There is a lot of startup advice that says you don’t have time to coach your team.

Ben is a legend and I don’t doubt his advice. A lot of what he says is right. You are hiring them for their ability and you do need them to scale their function without you. You also don’t have the experience to train them at their job.

All of that is true.

The part that isn’t true is that you’re building a team. Which means you care more about how the collective success over the individual pieces.

The best examples are in sports. As Malcolm Gladwell recently points out in this podcast…"But certainly, in this moment in basketball, it seems like it’s very coach-dependent. And when you see those..you then begin to wonder, how many players on basketball teams, who we consider mediocre, are actually really good but just in the wrong environment? Is Victor Oladipo an exception or is he part of a larger trend? I’m increasingly of the opinion that there must be lots of Victor Oladipos out there."

In the context of building a team, I agree with Malcolm more than Ben.

Granted, I don’t blitzscale. And in blitzscaling, Ben’s advice might be right on. You might not care about team performance. Instead you probably care about acquiring all-stars and assuming that they can play cohesively long enough to win.

Even if you aren’t blitzscaling you do need some all-stars on your team. It’s hard to build something great with zero talent. You just need to find the right all-stars that fit to your style of play.

Hiring A Leadership Team

I’ve built two leadership teams over 15 years.

The first time I followed the traditional, exec hiring process. I searched, met, sold, and hoped that they work out. I tried to set expectations and pretend that I knew what you’re doing in leading people more experience than myself. I even brought in an exec coach because that’s what happens when your own team complains about your immaturity.

The second time I built a team. I took a less experienced group of people and spent two years teaching them on how to become executives. They start as product owners, learning how to get a group to deliver. And over time you have to turn them into business owners that know how to make executive decisions about where to invest and why. The question now, is if they can continue to lead as the numbers become significantly larger than where they started.

Through it all I’ve learned a few things about hiring a leadership team.

1. You have to develop your team philosophy before you hire leaders. It’s on you to develop your own framework for how and when a team works together. You can’t ask a leadership team to build this for you. It has to be more defined than just…we’re succeeding.

2. You can hire well beyond your experience level, but it doesn’t mean you can coach it. People get confused in thinking that landing an all-star on the team means they have succeeded. It’s like saying that raising money means you’ve made it. Neither are true.

3. Melding experienced leaders to adopt your philosophy is much harder. When you hire a team leader they will say…oh yeah I believe in that same philosophy too. What you find, is that over time they really don’t change. They have their way of doing things and you need to know that is and understand how to manage it.

4. Don’t underestimate inexperience. Once people have success they forget that their inexperience was part of the formula to achieving success. Therefore don’t overlook inexperience as solutions to team leadership. Often times people just need a chance and direction to learn. And the hungriest can often outperform the experienced if given the right environment.

To Understand Before Coaching

There is something you have to understand about coaching. It only works if your resume is more successful than theirs. And it only lasts if you continue to develop as a coach.

For example, I would love to coach Barcelona. Except I can’t because Messi would never meld to anything I’d put on the table. Forget my experience in playing college soccer, Messi has developed his way and unless my resume is better than his, he isn’t going to meld to my culture.

But Guardiola? They listened to him, at least for awhile. His championship resume was longer. Once it was shorter, his time was up. So what did he do? He moved to a club that needed his winning coaching. Until they too were too successful. He’s now on to his third club, teaching the next group how to win.

What you notice about the best sports coaches is they aren’t teaching each player how to be great at their function. They rely on the player to develop that on their own. Instead they focus their energy on the system, repeatable processes, and how the group works together. The more experienced your team is, the better you have to be at this.

Take Phil Jackson. He created a system and used psychology to keep his players motivated. The talent on his team was so great there wasn’t anything else he could do other than focus on their mental state.

How To Coach Your Team

There are lots of ways to do this.

I don’t believe you should outsource it. I’m doubtful that an exec coach shares your same team philosophy, which means what they teach could be in conflict to what you believe.

Instead I suggest learning how to coach it. The easiest place to start is in teaching your team how to run a business. Normally they get a lot of practice at their specific function but little experience translating their function into business speak, which is what is expected at a board level.

Here are a few ways I’ve coached my own team…

• Read Bezos annual share holder letters. Or have them read the annual letter from any public CEO they admire. Reading these teaches them business speak, which is a foreign language from their function speak. We talk about these in 1:1 sessions.

• Write business summaries. We hold six board meetings a year. At this point we don’t have that many strategic topics to fill six meetings, which means the reason for the meetings is to give the team more practice at a board level. Before every meeting they have to write a short summary. This isn’t a ppt deck, it’s a business summary in a google doc. They write it and I edit it. In the beginning you basically re-write it. But over time they get better and better where they don’t need your editing.

• Phone call before the board meeting. As part of their weekly 1:1 they will practice the meeting out loud. I’ll ask questions like a board member and then give them feedback on the structure of what they said. Generally what you are coaching is their language and how to succinctly summarizes their learnings. What you discuss at a board level is different from a daily team level so you need time to teach this.

• Learning how to win a market. Figuring out the quadrant you can win is hard and you need team leads that know how to do this. It’s not a skill that is taught and so I’ve run some sessions that teach them how to look at the existing market to then figure out how they could win it on a new paradigm.

• Tools they can use. Few executives have tools they use to break down problems, organize people, and communicate. I share my own tools and work with them to learn how to use them. Tools like a customer journey, a brief, and documentation. It gives them structure they can use with their own teams. It also make sure all of us are speaking the same language.

• Consistent 1:1 sessions. I call them workouts. They are an hour long, every week. And I do everything I can not to miss them. They set the agenda and although most of the time spent is on their projects they are a chance for me to provide coaching feedback.

In Summary

I believe you can coach your team.

If you are playing the long game, both at your company and as a member of the startup community then this work will pay back. Happiness is higher. Churn is lower. And team speed starts accelerating over time.

If you are looking to torch the earth and go fast, then coaching is a waste of time. You’d be better off learning how to manage and turn through all-stars. And as long as you are succeeding and stock value is rising, you can deal with the negative impact it can have on your culture.

If you have questions, email or dm me on twitter.