It is one of the most common — and most costly — patterns in growing organisations: a person who was exactly right for the business at one stage becomes a meaningful constraint on its growth at the next. The awareness of this tends to be widely shared and almost universally undiscussed. The reasons are human and understandable. The consequences are serious and compounding.

Why it persists

Loyalty is one reason. In founder-led businesses especially, the people who were there early carry a weight of gratitude and relationship that makes objective performance assessment genuinely difficult. The CFO who held the business together through its first funding crunch deserves enormous credit. That credit does not automatically transfer into the skill set required to lead finance through a Series C.

Conflict avoidance is another. Leadership transitions are uncomfortable. They require direct conversations that most people — including most leaders — find genuinely hard. Deferring the conversation is easy to justify: things are fine, the timing isn't right, we'll address it after the next milestone.

The third reason is underestimation of the cost. Keeping the wrong person in a senior role is not a neutral act. It affects the performance of every person who reports to them, the decisions that don't get made well, and the talent that leaves because it sees no path forward. These costs are real but diffuse — they don't appear on any dashboard.

What doing it well looks like

The organisations that handle role transitions with the least damage share a common approach: they treat it as a business decision first and a people decision second. They are clear about what the role requires now versus what it required before. They separate the question of someone's value to the organisation from the question of whether they are the right person for this specific role at this specific moment.

Done well, these transitions can be handled with dignity, generosity, and genuine care for the individual involved. Done badly — or not at all — they quietly shape the ceiling of what the business can become.

The conversation is always hard. It is never as hard as not having it.