If you own a family business, take a minute with this question. What do you think each person in your family believes will happen to the business when you step back?
Most owners haven’t looked at it that way. They’ve been carrying the transition privately, waiting until they have something solid enough to share. In the meantime, the people around them have been filling in the gaps on their own, and those private versions rarely agree. That disconnect is where a lot of family business tension about succession quietly begins, long before any formal planning gets underway.
I talk about this in a short video, The Story Your Family Tells Themselves When You Say Nothing.
What each person in the family is assuming
The stories differ from family to family, though certain ones come up again and again. A son or daughter who works outside the company believes that because it’s the family business, some of the ownership will naturally come their way. A sibling who has spent years inside the business has no interest in growing wealth for brothers and sisters who never put in the hours. Underneath many of these sits a quieter worry about what would happen to the business if something happened to mom or dad.
Each of those stories carries either a hope or a fear. When nobody checks them against one another, a family can end up with as many succession plans as it has members.
We once worked with a family of four in which the father and daughter ran the company together, while the son and mother were both outside the business. During their Transition Roadmap work, the son told us he had been interested in joining for a long time. He knew he’d always be welcome to a job, but he couldn’t see where he’d fit, and he didn’t want to step on his sister’s toes. From where he stood, his dad and sister were doing well together, so he kept his interest to himself.
Nobody in that family had done anything wrong. The topic simply hadn’t come up, and he had filled in the answer on his own.
Why silence makes a family business transition harder
Owners often stay quiet because they don’t want to stir anything up before they have answers, and I understand that instinct. The difficulty is that silence leaves space, and people fill it. Some family members start to feel left out. Others wonder whether they’re even allowed to ask.
Over time those stories harden. A thought like “I might be interested, but I don’t want to rock the boat” can turn, ten years later, into regret about never saying anything, along with sadness and distance between people who care about each other.
By the time succession finally comes up, the family has years of assumptions to work through first. When families come into our work carrying stories that have turned into hurt or conflict, we begin by gently undoing them. Planning can’t start until that’s done, and the whole family business transition takes longer as a result.
Start the conversation before you have a plan
You can begin talking long before you have answers. These early conversations tend to go better when you haven’t figured it all out, because their purpose is to understand what you want alongside what everyone else wants. That’s much easier while the plan is still open.
Many owners carry the whole weight of family business succession planning by themselves. When they do, they end up making decisions about other people’s lives without including those people. The family members and key employees who will carry the business forward need to say yes to something they want for themselves, and they can only do that if they’ve had a hand in shaping it. This is one of the most overlooked parts of succession planning for business owners.
It’s also the heart of what I call a win-win-win. The transitioner gets to watch the business continue with successors who are thriving, and the successor feels good about having bought in, whether with money or with commitment and energy. The third win belongs to the business itself, which has to stay healthy for everyone in the family who depends on it. I think of it as the goose that keeps laying the golden eggs.
Not everyone gets everything they want in a transition. A family can still carry the legacy of the business and its own harmony forward together.
A word to successors
If you’re a successor holding a story about your role or timeline that nobody has confirmed, I’d guess it’s costing you some anxiety. My encouragement is to ask.
I won’t pretend that’s easy. An owner can feel pushed when the subject comes up, and a successor who raises it can be seen as entitled or wanting too much too soon. That’s why your tone matters so much. Come to the conversation with humility and genuine interest in your parent’s perspective. Questions like “Do you think I could take this on?” or “Do you think this would be good for our family?” invite an honest answer without pressing for a decision.
If raising it on your own feels too risky, a facilitated conversation can help. Having a neutral person present gives everyone permission to put things on the table they might otherwise hold back.
Bringing everyone into one story
Every owner facing a business transition makes a choice about how to handle it. You can carry it on your own, or you can bring the people around you into the process. Including others can feel terrifying at first. As you wade in, I think you’ll find it’s one of the most energizing things you can do.
When an entire family is excited about one shared story and working in the same direction to make it happen, it’s an incredible feeling to be part of.
Laura Chiesman and I wrote It’s A Journey for families who want to keep both their business and their relationships intact through a transition. The Second Edition is out now.
If your family is ready to start these conversations, our team at The Transition Strategists would love to help. You can schedule time with us at transitionstrategists.com/discovery.
