“Call me when you’re serious.”
That’s what some next gens are essentially saying when they leave the family business.
And I get it.
In a recent podcast conversation with Meghan Lynch from Six-Point Strategy, we talked about something we both see all the time: next gens begging for a roadmap. They’re not leaving because they lack opportunity. They’re leaving because they lack clarity.
As Meghan put it: “I’ve seen next gens leave the family business because that’s not available to them. They just don’t see a path. So it’s like, hey, I have other opportunities. I’m gonna go.”
Why Do Next Gens Need More Than Just Opportunity?
Because opportunity without clarity is paralyzing.
Next gens are making life decisions—where to live, whether to pursue other careers, how to plan their futures—on almost no concrete information. They’re turning down job offers and putting major life decisions on hold, all waiting for a “someday” that never gets defined.
The gift isn’t just the opportunity to join or lead the family business. The gift is clarity about when and how that will happen.
I learned this watching my dad exit his technology business when I was in college. Seeing him go through that evolution—moving from founder and operator to exiting that role—taught me how important that clarity is for everyone involved.
What Does a Succession Roadmap Actually Look Like?
A succession roadmap is a co-created timeline that maps out the many transitions that will happen over 3-7 years. It answers: what will change, when will it change, and what needs to happen to prepare.
When my business partner Elizabeth Ledoux invited me to join the firm as her successor, we built a five to seven year roadmap together. Here’s what it included:
Clear milestones: I know by the beginning of 2028, I need to understand all the financials because that’s when Elizabeth steps out of that role.
Learning timelines: What do I need to learn by when to actually be able to take on each responsibility?
Flexibility to adjust: When I got pregnant after trying for a couple years, we adjusted the timeline. The roadmap gave us flexibility to pivot because we had clarity on the bigger picture.
That roadmap let me say yes with confidence.
Is Succession Planning One Event or Multiple Transitions?
Succession is multiple transitions over time, not one single event.
Most transitions involve at least three distinct types of changes:
Role transitions – When specific responsibilities transfer (operations, sales, client relationships, financials)
Strategic decision-making transitions – When the next gen gets a real voice in business direction
Equity transitions – When ownership actually transfers
These don’t all happen at once. And they shouldn’t.
For most of our clients, these transitions happen over three to seven years. You might transfer operational roles years before you transfer equity. Or someone might be making strategic decisions before they own any of the business.
Breaking it into multiple wins makes the journey manageable for everyone.
What Happens When There’s No Clear Succession Plan?
Without a roadmap, next gens eventually leave.
They spend years in limbo—waiting for “maybe someday” while making major life decisions with no information. They turn down job offers. They stay in cities they didn’t love. They put off starting families or buying homes.
And eventually, they stop waiting. They take other opportunities where the path forward is clear.
As Megan said: “They just don’t see a path. So it’s like, hey, I have other opportunities. I’m gonna go.”
The business loses talented leaders. The family loses connection. And everyone wonders what went wrong—when the real issue was lack of clarity from the start.
Should You Start Succession Planning with Money or Objectives?
Start with objectives, not money.
Most succession planning jumps straight to: How much money do I need to retire? What’s the tax strategy? What legal structures do we need?
But we start with what everyone actually wants. We ask every member of the family: What do you want for yourself? Your spouse? Your business? Your employees? Your family?
Because sometimes there are leadership aspirations a next gen will have, and people just don’t talk about those things that are important to them.
For example, Elizabeth and I had objectives in opposition. She wanted to remain majority owner until she was officially transacting out. I wanted to be an equal partner sooner.
That led to a very rich discussion. For her, the financial security of maintaining control made it a deal breaker. It wasn’t for me.
But we talked it out, so I didn’t come in with resentment.
Starting with objectives ensures the legal and financial structures you build actually support what matters to everyone—not just what’s most tax-efficient on paper.
Why Is Succession Planning More Urgent for Next Gens Than Owners?
Because the current and next generations are operating on completely different timelines.
The current generation might be thinking, “We’ve got time. I’m not ready to retire yet.”
But the next generation is thinking, “I need to know now so I can plan my life.”
Next gens have career decisions to make, families to start, homes to buy, and opportunities to accept or decline. Every year without clarity is another year of their life on hold.
What a gift it is to offer that clarity. Because it gives people space to say, yes, I’m in. Yes, I’m out. And then at least we all know.
No one’s stuck in this space of, “Well, maybe it’s gonna happen someday, but we haven’t actually talked about it yet.”
How Do You Start Creating a Succession Roadmap?
You don’t need all the answers today. Start with these four questions:
What are your objectives? Not just financially—what do you actually want for your life, your family, your business?
What are your next gen’s objectives? Have you actually asked them? What’s a deal-breaker for them?
What does “success” look like? For you, for them, for the business, for the family staying together?
What are the many wins along the way? What role transitions could happen in the next year? What decisions could they start being part of?
Start there. Have those conversations. Co-create the roadmap together.
You don’t need to know exactly when you’re retiring or exactly how equity will transfer. But you can start mapping the journey.
Because at the end of the day, your next generation can’t plan their lives without knowing the plan.
And “call me when you’re serious” is not the message you want them walking away with.
Want Help Building Your Roadmap?
Join our free workshop: How to Hand Over Your Family Business Without Destroying Your Relationships
In 60 minutes, you’ll learn:
- The “First Conversation” Framework to start planning without creating family tension
- The 3-Timeline Method for mapping transitions over 3-7 years
- How to turn succession into multiple wins (not one scary leap)
Upcoming Live Sessions:
- October 27 – 1:00 pm MT
- October 28 – 9:00 am MT
Andrea Carpenter is the President of The Transition Strategists and host of Your Next Gen Friend, where she helps rising generation leaders in family businesses navigate succession with authenticity and purpose.
