Recipe #1: Confronting Your Fears About Succession Planning (Moving from the Known to the Unknown)
- Harry T. Jones
- 12 minutes ago
- 5 min read
Part 1 of the 7-week “Recipe for Executing a Succession Plan” series
Succession planning is scary.
I know it.
You know it.
Every founder we’ve ever worked with knows it.
And here’s why: You’re moving from the known to the unknown.
You know how to run your business.
You know your customers, your team, your processes.
You know what it feels like to be the one making the decisions, solving the problems, steering the ship.
But succession planning? That’s asking you to imagine a future where you’re not in control anymore. Where someone else is making the calls. Where your business continues… without you.
And that? That’s terrifying.
But here’s what I want you to know: It’s also completely normal.
Every founder we work with struggles with this. And the ones who finish well? They’re the ones who confronted it head-on.
So today, we’re going to talk about how to do exactly that.
The Key Ingredients: Three Fears Every Founder Faces
When it comes to succession planning, there are three core fears that show up again and again.
We call them the Three Pillars of Fear:
1. Fear of Loss of Identity“If I’m not running this business, who am I?”
2. Fear That Someone Else Will Do It Better“What if my successor is more successful than I was?” Fear of someone else doing a better job.
3. Fear of Too Many Unanswered Questions“I don’t even know where to start. There’s too much
I don’t know.”
Sound familiar?
If you’re nodding your head right now, you’re not alone. These fears are universal. And the first step to confronting them is simply naming them.
Because once you name the fear, you can start to work through it.
The Measurements and Timing: What Do You Actually Want?
Here’s something Donald—one of our Breakthrough Group members—said that really stuck with me:
“You’ve got to learn what each other wants. But the starting point is learning what YOU want.”
Donald’s talking about his son, who’s now his successor. And he’s right: You can’t plan a successful transition if you don’t know what you want.
So let me ask you:
What do you want?
Not what you should want.
Not what your spouse wants or what your team expects.
What do YOU want?
How do you want your life to look in 1 year? 5 years? 10 years?
What role (if any) do you want to play in the business after you transition?
What does “finishing well” actually mean to you?
Most founders I talk to have never asked themselves these questions. They’re so busy running the business that they haven’t stopped to think about what they actually want their future to look like.
But you can’t move from the known to the unknown if you don’t know where you’re going.
Real Stories: When You Can’t Even Think 30 Days Ahead
Let me tell you about a moment that happened in one of our Breakthrough Group retreats.
We were working through a planning exercise. I asked each founder to articulate their 10-5-1 vision—where they want to be in 10 years, 5 years, and 1 year.
One person couldn’t answer.
So we simplified it. We tried the “Bus Test”: “What if you got hit by a bus tomorrow and were out for 90 days? What would need to be in place?”
Still nothing.
So we tried one more time. We asked: “What if you had to take a three-month vacation with no phone or internet, and you’re leaving in 30 days? What preparation would you need to make?”
And here’s what he said:
“I can’t even think 30 days ahead. I’m just trying to get through today.”
Friend, if that’s you—if you’re so deep in the day-to-day that you can’t even imagine 30 days from now—I get it.
And I want you to know: That’s exactly why you need to start this process.
Because if you can’t think 30 days ahead, you’re definitely not ready for what happens when life forces your hand—through health issues, burnout, or an unexpected opportunity
Action Steps: Stage Your Death (Yes, Really)
I know that sounds dramatic. But hear me out.
One of the most powerful exercises I’ve seen founders do is what I call “Staging Your Death.”
Here’s how it works:
Sit down with your spouse, your key team members, or your lawyer and ask:
“What happens if I die today?”
Who takes over?
What decisions can’t be made without you?
What falls apart?
What keeps running smoothly?
One of our members did this with his family—his wife, his son (the heir apparent), and his daughter. He said:
“I staged my death so we could all see what would happen. Not to scare anyone, but so we could make a plan NOW—while I’m still here to help.”
Another founder went to his lawyer and said, “Tell me exactly what happens if I die tomorrow.”
Both of these exercises forced them to confront their fears and start making decisions.
And that’s what I want for you.
The Founder’s Legacy Audit: 5 Questions to Identify Your Succession Gap
Okay, so here’s where the rubber meets the road.
A couple of weeks ago, I shared a simple audit to help you identify where you are in the succession planning process. Some of you responded—and thank you! Your answers were so helpful.
But if you missed it (or if you need a reminder), I’m sharing it again today.
Answer these 5 questions honestly:
1. The Vacation TestIf you were completely unreachable for 30 days, would your business be:
More profitable?
Less profitable?
In total chaos when you return?
2. The Operational Star vs. Strategic LeaderDo you have someone on your team who can make a $100,000 strategic decision without calling you first?
3. The Identity TestIf you retired tomorrow, can you name three non-business activities that would give you the same sense of purpose your company does today?
4. The Soul TestIs the secret sauce of your brand—your mission, values, and promise—documented so a new owner could replicate it without you?
5. The Baton TestDo you have a written, step-by-step timeline for your leadership handover? Or is your exit strategy: “I’ll know when it’s time”?
If you answered “no” or hesitated on more than two of these questions, you have a succession gap.
But here’s the good news: Recognizing the gap is the first step toward closing it.
Your Next Step: Take the Audit (And Let’s Talk)
Here’s what I want you to do this week:
✅ Take the Founder’s Legacy Audit (answer those 5 questions honestly)
✅ Stage your death (have the conversation with your spouse, your team, or your lawyer)
✅ Ask yourself: What do I actually want?
And if you’re ready to go deeper—if you want help working through these fears with a trusted coach and a community of founders who get it—we have two spots available in our Finishing Well Breakthrough Groups.
Because here’s the truth, friend:
You don’t have to do this alone. And you don’t have to figure it all out by yourself.
Our goal is to help 100 founders execute a succession plan and finish well. And we’re offering resources at every level:
Free: Read our emails, visit our website, follow us on LinkedIn
$10: Get the book and workbook on Kindle
Community: Join a Breakthrough Group and work through this with others
Custom: Engage Cultivating Impact one-to-one for effective succession planning. One month or years. Payment is based on the success we help you achieve.
Let nothing stop you—especially not a lack of resources.
P.S. If you can’t think 30 days ahead, start with the Bus Test. If you got hit by a bus tomorrow, what would NOT get done? That’s your starting point.
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