There’s a tenuous balance between telling someone what to do and giving advice. It’s especially difficult as a mentor, especially if you’ve previously been a CEO and are used to being “the decider.”
As a mentor, you aren’t the decider. The CEO you are mentoring is the decider.
This dynamic is also true for many board / CEO relationships, where the board wants the CEO to make the ultimate decision. As I’ve often said, my goal as a VC is only to make one decision about a company – whether or not I support the CEO. If I do, I work for the CEO. If I don’t, it’s my job to do something about the CEO.
While this is nice in theory, it’s difficult in practice. One of my strengths is that I tell a lot of stories. One of my weaknesses is that, according to my wife Amy, my stories go on 20% too long (she is correct.) Here’s an example.
I’m at a board meeting. The CEO, which I love working with, is trying to figure out what to do about a particularly thorny issue. I tell a story. He reacts with a little more data. I tell another story. Another board member asks a question. I tell another story. This one goes on a bit too long.
The CEO looks directly at me and says, very firmly, “Will you just tell me the fucking answer for once?”
I tell him the answer.
He was looking for specific, actionable advice. I was telling him stories. If he spent enough time processing the stories, he might be able to come up with the right answer. Or, since they are stories, he might draw the wrong inference and decide to do something different from where the stories were leading him. This CEO was aware of that and, in real time was having trouble processing the point of the stories in his context.
Fortunately, this CEO was self-aware enough to ask for specific, actionable advice in a moment where he needed it.
Also published on Medium.