It often starts with a sense of alignment.
There is agreement that something needs to change, that the business has reached a point where additional leadership is required, and that bringing someone in from outside is the right next step. The conversations feel constructive, the intent is there, and on the surface it appears that everyone is moving in the same direction.
That is usually how it is described at the outset.
“We all agree we need this role.”
And in many ways, that is true.
What becomes clearer, though, as the conversation deepens, is that the agreement rarely extends much further than that.
Everyone agrees on the need for the hire. Alignment tends to stop there.
Spend a little more time with the different stakeholders, and the picture begins to shift. The role starts to take on slightly different meanings depending on who is describing it. The founder may be looking for someone they trust, someone who can work closely alongside them and take on responsibility without disrupting how things have always been done. A board member may be thinking more about structure, governance, and the need for challenge. A senior executive might be hoping for additional capacity, someone who can share the load and ease the pressure on an already stretched team.
Each of these perspectives makes sense in isolation.
Taken together, they create something less clear.
A role carrying too much weight
The difficulty is not that these views exist, but that they are rarely brought together properly before the process begins. They tend to sit alongside one another, untested and often unspoken, shaping expectations in ways that only become visible later.
At that point, the role starts to carry more than it realistically can.
It is expected to solve multiple problems at once, some of which are not entirely compatible. The brief becomes a blend of different priorities rather than a clear expression of what the business most needs, and the search begins with a sense that the right person will somehow reconcile those differences.
From the outside, the process can appear straightforward. There is a defined role, a set of stakeholders, and a shared intention to make a strong appointment. From the inside, the experience is often less certain. Conversations move, subtly, depending on who is in the room. What feels like a clear direction one week becomes less so the next. Candidates are discussed in different terms, sometimes positively by one person and less so by another, without it being entirely obvious why.
None of this tends to be deliberate.
It is simply the result of different people solving for different things.
The role becomes a compromise between perspectives, rather than a clear definition of need.
This is particularly common in founder-led and family businesses, where leadership decisions sit at the intersection of multiple interests. There is the business itself, with its operational and strategic requirements. There are the individuals running it day to day, each with their own pressures and priorities. And, in many cases, there is a family perspective, which brings its own considerations around continuity, stability and trust.
Those layers are part of what makes these businesses work.
They also make alignment more complex.
Because what looks like a single decision from the outside is often carrying several different expectations beneath the surface. The hire is not just about capability, but about how authority will be shared, how decisions will be made, and how the business will feel as it continues to grow.
When those expectations are not fully aligned, they tend to show up in the process itself.
The brief evolves as conversations progress. Feedback on candidates becomes less consistent. Decisions take longer than expected, not because people are being difficult, but because they are applying different criteria, often without realising it.
In some cases, the search becomes an attempt to find someone who can satisfy everyone.
That is rarely a realistic outcome.
There is also something else at play, which is less visible but just as important.
A natural desire to maintain consensus.
In many of these situations, there is an instinct to keep everyone aligned by finding a middle ground. To define the role in a way that incorporates each perspective, rather than forcing a more explicit conversation about priorities and trade-offs. It feels constructive in the moment, but it often leads to a brief that lacks clarity.
The result is not disagreement, but ambiguity.
And ambiguity at this level tends to carry through into the appointment itself.
What makes this moment important is that it sits before the market is engaged.
Once the search is underway, it becomes harder to step back and revisit the fundamentals. The process has momentum, candidates are in play, and the focus naturally shifts towards making a decision. If the underlying alignment has not been established by that point, it tends to surface later, often when choices need to be made.
That is when the differences become more pronounced.
One candidate may feel right to one part of the group and less so to another. Feedback can become difficult to reconcile. Progress slows, and the sense of clarity that was there at the beginning begins to erode.
From the outside, it can look like a challenging search.
From the inside, it is often a question of alignment that has not yet been resolved.
Handled well, this stage of the process can look quite different.
It requires a willingness to pause, however briefly, and bring those perspectives into the open. Not to eliminate them, but to understand them properly and to agree what matters most.
What is this role truly there to do?
Which outcomes are non-negotiable?
Where is there flexibility?
And, importantly, who ultimately owns the decision?
These are not always straightforward conversations, particularly where there are established relationships and sensitivities at play. But they are the ones that shape whether the brief becomes a clear direction or remains a compromise.
Once that clarity is established, the search itself tends to move differently.
The role is more focused, the criteria for assessment are more consistent, and candidates experience a clearer sense of what they are being considered for. Decisions become easier to make, not because they are simple, but because they are anchored in a shared understanding.
Without that, even strong candidates can struggle to gain traction.
Not because they lack capability, but because they are being evaluated against a set of expectations that were never fully aligned.
For founders and leadership teams, this is often one of the less visible aspects of making senior appointments.
The assumption is that success depends on finding the right individual, when in practice it depends just as much on agreeing what “right” actually means.
That agreement does not always come naturally.
It requires time, conversation and, occasionally, a willingness to challenge initial assumptions.
But it is what allows the appointment to do what it is intended to do.
Without it, the role can become a holding place for unresolved questions, and the individual stepping into it is left to make sense of something that was never fully defined.
Most senior appointments bring a degree of complexity.
That is part of their nature.
What determines their success is not whether that complexity exists, but whether it has been understood and aligned before the decision is made.
About the author
David Twiddle is the Managing Partner and Founder of TWYD. He works with founders, family businesses and family offices on senior leadership appointments, often where multiple stakeholders are involved and alignment is as important as the hire itself.
His work focuses on bringing clarity to these situations before the market is engaged, helping businesses define roles properly, align expectations and create the conditions for appointments to succeed.