Startup Boards, 2nd Edition

Chapter 21Mentors and Learning by Doing

Some CEOs feel they should never show any weaknesses. One VC remarked that one of their portfolio CEOs once said, “Hey, you need to know this. My father passed away unexpectedly.” He shared this news with his board members several days after this event occurred. The CEO may have felt the need not to show any weakness in this case. This board member quickly offered the CEO the following advice: “No one expects you to be a robot, carrying the weight of the world around with no emotion. Things are much easier to deal with when you get them out in the open.”

Mentorship and Vulnerability

In another situation, a CEO described dealing with a suicidal employee. “So yesterday, this guy put a gun in his mouth and threatened to kill himself. Two other employees went to his house to talk with him and essentially rescue him from himself. And then today, he showed up to work. What should I do? I can't cry in my chairman's beer.”

We disagree. While having deep personal relationships with each of your board members is unlikely, it's helpful to be vulnerable with at least one of your board members. Furthermore, some board members are willing to engage in mentorship-type relationships, where there is an explicit understanding that you will share things with them about what you are personally struggling with to be more effective.

Nicole Glaros (Chief Investment Strategy Officer, Techstars) gives the following advice to board members:

If you're a mentor, ...