Real Questions from CEOs in our Masterminds

Start with questions, not answers. As Don's friend advised: 'With the right questions, the facts become clear, and solutions will jump out at you.'

Have you ever wondered what keeps successful CEOs up at night when they think about succession planning? Working closely with our Succession Planning for Impact mastermind groups, we have the privilege of hearing the raw, unfiltered questions that emerge when leaders get serious about their legacy.

Want to hear some of them?

What Happens If I Don’t Show Up?

Don, a 69-year-old business owner, recently posed this challenging question to our mastermind group: “If I didn’t show up to lead the business tomorrow, would the doors soon close?” This sparked a crucial discussion about self-awareness, leading to more probing questions:

• “What do I actually DO versus what I think I do?”

• “How do people act when I’m present versus absent?”

• “What decisions never get made without me?”

John Maxwell reminds us, “Real leadership is demonstrated when you are not around.” Yet, as one mastermind member confessed, “Most CEOs aren’t self-aware enough to accept how things really work in their absence.”

Speaking the Same Language

Clark, one of our most proactive members, buys our “Succession Planning for Impact” book by the case and distributes it to his entire team.

Why? Because he recognizes a critical issue: “Are we all speaking the same language about succession?”

This leads to essential questions:

• “Is the founder speaking the same language as the team?”

• “Are we having conversations that actually lead to succession decisions?”

• “Are we all thinking toward the same end goal?”

The “Last Day” Exercise

One of our most powerful discussions started with this scenario: “What if today was your last day in the office?”

1. What urgent conversations would you have?

2. What decisions would you make immediately?

3. How would your succession plan change?

   
   

The Lifestyle Questions

Real CEOs in our mastermind are asking practical questions about their future:

• “What lifestyle do I desire post-transition?”

• “Where do I want to live?”

• “How much capital do I have versus how much I need?”

• “What’s my real appetite for debt?”

Measuring Progress Differently

A breakthrough insight from our mastermind: Stop looking at the gap ahead and start measuring backward. All you can see is your shortfall when looking ahead, but looking backward shows how far you’ve come.

This leads to an important point: comparison is the thief of joy. Instead of comparing yourself to an ideal future state, measure progress from where you started.

Starting the Conversation

Thomas, who spent five years selecting and developing his successor, now manages his family foundation and serves as his successor’s greatest encourager. His journey began with one conversation.

Ready to Start Your Succession Planning Journey?

Begin with these steps:

1. Join one of our Succession Planning for Impact masterminds where leaders tackle these questions together

2. Start the seven conversations outlined in our book, Succession Planning For Impact

3. Create your own “last day” scenario plan

   
   

Don’t wait until it’s too late. As one of our mastermind members says, “Each day ask yourself: if I’m not here tomorrow, how will the business continue?”

Want to join other leaders asking these crucial and real questions? Email Sunshine@cultivatingimpact.bizwith “Mastermind” in the subject line.

Remember, succession planning begins with strategic conversations. During these conversations, answers will begin to surface. The question is: are you ready to start the conversation?

In your corner!

Harry T. Jones