On an island
In 2021, my friend Nick Moryl wrote “Don’t hire a chief of staff”. He argues that founders hire one because they don’t feel on top of things, but it just buys them a few more months of treading water and replicates their faults, not just their strengths. The real fix is two or three strong senior leaders.
I’ve been a chief of staff twice. He’s 100% right.
I’d go one step further. A chief of staff hire is usually trying to fill three jobs at once. Senior leaders for the team, a coach for the founder, and a thought partner for the hard calls.
Let’s talk about that third one.
Ask a founder who they call about the hardest decision on their mind, whether it’s an exec hire, a cofounder rift, an org change, or a big pivot. Sometimes you’ll hear about a board member. Or maybe a friend, or a coach, or Claude. But most often, it’s nobody.
Your board is there to help, and they mean well! But most of the time, they just don’t have the capacity (or the objectivity) to be the thought partner you need. Your senior leaders—if you have them—are heads-down running their own teams, where they need to stay. A friend (or Claude) will listen, but they only know your side of it. And an executive coach works on the person, not the business.
So the founder ends up on an island, making the hard calls alone.
Like Nick says, don’t hire a chief of staff. An inexperienced 27-year-old (that was literally me, 10 years ago) won’t solve your problems. Build your leadership team. Find an incredible executive coach. And then find yourself an experienced, objective thought partner.
This third role has been my job, in one way or another, my whole career. Employee 35 at Uber and later chief of staff there, helping grow the company to more than 25,000 employees. Chief of staff again at Wheel through its Series B and C. And an advisor to founders since, with operating, investing, founding, and tinkering through it all.
I flag things that don’t make sense and offer criticism when it’s useful. I don’t bullshit, and I don’t create work (an advisor who invents work to justify the retainer is just one more person to manage). And I’ve learned not to drift into being a part-time executive—a full-time job in a part-time structure, more connected to the junior team than to the founder. The closer I stay to the founder, the better the work gets.
If you’re a founder and you can’t name the person who tells you the truth, I’d like that person to be me. Here’s how I work.