How to Hire a Chief of Staff
A Chief of Staff is one of the highest-leverage hires a CEO can make — and one of the hardest to get right. The role is genuinely different in every company, which makes defining success criteria critical before you start. This guide helps you hire a CoS who will multiply your impact, not just manage your calendar.
Hiring Process
Define the role clearly before posting
Is this CoS focused on strategy (board prep, OKRs, initiatives) or operations (process, systems, team coordination)? The answer determines your ideal candidate profile completely.
Structured first interview with the CEO
Test for: communication clarity, strategic thinking under pressure, ability to challenge ideas respectfully, and cultural alignment. This is a proximity role — fit with the CEO matters enormously.
Written exercise or case study
Give a real business problem — a messy strategic question or an operational challenge. Assess their structured thinking, written communication, and ability to navigate ambiguity.
Stakeholder panel interviews
Have them meet 3-4 people they'd work closely with (key direct reports, department heads). The CoS needs to earn trust across the org — not just with the CEO.
Reference checks
Call references directly — especially prior managers. Ask specifically about how they handle disagreement with leadership and how they manage confidential information.
Trial project (optional)
For final candidates, consider a paid 1-2 day project on a real company challenge. Nothing reveals readiness like an actual work sample.
Where to Find Chief of Staffs
Primary channel for experienced operations and strategy professionals. Targeted to people with consulting or strategy backgrounds.
Former McKinsey, Bain, and BCG consultants are common CoS profiles — alumni communities and LinkedIn alumni groups are good sourcing vectors.
Ask your investors for referrals — their portfolio operations teams often have a pipeline of CoS candidates.
Ask other founders who've hired a CoS for referrals — this role is almost always better filled through trusted referral than job boards.
Good for startup-oriented CoS candidates who are excited by growth-stage environments.
Common Hiring Mistakes
- Hiring a glorified EA rather than a strategic partner — undervaluing the role leads to wrong candidates
- Not involving the leadership team in the process — the CoS must earn their trust, not just the CEO's
- Skipping written exercises — verbal performance doesn't predict written communication quality
- Over-indexing on credentials (MBB, MBA) and under-indexing on judgment and EQ
Top Skills to Assess
Compensation Guide
$120,000 – $170,000
Senior CoS roles at well-funded companies can reach $200k+
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