The Executive Search Playbook

Subject: Confidential — Leadership opportunity

Dear [First Name],

[Mutual connection] suggested I reach out to you regarding a senior leadership opportunity.

I'm working with [Company/Board description — no name if confidential] on a [C-level/VP] search. Given your track record at [Current Company] — particularly [specific achievement or initiative] — you're exactly the kind of leader they're looking for.

This is a [brief value proposition: growth stage, market opportunity, team size, etc.].

I'd welcome a confidential, no-commitment conversation at your convenience. Would next week work?

Warm regards,
[Your Name]

LEADERSHIP & STRATEGY:
1. How would you describe [Name]'s strategic vision? Can you give an example?
2. How do they handle disagreement from their direct reports or board?
3. What's their approach to building and developing a leadership team?

RESULTS & ACCOUNTABILITY:
4. What's the most significant business outcome they delivered?
5. How did they handle a situation that didn't go as planned?
6. How do they balance short-term results with long-term building?

CULTURE & CHARACTER:
7. How would their direct reports describe working for them?
8. What should the hiring organization know before making this hire?
9. Would you hire/work with this person again? In what capacity?

A well-run executive search takes 60-120 days from briefing to signed offer. Rushing this process leads to misalignment — the cost of a wrong C-level hire (typically 5-15x annual salary) far exceeds the cost of extra time.

For confidential or board-level searches, external firms add value through discretion and market access. For VP-level roles where your brand is strong, internal executive recruiters with the right tools can deliver comparable results at lower cost.