Succession Isn’t Just Strategy—It’s Human: How Visionary Leaders Can Transition with Intention
For many founders, succession planning feels like a legal checklist or a financial transaction. But as Andrea Carpenter, President of The Transition Strategists, explains in our latest episode of the Scale Smart ,Grow Fast podcast—it’s so much more than that. Succession is personal. It’s emotional. It’s about legacy, identity, and preparing the next generation to lead.
Preferred listening on the go? Catch the full podcast episode on Spotify and Apple Podcasts.
Why Succession Planning Starts with Self-Awareness
Andrea, a next-gen successor herself, is walking the same roadmap she guides her clients through. Her transition into leadership within Elizabeth Ledoux’s company shows firsthand how complex and meaningful internal business transitions can be. From leadership development to defining fair equity deals, the process is never as straightforward—or as quick—as many founders expect.
“The biggest surprise? Timelines. What you think will take a year can easily stretch into three or more,” Andrea shares.
Mindset Shifts Every Founder Needs
Many visionary leaders delay succession planning due to fear: fear of letting go, fear of family conflict, or simply not knowing what comes next. Andrea emphasizes that successful transitions require a clear vision of your “next adventure” as much as a plan for who will lead the business.
Common mindset shifts include:
- Redefining your role as a mentor or advisor, not just the CEO
- Decoupling your identity from your company
- Designing a legacy that supports both the business and your family
Don’t Wait Until It’s Urgent
Andrea recommends starting the process 3–5 years before your desired exit. Whether it’s an internal succession, employee buyout, or third-party sale, you need time to develop leaders, align your values, and structure a deal that’s fair, strategic, and tax-efficient.
“The sooner you start, the more options you’ll have—and the more intentional your legacy can be.”
Tools for Intentional Transition
Andrea shares two powerful tools they use at The Transition Strategists:
- The IMAP Assessment – to understand individual wiring and communication styles
- The Objectives Matrix – to clarify what’s most important to each stakeholder in the transition
These tools help families and leadership teams move from conflict and assumption to alignment and trust.
💡 Key Takeaway: Succession Is About People, Not Just Process
If you want to pass your business on without breaking what you built, the time to start planning is now. Don’t wait until it’s urgent—start having the right conversations today.
🔗 Resources & Links:
- The Transition Strategists: https://transitionstrategists.com/
- Andrea Carpenter on LinkedIn: https://www.linkedin.com/in/andreashaver/
- Get the Objectives Matrix Tool: https://transitionstrategists.com/workergenix
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Transcript
Harley Green: All right. Hey, everybody. Welcome back to the Scale Smart Grow Fast podcast. Succession isn’t just a legal or financial process. It’s a human one. In this episode, Andrea Carpenter, president of The Transition Strategists and host of Your Next Gen Friend, shares how visionary leaders can prepare for transition with intention. Drawing from her own journey as a next-gen successor, Andrea offers practical and heartfelt insights for business owners who want to plan for the future, nurture rising leaders, and build a legacy that outlives their calendar.
Andrea Carpenter: I’m good, thanks for having me, Harley.
Harley Green: Awesome. Andrea, how did you get into this line of business? It’s quite unique.
Andrea Carpenter: It is quite unique. When I left my full-time W2, I thought I was going to grow and start my own business. Long story short, there was this period of figuring out who I wanted to serve. I’m second generation in my own family. My dad built and scaled a very successful business, which he ultimately exited. When your family has some type of wealth event, for some next-gens it happens early in their life or they’re born into it, their family already has the money. In some families it happens later. Suddenly there’s this shifting of identity and questions around, “What am I doing? What is my relationship with money?” For many next-gens, there’s a tipping point where they start to think about these things.
I thought it would be great if I could serve next-gens in some capacity. I met Elizabeth Ledoux, who’s now my business partner. She has always focused on internal transitions—how to help families stay together when parents are thinking about passing the business to their kids. It’s really about the whole person, the human side of families and business. A lot of people think it’s an either-or choice: my business stays together or my family does. We’ve proven that’s not true. The process we use also helps people decide what their options are. So people start thinking about what’s important to them and what the right path looks like. I began to think about all this in the context of successors and next-gens in families making a decision to come into a business they didn’t start. It’s a very different journey.
If you’re the founder, your identity is tied to the business. But for someone coming in as a second generation, it’s different. That fit really well with my experience and my desire to help next-gens. It’s turned a bit meta now because I’m a successor in Elizabeth’s business. We’re on a five to seven-year roadmap where she will transition and sell her equity to me. We get to decide that together, now that we’re on the roadmap together.
Harley Green: I love it. You’ve lived it, experienced it, and are continuing to experience it. What has surprised you the most about transitioning from the outside in?
Andrea Carpenter: Timelines are crazy. You look at a situation and think, “This will take a year and a half, maybe two.” You imagine you’ll be ready to take over, be the greatest leader in the world—but that’s not how it works. Even selling a business to the market can take two to three years. When it’s an internal transition, the leadership development required, the understanding of the business, the relationships with vendors—there’s so much a founder does that takes time to transfer.
From when Elizabeth invited me to be a potential successor, it took about a year and a half before our first legal documents were done. Deciding the purchase price—what I can afford, what she’s willing to accept, what’s fair—takes time. Our process focuses on what’s important to the people involved. Elizabeth thought she had 10 years left before retirement. Her husband said, “I’m retiring in six or seven—can we retire together?” It’s not just your decision. Other people’s lives are involved.
In my case, I was 30 and my husband and I were thinking about starting a family. I got pregnant in the middle of the process. Life happens. When you’ve thought about succession early and know your direction, your ability to pivot and respond is much greater. You’re aligned and can have good conversations when things change.
Harley Green: Many founders might struggle with letting go. Are there certain mindset shifts you believe are essential?
Andrea Carpenter: We use the word “metamorphosis.” We talk about six areas: role shifts, power dynamics, and legacy. Maybe you transfer bookkeeping but keep business development. That’s okay. It’s not all-or-nothing. The legacy piece is big—thinking, “My business is my legacy,” then realizing, “Now my legacy is letting it live on.”
Every owner needs an idea of their next adventure. The successor also has a next adventure—the business. My next adventure is hopefully owning The Transition Strategists. Right now, I’m a partial owner. Elizabeth’s next adventure will be stepping out—maybe still doing something she enjoys. Some people want to be with family, travel, golf, or get involved in philanthropy or mentoring. If you don’t have something to move toward, you’ll never fully step out of the way. That’s true even if you’re selling. We’ve met so many people who sell and are unhappy—not because of the deal, but because they didn’t plan what comes next.
Harley Green: How can leaders start thinking about succession before it becomes urgent? And what mistakes do you see when they don’t?
Andrea Carpenter: Give yourself as much time as possible. I’m a futurist by nature. If I don’t see the big picture, I struggle with making aligned decisions. The furthest out we’ve seen someone plan is 10–15 years, especially in family business. One client’s son is joining the Marines—he may be ready in 10 years, but the founder wants to be out in five. That disconnect creates challenges.
We started asking: does he need to hire a management team to bridge the gap? Are there key hires that can maintain the business in the meantime? When family’s involved, it’s never too early to start. Even employee buyouts require deep relationship and leadership development. If you’re selling, the market changes. Start 3–5 years before approaching an investment bank or broker. Know what your business needs to be worth. What’s your number? Will the sale give you the income you need, or will you need to keep working?
A lot of people avoid this due to fear—fear that their family will push them out, that conflict will arise, that they don’t know what to do next. That fear leads to waiting. And waiting shortens your timeline and limits your options.
Harley Green: What about when founders have multiple children involved? How do you navigate the fairness factor?
Andrea Carpenter: As a second-gen myself, the best thing my parents did was keep communication open. Families that fall apart during transition usually weren’t talking to begin with. Starting a dialogue, even without having the answers, is powerful.
You might have three kids—one wants in, one doesn’t, one wants equity. Maybe they’re friends, maybe they’re not. We’ve seen families where one child works in the business, and the siblings don’t think it’s fair. If no one understands the value of the business or what it means to sell, resentment builds. A key question: is your business a family asset, or is it a business asset that family members can choose to buy into? That distinction determines how we write the transition plan.
Harley Green: Can you share a success story from a family that got it right?
Andrea Carpenter: Yes. One family came in with tension—arms crossed, unsure, not believing the process would help. Parents assumed kids wouldn’t show up. Kids assumed parents wouldn’t change.
We started with the IMAP assessment. It shows how people are wired and how they prefer to be influenced. Suddenly, they saw each other clearly—why someone hesitates, why someone pushes. They started using language like, “Your persuader is a little strong” or “Your adaptability is clashing with my planning.” It opened up a whole new way to talk.
Then we used the Objectives Matrix—each person shares what’s most important to them in the transition. The emotional shift was huge. One family passed the tissue box around the table. For many, it was the first time they’d really talked about what matters to them.
That’s when the real success happens—when families stop defending and start designing. “I want to start a nonprofit.” “I want to grow the business.” Now they can create a plan that honors both.
Harley Green: That’s incredible. For leaders ready to define their next adventure, where should they begin?
Andrea Carpenter: Start with the Objectives Matrix. It helps you think about your goals—what you want to continue doing, what’s short-term, long-term. What’s important to your spouse? Your kids? Your employees?
You can get it at transitionstrategists.com/workergenix. It’s a great tool to begin visualizing a future beyond the business. If what you want to keep doing is working—that’s fine! But this tool will show you when your work no longer supports your life goals. When that happens, it’s time to design a plan that aligns both.
Harley Green: So many great insights and takeaways, Andrea. Thank you for sharing. Where can people connect with you?
Andrea Carpenter: Find me on LinkedIn at Andrea Carpenter and follow my podcast, Your Next Gen Friend. You can also get the free Objectives Matrix at transitionstrategists.com/workergenix.
Harley Green: Amazing. Thanks again, Andrea. If you found value in this episode, be sure to like, subscribe, and share it with a fellow business owner who needs to hear it. See you on the next one!