The Conversation That Never Quite Happens

Why families stall around people and leadership—and what helps move things forward

Most families don’t call us in a crisis.

They get in touch when something’s been hanging in the air for a while. Talked about. Circulated. Tension rising—but no real movement.

You know the kind of thing:

• “We’ve talked about it loads—but nothing’s actually happened.”

• “We think we need someone—but we’re not sure what for.”

• “We need to sort succession—but it’s never the right time to bring it up.”

These conversations get raised, then dropped. Everyone agrees there’s something to look at—but no one wants to push too hard. It’s rarely about strategy. It’s nearly always about people.

Who’s leading? Who’s stepping up? Who’s stepping back? What roles are needed? What decisions haven’t been made?

And most of the time, it’s not indecision—it’s lack of clarity.

A familiar example:

I worked with a family where the founder had been circling the idea of a CEO for years.

The daughter was capable, ready, and already doing much of the job. But nothing had been said out loud. The board didn’t want to interfere. The founder wasn’t quite ready to let go.

Everyone was waiting for someone else to name it. And because no one did, the conversation never quite landed.

They weren’t confused. They just hadn’t put the people and leadership piece on the table properly.

This is the moment I’m most often called in.

Not when the board is imploding. Not when someone’s walking out the door. But when something about leadership isn’t working—and no one knows how to say it.

That’s where we’re useful.

We’re not consultants. We’re not coaches. And we’re not a recruitment agency chasing roles.

We work with families to get clear on the leadership questions they’re sitting with.

What’s going on? What’s needed? What’s possible? And what’s in the way?

What helps?

Here’s what I’ve seen work again and again:

• Write it down. Once people can see the full picture in black and white, things tend to shift quickly.
  

• Ask better questions. Instead of “Should we hire someone?” try “What kind of leadership do we actually need—and why now?”
  

• Don’t rush the action. You don’t have to decide straight away. But until you’ve got clarity, you’re not deciding anything at all.

One Final Thought

Family businesses don’t stall because they don’t care. They stall because people and leadership issues are personal—and hard to untangle when you’re inside them.

But once things are out in the open—clear, calm, and properly understood—families almost always know what to do.

And that’s when the real conversation starts.

About the Author David Twiddle is the Managing Partner of TWYD & Co, a specialist executive search and leadership advisory firm working with family businesses, family offices, and founders. With decades of experience helping families make confident decisions about leadership and succession, David brings calm, clarity, and a strong instinct for people to situations where things often feel unclear. He writes regularly about the human side of family enterprise—where business, family, and leadership all come together.