The Candidate Who Looked Right
There is a particular moment that comes up surprisingly often in conversations about senior appointments.
The founder has met someone they like. The CV is strong, the references are good, the experience appears relevant and the candidate has held roles that, at first glance, seem to prepare them for almost everything the business needs. There is a sense that the search has finally produced the person everyone was hoping to find.
Then, usually quite quietly, someone says something along the lines of, “I just don’t know whether they are right for us.”
It is an interesting phrase because it rarely means that anything obvious is wrong. The candidate may be entirely capable of doing the job. They may have more experience than anyone else in the process. They may have worked in larger businesses, managed greater numbers of people and dealt with considerably more complicated commercial situations.
And yet something is not quite sitting comfortably.
The candidate has not suddenly become less capable. The conditions have changed.
Equally, someone who has spent their career in entrepreneurial businesses can find themselves frustrated by a family that wants more governance, more accountability and greater discipline. They may regard some of the family’s involvement as interference when, from the family’s perspective, it is part of responsible ownership.
Both sides can be behaving rationally from where they are standing.
That is what makes these appointments so difficult.
The person behind the appointment
There is another part of the process which is easily overlooked because it is harder to articulate.
The business is often recruiting for what it needs next while the founder is still carrying a strong memory of what worked before.
A founder might say they need someone who will challenge them. They may genuinely mean it. But when that challenge arrives, particularly on an issue that matters personally, it can feel very different from the idea of wanting constructive challenge discussed during the search.
Similarly, a family may say it wants an independent leader who will professionalise the business. Yet when that leader starts questioning long-standing practices, changing people who have been with the family for years or asking difficult questions about capital allocation, the emotional reality of the appointment can become considerably more complicated.
None of this means that founders or families are being unreasonable.
There is a history behind these businesses that an outsider cannot acquire simply by reading the annual accounts or spending a few hours with the leadership team. Decisions made twenty years ago can still influence today’s relationships. Employees may have deep personal loyalty to the family. A particular site, product or division may mean considerably more to the owners than its financial contribution would suggest.
The incoming executive is therefore entering an existing system of relationships, loyalties and expectations.
The question is not simply whether they can perform the role. It is whether they can perform the role in this particular environment, with these particular people, at this particular point in the company’s history.
That is a much harder question.
It is also why two candidates with almost identical experience can create very different reactions around a board table.
One may have the ability to walk into the business and understand its character quickly. They know when to challenge, when to listen and when something that looks like a commercial disagreement is actually about something deeper.
The other may be equally talented but arrive with a very strong view of how things should be done, based on environments where that approach has served them well.
Sometimes the second candidate is the one who looks stronger during the formal process.
That does not necessarily make them the better appointment.
The hardest part of a senior appointment is often not establishing what someone can do, but understanding how they will do it with the people who already matter.
This becomes particularly important when a business is appointing someone to take pressure away from the founder.
It sounds straightforward. The founder wants to step back, the business needs greater leadership capacity and a new executive is brought in to take responsibility.
But stepping back is rarely a single decision.
Founders can want succession and continuity at the same time. They can want someone to take charge while still wanting to remain close to the decisions. They can want the business to become less dependent on them while finding it difficult to watch someone make decisions differently.
Again, this is not a criticism. It is simply what ownership can feel like after many years of personal involvement.
A candidate who understands this is likely to behave differently from one who sees the founder’s involvement simply as an obstacle to their authority.
That distinction can determine whether an appointment develops into a genuine partnership or gradually becomes a contest over where authority sits.
I have come to think that this is one of the most difficult judgements in senior recruitment, particularly in founder-led and family businesses, because the person who looks strongest when reduced to a CV can sometimes be the person who creates the greatest uncertainty once you imagine them actually sitting around the table.
The difficulty is that the things which make someone look impressive are often much easier to see than the things which make someone work well in a particular business.
A CV tells you where somebody has been. It tells you what they have been responsible for and, to an extent, what they have achieved. It cannot easily tell you how they behave when a founder changes their mind halfway through a meeting, how they respond when a family shareholder challenges a decision they thought had already been agreed, or whether they can disagree with a strong-willed owner without making the relationship unnecessarily difficult.
Those things tend not to appear in an executive biography.
When the CV starts to tell too much
There is an understandable instinct, particularly when an appointment feels important, to look for reassurance in the candidate’s background.
A well-known company. A bigger title. A larger team. An impressive turnover figure. Perhaps experience of a business transformation that sounds remarkably similar to the challenge currently facing the organisation.
None of these things are irrelevant. In fact, they can be very useful indicators of capability. The problem begins when evidence of capability becomes confused with evidence of fit.
A family business is rarely just a business with a family attached to it.
The ownership structure affects how decisions are made, how disagreement is expressed and how trust is built. The history of the organisation is usually present in the room, even when nobody mentions it. There may be family members who have worked in the company for decades alongside executives who joined much more recently. There may be shareholders who are not involved operationally but whose views carry considerable weight. There may be a founder who has spent thirty years making decisions instinctively and now wants someone else to take greater responsibility without quite being ready to relinquish control.
An incoming leader can understand all of this intellectually and still struggle with it in practice.
That is why some appointments become difficult in ways that nobody predicted during the search.
The candidate was not necessarily wrong. The business was not necessarily wrong either. What had been missed was the relationship between the two.
A strong candidate can still be the wrong appointment when the context in which they have succeeded is fundamentally different from the one they are entering.
I have seen situations where a candidate’s previous success has actually become part of the problem.
Someone who has spent fifteen years in a highly structured corporate environment may have become exceptionally good at operating within clear authority, defined governance and established reporting lines. They may be accustomed to a board that challenges management in one way, shareholders in another and executives in another.
Then they arrive in a family business where the chairman is also the founder, where a family member who is not formally involved in the business still has an influential voice, and where decisions that appear operational can have a personal or historical dimension.
What is really being appointed?
Perhaps the most revealing conversations in a senior search are not always the ones about the candidate.
They are the conversations about what the business is actually asking another person to take on.
Sometimes the advertised role sounds like a Managing Director, but what the family really needs is someone who can create confidence that the business can operate successfully without the founder being involved in every important decision.
Sometimes the requirement appears to be for a transformational leader, when the underlying need is someone who will bring consistency and discipline without destroying the character that made the company successful.
And sometimes a family says it wants a particular type of executive because that is what it believes a modern business should have, when the real question is whether the owners themselves are ready for the consequences of appointing that person.
These are not recruitment problems in the conventional sense.
They are questions about the relationship between ownership, leadership and the future of the business.
This is where a candidate who looks slightly less impressive on paper can sometimes become much more interesting.
They may not have worked for the largest organisation. They may not have managed the biggest team. They may not have the most recognisable corporate names on their CV.
But perhaps they have spent ten years working alongside an entrepreneurial owner. Perhaps they have taken responsibility gradually rather than inheriting authority. Perhaps they have experienced disagreement without allowing it to become personal. Perhaps they understand that a family business can require a different form of leadership because the consequences of decisions extend beyond the management team.
Those qualities can be difficult to score.
They are also difficult to manufacture.
The danger in recruitment is that the things which are easiest to compare become the things that receive the most attention. Experience becomes a proxy for suitability. Seniority becomes a proxy for authority. Achievement becomes a proxy for judgement.
Yet senior leadership is rarely that simple.
The person who has done the biggest job may not necessarily be the person who can do this job. The person with the most impressive history may not necessarily be the person who can build trust with the people who own the business. And the person who gives the most confident interview may not necessarily be the person who will be most comfortable when the certainty of the interview room disappears.
That is often when the real appointment begins.
Not when the contract is signed, but when the candidate encounters the first disagreement that cannot be resolved by reference to a job description.
A founder wants one thing. A board member wants another. A family shareholder raises an unexpected concern. A long-serving employee reacts badly to a decision. The new leader has to decide whether to press ahead, slow down, listen, challenge or compromise.
Those moments reveal rather more than a polished career history.
They reveal judgement.
And judgement is deeply contextual.
For founders and families considering a senior appointment, perhaps the most useful question is therefore not simply whether a candidate has done the job before. It is whether they understand the particular circumstances in which they are now being asked to do it.
There is a temptation to believe that the right appointment will remove uncertainty.
In reality, the right person may simply be someone whose way of dealing with uncertainty is compatible with the business, the family and the stage it has reached.
That is a less tidy proposition than choosing the strongest CV. It is also closer to what actually happens once the recruitment process is over.
Because ultimately, a senior appointment is not made between a business and a CV.
It is made between people.
And in a family business, those relationships carry a history that no CV can fully describe.
About the author
Oliver Denton is an Associate Partner at TWYD & Co, working with founders and family businesses on senior leadership and executive appointments. His work often involves looking beyond conventional measures of experience to understand the individual circumstances in which a leader will actually be expected to operate.