Initiating the Legacy Conversation

Two Men Having a Difficult Legacy Conversation

Polish your legacy conversation skills. Sign up for Initiating Legacy Conversations with Jonathan Gudema, Esq.

Talking about planned giving can be the toughest job of all

My Dad never wanted to talk about creating a will. “Don’t worry,” he’d say, “It’s not like I’m going to die tomorrow.” Then he’d change the subject—usually to the tomatoes he was growing—because he found talking about planning his estate too uncomfortable.

I was met with this same response every time I tried to bring up legacy planning. And it was uncomfortable for me, too—no one wants to talk with their parents about dying. But I knew Dad was ignoring one of the most important tasks any of us will ever complete, and that if he didn’t create a will, he’d leave my Mom (and the rest of us) with a huge mess to sort out.

He’d also lose out on the chance to create his own legacy and make a measurable impact at his favorite charities. Still, I brought it up less and less over the years, knowing I’d get the same response.

Guess what? My Dad died without ever making that estate plan (just like these rich and famous such as Abraham Lincoln, Prince, Aretha Franklin, Bob Marley …). We had no idea what he’d planned to give his favorite charities. He left a gigantic mess, including hefty legal fees, for my family to deal with.

And he’s a prime example for why anyone in planned giving must be able to initiate a legacy conversation. Maybe if Dad’s favorite NPOs had reached out over the years and opened a dialogue with him, the outcome would have been different—and they’d have much heftier endowments.

Keys to the Kingdom

When you learn how to have effective conversations with donors and prospects about planned giving, it’s like getting the keys to your nonprofit’s future. Here are a set of questions (PDF; with explanations behind each) to get you started.

Among the things that help are:

  • Understanding mindsets, motivations and aspirations.
    Age, physical and mental health, family matters and current events all affect your donors’ thinking. Get to know your prospect and listen. Is creating a legacy a priority? How do they wish to be remembered?
  • Knowing what makes a good prospect.
    How many times have they donated to your organization? What’s their age and income level? What’s your screening process?
  • Knowing which life events are good triggers for opening up a dialogue.
    Divorce, the arrival of a child or grandchild, a change in business ownership or employment, even a death in the family are among the many reasons people should update their will (and their legacy plan).
  • Learning how to develop a “Legacy Opener.”
    You need a simple, effective planned giving conversation starter to set your prospects at ease.
  • Overcoming the greatest hurdles to a legacy conversation.
    Oftentimes, fear holds us back. 
  • Determining whether they have a will or an estate plan, and knowing what to suggest if they don’t.
    Like my Dad, your prospect may be putting their will on the back burner. You’ll need skill to motivate them.
  • Knowing how to close on a gift.
    Getting a prospect to talk about planned giving is one thing. Getting them to commit to a gift is another. What’s your plan?

Initiating a legacy conversation can be uncomfortable, to say the least. It’s rife with the potential for conflict. You’ll be reminding your prospect about their mortality, and potentially bringing up triggers from their past.

But the alternative is silence, unwritten wills, family chaos, and empty endowments. You cannot be an effective planned giving fundraiser if you don’t know how to initiate a conversation with prospective donors. And you won’t be doing your supporters any favors if you can’t convince them that they need a will to protect their family and their legacy.

We’ve always said that people skills are the most important aspect of planned giving—and knowing how to initiate a legacy conversation is at the very top of that skills list. So what are you waiting for?

And by the way, as my dad always said “I’m not going to die tomorrow,” well, he did “die tomorrow.”

Polish your legacy conversation skills. Sign up for Initiating Legacy Conversations with Jonathan Gudema, Esq.

All of our blogs, products and services are proudly conceived, created, reviewed, and disseminated by real humans — not A.I. (artificial “intelligence.”)

Legacy Planner Logo

Making Estate Planning Accessible, Simple, Personal, Secure and FREE!

Bequests are up, cash is down. Empower your donors to plan their will and invest their legacy in the cause they support the most.

Planned Giving Marketing Authority:

Leave a Reply

Reach out! We look forward to hearing from you.


We value your privacy and keep your
information private. We do not spam.