Startup CEO, 2nd Edition

Chapter 43Working with a Coach

When a member of our board first suggested I work with a coach, I thought it would be a good idea for one reason: to learn how to get people to stop suggesting I work with a coach. A decade later, my coach, Marc Maltz, is one of my most valuable assets and advisers.

CEO coaches come in lots of shapes and sizes. Some are almost therapists while others are retired CEOs themselves. Some are quiet and lead you to conclusions on your own and some are more in your face. You have to find one who's a good fit with your style, your pace of work, and your ability to pay. It's one investment that I wouldn't shortchange as you try to grow your business and your career – even if you have done it all three times before.

The Value of Executive Coaches

We started Return Path in December 1999. Within 10 months, the company hadn't had time to turn into much of anything at all when the great Internet bust happened. We kept grinding forward in 2000 and 2001 and the end of that year had us going through a painful 50/50 merger with our only direct competitor and recapitalizing the company. We were still alive, even kicking, but things were not going well.

When one of our board members, Fred Wilson, sat down with me to give feedback that I could be doing a better job in a few specific ways and perhaps I might benefit from working with a CEO coach, my immediate thought was, “Clearly, the one part of my job that I'm not great at is managing my board, otherwise Fred ...