The last will and testament: why the legacy journey belongs to more than one person.

Part 2 of 2.

My Dad died two years ago. He was, by common agreement among those who knew him, the tightest man in the north of England. Not mean - just amazingly and reputably careful with money. So when we came to sorting through his affairs, I wasn’t expecting many surprises on the charitable giving front.

Having spent a significant part of my career leading Cancer Research UK’s legacy programme, I knew he’d used their Free Will Service at some point - not one to pass up a freebie. And I fully expected him to be among the c40% of users who don’t ultimately leave a gift. He’d never mentioned it. We’d never talked about it.

But as we cleared through his belongings, I found a CRUK-branded diary for every year since 2004 - the year I first joined the organisation. And a CRUK volunteering badge - I had no idea he’d been helping out in the local shop! The small pecuniary gift he left was, I realised, anything but a token gift.

What stayed with me most though was what came out of the conversations at his memorial. Causes and organisations I’d never known he cared about. Friends sharing stories that painted a picture of a man whose charitable instincts ran deeper and wider than his family had ever understood: protecting the birds off the the north shore of Walney Island, daily work at the community allotment which provides fresh fruit and veg to the local food bank and the Lake District Mountain Rescue. We were, as most families tend to be, brilliantly awkward at those kinds of conversations. And I wish we’d made time for more of them.

I’m sharing this because it sits at the heart of what Part 2 of this post is really about. The gap between what a supporter cares about and what the people around them actually know. And what happens to that gap when the will is eventually administered.

The numbers behind the family picture

A will is the most personal legal document most people will ever make but it is administered by others, in circumstances the person who wrote it can often never anticipate. And often by family members who are navigating grief, financial pressures and complicated relationships at the same time.

The scale of that challenge is growing. Formal challenges to wills in England and Wales reached 11,362 in 2024 - a 56% rise over 5 years, according to HM Courts and Tribunals Service data. The drivers are well documented and structural: blended families, questions around mental capacity, the growth of DIY and online wills and estates that are simply worth more and therefore worth disputing. In Australia, Bequest Assist found that an estimated 3% of wills included a gift promised to a charity that was never paid - representing more than $40 million every year!

The legacy gift that a supporter writes into their will is not automatically that legacy gift their charity receives. The journey from intention to income passes through people, relationships and circumstances that most legacy programmes have barely begun to map.

Charities are strangers to the people who matter most

Most legacy programmes are build around one relationship: the charity and the pledger. Fair enough. The family is fairly invisible until the estate is in administration. By that point the charity is arriving as a stranger into what is often an emotionally charged and legally complex situation.

Think about this from a behavioural standpoint. The executor - often a son, daughter or close friend - is navigating grief, paperwork, family dynamics and financial decisions all at the same time. In that state, how an organisation shows up matters. A charity that arrives with warmth, clarity and genuine humanity will be experienced very differently to one that sends a standard notification letter and a request for documentation. The impression formed in that moment extends well beyond the administration of one estate.

I wrote about executor stewardship in an earlier post and I won’t repeat myself here. The core of it is this: the legacy journey doesn't end when the gift is confirmed. It doesn't really begin in any meaningful relational sense until the people administering the estate feel that the charity understands what this gift meant, and that the supporter who made it is being acknowledged as more than a line on a bank statement.

Bringing families along the journey earlier

Executor engagement matters, but there’s an opportunity to close a relationship gap much earlier in the journey.

If the Boomer legator is making more deliberate choices about which charities earn a place in their will - under the kind of pressure I described in part one - then the relationship a charity has with the wider family of that supporter starts to matter in a way it hasn't before.

This is not about asking family members for money. The son or daughter who has heard their parent speak about a cause with genuine feeling. The grandchild who understands why this gift matters to their family. The partner who knows that this is something their loved one cared about deeply. These are not peripheral relationships to the legacy decision. They are part of the conditions in which it survives or doesn't.

Behavioural research tells us that social identity and shared narrative are powerful reinforcers of intention. When a charitable gift is understood and valued by the people closest to the donor, it is more likely to be protected, respected, and sometimes extended into the next generation. When it exists only in a document that the family encounters for the first time at probate, it is in a more fragile position than most legacy programmes acknowledge.

My Dad's CRUK diaries didn't make it into a conversation while he was alive. The causes his friends mentioned at his memorial never made it into a will at all. That isn't a failure of fundraising. It's a reflection of the conditions in which those conversations either happen or don't. Charities can't manufacture those conversations, but they can create the environment in which they become more likely.

What this means in practice

None of this requires charities to reinvent their legacy programmes but it does ask for a shift in how the journey is framed when you’re putting the supporter first.

The pledger is not the only person on the legacy journey. They are the most important person, but they exist inside a family, a set of relationships, and an estate that will eventually be administered by people the charity has probably never spoken to. Building a stewardship approach that creates optional, low-pressure touchpoints for families that thinks about how the donor’s values can be made visible and meaningful to the people around them, reflects the reality of how legacies actually land.

This is a VERY long-winded way of suggesting, the charity of share of will is contracting because the Boomer will is under pressure. The organisations that hold their place in that environment are the ones that have built relationships deep enough to survive it. That means thinking about who is in the room when the decision is made, who is the room when the estate is administered and what kind of relationship your charity has with both.

If this has prompted more questions than answers, let’s unpick them together.