Start-up CEOs: Do You Even Need a Mentor?

Guest Blog Post: Richard C. Harris, PhD

Last month I wrote about what angel investors need to learn in order to become better mentors. A recent blog post by Fred Wilson raises the mirror-opposite question: can entrepreneurs learn how to use a mentor? Wilson argues that they need to, and he cites another blog post, this one by Ben Horowitz on the challenges that office politics play for the CEO who is trying to get a company ramped up: what do you do as CEO when one of your lieutenants comes to you complaining about the performance of one of his peers.

But the issue for CEOs is even larger than the political infighting that goes on between the super-bright, super-confident team of people the CEO has to manage. There are also day to day issues: what to do about the software team leader whose programmers seem to be leaving all too frequently; or the call center worker whose choice of food smells up everybody’s workspace. Former Pyramid Digital Solutions CEO Dharmesh Shah (now CTO at Hubspot) tweeted recently that he was spending the afternoon writing code. And he ended the tweet with one word: “Bliss”. Everybody thinks the CEO is in charge, but for the CEO, it doesn’t always seem that way.

Some CEOs have the knack for getting a team working at a high level—and for sustaining that performance over time. Others (most, in my experience) find themselves wondering what’s going wrong once the initial adrenalin burst that comes with seed money wears off. If your team is in danger of coming off the rails—for BIG issues or tiny ones—you’ve got two choices: try to resolve the issue based on your quick thinking and superior intellect, or ask for help.

In my experience, the first route rarely works. Human beings (that’s you) are not wired to explore conflicting situations. Our fight or flight mechanism makes us want to either squash the conflict or avoid it. That’s right. Powerful CEOs who have no problem putting millions of dollars at risk wimp out when those pesky people issues pop up. But if you don’t deal with them, they can take your company down…and you with it.

If you’re a CEO facing a difficult people-issue, here are three things to keep in mind:

  1. Find somebody you can trust to talk through the situation, a mentor. The word “mentor” implies some sort of wise counsel. It’s useful to have wise counsel, but you also want someone who can empathize with your situation. Donald Trump only qualifies on one of these criteria. Remember trust gets built on three things: empathy, insight, and reliability. Look for all three in a good mentor.
  2. Your investor pool, experienced as they may be, are not always a good source of help for these problems. If you’re working with angel investors, there’s a good chance that they may have been a CEO, but there’s also a good chance that their ability to help you will lie in an entirely different arena—like identifying future funding sources, or lining up a good outside auditor. Also, it’s hard to open up to someone who is (no matter how benignly) in a position to judge your performance.
  3. It’s useful if your mentor has also been a CEO, but it’s not absolutely necessary. There are plenty of people who are mentors and coaches whose primary contribution is to help you think through your issue, not give you advice based on their first-hand experience. Think of them as your own private Yoda.

One of the most successful CEOs I know doesn’t have just one mentor. She has a number of experienced people whom she turns to depending on the issues she is facing—financial structure, board relationships, leadership issues. It’s something that she’s learned to use to great advantage.

Fred Wilson is clear on those areas where he can help, and where he can’t. It pays for the CEO to match that self-awareness.


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