I’ve worked with hundreds of business owners through business and family asset transitions, and I can usually tell in our first meeting whether someone is going to move forward. Some owners leave that conversation ready to act. Others stay stuck for another two years, or drift into what I call the five-year rolling retirement plan, where the target date slides out a little further every time someone asks.
When people ask me why business owners delay succession planning, they usually expect the answer to involve taxes or valuation. Those matter, and they come later. What separates the owners who move from the owners who stall tends to come out when I ask one question. What do you want your life to look like five years from now?
I’m asking about your life, with the business set to one side for a moment. Owners who can answer tend to move through business transition planning with surprising speed, because they have a next adventure pulling them forward. Owners who can’t often have plenty of information and capable advisors around them, and they still freeze.
Why the personal side of succession planning comes first
People rarely make big changes willingly unless they’re heading toward something they want more than what they have now. For a founder who has spent thirty or forty years building a company, the business is often the most compelling thing in their life. It has given them purpose and a daily rhythm, and for many of them it has quietly become the answer to the question of who they are. Stepping away from that with nothing on the other side feels a lot like stepping off a ledge.
That’s why so many decisive, successful owners become uncharacteristically paralyzed when transition comes up. They’re used to being the one with the plan. When the conversation shifts from what’s next for the business to what’s next for them, many don’t have a ready answer, and every decision about timing or deal structure starts to feel heavier than it is. I’ve had owners tell me they assumed they needed more data or a better advisor. Most of them came to see that the missing piece was personal, a clearer picture of who they wanted to be once they stepped back.
Succession planning for business owners has a technical side that deserves excellent attorneys and CPAs. That work goes much further once the owner knows what the documents are meant to serve.
Transition happens to you or for you
Every business transition happens eventually, whether it’s planned or not. It can happen to you, or you can let it happen for you, and that choice belongs to you. In the meantime, every month without clarity, your best people are making decisions based on what they think is going on. Many of us are baby boomers reaching this season of life, and the employees and family around us are already sketching out our transition in their own heads. I hear it constantly in some version of “Oh, she’ll never leave,” and I always want to ask how they could possibly know.
Getting clear on your next chapter is what lets you orchestrate the rest on your own terms. In family business succession planning, transition tends to happen in layers. You might step out of the CEO role well before you step back from decision-making, and the question of when ownership moves to someone you trust may come later still. When you know where you’re headed, you get to set the pace for each of those. When you don’t, the people around you fill the gaps with their own assumptions, and you end up with a transition by default.
I talk through this question in a short video, including what I see happen when owners stay stuck and how successors can help get things moving again.
When a business owner won’t let go, try a different question
This part is for successors, since many of you read these too. If the owner in your life seems stuck, or you’ve started to wonder whether they’ll ever let go, pushing harder on the timeline usually backfires. I’ve watched it play out many times. The owner feels pressured and pulls back, tension builds between you, and the whole process slows down.
If you’ve been wondering how to talk to a parent about succession, start with their future instead of the calendar. Ask what they’re excited about next, or what a good outcome would look like for them personally once the business is in other hands. Those questions tend to open a much better conversation, and sometimes they help the owner find an answer they didn’t know they had.
Emotional readiness takes time, so think in decades
I won’t pretend this question is easy. Emotional readiness for a business transition rarely arrives on schedule. I often encourage owners to think in decades, picturing life five years out, then ten, and even twenty. At 65 or 70 that can feel like looking into fog, especially when the business has been woven into your identity for most of your adult life.
The picture comes into focus gradually, with some honest reflection and usually someone asking good questions alongside you. Once it forms, it becomes a North Star you can steer by. The timing and tax conversations get easier because you finally know what they’re serving.
Transition is not an individual sport
Some founders carry transition as if the whole weight sits on their shoulders. Since you’re building what comes next for the people who will carry the business forward, it makes sense to bring them in and ask what they see. That’s the heart of what we call Transition 3.0, where both generations build the plan together.
When I started my own transition, I didn’t know who my successor would be. I began by imagining what the future could look like for me and for the company, I got excited about it, and that excitement is what sent me looking for the right person.
Where to start
If you’re considering a transition in the next three to ten years, or sooner, set the timeline aside for a while and spend some time with the question of what you want your life to look like. Clarity on your next chapter after the business makes every other decision lighter.
That personal work is where our Transition Compass begins, and it’s the first step inside Evolve, our 12-month guided transition program. If you’d like to talk through where you are on your own transition journey, you’re welcome to schedule a Discovery Call at transitionstrategists.com/discovery.
Laura Chiesman and I explore these ideas in more depth in It’s A Journey, now available in its Second Edition.
Elizabeth Ledoux is the founder of The Transition Strategists and host of The Business Transition Roadmap podcast.
