When Selling The Family Business Becomes A Leadership Decision

It usually starts quietly - on the drive back from a board meeting, or over a drink between siblings. A question, half-joking at first: Would you ever sell? And then, just as quickly: Really? Would you actually do that?

Not because the business is in trouble. Not because there’s a buyer at the door. But because something has shifted. Energy is dipping. Alignment is harder to find. The next generation have different priorities. And everyone’s wondering what the future really looks like, they’re just not saying it out loud.

For many families, selling the business still feels like the ultimate line you don’t cross. The name’s been above the door for decades. Clients know it. People trust it. Letting it go feels like letting go of something much bigger than a company.

But what if that reluctance becomes the reason the business starts to drift?

This is the tension many families face. A deep loyalty to what came before, and a growing awareness that what comes next may need something different. Holding on feels safe, but it can quietly become the risk.

It’s not simply a financial decision. It’s not just an emotional one either. This is a question of leadership. Of whether the current generation is willing to ask the difficult questions, look clearly at the facts, and make a decision that’s considered, not delayed.

I spoke recently with the Chair of a long-established family firm. We were talking about this exact moment, and he put it well:

“Nobody wants to be remembered as the ones who sold the business. But do they really want to be remembered as the ones who missed the moment?”

He’s right. In many businesses, there’s a window - sometimes brief, sometimes a few years wide - when the business still has momentum, and the family still has options. Miss it, and the outlook changes.

The business starts to feel tired. Buyers pull back and confidence dips. Family conversations become more tense. Nothing falls apart, but progress slows and everyone senses it.

And when that happens, decision-making gets harder, not easier. There’s more pressure. More complexity, more emotional weight, - and often less value on the table.

What’s striking is that this moment rarely arrives with a single trigger. It tends to build quietly. One senior leader starts thinking about retirement. The family board meets less often, or avoids certain topics. A few promising non-family executives leave. Suddenly, what was once a confident business starts feeling cautious. And once that happens, everyone feels it.

In some cases, families respond by doubling down. They invest in new leadership, rethink the structure, and create a clear next chapter. That’s a valid path. But it still requires the same level of reflection: What are we trying to protect? What are we willing to change? What does success actually look like from here?

What matters is that the question is asked directly - and answered with care.

That’s why the conversation about a possible sale should never come as a surprise. It shouldn’t be something that catches people off guard. It should happen early, and with structure. Not because selling is always the answer. Often, it isn’t. But if the question isn’t addressed, families lose the chance to shape their own future. They react to circumstances instead of leading through them.

The families who handle this well don’t have all the answers. But they are willing to ask better questions. They take the time to understand what the business needs, what each generation wants, and what would have to be true for everyone to move forward with confidence.

They don’t assume everyone wants the same thing - or that the past automatically defines the future. They test their thinking and they listen to perspectives that feel uncomfortable. And they take the long view, even when the next step feels unclear.

They see it for what it is: a leadership call. Not a shortcut or a failure. A leadership call made in full view of the facts and with responsibility to those who came before, and those who’ll come next.

And when the decision is made, they act with clarity. Not with caution or regret.

Because the real risk isn’t getting it wrong. It’s waiting until the decision makes itself.

About the author David Twiddle is the founder of TWYD & Co, an advisory firm that supports families in business through moments of leadership change. With over 25 years' experience in executive search and leadership advisory, he works closely with owners, boards, and rising generation leaders to bring clarity to complex moments. His focus is on helping families move forward with confidence, even when the next step feels uncertain.