Ben Thomas

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Chief of Staff

Sep 29, 2023, 6 min read

0. Why I’m interested

Executives at businesses of all kinds are hiring for a “chief of staff” (CoS) type role. I think that type of job seems interesting. It’s also similar to what I’ve done in a couple contexts. So, I am writing about what I learn and think about this job category. I want to be intentional about the types of roles I take on.

I’m using “chief of staff” here as shorthand for a bunch of different roles that may or may not actually have that title. The main difference between a general “Strategy & Operations” role versus “CoS” is how much you work with the CEO or executive leadership team.

1. What is a “chief of staff”?

Originally a role mostly in government and military institutions, executives at a wide variety of organizations now hire roles under a title of CoS or other similarly vague titles like “Special Projects” or “Strategy & Operations” or “Exec Ops”.

I think of a “chief of staff” as a good descriptor for someone who:

  • (A) Has no (or few) direct reports
  • (B) Reports direct to an executive
  • (C) Works as a highly capacity generalist

Some job descriptions from Q4 2023:

There’s quite a range of industries and scopes of responsibility for the same job title. I think that shows lots of organizations feel a need for someone who can handle variety and ambiguity. Does that “felt need” actually mean they should hire a CoS? Maybe, maybe not.

2. Why would you hire one?

A CoS augments leadership’s capacity. Leaders are increasingly busy and stretched thin as the world moves faster, work becomes more complex, and society expects more of businesses (see CEO Excellence by Carolyn Dewar, Deep Work by Cal Newport). Couldn’t it be nice to have a right-hand who could problem-solve with you, run meetings in your stead, and lead projects? Another way to put it is that creating leverage is the meta-responsibility of the role

Matt Mochary recommends an Exec Ops role (formerly CoS) as the first hire a startup should make.

Another type of leverage would be someone who can kickstart research ideas from leadership without distracting another team. Call it a technical chief of staff. That would be more of a hybrid of a Special Projects and CoS role.

Also, a CoS (or COO for that matter) helps round out a leadership team. No one is perfect — instead of a founder or CEO trying to be perfect, they can look for someone with complementary strengths (see The Dynamics of a Founder and COO with Chris Monk and David Perell - Secret Ops | Podcast on Spotify). Not as an excuse to be bad at certain parts of the job, but as a way to run a better company without trying for individual perfection.

3. Is it for me?

Over time I’m learning more about my strengths and interests:

I seem to be a generalist.

  • I enjoy being a generalist in life and work. I try to write about a variety of interests. In management consulting I liked working in a variety of industries.
  • I’m pretty good as a generalist already. I did well in management consulting as a generalist, and my next role after that was also quite generalist (see About)
  • I seem to be better at this type of role than others. I don’t seem to like doing the same work over and over again. I like to change up projects pretty often. I also don’t think I’m that good at managing people — yet; I’m getting better.
  • I’m working on my toolkit. I’m learning to code more, tinkering with AI projects, writing more, and testing/proving my assumptions about what I like and don’t in my current role 

I like working with exec leadership.

  • I want to have the C-Suite perspective on a business. I want to work where on the problems with the most impact. I don’t mind getting into the weeds but it takes more energy for me to focus on problems that ”feel small”
  • I like to be in the room where it happens.
  • You can “punch above your weight” in impact, because you can often work in these roles at a much younger age / with less experience than the executive role.

I want to learn a lot quickly.

  • You can learn from the decision maker instead of actually being in the hot seat for big decisions.
  • You (hopefully) receive high quality mentoring/coaching and access to soft networks that wouldn’t otherwise be available.

4. What are the challenges?

Much of these notes are drawn from 10,000 Hours with Reid Hoffman which is a great read.

  • You’ll usually work the executive’s hours. I can grind. But be clear eyed that these roles are not a clear nine to five.
  • Job description will be unclear and scope will be unclear. Even with a well written RD — which I’ve had in a generalist role — usually that is still just clearly writing down vague responsibilities. Be ready to deal with ambiguity.
  • High risk / high reward type of role. One person in particular — your boss — shapes almost all of the experience. That’s more true than a typical manager because you might not have a larger team or a skip-level manager or other teams where the role could fit at all. Be discerning and ready to move on at the right time.

Beware the status cycle. There’s often a title getting attention every few years as the “generalist role for the hotshot ex-consultants.” Karl Yang calls this The Status Cycle and suggested a couple years ago that “CoS” was on the decline phase. Two notes: Don’t pick a role because it feels “high status.” And be discerning about roles when the job title has become overrated.

Yes “generalist role for the hotshot ex-consultants” hits a bit close to home — that’s why I want to be thoughtful about what specifically I’m good at and what I’m looking for.

5. Some further reading:

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