Template · 12 min read

Chief of Staff Job Description, Duties & Interview Questions

vChief Free Intermediate

This is the concrete, copy-paste artifact the other two essays lack: a real JD skeleton (summary, Who You Are, nine responsibilities, qualifications) plus ten interview questions you can lift straight into a scorecard. It explicitly leaves 10 to 20% of the mandate undefined for the hire to shape, and shows how to swap in your gap areas (finance, HR, sales ops) so a 10 to 20 person startup can spec the exact boring load-bearing surface, vendor payments, onboarding, tooling, that you are trying to offload.

  • Ships a fillable JD plus interview-question set you can drop into a hiring scorecard the same day
  • Deliberately leaves 10 to 20% of the role undefined so the first hire shapes the messy edges you cannot pre-spec
  • Prompts you to name your own gap areas (finance, HR, ops), which is exactly how you decide what stays with the founder versus what they own
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The question it answers

  1. When should I hire my first operations or 'chief of staff' person, and what should they own?

Read with it

  1. Written by PostHog's operations lead, this is the sharpest piece on hiring for judgment over resume. Its core claim, attributes... PostHog Article · 10 min read Making your first startup ops hire: what founders should look for Charles Cook
  2. The canonical piece for avoiding exactly the vanity-title trap you warn against. It caps the role at about 20% admin work (so... a16z Article · 15 min read How to Hire a Chief of Staff Andreessen Horowitz (a16z)
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