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Don, Succession Planning & The First Conversation

Updated: Jun 29, 2023


Don is 69. He started and built his business. He used up his savings in the first three years. In year four, he could pay himself a meager salary. For thirty years now, the business has made a profit and blessed his community.


Don is the heart and soul of the business. His name is on the business and his picture is on all the marketing collateral. At every major business function, he is front and center. He has achieved success.


But Don and his wife have had health issues. Both have had bouts of cancer. This influences his thinking. The reality that he won't be able to steer his business forever grows stronger in his heart daily. If he didn’t show up to lead the business tomorrow, he knows the doors would shortly close and many people’s lives would be negatively affected.


A friend who has some experience in succession planning encourages Don to start with twelve conversations with key people over the next year. These conversations will center on what it would take for his business to thrive in his absence. His friend is wise and advises Don how to make these conversations happen.


His first advice for Don is to limit the number and quality of people to have these conversations with. It is important, his friend tells him, that the meetings only involve a few select people. When he asks why, his friend’s answer provokes him.


“Don,” his friend says sternly, “the smallest minds in a room can shut down the biggest ideas.” For this reason, his friend suggests a group of three to five people. “You can invite more people in later, but dialogue will be easier with fewer voices.”


...the smallest minds in a room can shut down the biggest ideas. click to tweet

He explains how succession planning conversations are often sabotaged before they get traction because the wrong people are in the room. “This can happen when people who are tens on a leadership scale are forced to work closely with people who are fours and fives.”


“Don, let me tell you something profound. In that scenario, the tens will often defer to the fours and fives, who can then monopolize the thought process. And when people who are fours and fives monopolize the thought process, the people who are tens will tune out. This is tragic and results in unproductive conversations."


On a leadership and confidence scale, the small group should be compatible.


“You want to get a variety of viewpoints,” his friend says. “Pick some people who have already been where you want to go. Look for those who have been fruitful in their own endeavors at a scale you want to achieve. Finding those who have been involved in succession planning will be a plus,” he says.


He also advises Don to find people who ask brilliant questions. “With the right questions, the facts get clear and solutions will just jump out at you,” his friend says with a smile. “They should be people who can candidly ask hard questions and speak the truth. They should also align with the values you desire for your future leadership.”


His friend cautions Don about some people he should avoid. “Just because someone has been an ally or team member doesn’t mean they should be a part of the group.” He elaborates on involving people who are stuck in the past, have a personal agenda, or can’t perceive the values that made his business impactful.


Don’s friend has one more warning about the process: “It is inevitable, someone will get their feelings hurt; be prepared for it. This is leadership.”


It is inevitable, someone will get their feelings hurt; be prepared for it. This is leadership. click to tweet

“When you meet, don’t start with the answers Don, start with provoking questions,” he says. He then leads Don in a list of some questions to ask and begin to answer in these twelve conversations.


Conversation One

“The first conversation should help you recognize your impact. This comes from awareness, intentionality, and movement (AIM). You are more likely to hit a target you aim for.”


  • Awareness starts with clarifying what is the impact of the organization that should continue. What are the values you want to succeed the founder?

  • Intentionality has to do with actions you might take to make sure this impact continues and increases.

  • Movement has to do with structuring the business so the impact can continue to grow.


The first conversation will center around Awareness. Ask and discuss:


If this organization shuts down in ninety days, why would that be bad?

  • What would the repercussions be?

  • What would the consequences be?

  • for the employees?

  • for the vendors?

  • for the community?

  • For the owner’s children, grandchildren, and great-grandchildren?

Don’s friend encourages him to understand that just having these conversations about the business over the next year will be eye-opening. “Go as far as you can see, and when you get there, you will see further!”

Go as far as you can see, and when you get there, you will see further! click to tweet

“Next time we meet,” Don’s friend says, “I will coach you on the second conversation centered around Intentionality.”



Harry T. Jones



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