There is usually a moment in a succession conversation when somebody says, almost casually, “We just need to find the right person.”
It is an understandable place to arrive. A founder is thinking about stepping back, the business has reached a point where the existing leadership arrangements no longer feel quite right, or a family has begun to recognise that the next generation may not be ready, willing or suitable to take on the chief executive role. The instinct is to think about the appointment. Who could do it? Where might they come from? What sort of experience should they have?
The conversation can become very quickly about people.
Yet, after enough conversations with founders and families, I have become increasingly conscious that succession is rarely one thing. The appointment of a new leader may be the most visible part of it, but it is often only one part of a much larger change taking place underneath.
A founder may say they want to retire, while still wanting to know what happens every morning. A family may say that ownership should remain within the family, while accepting that the business may need an external chief executive. A second-generation family member may be entirely capable of leading the company, but may not actually want the responsibility. Another may want the role very badly, but have spent their whole career being treated as the founder’s son or daughter rather than as a leader in their own right.
All of these things can sit inside the same succession conversation.
And they do not necessarily point in the same direction.
Succession becomes difficult when everybody agrees on the word, but means something different by it.
This is one reason why apparently straightforward appointments can take considerably longer than expected. The difficulty is not always finding someone who could do the job. Sometimes the harder question is understanding what the organisation, the family and the outgoing leader are actually asking that person to do.
The person being appointed is only part of the change
In a professionally managed business, there is often a reasonably clear distinction between the individual leaving, the role they occupy and the person who will replace them. There are still emotions and practical difficulties, of course, but the boundaries are usually more defined.
Founder-led and family businesses are different because the person at the top may have been part of almost every important decision for decades. Their influence can extend far beyond their formal role. They may have relationships with customers that pre-date the current management team, know suppliers personally, retain the confidence of the bank, understand the history behind particular decisions and carry an almost instinctive sense of what does and does not feel right.
More importantly, the business may have grown around them.
That creates a particular difficulty when the conversation turns to succession. The question is not simply whether another person can perform the role. It is whether the organisation is ready for the role to be performed differently.
I have seen businesses spend considerable time defining the characteristics of a successor, only to discover that the real difficulty lies elsewhere. The founder is looking for somebody who will bring fresh thinking, but also wants them to protect everything that has been built. The family wants greater professionalisation, but remains uncomfortable with decisions being made without a family member in the room. The board wants a chief executive who will take full responsibility, while important decisions continue to find their way back to the founder.
None of these positions is necessarily unreasonable.
The difficulty is that they can be very difficult to reconcile.
There is also a tendency to assume that the next leader should somehow resemble the person who came before. This is particularly understandable where the founder has been successful. The business has grown because of their instincts, relationships and determination, and there can be an almost unconscious desire to reproduce those qualities in another person.
But the person who follows a founder is taking over a business that is no longer the business the founder originally built.
The requirements may have changed. The scale may have changed. The people may have changed. The family may have changed. Even the founder’s own relationship with the business may have changed.
That is why succession can become uncomfortable when the search for a successor begins before the family has really considered what it wants the business to become.
What does the founder actually want to leave?
This is often where the more personal part of succession emerges.
Founders can be remarkably clear about wanting the business to continue, while being less clear about what their own role should become once somebody else is running it. That is entirely understandable. A business built over thirty or forty years is rarely just an economic asset. It can be intertwined with identity, reputation, family history and a sense of personal achievement.
Stepping away from it is therefore not simply a matter of changing a job title.
There are founders who genuinely want to retire and discover that they still have strong views about the way the business should be run. There are others who say they want to remain involved but are, in reality, looking for a different kind of relationship with the company. Some want to remain close to strategic decisions. Some want to be available when asked. Some simply want reassurance that what they built is in safe hands.
The distinction matters because the incoming leader will feel it, whether or not it is ever discussed openly.
A chief executive cannot easily take full responsibility for a business while believing that the founder may overturn a decision at any moment. Equally, it is unrealistic to expect a founder to become emotionally indifferent simply because a succession plan says that they have retired.
The hardest part of succession is sometimes not deciding who should lead, but deciding what the person who has always led should become.
Family businesses add another layer because ownership and leadership do not necessarily travel together.
A family can quite reasonably decide that the shares should remain within the family while the executive leadership passes to somebody outside it. Equally, a family member may be the right person to lead the business, but that decision should not be confused with the fact that they happen to be a shareholder or potential heir.
This is where conversations about succession can become particularly delicate. The family is not only deciding who should run the business. It may also be deciding what family membership means in relation to the business.
For one generation, being part of the company may have meant working in it. For the next, it may mean being an owner without having an executive role. For another family member, it may mean having no operational involvement at all but still wanting to play a meaningful part in the future of the family enterprise.
These are very different forms of involvement.
They can coexist, but they require an understanding that ownership, leadership and family influence are not interchangeable.
The appointment reveals what was unresolved
Perhaps the most revealing part of a succession process is what begins to surface once a real candidate is being considered.
A family may have spent months discussing the future in broad terms, but a particular person has a way of making the questions tangible. Would the founder genuinely allow them to make the decisions? Would the family accept them challenging established ways of working? Would the existing management team follow them? Would the next generation see them as a leader or simply as an employee brought in by the board?
These questions can be uncomfortable because they expose things that were easier to leave unresolved.
Sometimes a candidate is rejected because they are not quite right. Sometimes the reasons given are entirely sensible. But occasionally, the further the process goes, the more apparent it becomes that the candidate is not the real problem.
The business is not yet ready for what their appointment would represent.
That can happen when an incoming chief executive would have to inherit authority that has never properly been released. It can happen when family members have different ideas about the future but have avoided discussing them. It can happen when the board has agreed that professional leadership is required but has not really considered what professional leadership will mean for the family’s role.
And sometimes it happens because the organisation has become so accustomed to one individual that it has forgotten how to operate without them at the centre.
This is why succession is often less tidy than the word suggests. There may be a planned retirement date, a board process, a shortlist and a preferred candidate, yet the most consequential part of the process may be happening in conversations that never appear on a succession timetable.
People are working out what they are prepared to give up.
They are also working out what they are not.
There is a temptation to see succession as an event: one person leaves, another arrives, and the business carries on. In reality, leadership appointments of this kind can take years to settle because authority does not always move at the same speed as the job title.
The incoming leader may need time to establish their own relationships and judgement. The outgoing founder may need time to find a different place in the life of the business. The family may need time to become comfortable with being owners rather than operators.
None of this necessarily means that anything has gone wrong.
It may simply mean that succession is doing what succession inevitably does. It is exposing the relationship between the people, the business and the ownership.
That is why the most interesting succession conversations I have been involved in are rarely just conversations about candidates.
They are conversations about what the business is becoming.
A founder who has spent decades making decisions is contemplating a future in which their judgement is no longer the final word. A family that has always understood the company through personal involvement is considering a more formal relationship with ownership. A new chief executive is being asked to bring their own authority into a business where the previous leader’s authority is still deeply present.
The appointment sits at the centre of all of this, but it cannot carry all of it.
Perhaps that is why the best succession processes do not always produce the most obvious successor. Sometimes they produce a clearer understanding of what the business actually needs from its leadership. Sometimes that means a family member. Sometimes it means an external appointment. Sometimes it means recognising that the timing is not yet right.
And sometimes the most important outcome is simply that people begin saying aloud what they had previously assumed everyone else understood.
A successor does not simply inherit a role; they inherit everything that the previous leader has left unresolved.
There is no single version of a successful succession because there is no single thing being succeeded.
For one business, it may principally be about leadership. For another, ownership. For another, the founder’s identity within the company. In a family business, all three can be intertwined, along with questions of legacy, family expectations and the future relationship between generations.
The mistake is perhaps not in thinking about succession as an appointment. The appointment matters enormously. The mistake is in believing that making the appointment completes the succession.
It rarely does.
The new leader still has to become the leader. The founder still has to discover what their next relationship with the business looks like. The family still has to decide what it means to own something they may no longer run.
Those things take time, and they cannot always be settled in a board paper.
The older I get, the more I think that succession is less about replacing one person with another and more about allowing a business to change its relationship with the people who have carried it this far.
That is a more complicated undertaking than appointing a chief executive.
It is also where the real succession begins.
About the author
Oliver Denton is an Associate Partner at TWYD, where he works with founders, family businesses and family offices on leadership, succession and the appointments that can have a lasting effect on an organisation. Much of his work involves understanding what sits behind an appointment, particularly where family, ownership, and executive responsibility intersect.