When to hire a chief of staff
Hire a chief of staff when the founder is the bottleneck for work that belongs to no team: planning, investor updates, hiring coordination, special projects.
The role in one sentence
Before writing a job post, say the role in one sentence. If you cannot, the role is not clear enough to hire for.
"We need a chief of staff to the CEO: three to six years in consulting, operations or an early startup, strong writer and analyst, who takes on projects that belong to no team."
Change the details to yours. In Evander this sentence is enough to create the job post, interview stages and scorecards as drafts; see how it works.
Job description template
[Company] is [N] people. As chief of staff you work directly with the CEO. You run the company's planning and reporting, take on projects that belong to no team, and make sure decisions turn into action.
What you will do
- Run planning, goals and the weekly and monthly rhythm.
- Prepare board and investor updates.
- Lead special projects: a new market, a pricing change, an office move.
- Coordinate hiring until there is a recruiter.
- Find what is stuck across teams and get it moving.
What we look for
- You have run projects across teams without formal authority.
- You are a strong writer and are comfortable in a spreadsheet.
- You have worked in a fast, unclear environment.
- People trust you with confidential information.
Add the location, the pay range and equity, and how the interview process runs. Several US states require a pay range in the post, and EU rules require telling candidates the range before the first interview.
Screening brief
A screening brief says who should get an interview. Use it yourself or give it to AI screening.
Must-haves
- Has led cross-team projects to a finish, because the role has no team of its own.
- Strong writing and analysis, shown in a work sample, because updates and plans are the output.
- Has worked closely with senior leaders, because the job is leverage for the CEO.
Either of these profiles works
- Consultant or banker who moved into a startup operations role.
- Early startup employee who has already done a bit of everything.
Bonuses
- Has run a fundraising process or board reporting.
- Has built a function and handed it over.
- Knows your industry.
Interview plan
| Stage | What it tests |
|---|---|
| Intro call (30 min, CEO) | Why this role, what they want to do after it. |
| Project review (60 min) | Two projects they led: goal, obstacles, result, what they did themselves. |
| Written exercise (paid, 2 hours) | A one-page memo on a real question the company faces. Tests structure and judgment. |
| Team conversations and references (90 min) | With two leaders they would work with. References from a former manager. |
Scorecard
Rate each criterion from 1 to 4 with a written example, before the debrief and without seeing other ratings. More in interview scorecards.
| Criterion | What strong looks like |
|---|---|
| Structured thinking | Breaks a vague problem into clear parts and a recommendation. |
| Writing | Memo is short, specific and takes a position. |
| Getting things done without authority | Examples of moving people who did not report to them. |
| Judgment and discretion | Knows what to decide alone and what to bring to the CEO. |
| Range | Has switched between very different kinds of work and delivered. |
Interview questions
- Tell me about a project that had no owner until you took it. What happened?
- Describe a time you had to get a senior person to do something they did not want to do.
- What would you want to know about how our CEO works before starting?
- Tell me about a recommendation of yours that was rejected.
- What do you want to be doing in two years?
Common mistakes
- Hiring a chief of staff when the real need is an executive assistant or a COO.
- No defined first projects, so the role becomes a catch-all.
- Hiring someone the leadership team will not accept as a peer.
This kit is also available as Markdown, free to copy and adapt, in the hiring-templates repository on GitHub.
Questions
When should a startup hire a chief of staff?
Hire a chief of staff when the founder is the bottleneck for work that belongs to no team: planning, investor updates, hiring coordination, special projects.
What should a job description for a chief of staff include?
A short summary of the company and the role, four or five things the person will do, three or four requirements that can be checked, the location, the pay range and equity, and the interview process. Start from one sentence, for example: "We need a chief of staff to the CEO: three to six years in consulting, operations or an early startup, strong writer and analyst, who takes on projects that belong to no team."
What interview questions should I ask a chief of staff?
Tell me about a project that had no owner until you took it. What happened? Describe a time you had to get a senior person to do something they did not want to do. What would you want to know about how our CEO works before starting?
What are common mistakes when hiring a chief of staff?
Hiring a chief of staff when the real need is an executive assistant or a COO. No defined first projects, so the role becomes a catch-all. Hiring someone the leadership team will not accept as a peer.