Every world-class athlete has a coach: every tennis player at Wimbledon, every golfer in the PGA, and every batter in the MLB. An athlete without a coach is incomplete.
The sports world figured out long ago that athletes with coaches win. The business world is just catching up.
Great coaches hold up a mirror so you understand yourself better. They provide feedback and hold you accountable. They're a sounding board to debate ideas with, and a shoulder to lean on in hard times.
At Clearbit, we allow any senior manager to expense coaching. If coaching is so useful, why doesn't everyone at the company have an external coach? Well, unfortunately it comes down to cost. At the current size of our business, it's just not viable.
That said, there is an excellent back-up option, and that is your direct manager. Part of great management is coaching, and one of the reasons we've written this book is to turn our managers into great coaches.
The best way to find a coach that works for you is the same way you find anyone good: ask your network. Failing that, we keep a list of recommended coaches. And finally, we recommend using Torch, a coaching service.
As the company grows, it is only natural that issues crop up outside of your experience. The worst way to deal with this is to blunder forward, pretending to know what you're talking about. A better approach is to ask for help—and who better to ask for help than a board of advisors.
An advisory board is a set of three to five people who have experience in your domain and have committed to helping you. They are there to answer the odd question over email, pop on the phone with you, and if needed, come by the office. Their networks are also incredibly useful.
An advisory board is a requirement for anyone on Clearbit's leadership team.
When I think of how critical advisory boards can be, one example stands out. Clearbit was going through the process of raising venture debt and had been given some conflicting information around the kind of debt we should raise.
I reached out to Patrick Grady, a member of my advisory board, for help. Patrick is an ex-CEO and has raised hundreds of millions in both equity and venture debt rounds, he's seen it all and has a wealth of experience. Patrick not only came by the office to take us through the whole process, but introduced us to an ex-banker who had been on both sides of the table negotiating venture debt. They aided us with the process, reviewed the debt term sheets, and helped us avoid making any mistakes.
Advisory boards sound great in principle, but a common objection I hear to them is: "Why would anyone help me? Won't they require compensation?"
Perhaps they will ask for some kind of compensation, but we have found that the vast majority of people are willing to set aside time for you as a way of paying it forward. Every successful person has been helped by other people, and most of them are willing to give back to the community. And a lot of advisors simply enjoy the feeling of creating value. In fact, who doesn't?!
That is one of the very special things about the tech community. Indeed, one day it might just so happen that you too will help some less experienced leader with their own questions.
Pick three to six people in your network who are either a few years ahead of you in their careers or are semi-retired. Reach out to them, perhaps buy them coffee or dinner, and broach the subject.
We don't recommend opening with any talk about compensation; it changes the tenor of the conversation. It turns out that people feel a lot more satisfaction when they help others out of the kindness of their hearts.
We recommend making the barriers to contacting your board as low as possible. One such way is by putting your board into a CRM like Streak, so that you can easily reach out and customize the email with a mail merge.