Walk me through how you would approach your first 90 days supporting a chief executive who is new to the organisation.

The panel wants to see whether you understand that earning trust comes before changing anything, and whether you can structure an unstructured situation. A three-phase walk-through. Name the phases, say what you would do in each, and finish with what you would expect to have produced by day 90. Be specific about who you would meet and what you would read.

Tell me about a time you had to influence a senior leader who did not report to you to keep a priority on track.

Cross-functional influence without authority is the core of the job, and the panel is listening for how you handled resistance rather than whether the project succeeded. Use STAR. Keep the situation and task short, spend most of the time on the specific actions you took to bring the person onside, and give a clear result with what you learned about influencing at that level.

You are preparing a board paper on a decision where the financial model points one way and the operational leaders argue the other. How do you handle it?

This tests analytical discipline and whether you can hold a neutral position when senior people disagree, which is exactly what a chief of staff has to do. Separate facts from positions, state how you would test the assumptions behind each view, then describe how you would present the options rather than forcing a single answer.

A strategic project you are overseeing slips by three weeks, and the board meets in a week. What do you do?

Scenario questions like this check composure, honesty and whether you protect the executive's credibility rather than just the project timeline. Work through it in order: establish the facts, decide what needs to change, brief the chief executive before they are caught out, then manage the board communication.

Give me an example of handling confidential information about a restructure that affected people you work closely with.

The role sits inside sensitive information constantly, and the panel needs confidence that you can hold it without either leaking it or becoming cold and evasive with colleagues. STAR plus a short reflection on judgement. The key part is what you did to protect the information while still behaving honestly with people.

How do you decide what actually gets the chief executive's time?

This is the central judgement of the role, and the panel wants a method rather than an instinct. Answer with criteria first, then the mechanism you use to apply them. Name what you would escalate immediately and what you would handle yourself.

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Chief of Staff interview questions

The questions people actually get asked for this role, and what each one is really testing.

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What to expect

A chief of staff interview tests judgement and trust as much as skill. The panel is usually trying to work out whether you can represent the executive credibly, handle information discreetly, and keep multiple workstreams moving without needing to be managed.

Judgement and prioritisation: Questions about how you decide what reaches the chief executive and what does not, and how you handle competing demands on their time.
Behavioural: Stories about influencing people who do not report to you, managing a senior stakeholder relationship, or delivering a project across departments.
Analytical and technical: How you build a board paper, a business case, a financial model or a dashboard, and how you test the numbers behind a recommendation.
Scenario: A live problem, often a project slipping or a sensitive decision landing without warning, to see how you think under pressure.
Confidentiality and trust: How you handle sensitive information about restructures, executive performance or commercial negotiations.
Process: Questions about how you would structure your first months in the role, or how you would run a planning cycle from scratch.

Expect a recruiter or HR screen first, then a panel with the chief executive and often one or two direct reports. Many organisations add a short written exercise, a board paper or a one page briefing note under time pressure, because the role is largely written and analytical. A final conversation may involve a board member or another executive who wants to test how you handle a senior external audience.

1
Walk me through how you would approach your first 90 days supporting a chief executive who is new to the organisation.
Why they ask: The panel wants to see whether you understand that earning trust comes before changing anything, and whether you can structure an unstructured situation.
How to structure your answer: A three-phase walk-through. Name the phases, say what you would do in each, and finish with what you would expect to have produced by day 90. Be specific about who you would meet and what you would read.
Example answer
“I would split it into three phases. In the first month I would mostly listen. I would map the business by meeting the direct reports, the finance lead and a sample of people two levels down, read the last four board packs and the strategy papers, and build a one page view of who decides what. I would not propose changes to meetings or reporting in that month. In weeks five to eight I would establish the rhythms, so a weekly executive agenda tied to the top three priorities, a standard format for board papers, and a simple tracker for strategic projects that shows status without needing a meeting to interpret. In the last month I would pick one visible thing to deliver, something like a consolidated performance dashboard or a clear process for how proposals reach the executive, so the role has produced something concrete rather than just coordination. By day 90 I would want the chief executive to say they trust my read on what deserves their attention.”
2
Tell me about a time you had to influence a senior leader who did not report to you to keep a priority on track.
Why they ask: Cross-functional influence without authority is the core of the job, and the panel is listening for how you handled resistance rather than whether the project succeeded.
How to structure your answer: Use STAR. Keep the situation and task short, spend most of the time on the specific actions you took to bring the person onside, and give a clear result with what you learned about influencing at that level.
Example answer
“We were rolling out a new pricing model across three regions, and the general manager of one region had stopped attending the working group because he thought the model would cost him margin in his largest accounts. My task was to get him back to the table without escalating over his head. I asked for 30 minutes with him and brought his own regional numbers, modelled both under the new pricing and under his preferred approach, and we went through the two accounts he was worried about line by line. He was right about one of them, so we built an exception into the rollout for accounts above a certain contract value. He rejoined the group and became one of the louder advocates for the change because his concern had been treated as a real issue rather than an objection to manage. What I took from it is that senior resistance is usually a specific problem in disguise, and my job is to find the specific problem.”
3
You are preparing a board paper on a decision where the financial model points one way and the operational leaders argue the other. How do you handle it?
Why they ask: This tests analytical discipline and whether you can hold a neutral position when senior people disagree, which is exactly what a chief of staff has to do.
How to structure your answer: Separate facts from positions, state how you would test the assumptions behind each view, then describe how you would present the options rather than forcing a single answer.
Example answer
“First I would check whether the two views are actually in conflict or just using different assumptions. Usually the model embeds a cost or volume assumption the operational leaders dispute, so I would sit with each side and line up the inputs side by side. If the disagreement is a genuine assumption, I would model it both ways and show the decision point, that is, at what volume the answer flips. Then I would write the paper with three options, the financial case for each, the operational risk for each, and a recommendation with the reasoning shown. I would not hide the disagreement; boards usually trust a paper more when it says plainly where reasonable people differ. I would also flag what we would need to monitor after the decision so we know early if the assumptions were wrong.”
4
A strategic project you are overseeing slips by three weeks, and the board meets in a week. What do you do?
Why they ask: Scenario questions like this check composure, honesty and whether you protect the executive's credibility rather than just the project timeline.
How to structure your answer: Work through it in order: establish the facts, decide what needs to change, brief the chief executive before they are caught out, then manage the board communication.
Example answer
“I would spend the first day finding out why, because three weeks usually means either a dependency nobody owned or a scope decision that was never made. I would get the project lead to give me the real critical path, not the optimistic version. Then I would decide whether the deadline can be recovered, say by adding resource or cutting scope, or whether it genuinely moves. Either way the chief executive needs to know before the board does, so I would brief them with the cause, the revised date, the options and what I plan to say. In the board paper I would not bury it. I would state the delay, the reason and the recovery plan in the first page, because a board forgives a slip that is disclosed early and does not forgive one they discover themselves. After that I would fix the underlying gap, which is usually a decision right or a reporting line rather than a person.”
5
Give me an example of handling confidential information about a restructure that affected people you work closely with.
Why they ask: The role sits inside sensitive information constantly, and the panel needs confidence that you can hold it without either leaking it or becoming cold and evasive with colleagues.
How to structure your answer: STAR plus a short reflection on judgement. The key part is what you did to protect the information while still behaving honestly with people.
Example answer
“I was in the small group planning a restructure that would affect a team I worked with daily, and one of the managers in that team was a friend. For six weeks I knew his role was in scope and could not say anything. What I did was stay consistent: I did not avoid him, I did not give hints, and I did not join speculation about the restructure when it came up in the kitchen. When I was asked directly whether I knew something, I said I could not discuss it and that announcements would come through the proper channel. That was uncomfortable, but it meant that when the announcement came, no one could point to me as the source. Afterwards I checked in with him as a colleague and was honest that I had known, and he respected that I had not told him. The lesson is that you protect the process and the people at the same time by being predictable rather than by disappearing.”
6
How do you decide what actually gets the chief executive's time?
Why they ask: This is the central judgement of the role, and the panel wants a method rather than an instinct.
How to structure your answer: Answer with criteria first, then the mechanism you use to apply them. Name what you would escalate immediately and what you would handle yourself.
Example answer
“I use a few filters. Is this a decision only the chief executive can make, either because of decision rights or because it sets a precedent. Is it irreversible or expensive to get wrong. Is there an external commitment, so a regulator, an investor or a board matter, with a deadline attached. Does it relate to one of the top three priorities we have agreed for the quarter. If it fails all of those, it usually goes to the relevant executive or comes back through me with a recommendation attached. I would also say what I escalate immediately regardless: anything involving legal exposure, a serious safety or people matter, or a significant external relationship. The mechanism matters as much as the criteria, so I would keep a live list with the chief executive, review it weekly, and make sure the things I filter out still get a decision from someone rather than sitting with me.”