Blog

Transitioning into this role has come with a steep learning curve. I stepped into a company with history, structure, and strong principles. And that’s exactly what drew me here—because I didn’t want to start from scratch. I wanted to build on something meaningful.

That said, I’ve been in sponge mode. Absorbing what works. Questioning what could be better. Figuring out what to preserve and where to innovate. And—maybe most importantly—learning to say, “I don’t know yet, but I trust myself to figure it out.”

When I first started my business in high school, I named it “Flaming Squirrel Design.” I was seventeen, designing logos and building websites. How does this tie into what I do now as a Transition Guide helping family businesses? Well… there are lots of valuable skills I learned that have come with me into my family’s limited partnership and my role as a successor in a private firm.

That’s the thing about succession journeys—they rarely follow a straight line. And whether you’re taking over your family’s business, stepping into leadership at a company where you’ve built your career, or joining an enterprise with the intention to lead it someday, there are universal truths about the successor experience that nobody really tells you about.

Owners wonder, “How do I let go of what I’ve built?”
Successors ask, “When will I finally get to lead?”
This tension isn’t just about assets—it’s about two different realities colliding.
And until you create a timeline, both sides are stuck waiting.

Recently, during our Transition Timeline workshop, one owner put it best: “My job isn’t to lead anymore. It’s to mentor and teach them how to do it without me. It’s to help them design it for them, not me.”

You’ve built a successful business through years of dedication, vision, and hard work. Now, as you consider what comes next, one question looms larger than all others: how do you talk to your family about business succession?
If you’re like most business owners, the mere thought of initiating this conversation creates knots in your stomach. You’re not alone. According to our research, the fear of damaging family relationships is one of the top concerns that prevents owners from beginning their business transition journey.

“I thought having all the plans in place before telling my kids was the responsible thing to do,” a business owner recently shared with me. “But when I announced my succession decision, you could feel the temperature in the room drop 20 degrees. Now my daughter won’t return my calls, and my son is talking about leaving the company entirely.” This scenario plays out more frequently than you might imagine. Statistics show that only 30% of family businesses survive into the second generation, and merely 12% make it to the

“I know I need to plan my transition, but there’s always something more urgent to handle.”

I hear this from business owners almost daily. You’re managing daily operations, dealing with employees, keeping customers happy, and trying to grow your business. The thought of planning your eventual transition feels overwhelming – especially when you’re not even sure where to start.

But here’s what I’ve learned: time is your most powerful ally in creating a successful transition.

As a potential successor, one of the most challenging questions we face is: “Is this truly my dream, or am I just following someone else’s path?” As the daughter of a successful business owner and now a potential successor at The Transition Strategists, one of North America’s leading business succession consulting firms, I’ve wrestled with this question from multiple angles. Today, I want to share my journey of discovering authentic purpose in business succession, hoping it might help others facing similar questions. 

One of our favorite books by Patrick Lencioni is “The Five Dysfunctions of a Team.” (If you haven’t read it, we highly recommend it.) He’s also the author of an article in the Harvard Business Review about corporate values.  In this article, Lencioni asks readers if four values — communication, respect, integrity and excellence —resemble their own companies’ values and then drops a bombshell: These are the values of Enron, the energy company that declared bankruptcy after committing one of the biggest accounting frauds of this century.  Not surprisingly, there’s

Stepping out of and into business ownership are huge career and life transitions. Owners stepping out have reached a high level of competency and need to transfer the knowledge of what they do and how they do it to their successors. Organizing that transfer is just one reason we include a Transition Timeline™ in the Transition Roadmap documents we create for owners and their successors.  Business owners, however, don’t just step out of ownership; they also step into the next great adventure of their lives. And that transition from business