Why Founders Should Hire a Chief of Staff

And why it's different for generalist vs specialist founders

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When I first heard startups were hiring people as a “Chief of Staff” I was confused. In all honesty, it sounded kind of strange and unnecessary.

I was working at Uber in 2018 and was in my first meeting with Jason Droege, who led Uber Eats at the time. The meeting had our head of business development and others — about ~8 people in total.

The conversation was structured and occasionally led by Droege’s Chief of Staff. They seemed very sharp and like they knew exactly what they were supposed to do — but I had no idea.

Yet when Houck’s Newsletter started generating meaningful revenue last spring one of the first things I did was hire a Chief of Staff.

I had actually set out to hire a research analyst (here’s the "JD”) but as I talked to candidates I realized my needs were more broad and rapidly changing than just research.

It’s one of the best decisions I’ve made for the business.

This week I’m sharing why my thoughts on a CoS changed and:

  • What is a Chief of Staff?

  • Why a CoS is valuable to founders

  • A framework for when to hire a CoS (and why I recommend it)

  • What qualities to look for when hiring a CoS

Why Founders Should Hire a Chief of Staff

What is a Chief of Staff?

A surprisingly common misconception is that a Chief of Staff is a glorified executive assistant.

I can’t find it now, unfortunately, but I remember seeing a tweet that said giving out the title “Chief of Staff” is how you convince MBAs and management consultants to become executive assistants.

Pretty funny, but not accurate.

Instead a CoS handles high-leverage, often cross-functional projects that the founder(s) doesn’t have bandwidth to take on. The CoS is there to jump in on critical projects and take ownership of them.

Typically a founder will give their CoS a goal and some context on a project, but a good CoS can handle ambiguity.

These are projects that require the creation of new processes or systems, and the CoS can either maintain those themselves or offload them to others on the team once they get things working.

Some examples I’ve asked my CoS to do in the last 6 months:

Additionally a CoS typically has full business transparency from founders and are aware of all workstreams that are going on. They maintain a tight feedback loop with the founders on their areas of ownership via 1:1s (but are often in many if not all other major meetings as well).

A good working relationship with a CoS is to make it so that whatever you know, they know too. And as a result, the CoS is able to make decisions and operate without needing your input on everything.

Top tier executive assistants are great at many things but have critical core operational tasks and simply don’t have the wide strategic business context required for CoS-style work.

In fact, having a great CoS and a great EA is an incredibly powerful and complimentary combination.

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