I’ve been immersed in the world of charitable bequests since my fellow Good Workers and I conducted our first donor poll on the subject way back in 2003.

In the years since, I’ve learned dozens of valuable lessons about where legacy gifts come from, who makes them, why they get made and how to persuade people to give them. It’s been a fascinating journey for me – one that isn’t by any means over…

If I had to pick one roadblock that gets in the way of our success as fundraisers in convincing supporters to leave bequests, it would be this:


What do I mean by that?

When I speak at fundraising conferences, my audiences are – on average – people in their mid to late 30s, or perhaps early 40s. Yet, I know from our State of the Legacy Nation polling that the vast majority of bequests come from people in their 60s, 70s or even 80s. There’s a good generation between the average legacy fundraiser and the average legacy prospect – sometimes two generations!

A working mom fundraiser in her late 30s is in a VERY different mindspace than a retired, empty-nester prospect in her 70s. As fundraisers, it’s our job to understand our audience – it’s NOT our audience’s responsibility to understand us!!

If we’re to be successful legacy gift persuaders, we MUST have a deeper understanding of what it’s like to live in a later stage of life. We must study it. We must ponder it. We must imagine it. We must embrace it.

So, I’m going to give you four tips to help you bridge your generation gap – and to crawl inside the head of those older legacy prospects you so desperately want to connect with:

Your older prospects are thinking about their life’s PURPOSE and MEANING

They’ve given thought to the existential questions like ‘Why am I here?’ and ‘What does my life mean?’ While you’re scrambling from soccer practice to daycare pickups, your prospect could well be sorting out the meaning of life. To connect with this prospect, you must learn to speak existentially.

Your prospect cares less about STUFF and more about EXPERIENCE

This is especially true of Baby Boomers (who today are aged between 51 and 71). When you talk to them about bequests, don’t talk so much about the money as about the act of giving. There’s a big difference here – one that many planned giving professionals don’t appreciate.

Your prospect probably has TIME that you don’t

As you scramble to get your dog walked and your family out the door in the morning, your prospect could well have time to sit at the kitchen table with a cup of tea and read that legacy booklet (or the legacy section of your website). I’m 61 years old – and I’ve just had my nest empty in the past year. I have time I couldn’t have imagined a couple of short years ago. So – in a nine-second, get their attention in a hurry world, you can actually take your time communicating with this audience.

Follow the source of the gift

While most charitable giving comes from the empathy centre of the brain, bequests come from the AUTOBIOGRAPHICAL centre. This is the place in the brain where (in later years), we construct the story of our lives. We try to bring that story into a cohesive whole and we try to attribute ourselves with consistent desirable qualities (like love and generosity). When I interview legacy donors for testimonials messages, I always like to start with two questions:

  • Would you tell me about your childhood? What was it like growing up?
  • Who taught you to be generous?

Questions like these help the interviewee to get into a very autobiographical mindset – and this mindset usually lasts for the rest of the interview.

These are just four simple tips to help you bridge the generation gap that exists between you and your legacy prospects. My final idea is this: just try to spend some time with older people. Watch them. Talk to them. Listen to them. Study them.

I promise you that  it will be time well spent…