By Chief Maker Executive Development Academy

For ambitious professionals with their sights set on the C-Suite, the guidance of an experienced mentor can be the critical difference that makes the difference.  

CEOs, in particular, offer invaluable wisdom gained through years of leadership experience. But how do you convince someone with such limited time to invest in your development? 

Here's a strategic approach to securing and maintaining a CEO mentor relationship. 

 

Finding the Right Mentor Match 

The foundation of any successful mentoring relationship begins with thoughtful selection: 

  • Look for potential mentors 2-3 levels above your current position (4 levels is ambitious, but possible) 
  • If there’s common ground, you’ll more likely get a positive response 
  • Choose someone you genuinely admire and trust based on their leadership style 
  • Aim to make organic connections rather than using pre-arranged mentor programs 
  • Look for a person you can see yourself having authentic conversations with 

 

Building Connection & Making Your Request 

Start by establishing a foundation of meaningful interactions in low-pressure settings first. 

  • Engage with them at company functions or industry events 
  • Ask genuine questions during these casual encounters 

 

Once you’ve established familiarity, reach out with a well crafted email that includes: 

  • Specific insights you’ve taken from their presentations or published content 
  • Your current role and relevant challenges 
  • Your willingness to learn and make bold changes 
  • How you’re giving back by mentoring younger leaders (If you’re not - get started now. It’s a great way to learn in itself)  

Acknowledge their busy schedule and make the meeting as convenient as possible for them. Start with a simple coffee, that’s all. 

 

Managing the Mentor Relationship 

If your coffee request is successful, the responsibility falls on you to maintain the relationship effectively: 

  • Prepare a focused agenda for each meeting (aim for quarterly sessions) 
  • Coordinate meeting logistics through their Executive Assistant 
  • Begin each meeting by establishing rapport  
  • Provide updates on how you've implemented their advice and the results achieved 
  • Ask specific questions about your current professional challenges 
  • Express genuine gratitude for their time 

 

Demonstrating Your Commitment 

CEOs want to mentor people who take action on advice and show growth.  

  • If they recommend a book, read it and take notes 
  • Send brief follow-up messages sharing key insights you've gained 
  • Be open about your development areas and challenges 
  • Show them that you're actively applying their guidance 

 

CEOs mentor others primarily because they want to give back. While they're exceptionally busy, most successful executives have had mentors themselves and understand the value of passing on their knowledge. By following this structured approach, you make it easy for them to help you without adding significant burden to their schedule. 

Just remember, rejection is possible but it doesn't reflect your value. If one CEO declines, try approaching another potential mentor using the same thoughtful strategy. The right mentoring relationship comes down to timing, chemistry, and persistence.