Who do you fear losing — and what are you doing about it?
When I speak with senior leaders, one question often reveals more than any talent grid or succession plan: who are you most afraid of losing?
My honest answer is this: I was never really kept awake by the difficult decisions I had to make or the scrutiny that came with them. What troubled me most was the possibility of losing the brilliant leaders I had worked hard to build around me — because when your best leaders begin to drift, your strategy, culture and delivery capacity are already at risk.
In every leadership role I’ve held — especially where significant change was required — my first priority has been to build a strong leadership team around me. As I’ve said before, transformation is not delivered by one heroic individual; it depends on a coherent, credible group of leaders who can carry the work, challenge the thinking and build momentum and role-model process and behaviour changes alongside the accountable senior leader.
These are people I can trust, learn from, be challenged by, build bonds with and create a project around. But the flipside of the energy working with brilliant people is the fear of losing them, and that fear – I find – is multiplied when those people are your best leaders.
That is why leadership development should never be treated as a reward for good performance or a training line in a budget. Done properly, it is a form of risk management: a deliberate, explicit and logical way of keeping your best people stretched, committed and connected to the future of what you’re trying to build.
When I talk about ‘losing’ someone, I mean one of three things — and only one of them is healthy.
1. They leave for an exceptional opportunity elsewhere, continue to make impact, and develop in ways your organisation genuinely could not offer at that point (healthy, if handled well).
2. They outgrow the role but cannot see any serious route to stretch, progression or purposeful challenge inside your organisation (bad, and usually predictable).
3. They lose faith in the strategy, culture or purpose of the team and decide they are no longer the right fit. Sometimes they leave; sometimes, more dangerously, they stay but quietly withdraw their energy and belief (bad, and corrosive).
A useful test is this: if one of your best leaders told you tomorrow that they were leaving, would you be surprised — or would you realise the warning signs had been there for months?
In my experience, organisations rarely put enough deliberate time, energy, creativity or resource into developing and retaining the leaders who create the most impact — even though those are often the very people whose departure would hurt most.
One reason is discomfort. In sectors such as charities and public services, leaders can be understandably wary of appearing to single out, reward or invest disproportionately in high-impact talent. Concerns about bias, favouritism and unclear recognition frameworks are real — but avoiding the issue does not make it fairer; it simply makes talent development more accidental.
Another reason is that organisations often staff important work by defaulting to job title, hierarchy or technical ownership rather than asking who would bring the greatest judgement, energy and impact to the task. That can unintentionally exclude the very leaders who would grow fastest — and contribute most — if they were trusted with higher-stakes work.
Finally, career planning often avoids the most honest conversation until it is too late: brilliant, ambitious people may need to leave for a period to gain different experiences, build wider perspective and grow in ways your organisation cannot currently offer. The question is whether you make that conversation safe enough to preserve the relationship — and perhaps create the conditions for them to return.
So, if the fear of losing your best leaders keeps you awake, here are three practical things to do before the risk becomes a resignation conversation.
1. Ask, don’t tell. Make time to understand what your strongest leaders want from their careers: the impact they want to make, the skills they want to build and the kind of work that gives them energy. The conversation itself can be transformational, even when the honest answer is that they may need to move role — or organisation — to keep growing.
2. Invest in your talented leaders. Give them time and space to reflect, test ideas with other high-impact people — ideally from different organisations and sectors — and encourage learning that stretches them. Just as importantly, connect that investment to the contribution they can make, so development feels tangibly related to the impact you – and they – are paid to make.
3. Put your highest-impact people onto your highest-stakes work, whatever their job title or formal position. If impact is the goal, the project team should be shaped around judgement, energy, critical thinking and delivery — not just hierarchy or technical ownership. Done well, this motivates talented leaders, raises standards and creates healthy competition for the work that matters most.
If you lead an organisation and recognise this tension — wanting to stretch your best people while fearing the moment they might outgrow you — that is exactly the kind of leadership challenge I help clients work through. The goal is not to keep talented leaders at all costs; it is to create the conditions in which they keep choosing to contribute their best work while they are with you.