Questions to ask a founder before accepting a Chief of Staff role
By Alice Huang, Chief of Staff and operator
Questions to ask a founder about a Chief of Staff role: priorities, authority, access, working style and what success will look like.
The title can sound right while the job is wrong. Before you accept, find out what this founder needs, what you will own and how the two of you will work together.
a16z's Executive Talent team stresses that Chief of Staff responsibilities vary and need to be clear up front. Use that as the starting point for your questions.
Ask about the problem
- Why are you hiring this role now?
- What keeps coming back to you that should not?
- What would you want to be different after six months?
- What has already been tried?
Listen for a problem you can help solve. A list of everything the founder dislikes is not yet a job description. Ask which outcomes come first and what can wait.
Ask about authority and access
Who do you report to? Which decisions can you make, which can you recommend and which can you only coordinate? What information will you have access to? How will the founder introduce your role to the leadership team?
Do not assume that being close to the CEO gives you permission to manage everybody. a16z recommends a single executive reporting relationship; the exact arrangement still needs to be agreed in this company.
Ask about the working relationship
How do you prefer to receive bad news? What happens when we disagree? When will we review priorities? What does support look like when another leader challenges the role?
Ask about the work beyond the initial period, too. Do not treat a suggested tenure in a hiring guide as a rule for your career. Discuss the founder's expectations and your own.
Write back what you heard
Before accepting, summarize the outcomes, scope, reporting line, decision rights and review rhythm. Ask the founder to correct anything you misunderstood. If important promises are part of your decision, have them reflected in the appropriate written agreement.
Your goal is not to catch the founder out. It is to discover whether the job both of you are imagining is the same job.