Hiring guide
How to Hire a Chief of Staff
When to hire a chief of staff, where to find them, the judgement and operating skills to test, a leadership-meeting work sample, red flags and onboarding.
The short answer
Hiring a Chief of Staff comes down to verifying judgement about what the executive should and should not see, running an operating cadence: leadership meetings, planning cycles, okrs or quarterly goals and clear, concise writing: briefs, decision memos and board or investor updates before you commit interview time. The process below runs 5 stages, screens on evidence rather than résumé claims, and scores every candidate against the same criteria.
- Watch for: Sees the role mainly as a stepping stone and wants to manage people from day one
- Watch for: Talks about controlling access to the executive more than helping others get decisions
- Score on: Clarity and prioritisation in the one-page summary
- Score on: Quality of judgement in the strategic case
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Applying for a role like this? Practise the assessment free →Before you hire a chief of staff, decide which version of the role you need: a strategic partner who runs planning and special projects, an operator who drives the leadership team's cadence, or a mix of both. The title means different things at different companies, so candidates will read your job description very differently unless you are specific. This guide covers when the role makes sense, where to find strong candidates, what to test, a practical work sample, red flags and how to make the first months work.
Why this role matters
A chief of staff extends the executive's capacity. They make sure leadership meetings lead to decisions, decisions turn into owned actions, cross-team projects move and the executive spends time on what only they can do. A good one is trusted by the whole leadership team. A poor fit becomes a gatekeeper or an expensive assistant, and can damage relationships between the executive and their direct reports.
Where to find candidates
- Alumni of strategy consulting firms who want an operating role, found through LinkedIn and alumni networks
- MBA and executive education alumni networks at business schools
- Your own company: strong project leads, business operations staff or senior analysts who already know how the organisation works
- Former government, military or political staff, where the chief of staff role has a long history
- Referrals from investors and executives who have worked with an effective chief of staff
- Business operations and strategy and operations communities on LinkedIn
Skills to look for
Red flags
- Sees the role mainly as a stepping stone and wants to manage people from day one
- Talks about controlling access to the executive more than helping others get decisions
- Cannot give an example of influencing a senior person who disagreed with them
- Shares confidential details about a previous employer during the interview
- Writing samples are long and unclear, with no recommendation
- Values do not match the executive's working style, which the role cannot survive
The interview process
- 1
Executive conversation
The executive meets the candidate to discuss what they want help with and how they work. Both sides should test fit honestly, because this relationship is the job.
- 2
Leadership team interviews
Two or three direct reports interview the candidate. Ask them to judge whether they would trust this person to represent the executive.
- 3
Leadership-meeting work sample
Give a set of messy inputs: notes from a leadership meeting, a few metrics and conflicting team updates. Ask for a one-page summary of decisions, owners and open issues, plus a draft agenda for the next meeting. A job simulation of this kind of work is one option when comparing several candidates.
- 4
Strategic case
Discuss a real issue the company faces, such as entering a new market or reorganising a team, and ask how they would structure the work and who they would involve.
- 5
References
Speak to executives they supported and peers they worked alongside. Ask about discretion, follow-through and how they handled conflict.
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How to evaluate
- Clarity and prioritisation in the one-page summary
- Quality of judgement in the strategic case
- Trust and credibility with the leadership team interviewers
- Evidence of influence without authority in past roles
- Discretion and integrity
- Working-style fit with the executive
Onboarding
- 1Write down the role's scope, decision rights and what is explicitly out of scope, and share it with the leadership team
- 2Have the executive announce the hire and explain how the role will work
- 3Give access to the executive's calendar, key documents and board materials from the start
- 4Hold a short daily check-in for the first weeks, then move to a weekly one
- 5Give them one visible project early so they build credibility with the team
Common questions
When should a company hire a chief of staff?
Usually when the executive's time is the bottleneck: too many meetings, decisions not followed through and cross-team projects stalling. If the need is mainly scheduling and inbox management, an executive assistant is the better hire.
What is the difference between a chief of staff and an executive assistant?
An executive assistant manages the executive's time, travel and communications. A chief of staff works on priorities, decisions and cross-team projects, and often acts on the executive's behalf with the leadership team. Many executives have both.
What background makes a good chief of staff?
Common backgrounds include strategy consulting, business operations, finance and internal project leadership. The shared traits are judgement, discretion, clear writing and comfort working across teams.
What does a chief of staff do after the role?
Many move into operating roles such as heading a function or business unit. Being open about this in hiring helps attract strong candidates and plan succession.
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