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?'