It was a passing comment at the end of a meeting that stayed with me.
“We’ve had more applicants than ever for our graduate roles,” the founder said. “Hundreds of them. Good people too. But ask me where I’m finding my next Managing Director, and I honestly couldn’t tell you.”
It wasn’t frustration so much as disbelief. The business had continued to grow, the brand was respected, people wanted to work there, and yet one appointment seemed permanently just beyond reach. As the conversation continued, it became clear this wasn’t really about recruitment. It was about something much harder to define.
Over the past year, I’ve heard versions of that conversation time and again. Family businesses rarely struggle to attract talented people at the beginning of their careers. Apprenticeships fill quickly. Graduate schemes are oversubscribed. Operational and technical roles often receive a healthy response. Young people still see something appealing in businesses where decisions feel closer to the work, where people know each other, and where careers appear less anonymous than they might inside a large corporate.
The difficulty begins further up the organisation.
Finding experienced leaders who genuinely want to build the next chapter of a family business has become noticeably harder. Not impossible, but harder than many founders remember. Lengthy searches are becoming commonplace, appointments take months longer than expected, and more processes conclude without anyone being appointed at all.
At first glance, this can feel surprising. Many family businesses are performing well. They have stable ownership, clear identities and long-term thinking that many larger organisations would envy. Yet those strengths do not always translate into an obvious attraction for experienced executives.
Sometimes the explanation is put down to a shortage of talent. Sometimes it is blamed on changing expectations around remuneration or flexible working. Those things may play a part, but they rarely explain the whole picture. The more conversations I have with founders and senior candidates, the more it feels as though they are often looking at the same opportunity through entirely different lenses.
Looking Beyond the CV
Experienced leaders have far more choice than they once did.
Many have already built successful careers in listed companies, private equity-backed businesses or international groups. They are selective, not simply because of financial considerations, but because they have become increasingly thoughtful about where they can make their best contribution. They want clarity over decision-making, confidence in governance, and an honest understanding of what success will really look like.
Family businesses often assume their reputation will answer those questions for them. From the inside, it is obvious why the business is special. The values are lived rather than written down. Relationships stretch back decades. Decisions can be made quickly because trust already exists. The family’s commitment feels reassuring rather than restrictive.
From the outside, those same characteristics can appear far less certain.
Candidates wonder where authority genuinely sits. They ask themselves whether difficult decisions will be supported when family relationships become involved. They look for evidence that the role has room to shape the future rather than simply preserve the past. None of these questions are unreasonable. In fact, the strongest candidates almost always ask them.
The best leadership appointments rarely depend on finding someone exceptional. They depend on whether an exceptional person can genuinely see where they fit.
There is another reality that founders often underestimate.
By the time someone reaches executive leadership level, they are no longer choosing only a business. They are choosing the people they will spend the next five or ten years working alongside. They are assessing trust, openness, ambition and the quality of conversation just as carefully as they assess financial performance.
That is considerably harder to communicate than a balance sheet.
Many founders tell compelling stories about where the business has come from. Fewer find it easy to describe what leadership actually feels like inside the organisation today. The distinction matters because experienced candidates are making decisions with both their heads and their instincts.
The Weight of Continuity
Family businesses are unusual places because continuity carries enormous value.
People remain for decades. Customers often become friends. Suppliers become trusted advisers. The business develops a collective memory that extends well beyond individual careers. Those qualities create resilience that is difficult to manufacture elsewhere.
Yet continuity also creates expectations that are rarely written down.
Incoming leaders are expected to respect traditions they had no part in creating. They inherit relationships built over generations. They are asked to introduce fresh thinking while recognising that some decisions have emotional as well as commercial consequences. They must earn credibility with people whose loyalty has often been built over many years.
None of this appears on a job description.
The result is that recruitment processes sometimes become exercises in searching for certainty. Every interview raises another question. Every strong candidate seems to have one perceived gap. One person has outstanding commercial experience but limited exposure to founder-led businesses. Another understands family ownership but lacks international growth experience. Another feels culturally right but perhaps isn’t transformational enough.
Eventually the conversation becomes less about who could succeed and more about who carries the least perceived risk.
Ironically, the longer the search continues, the more difficult it often becomes.
Boards become cautious. Expectations quietly rise. The description of the ideal candidate grows broader rather than sharper. Candidates sense hesitation, even if nobody says it aloud. Some withdraw because they accept other opportunities. Others begin to wonder whether the organisation is fully aligned around what it actually wants.
None of this reflects badly on the business. It simply reflects how significant these appointments have become.
Leadership searches often become difficult long before the recruitment process begins, because uncertainty has been building quietly inside the business itself.
That uncertainty is rarely about capability.
More often it concerns readiness.
Founders who have carried responsibility for decades understandably find it difficult to imagine precisely how another leader will carry it differently. Families may agree broadly on the future while holding subtly different expectations of what the next executive should protect, improve or challenge. Boards can all describe the role in similar language whilst quietly imagining different people performing it.
These differences are seldom obvious until recruitment begins.
Candidates notice them remarkably quickly.
An experienced executive does not expect complete certainty. Every organisation has complexity. Every leadership role involves ambiguity. What they are looking for is consistency. They want confidence that the people making the appointment share a common understanding of what success will actually require.
When that confidence exists, conversations become noticeably easier. Questions become more open. The relationship begins to develop naturally because both sides are exploring the opportunity rather than defending assumptions.
Perhaps that is why the businesses that make outstanding appointments often appear surprisingly calm throughout the process. They are not calmer because recruitment is easier. They are calmer because they have already had the difficult conversations internally.
The shortage of experienced leadership is real enough, but it is only part of the story. There are exceptional leaders looking for businesses where they can contribute meaningfully over the long term. Equally, there are remarkable family businesses looking for exactly those people.
The challenge lies in the distance between those two perspectives.
Bridging that distance requires more than a well-written role profile or an extensive search. It begins with understanding how the opportunity is genuinely experienced by someone who has never lived inside the business before.
That can be uncomfortable because it asks founders to see their own organisation with fresh eyes. Yet those moments of reflection often become the point at which recruitment stops feeling like a search for the perfect individual and starts becoming a conversation about the future of the business itself.
In the end, leadership appointments inside family businesses have never been purely transactional. They are invitations into something much deeper than a role. They ask someone to become part of a story that began long before they arrived and, if the appointment is successful, will continue long after both founder and executive have moved on.
That is precisely what makes these appointments so rewarding when they are right, and so difficult when they are not.
About the author
Oliver Denton is an Associate Partner at TWYD & Co, where he works with founders and family businesses on senior leadership and board appointments. His work centres on understanding the people behind the business as much as the roles they seek to fill.
Through conversations with owners, directors and leadership teams across a wide range of sectors, Oliver has seen how the most successful appointments begin long before candidates enter the process. They emerge from a shared understanding of the future the business is genuinely trying to build.