Many professionals considering a charity trustee role focus immediately on how to get one. The networking, the search firms, the applications. Our experience with our clients suggests a prior step: honest reflection on whether the role – and the charity – is right for you.

The expectations gap

Writing recently in the Financial Times[1], Craig Coben describes a friend who, after a long career in finance, joined the board of a regional theatre. He loved the stage and hoped to take part in creative discussions about the coming season. Instead, the charity welcomed him as the “numbers guy” – reviewing budgets and soliciting donations. What he hoped would be a fresh chapter felt more like a diminished version of his former job.

The story captures a common risk: the gap between what you expect from a role and what the organisation expects from you. Neither party had the honest conversation, neither asked the difficult questions.

Skills must be adapted, not transplanted

Professional experience is valuable, but it must be reshaped for a mission-driven context. Financial discipline applied to charitable priorities looks different from commercial oversight. Governance for organisations where impact matters more than returns requires a different mindset. Without that adaptation, the experience risks becoming a pale echo of your old role.

The harder question

Coben makes a sharp observation: “Many people leaving finance miss institutional clout more than they expect. Board roles can become a way of preserving that authority in soft focus.”

So are you pursuing the role because you genuinely want to contribute to a cause? Or because you are looking for a softer version of the status you are leaving behind? Both you and the charity deserve an honest answer.

Three questions to ask – both of yourself and the charity

Before committing to any role:

– What does this organisation need?

– Where can I contribute that is not simply a replay of my old job?

– Do they want something more than my money and my contacts?

These are not comfortable questions. Charities sometimes avoid them because they do not want to discourage a willing volunteer. Candidates avoid them because they do not want to seem demanding. Yet failing to address them all too often leads to misaligned expectations and frustration.

The professionals who thrive in trustee roles approach them with genuine curiosity about the organisation, honest self-awareness about their motivations, and a willingness to adapt. Fit matters.

If you would like to explore these questions further, Milestones can help. Contact: George Wilkinson on 07875 570 365 (george@careermilestones.com)

[1] Doing good in retirement requires more than just turning up, Craig Coben FT Jan 26, 2026

Download a copy of Thinking about a charity trustee role February 2026