The Conversations That Stick: Reflections Of A Family Business Headhunter

Over the years, I’ve sat in dozens of briefing meetings about senior hires in family businesses. On the surface, they often start the same way: a job title, a list of desired qualities, maybe a comment about wanting someone who can “hit the ground running.”

But the conversations that stick with me — the ones I find myself thinking about long afterwards — tend to come a little later, once the room relaxes and there’s permission to say what’s really on people’s minds.

Like the founder who said, quietly: “We’ve never hired outside the family before. How do we know someone else won’t just come in and try to change everything?”

Or the board member who sighed and said: “We want someone exceptional, but let’s be honest — we’re not paying at that level. How are we going to make this work?”

These are the moments where the real brief starts to emerge. Because hiring in a family business is never just about finding a set of skills — it’s about legacy, relationships, and trust.

When The Pay Question Hangs In The Air

One of the most common tensions is around what the business is prepared — or able — to pay. In many family firms, senior leaders have been with the business for years. They’ve grown alongside it. Their packages reflect loyalty, not market trends. So when the family decides to bring in new leadership — someone with external experience or specialist skills — the expectations around pay don’t always align with the reality of the market.

There’s often a moment when someone says: “I know we’re asking for a lot, but I just don’t think we can go above £X. It wouldn’t sit right with the others internally or even what the family earn.”

And that’s a fair concern. Because it’s not just about the budget — it’s about the message it sends. How will it land with the long-serving FD who’s been steadying the ship for 15 years? Or the sibling who’s been quietly underpaid for a decade?

These are sensitive conversations, but they’re essential. That’s why we often start with benchmarking — not just to understand what the market says, but to give the family a clearer sense of what’s possible, and how to approach it in a way that feels fair.

“They Must Fit” — But What Does That Really Mean?

Perhaps the most common phrase I hear is: “They’ve got to fit.” And they’re right — fit is everything. In a family business, the wrong hire can create friction fast. But when I ask, “What does fit mean to you?” — there’s often a pause.

One client said: “They just need to ‘get us’… but I’m not quite sure how to define that.”

Another said: “We’re a bit of an odd bunch — you either click with us or you don’t.”

Often, “fit” comes down to emotional intelligence. It’s about how someone listens, how they handle grey areas, whether they can build trust without demanding it. But unless that’s unpacked and defined, it becomes a moving target — and that’s not fair on the candidate or the business.

Helping families put language around this — to get clearer on what kind of leader will thrive in their environment — is a big part of the value we try to bring.

When Not Everyone Agrees

In many cases, the family isn’t fully aligned on what they want — and that’s OK. One sees the role as strategic, another wants someone who’ll stay close to the detail. One thinks it’s time to hand over more responsibility, another isn’t quite ready to let go.

As one founder put it, in a moment of real honesty: “I want to step back a bit… but not totally. I still want to be involved.”

It’s a completely understandable position — but if that isn’t clear from the outset, it can lead to confusion and frustration later on. Is the new person there to lead? Or to support? Are they expected to take charge, or to defer?

These differences aren’t a problem — unless they’re left unspoken. That’s why one of the most powerful questions we ask early on is: “What will success look like 12 months after this person joins?”

It’s amazing how often that opens up something new. Not just about the role, but about the business more broadly. Sometimes, it even leads to a rethink of what they’re hiring for in the first place.

This Is Where The Real Work Begins

At TWYD, we’ve learned that the real value in any senior appointment lies in the conversations before the search begins. We take time to understand the personalities, the history, the points of tension, and the ambitions that don’t always get said out loud. We ask the questions that create clarity — about role design, expectations, pay, fit, and family alignment.

Sometimes, we help shape the role. Sometimes, we suggest a Viability Assessment before diving into recruitment. And sometimes, we say: “Not yet. There’s a bigger conversation to have first.”

Why It Matters

The right hire can be a turning point for a family business. But only if the process is thoughtful, honest, and grounded in a shared understanding of what’s needed — and what’s possible.

That’s why the conversations that stick — the ones about identity, trust, culture and care — are the ones that matter most.

They’re where the real work begins.

And they’re why I do what I do.

About the author - David Twiddle is the Managing Partner of TWYD & Co, a leadership advisory firm working exclusively with family businesses and family offices. With over 30 years’ experience in executive search and leadership advisory, David brings a commercial mindset, a calm, considered approach, and a deep understanding of the unique dynamics at play in family enterprises. He works closely with clients to make confident leadership decisions — whether that’s planning succession, hiring a non-family executive, or building alignment at board level.