Don’t Hire a Chief of Staff

Chief of Staff has been the hottest job in the valley since about 2015. It makes sense to have one if you’re the CEO of a 10,000 person company and you have a 12 person executive staff to oversee, but more and more Seed and Series A stage companies are hiring Chiefs of Staff. If you’re at this stage and are considering hiring a Chief of Staff: don’t. 9 times out of 10, it’s the wrong answer.

Most early stage companies who hire Chief of Staff roles would be better served by hiring stronger senior leadership. There are usually only 2–3 things that really, really matter at a given time at an early company, so hire 2–3 exceptional leaders to own those problems and forget the Chief of Staff. Hiring a Chief of Staff at the Seed or Series A stage (or even Series B) sends the message that the CEO thinks they need to do it all themselves. If you hire a Chief of Staff, at best that will buy you a couple more months of staying on top of everything — barely. You’ll tread water at best, and the fundamental problem still isn’t solved: your teams and functions aren’t scaling, and you don’t have capacity to lead all of them.

One common fault line that has emerged since the beginning of 2020, accelerating the Chief of Staff trend, is the shift to remote-first work. More junior teams (and leaders) struggle in a remote world. In an in-person world, a founder/CEO can get by with having managers with 6 total years of experience reporting to them. Teams can skate by with informal cross-team communications in an in-person world because people can fill in the gaps at lunch, at the water cooler, at someone’s desk, etc. Remote work wipes all of that out. You have to rely on formal communication channels, both up-and-down and across teams. This is where junior management breaks down and more experienced management excels.

Here’s the dirty secret: with better senior leadership, you don’t get much better decision-making. That skill reaches diminishing marginal returns after a decade or so of experience in startups (often less with the best people). But you do get better management abilities, which means better team leadership, better managing upwards, and better coordination across the company. If you hire senior leaders focused in each of your company’s critical areas — the areas that really matter in the next 12 months — that will do far, far more to improve both your company’s execution and your ability to stay on top of things than hiring a Chief of Staff.

What does “more senior leadership” look like? Don’t hire anyone more junior than Director-level to lead a function: at that level, they’re still hungry enough to roll up their sleeves and execute, yet they’re experienced enough to effectively communicate upwards and across the team. Communication is really the thing many founder/CEOs are solving for with the Chief of Staff role: they don’t feel on top of things, so they hire a Chief of Staff to solve for that. (Or, in the other primary motivator: there are point problems that need to be solved that the existing team can’t handle, in which case the solution is still the same — hire better leadership.)

We lionize founders and CEOs and some actually believe they are the company. In most cases — especially when you’ve raised money, have customers and a team, etc. — this is simply not true. The CEO or founder is not the company, but they are the ones who build the best leadership team. That leadership team is what enables the CEO to both (a) get the information they need to make decisions and (b) execute in all functions.

Jack Dorsey is an exceptional founder and CEO, but his secret isn’t that he’s a superhuman who does everything; his secret is he recruits excellent executive talent who enable him to do everything he can do. (How do you think he runs 2 public companies? It’s certainly not because he works twice as many hours.) Steve Jobs never had a Chief of Staff (certainly not in the contemporary Silicon Valley sense)— but he did have an absolutely world-class leadership team that made Apple what it is today, and continued to run the company just as well after he passed.

If you’re tempted to hire a Chief of Staff, ask yourself: why do you really need this person? What problems in your company do you actually need to solve? If you’re underwater in any area of the company that’s critical to your success between now and your next fundraise milestone, that’s a sign that your leadership in that area isn’t meeting the bar and you need to upgrade it. Making those key hires will do orders of magnitude more to speed your company up vs. hiring someone 2-4 years out of college to act as an extension of you — which, by the way, also replicates your faults, not just your strengths.

Don’t hire a Chief of Staff.

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