Questions to Ask a Chief of Staff
Questions for anyone sitting across from a chief of staff: a candidate you are interviewing, someone you are considering hiring for the first time, a person you are meeting to learn about the role, or the chief of staff you already work alongside. They focus on scope, authority, the relationship with the principal, and how the job actually gets measured.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
How would you describe what the job is, in one sentence?
Chief of staff means at least four different jobs depending on the organization: an operator, a strategist, a proxy for the principal, or an elevated executive assistant. The first sentence someone reaches for tells you which version they have lived.
- 2
What did you spend the most hours on last month?
The written scope of a chief of staff role is always broad and always aspirational. A month of actual hours cuts through it, and if the honest answer is calendars and slide decks, that is worth knowing before anyone uses the word strategy again.
- 3
Who do you report to, and does anyone report to you?
Some chiefs of staff run a team, some run none, and the difference changes the job entirely. It also tells you whether the role is a leadership position or an influence position, which is the harder version to do well.
- 4
What decisions can you make without checking?
This is the single best question about a chief of staff role, because the job runs on borrowed authority. Someone who can name the categories they decide alone has a real remit. Someone who cannot has a coordination job with a senior title.
- 5
How do people know when you are speaking for your principal and when you are not?
Ambiguity here causes more damage than any other part of the role. Listen for an explicit mechanism, such as a phrase they use or a habit of naming which hat they are wearing, rather than an assurance that people just know.
- 6
What does your principal actually want from you that they have never said out loud?
Every chief of staff is partly hired to fix something the leader will not name: a broken leadership team, their own disorganization, a communication problem. A candid answer here shows real self-awareness about the position.
- 7
What do you say no to on their behalf?
Filtering is where the value is and where the resentment collects. Ask for a recent example and how the person on the other end took it, because a chief of staff who has never absorbed anyone's irritation is probably not filtering anything.
- 8
How often do you disagree with your principal, and how do you do it?
Never is a bad answer and constantly is a different bad answer. What you want is a description of the setting: privately, before a decision is public, with an alternative attached. This is the part of the job that protects an organization from a bad call.
- 9
What is on your desk that should belong to someone else?
Chief of staff roles accumulate orphaned work, which is useful for a year and corrosive after that. Someone who can name what they are holding temporarily against what has quietly become permanent understands the trap the role sets.
- 10
How do you handle information that people give you assuming it will not reach your principal?
The role sits between a leader and everyone who is careful around that leader. There is no clean answer, but a thoughtful one describes a rule they apply consistently, because inconsistency is what stops people telling a chief of staff anything true.
- 11
What have you stopped doing since you started?
A good chief of staff kills meetings, reports and processes. If nothing has been removed in a year, the role has been additive only, which usually means the organization has one more layer rather than one less problem.
- 12
How is your performance measured?
This is genuinely difficult for the role, since most of the output belongs to someone else. Answers that involve the principal's outcomes or the leadership team's functioning are more credible than a list of projects with the chief of staff's name on them.
- 13
Tell me about something that failed while you were responsible for it.
Chiefs of staff can hide behind shared ownership, so push for one where the call was theirs. What you are listening for is whether they take the failure cleanly or distribute it across the leadership team they were coordinating.
- 14
How do you work with the executive assistant and the operations team?
These boundaries are where chief of staff roles most often go wrong, particularly with a long-serving executive assistant who has real influence. A candidate who has thought about this relationship has done the job. One who has not will find out in week two.
- 15
What do you do when two executives want opposite things and both think you are on their side?
This is a weekly occurrence in the role, not a hypothetical. Watch whether they describe escalating, brokering, or quietly deciding, because each says something different about how they use the authority they have been lent.
- 16
What information do you see that nobody else sees, and how do you handle it?
Compensation, restructures, departures and board material all pass through the role. Ask how they hold that alongside daily relationships with people who are affected by it and do not know yet.
- 17
How do you know when to insert yourself and when to stay out?
Overreach is the most common failure of a chief of staff, and it looks like helpfulness from the inside. A candidate with a working rule for when not to get involved is describing a skill that took a while to learn.
- 18
Who owns the relationship after you leave a project?
The role is meant to be temporary in each area, which means handing work back cleanly. Someone who cannot describe a handover has been accumulating rather than delivering, and the organization will feel that when they move on.
- 19
How long do you expect to do this job, and what comes after?
Most chief of staff roles are two to three years by design and the exit is part of the deal. An answer involving a specific next role is normal and healthy. No answer at all suggests the role has no defined end, which becomes a problem for both sides.
- 20
What would make you say the role is not working?
Ask this whether you are hiring or already working with them. Naming the conditions in advance, such as being cut out of decisions or having no authority to match the scope, gives both of you a way to raise it later without it becoming a resignation.
Using these questions well
Practical guidance for the conversation itself.
If you are hiring a chief of staff
If you are hiring a chief of staff
Define the version of the role first
Write down which of the common shapes you are hiring for: running the operating rhythm, doing analysis and special projects, acting as a proxy in rooms you cannot attend, or managing the leadership team's functioning. Candidates cannot answer well against an undefined role, and a bad hire here is usually a definition problem rather than a person problem.
Test the authority question directly
Ask what you would need to delegate for the role to work, and see whether the candidate names things you are not willing to give up. That conversation is uncomfortable in an interview and much worse six months in.
Check the exit plan before the start date
Agree roughly how long the role lasts and what it leads to. Chief of staff roles that run indefinitely tend to end badly, because the person becomes structurally senior with no defined function of their own.
If you are meeting one to learn about the role
If you are meeting one to learn about the role
- Ask about the worst quarter rather than the best. The role is defined by what happens when the organization is under pressure.
- Ask how they got the job. A large share of chiefs of staff were hired internally by someone who already trusted them, which tells you something about how to position yourself.
- Ask what they would need to learn to run a function instead. The most common next step is a line role, and the gap is usually direct people management.
- Ask what they miss about their previous job. The role trades depth for breadth and not everyone is happy with the exchange.
- Ask whether they would take the job again, and listen to the pause before the answer.
If you already work with one
If you already work with one
- Ask what they need from you that they have not asked for. The role tends to absorb friction quietly rather than report it.
- Ask which of your requests cost the most and deliver the least. They will know and they will rarely volunteer it.
- Be explicit about when you want their own view rather than the principal's. It is the fastest way to get honest input from someone trained to represent someone else.
- Check whether anything you delegated as temporary has quietly become permanent.
- Ask what would need to be true for them to still be doing this in two years.