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DavidSaint
David Saint

Feb 17, 2026, 10:00 AM

Challenge with positive intent

An interesting theme has been emerging in recent months, as I’ve carried out governance reviews for a number of diverse clients.

In a nutshell: many charity executives want to be challenged by their trustees, yet many trustees are reluctant to offer that challenge.

The title of this article is taken from the Governance Handbook of one of those clients, which explicitly states that one of the roles of a trustee is to “challenge with positive intent”. And yet, even in that charity, trustees generally seemed to feel that their role was to encourage, affirm and congratulate the executives, rather than to challenge.

Push for better?
It struck me that adding “with positive intent” to the word “challenge” was highly significant, and helpful. In charities where trustees are “challenging”, this can often be quite aggressive and unhelpful, with the result that executives come to dread Trustees meetings, and breathe a sigh of relief when they are over. But “with positive intent” is exactly the point – challenge is not about point-scoring, or keeping people in line. It’s about exploring how can we do more, do better, be more creative, or whatever? Can our challenge be used to have a positive impact on the charity?

I do understand why trustees can be reluctant to challenge. I have been a trustee myself and understand the tensions. You don’t want to show up, undermine or demoralise your executives, and it can be so much easier simply to say “well done” and move on, rather than ask a really incisive or insightful question that might cause embarrassment.

Dumb is better than shtum
And then, of course, there is our fear of asking the dumb question. Is what we think is incisive or insightful actually going to be shown to be ignorant? Trustees generally have much less detailed knowledge of the workings of the charity than the executives who are working in it every day. As trustees can we really know enough to question them? Isn’t it almost impertinent to do so?

Let me reassure trustees of a few things.

First, your executives are highly likely to warmly welcome “challenge with positive intent”. Such challenge needs to be clearly framed in that context, as it may come as a bit of a surprise to executives the first few times, if they have not been used to this approach.

Second, dumb questions are much better than no questions – and very often the questions are much less dumb than you might think. I well remember a meeting in which acronyms were being used extensively, and one of them repeatedly. In the end I had to stop them to ask what those initials stood for – and 6 other people in the room said they were so glad I had asked, as they didn’t know either!

Add real value
Finally, you may find it helpful to think of yourselves as coaches. Even the top athletes – in fact especially the top athletes – have coaches, whose job it is to give them a hard time; to challenge them to do even better than they ever thought they could. In fact, to challenge them with positive intent.

This is a great way – an important way – a required way – for trustees to add real value to their charities, helping their executives achieve even more than they think they can.

If you would like help to strengthen the governance of your charity, get in touch. Email office@actionplanning.co.uk

ABOUT DAVID SAINT

David Saint Action Planning Charity Consultant

David established Action Planning in 1990 after a 16 year fundraising career with Scope, Sense, SANE and Arthritis Care. He is recognised as one of the not-for-profit sector’s leading authorities on strategy, management and fundraising, and has advised the Boards and Senior Management Teams of some of the most significant organisations in the sector.


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