I’ve asked “is my successor ready?” as an owner, and I’ve watched our own team live that question as Andrea Carpenter steps into leadership at The Transition Strategists. It’s one of the most natural things to wonder in a family business transition, and it’s the question owners bring to me more than any other. Over the years, though, I’ve noticed it tends to leave someone out. https://youtu.be/XN9ANhKvYqA Successor readiness matters, of course. The trouble is that most people ask about it in a way that only has room for one
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,
Ariel Steele works two days a week and still owns one hundred percent of her company. It took her three years to build that, and about twenty to get out of her own way. She has owned her business in Colorado for twenty one years. Her team of five now runs everything from the prospecting through the closings, work she spent most of those years believing only she could do. When she came on the Business Transition Roadmap to talk about how it happened, she did not point to the
Owners ask me this constantly, and it is almost always the ones who have already built a strong team around them. They have a tax advisor they trust, an attorney who has handled their work for twenty years, and a financial professional who knows every line of the balance sheet. So the question tends to arrive with a little hesitation, as though asking it might insult the professionals they already rely on. It never does. What is a transition strategist, or what we call a transition guide, doing that those
A private equity group came knocking on a company doing more than forty million in revenue. The owner had not gone looking for a buyer and had no particular plans to sell. The group opened his financials, spent some time with what they found, and passed. Nothing was wrong with the business. It had grown from around seven million to more than forty million in five years, which is the kind of trajectory that brings buyers to your door in the first place. The problem was the record of that
Founders rarely reach out because the numbers confuse them. They reach out because they have started to picture life on the other side of the business and the picture comes back blank. The company has a plan for almost everything. There is a plan for hiring, and a plan for the equipment that gives out in year seven. Then the owner sits down to think about their own next chapter and finds nothing to work from. Thirty years of energy went into building something, and very little of it went
Five years ago, Elizabeth Ledoux and Laura Chiesman sat down to write a book about business transition planning. They had watched too many owners arrive at the most significant decision of their working lives with no roadmap in front of them, and they wanted to put one in their hands. What neither of them fully knew at the time was how much of that roadmap they would end up walking themselves. Since the first edition, Laura has completed her second transition and Elizabeth is three years into her own. That
When a business owner sits down with me to talk about their transition, they usually come prepared. They can talk about valuation. They can walk me through who might take over and roughly when. Many of them can describe the legacy they hope to leave with genuine feeling, because they have thought about it for years. Then I ask a much smaller question. What will an ordinary Tuesday look like after the transition? I am not asking about the celebration dinner or the trip you have been promising your spouse
Many business owners delay transition planning because they believe it signals the beginning of the end. The opposite is true. A business transition strategy starts creating value the moment you begin, long before any change in ownership or leadership takes place. We call this the multiplier effect, and it shows up in five measurable ways: your people, your business value, your time, your conversations, and your decisions. This post breaks down each one, drawing on Episode 87 of The Business Transition Roadmap podcast, where Elizabeth Ledoux explains what compounds when
