There is a particular moment I have come to recognise in family businesses. Everyone around the table is talking about the need for a new CEO, and everyone appears to agree about what the business needs. Then, usually some way into the conversation, it becomes clear that they are not actually looking for the same person.
The family may be talking about growth, professionalisation and the next stage of the business. The outgoing founder may be talking about someone who understands how things have always been done. The board may want stronger challenge and accountability. Meanwhile, the CEO they eventually appoint discovers that the family’s idea of “the next stage” means something rather different from theirs.
None of this is particularly unusual. It is one of the more difficult realities of appointing leadership into a family-owned business.
The appointment is rarely just an appointment
The instinctive response is often to look outside and find the right person. A search begins, candidates are interviewed and experience is carefully considered. There is nothing wrong with that process, but it can disguise the more important question sitting underneath it.
What, exactly, does the family want this person to do?
That sounds straightforward until the answer is tested properly.
One family member may want the business to become less dependent on the family. Another may be deeply uncomfortable with that prospect. One shareholder may want significant investment and expansion. Another may value dividends and stability. Someone may talk enthusiastically about professionalising the management team while still expecting the CEO to check important decisions with the family.
The candidate is therefore being appointed into a set of expectations that may never have been fully discussed.
The difficult part is often not finding a capable CEO. It is discovering whether everyone means the same thing when they say they want change.
I have seen situations where a candidate looks excellent on paper and performs strongly throughout the selection process, only for the appointment to become difficult because the family and the individual have fundamentally different ideas about the job.
The CEO thinks they have been brought in to lead. The family thinks they have been brought in to help them implement a direction they have already decided upon.
That difference can become uncomfortable very quickly.
What the family is really asking for
Family businesses have a history, and that history matters. A founder may have spent decades building something from very little. Family members may have grown up with the business around them. Employees may have worked there for twenty or thirty years.
A new CEO is therefore not simply taking responsibility for a company. They are stepping into something that carries emotional and personal meaning for people who own it.
That does not mean the family is unwilling to change. Often, quite the opposite. Families can be remarkably ambitious about what comes next. The difficulty is that ambition can coexist with a strong attachment to what came before.
This is where appointments can become confused.
The family may say it wants an experienced external CEO because it needs someone who will challenge the business. But when that challenge arrives, it can feel very different from how it sounded during the recruitment process.
The CEO may conclude that their job is to make difficult decisions. The family may discover that some of those decisions touch things they never regarded as negotiable.
Neither side necessarily behaves badly. Both may simply be operating from a different understanding of what was agreed.
The conversation before the search
The strongest leadership appointments I have seen tend to have something in common: the difficult conversations happened before the appointment, rather than being left for the new CEO to discover.
That does not mean everyone has to agree. In fact, complete agreement may be unrealistic. What matters is that the disagreements are visible.
A family can want growth while still wanting control. It can want a CEO with independence while remaining closely involved. It can want professional management without wanting the character of the business to disappear.
Those tensions are not necessarily problems. They are part of the reality of family ownership.
The problem comes when they are hidden behind a job description.
A CEO cannot resolve an ownership disagreement simply by being a better CEO.
For founders and families considering a leadership appointment, the most revealing conversations are often not about the candidate at all. They are about what the owners expect the business to become, what they are prepared to let go of, and where they are not prepared to compromise.
That is the territory in which the eventual CEO will have to operate.
The best appointment is not always the person with the most impressive track record. It is the person whose understanding of the role genuinely matches the reality of the ownership.
And sometimes the most important thing a family can discover during a CEO search is that the disagreement is not about the candidate.
It is about them.
About the author
Oliver Denton is Associate Partner at TWYD & Co, working closely with founders, family businesses and Founder-led businesses on leadership appointments and the decisions that surround them. His work often sits at the point where ownership, leadership and the future direction of a business meet. He brings particular interest to the human realities behind senior appointments, especially where expectations are not quite as aligned as they first appear.