you can ask something like “how can I get my product and go-to-market leaders to work together more effectively?” The good news is there are CEO coaches out there who can talk through both types of questions with you in a confidential setting.
So what do I tell a CEO when they ask me whether I think they should work with a CEO coach or not? Here’s how I lay it out for them:
Every CEO needs someone they can talk to about anything—someone to whom they can ask the ‘How do I…?’ or ‘I don’t know how to …?’ type questions and not worry that they’ll be judged as not being capable of doing the CEO job when they do. I think this advice holds for any CEO, but is particularly helpful for “first time” CEOs who don’t fully realize the ‘multivariate calculus’ nature of what being a startup CEO entails.
An ideal CEO coach as someone the CEO can think of as an “independent independent”: the person that they’ll get everything out of as if they were an “independent board director”, but who is fully “independent” and therefore in service first and foremost to the CEO. The value of this ‘consiligere’-like leverage that a CEO coach provides is difficult to describe until you tap into it during a company crisis or when you’re stressed the night before a board meeting.
And a good CEO coach is a litmus test for your board and investors who may have been the folks recommending you work with a coach. Good board members and investors have seen the positive impact a CEO coach can bring to a company, and they don’t feel threatened that the CEO is talking to someone that they might never even meet. It’s the folks around your board who don’t embrace the privacy of this “CEO to CEO coach” relationship that you may need to wonder about.
If you’re in the midst of the startup CEO journey and climbing alone, I’d encourage you to re-read this post and listen to that voice in your head after you ask each of the questions above one more time. If you’re still feeling like “solo player” mode is right for you, great, no need for a CEO coach. But if asking yourself the questions above makes you anxious about walking the tightrope by yourself, make it a priority to find your “independent independent” in the coming weeks or months.
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