- Date: September 23, 2026
What Makes a Transition Strategist Different From Your Attorney and CPA
- 6 min read

I attended a workshop for business owners recently and heard many conversations about the search for successors. Several mentioned that because they couldn’t find “the right successor,” to continue their legacy, they were resigned to selling to an outside third party. When these owners explained to me why their children, business partners or longtime key employees weren’t “right,” I left these conversations wondering what ever happened to curiosity? I was tempted to ask, “Are you really open minded in your search for a business successor?” As I recall these conversations,

Believe it or not, tire alignment comes to mind when I see owners stuck between the reality of a business transition with its confusing number of options and cacophony of opinions and the ideal—a business transition that 1) meets their goals and 2) maintains their most important relationships. Mechanics align our cars’ tires so that we reach our chosen destinations safely. As Transition Strategists, we use The Transition Compass to help you reach your chosen business transition destination with your relationships intact. The Symptoms of Misalignment Perhaps you recognize one

The HBO series Succession is a dramatization of the transition of a business from one generation to the next, a morality tale about what can happen when a Generation 1 owner fails to create a coherent plan to pass a business to members of Generation 2. It has been successful with both critics and audiences, receiving nominations for 25 Emmy awards. Millions of viewers have watched the Roy family do everything wrong, destroying relationships while driving the family business to the brink of disaster. Succession planning done right may not

We’ve all heard the horror stories about family business transfers that create irreparable damage—parents estranged from children, children at war with siblings, and standoffs that endure for generations. It doesn’t have to be this way! We’ve worked with many families who have moved through business transitions and kept their relationships healthy. While every family is unique, we recommend that leaders take 4 steps to a successful family business transition. 4 Steps to a Successful Family Business Transition: The Foundation for a Successful Transition The transition of a business to an

As a longtime advisor who helps business owners craft plans to put their companies in the hands of successors, I’m often asked questions about how companies can be transitioned to their adult children. Before moving forward, I suggest that there are at least four questions to ask before passing a business to the next generation. Business transitions from one generation to the next are complicated because so much is at stake: owner’s financial and emotional wellbeing, the company’s success, and the wellbeing of the entire family. Yet the goal of

Resilience is a quality we cultivate in ourselves and try to instill in our businesses because the greatest life or business plan in the world can’t prepare us for every tough challenge or unforeseen situation. Well, the ongoing interruptions in the supply chain, the war in Ukraine, continual mutations in the COVID virus, a tight labor market, and rising rates of interest and inflation certainly check many of the tough challenges boxes. What lessons did you learn from the COVID pandemic and how have you positioned your company to meet

Owners wear many hats as they grow their businesses: rainmaker, HR manager, CEO, cheerleader, and director of finance, to name a few. Yet if they are still wearing all these hats as they move toward their business transitions and Next Adventures, that’s a problem. If you don’t cut the ties of dependency between you and your business, you face a huge obstacle on your road to a successful transition. Think for a moment: ???? Does the success of your company depend on your knowledge, skills, relationships, and experience? ???? Does

I spoke recently with the owner of a successful business whose two sons had been active in the company for the 20 or so years since they graduated from college. She told me that it was time for her to start putting the company into their hands, but just thinking about the process made her anxious. I had my suspicions about the causes of her anxiety because I work with owners every day who care deeply about their companies and their relationships. They are successful individuals, confident decision makers and

In my prior post, I wrote about how unspoken expectations, a lack of planning, and an unwillingness to ask for help doomed the transition of a successful business between generations. Today, I share with you another story about an owner who torpedoed her transition when she let her ego determine her legacy. I hope after reading this article, you’ll think about the goals for your business transition: Will it cement your legacy or stroke your ego? Janice owned a consulting company that managed medical practices. Janice ran the company for