Hiring a fractional CMO based on a 30-minute call is high-stakes. These are the questions we recommend founders and CEOs ask — and what good vs. concerning answers look like.
Ask 15 specific questions across: past outcomes, working style, capacity, business fit, and red flags. Don't accept generic answers ('I drive growth'); push for specifics ('What specifically did you do at [company] and what was the result?'). Verify everything with reference checks.
1. 'Walk me through a specific past engagement. Situation, what you did, results.' (Look for: specifics, numbers, honest assessment of what didn't work)
2. 'What's the biggest miss in your career? What did you learn?' (Look for: self-awareness, real reflection)
3. 'What percentage of your fractional engagements have led to good outcomes vs. mediocre vs. failed?' (Look for: honest distribution; 100% successful is a lie)
4. 'Can I talk to 2-3 of your past clients?' (Non-negotiable)
5. 'What's your typical engagement structure — hours per week, days per week, types of meetings?' (Look for: specific cadence, not 'whatever you need')
6. 'How hands-on are you? Do you produce work yourself or direct others?' (Look for: clear answer that matches your need)
7. 'How do you handle disagreement with the CEO?' (Look for: 'I'll push back, but you decide.' Avoid: 'I just do what you want.')
8. 'What does the first 90 days look like with a typical client?' (Look for: structured plan, not 'depends on the situation')
9. 'How many concurrent engagements are you running?' (Look for: 3-5 max; above 5 is a quality risk)
10. 'When are your busiest hours? When can I reach you?' (Look for: clear answer; avoid 'I'm always available')
11. 'When does your current engagement load free up?' (Helps you plan timing)
12. 'What experience do you have in [our industry]?' (Look for: relevant pattern recognition, even if not exact industry)
13. 'What kind of company should NOT hire you?' (Look for: real answer; everyone who passes this is more honest than the generic 'I work with everyone')
14. 'How do you bill — by the hour, by the month, or some other structure?' (Look for: monthly retainer or per-day rate; avoid hourly unless it's a short defined project)
15. 'What would you need from us to make this engagement succeed?' (Look for: clear ask, mature understanding of what success requires; avoid 'just need access to the team')
After the interview, ask references:
• 'Would you hire them again?' (Look for: immediate yes)
• 'What did they not do well?' (Everyone has weaknesses)
• 'How was the relationship at the end?' (Clean exits matter)
• 'What outcomes did they actually drive vs. promise?'
• 'Anything I should know that won't come up in the interview?'