Employing a Chief of Staff is a bad idea

Since around 2015, Chief of Staff has been the hottest job in the valley. It makes sense to have one if you're the CEO of a 10,000-person firm with a 12-person executive team to manage, but Chiefs of Staff are increasingly being hired by Seed and Series A stage companies. If you're at this point and thinking about employing a Chief of Staff, don't do it. It's the wrong response 9 times out of 10
Stronger senior leadership would be beneficial for most early-stage organisations that hire Chief of Staff roles. At an early stage company, there are usually just 2–3 things that really, truly matter at any given time, so select 2–3 exceptional executives to own those issues and forget about the Chief of Staff. Hiring a Chief of Staff at the Seed or Series A (or even Series B) stage suggests that the CEO believes they must handle everything themselves. Hiring a Chief of Staff will only buy you a few extra months of staying on top of everything – at best. You'll float along at best, and the core issue remains: your teams and functions aren't scaling, and you don't have the ability to lead them all

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The transition to remote-first work is one common fault line that has formed since the beginning of 2020, increasing the Chief of Staff trend. In a remote world, more junior teams (and leaders) suffer. In an in-person world, a founder/CEO can get by with having managers reporting to them with a total of 6 years of experience. In an in-person setting, teams may get by with informal cross-team communications because people can fill in the gaps during lunch, at the water cooler, at someone's desk, and so on. All of it is obliterated when you work from home. You must rely on established communication channels to communicate both up and down as well as between teams. This is where inexperienced management fails and more experienced management shines

Here's a nasty little secret: greater senior leadership doesn't necessarily mean better decision-making. After a decade or so at startups, that expertise achieves diminishing marginal returns (often less with the best people). However, you gain superior management skills, which means better team leadership, upward management, and cross-company cooperation. Employing senior leaders focused on each of your company's essential areas — the areas that actually matter in the next 12 months — will boost both your company's performance and your ability to remain on top of things considerably more than hiring a Chief of Staff

What does it mean to have "more senior leadership"? Don't recruit anyone below the Director level to head a function: they're still eager to roll up their sleeves and get things done, but they're also seasoned enough to communicate effectively upwardly and across the team. Many founder/CEOs use the Chief of Staff function to address a lack of communication: they don't feel on top of things, so they hire a Chief of Staff to help them. (Or, in the case of the other key incentive, there are specific difficulties that the current team is unable to address, in which case the solution remains the same – employ better leadership.)

We idolise CEOs and founders, and some even believe they are the firm. This is simply not true in most circumstances, especially when you've raised money, have clients and a team, and so on. The company is not run by the CEO or founder, but they are the ones that put together the greatest leadership team. The CEO's leadership team is what allows them to (a) receive the information they need to make decisions and (b) execute across the board

Jack Dorsey is a fantastic founder and CEO, but his secret isn't that he's a superhuman who can do it all; it's that he surrounds himself with superb executive talent who enable him to achieve everything he can. (How do you believe he manages two publicly traded corporations?) It's not because he works twice as many hours as you.) Steve Jobs never had a Chief of Staff (at least not in the modern Silicon Valley sense), but he did have a world-class leadership team that built Apple into what it is today and continued to operate it well after he died

If you're considering hiring a Chief of Staff, ask yourself why you need this person in the first place. What issues do you need to address in your organisation? If you're underwater in any area of the business that's crucial to your success between now and your next fundraise milestone, it's an indication that your leadership in that area isn't up to par and has to be upgraded. Those important employees will accelerate your firm by orders of magnitude more than employing someone 2-4 years out of college to serve as an extension of you — which, by the way, mimics your flaws as well as your strengths

Hiring a Chief of Staff is a bad idea