CEO Diligence Process

A comprehensive framework for conducting due diligence when hiring a CEO, focusing on thorough verification while maintaining trust.

Initial Assessment (Trust Phase)

• Trust your gut instinct as first screen
• Look for "creepy crawlies" - any uncomfortable feelings after meeting
• Assess if candidate makes you feel energized after meeting
• Consider if you'd trust them to "babysit your kids"
• Look for authenticity over polish
  • Prefer candidates who show genuine nervousness
  • Value those who scratch their face during hard questions
  • Avoid "slick" personalities

Secondary Verification (Team Review)

• Have 1-2 trusted team members interview candidate
• Get multiple perspectives on personality fit
• Look for consistent feedback across reviewers
• Ensure alignment with company culture and values

Deep Background Check (Verify Phase)

• Hire former CIA agents (Business Intelligence Advisors)
• Cost ranges from $10,000-$20,000
• Process includes:
  • Hour-long candidate interview
  • Document every claim made
  • Verify each statement independently
  • Contact 5+ former colleagues
  • Check legal records
  • Review payment history
  • Examine criminal background

Reference Check Strategies

• Never call provided references
• Use "scuttlebutt" method:
  • Contact friends who invested in previous companies
  • Ask CEOs about why person left
• Email trick for honest feedback:
  • Email multiple former colleagues
  • State "no response = negative reference"
  • Gives people safe way to indicate concerns
  • Helps avoid legal liability issues

Why This Matters

• Prevents expensive hiring mistakes
• Worth investment for key leadership roles
• Helps avoid "nightmare" scenarios
• Creates confidence in final hiring decision
• Reduces risk of misrepresentation