Hire your next chief of staff

A graduate degree such as an MBA can certainly help, particularly for roles supporting CEOs of larger or more complex companies, but it is rarely a hard requirement and you should not screen on it alone. Some of the strongest Chief of Staff hires come from backgrounds in management consulting, investment banking or internal operating roles where they have already demonstrated the ability to handle ambiguous problems and influence senior people. When evaluating candidates, you will get a much better signal by focusing on their judgment, the quality of their written communication and their track record of getting things done in messy environments than by reading the credentials at the top of the resume.

The two roles get confused regularly, but they actually operate quite differently in practice. A COO or VP of Operations typically holds formal authority over a defined set of functions and is directly accountable for the P&L outcomes of those areas, with a clear set of direct reports underneath them. A Chief of Staff usually has no direct reports of their own and no formal authority over other departments, yet they are still expected to drive priorities across the entire organization. They do this by working through influence, relationships and the credibility of operating on behalf of the CEO. In practice, the Chief of Staff acts as a force multiplier for the executive they support, whereas the COO is a senior operating leader running a function in their own right.

Most Chief of Staff tenures fall somewhere between two and three years, though some stretch longer when the working relationship with the executive is unusually strong or when the scope of the role keeps evolving. The job is often treated as a launching pad into a more senior operating role, either at the same company or somewhere new. Common next steps include Head of Strategy, VP of Business Operations, General Manager of a business unit and, in many cases, leaving to start a company as a founder.

Discretion sits at the very top of the list because the Chief of Staff is constantly exposed to sensitive information about people, compensation, finances and strategy that they cannot share broadly inside the company. Beyond discretion, the role demands strong judgment in the face of ambiguity, polished written communication that can credibly stand in for the executive when needed and the kind of social awareness that lets them read a room and adjust their approach in real time. The day to day reality of the job involves taking partially formed thoughts from the executive and translating them into clear, sequenced action that other leaders across the company can actually run with.

Prior experience in your specific industry is genuinely useful because it shortens the ramp-up period and gives the new hire credibility with other senior leaders from day one. That said, it should not be treated as a hard requirement that disqualifies otherwise strong candidates. The best Chief of Staff hires tend to learn a new business quickly and apply structured thinking effectively regardless of the domain they came from. If you operate a deeply technical company, it is worth looking for at least basic technical fluency in the candidate so they can hold their own in product and engineering conversations and engage credibly with the people leading those functions.

The most useful interview exercise is to walk the candidate through a genuinely ambiguous problem you are currently facing in your business and ask them to think out loud about how they would approach it. Pay attention to whether they take a moment to structure the problem cleanly before jumping to solutions, whether they surface the relevant tradeoffs rather than landing on a single answer too quickly and how they handle the parts of the prompt that are deliberately vague or incomplete. The strongest candidates will push back when something in the brief does not make sense to them, ask sharp clarifying questions and ultimately arrive at a recommendation they can defend with reasoning rather than just confidence.

The right level of seniority depends mainly on the executive the Chief of Staff will be supporting and on the complexity of the operating environment around them. A CEO running a $50M or larger company with multiple business lines and an active board of investors will generally want a Chief of Staff with somewhere in the range of 7 to 10 years of professional experience, ideally including some time in a high-context role like consulting, banking or senior operating leadership. An early-stage founder running a smaller team can often do extremely well with someone in the 3 to 5 year range, provided that person brings strong operator instincts and a willingness to roll up their sleeves on whatever needs doing.

Whether the role works remotely depends quite a bit on how the executive operates and on how the company is set up overall. The most effective Chief of Staff work tends to happen in close physical proximity to the CEO, because so much of the value comes from quick hallway conversations, picking up on context in real time and being in the room for unscheduled moments that you cannot put on a calendar. Hybrid arrangements with regular co-location each week tend to work well in practice, while fully remote setups are only really sustainable in companies that already have a strong async-first culture and disciplined written communication baked into how they operate.