Chief of Staff or Executive Assistant: which should a founder hire first?

I’ve been recruiting Executive Assistants for founders and chief executives for over a decade, and the brief that starts “I think I need a Chief of Staff” is one I hear often. Sometimes it’s right. More often, when we talk it through, the founder is drowning in their own week, and what they’re describing is a very good Executive Assistant. The two roles get confused because both sit next to the founder, both are trusted with everything, and both titles have been stretched to cover whatever the last person did. They are different jobs, and hiring the wrong one first is expensive in both directions.

What each one actually takes off your plate

An Executive Assistant runs your operating rhythm. Your time, your inbox, your travel, your meetings, the follow-through on what you said you’d do, and, at the senior end, the board pack, the investor updates and a set of decisions they take without asking you. The best ones, the people The Core Standard calls Executive Business Partners, read the commercial picture behind the inbox and act as an extension of you. What they don’t do is own outcomes across the company that belong to other people.

A Chief of Staff does. They sit between you and your leadership team, own the operating cadence of the business rather than of you, close decisions between function heads that would otherwise land on your desk, and carry the plan the whole team is held to. A good one is a leader in their own right, and is paid and treated as one. What they don’t do, and will quietly resent being asked to do, is run your diary.

The quickest test I know is to list what you’d hand over in the first month. If every item comes back to your own time, information and commitments, it’s an Executive Assistant. If the list is full of other people’s problems that you’re holding because nobody else can, it’s a Chief of Staff. If you want the longer version of that test, I’ve written eight questions to ask about the role you’re writing.

Why the Executive Assistant usually comes first

In the early years, almost all of the waste in a founder’s week is operational. Meetings that shouldn’t be in the diary, emails that should have been answered in your name, the investor who wanted ten minutes and got a week of chasing, the board pack built the night before. None of that needs a Chief of Staff, and a Chief of Staff hired into it will either do it badly or leave. An Executive Business Partner will do it well and give you back the hours that were the problem in the first place.

There’s a second reason. A Chief of Staff needs something to run. If the company is small enough that you still know every decision being made, there are no cross-functional problems to hand over yet, and the role has no content. In my experience the founders who hire a Chief of Staff at that stage end up with an expensive project manager and no projects, and the person leaves within the year because the job they were sold didn’t exist.

When the answer changes

It changes when you have a leadership team and the problems start falling between them. Some of the signs I’d look for: two function heads are each waiting for you to settle something that neither will raise directly, the plan you set in January is only being tracked in your head, you’re spending your week on the operating cadence of the business rather than on customers, product or fundraising, and your Executive Assistant, however good, is being asked to arbitrate things that aren’t theirs to arbitrate. At that point you don’t replace the Executive Assistant. You add the Chief of Staff, and the two roles work together, one running you and one running the team.

Some founders go straight to a Chief of Staff because they already have a strong Executive Assistant and the operational layer is covered. That’s the right order. The mistake is going to a Chief of Staff because you don’t have an Executive Assistant and the title sounds more serious.

What to write in the ad

Whichever you hire, describe the remit rather than the seniority. For an Executive Assistant, name the decisions they’ll make without asking you, the people they’ll deal with in your name, what a good first year looks like and the salary, and if it’s the top of the ladder, call it Executive Business Partner so the right people apply. For a Chief of Staff, say what they’ll own across the company, who they’ll hold to the plan, and what decisions are theirs to close. If you can’t fill that second list, you’ve just found out which role you’re hiring. There’s a fuller guide to writing the Executive Assistant description if you need it.

See them do the job before you offer it

Both roles are easy to interview well for and hard to assess in an interview, because what you’re buying is judgement under pressure and the interview tests how well someone describes it. For an Executive Assistant at any level, The Core Standard puts the candidate inside a realistic working day at the level you’re hiring, with the inbox, the stakeholders and the decisions, and a specialist reviewer scores it against a published rubric. For a Chief of Staff the assessment has to test something different, proxy decision-making, influence without authority and board-level writing, which is why it’s a separate stream built around a strategic week. It’s in development and you can register to be told the week it opens.

Both are sat online and scored remotely, so it makes no difference whether you’re in London or San Francisco. Reviewer calls are scheduled for your time zone, and pricing is available in US dollars on request.

Common questions

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