CEO Check-in Cadence

A guide for founders transitioning out of their CEO role and handing over control to a new CEO, focusing on the importance of clean breaks and proper delegation.

Initial Assessment Before Hiring

• Business must be ready for CEO transition
  • Have product-market fit
  • Minimum $300k in annual profit
  • Ability to make someone wealthy through compensation
• Founder must be mentally prepared
  • Willing to truly walk away
  • Accept that things will be done differently
  • Ready to empower new leadership fully

Transition Timeline

• First Month

  • Complete brain dumps with new CEO
  • Remove yourself from all communication channels (Slack, email)
  • Direct all executive team to new CEO
  • Only available for true emergencies

• Months 1-3

  • Check-ins every two weeks
  • No direct communication with other executives
  • Avoid "swoop and poop" management
  • Let CEO establish their authority

• Months 3-6

  • Reduce to monthly check-ins
  • Focus only on high-level metrics
  • Resist micromanaging decisions

• After 6 Months

  • Move to quarterly meetings
  • Review only major strategic decisions
  • Some CEOs may only need annual check-ins

Key Success Factors

• Clean Break

  • Must be "all in or all out"
  • No halfway measures
  • Don't undermine CEO's authority

• Communication Guidelines

  • Set clear spending thresholds requiring approval
  • Establish what requires consultation
  • Define emergency protocols

• Performance Evaluation

  • Accept some decline in areas of founder's expertise
  • Expect overall business health to improve
  • Allow for "flesh wounds, not mortal wounds"
  • Many businesses double in first year under new CEO

Common Mistakes to Avoid

• Maintaining direct contact with old executives
• Questioning every decision
• Requiring excessive reporting
• Being too present in day-to-day operations
• Not giving CEO enough autonomy to make changes