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Posted October 28th, 2026

Strategies for Effective Planned Giving Legacy Challenges

Most fundraisers are familiar with the strategy known as the gift challenge, where loyal donors pledge additional dollars to match new, current gifts. They can be especially effective during membership drives and capital campaigns.

A less common strategy is the legacy challenge, which is an opportunity to unlock future commitments while simultaneously generating immediate funding. On a recent episode of the Sharpe Insights Podcast, we were joined by John Jensen, the director of planned giving at Washington National Cathedral. John discussed how the Cathedral successfully used this concept to uncover bequest commitments they were unaware of and encourage new commitments.

What exactly is a legacy challenge?

A legacy challenge is simply a fundraising campaign designed to encourage donors to share their planned gift intentions with your organization. Unlike traditional matching campaigns, a legacy challenge incentivizes individuals to disclose their estate plans and the potential value of their future gifts.

Here are some of the advantages:

  • Increased transparency: Donors inform you about their planned gifts, helping your organization better understand future funding.
  • Immediate funding: Through matching commitments, charities can secure current funding based on future gifts.
  • Engagement: Encourages deeper relationships with donors by fostering open communication about their philanthropic intentions.

Getting started

  1. Define your goals, whether it’s increasing donor participation or boosting overall planned giving revenue.
  2. Engage major donors willing to match gifts disclosed during the campaign.
  3. Plan for a campaign duration of six months to two years, allowing ample time for donor engagement.
  4. Make sure your donors understand the matching process and the impact of their commitments.

Here are some potential pitfalls to be aware of:

  1. Avoid launching during peak annual giving seasons, which may distract donors from your campaign.
  2. Ensure donors are well-informed about the benefits of participating in the challenge.
  3. Regularly engage with potential donors to remind them of the campaign and encourage participation.

Real-World Insights From Washington National Cathedral

John outlined the Cathedral’s recent legacy challenge, which successfully engaged donors and secured more than $35 million in commitments.

Their strategy began with targeting their legacy society members. By focusing on existing members who had previously included the Cathedral in their estate plans, the Cathedral could unlock significant previously undocumented gifts. They also identified donors from the society who would be interested in helping the Cathedral by matching commitments.

John and his team established a limited time frame for the challenge that encouraged donors to act swiftly, enhancing participation rates. They also provided assurances that donor information would remain confidential to encourage openness in sharing gift amounts.

Key Takeaways

Engagement is key: Foster relationships with your donors, especially those who have already included you in their estate plans.

Communication matters: Ensure your messaging is clear about how the challenge works and its benefits.

Leverage success stories: Donor stories are extremely effective in encouraging new gifts. In the planned giving world, they also educate donors on additional ways to give they may not have thought of.

A well-structured legacy challenge can not only secure future commitments but also generate immediate funding for your organization. By fostering open communication and effectively engaging donors, your planned giving program can thrive.

Explore additional episodes of our podcast, Sharpe Insights: Conversations With Your Planned Giving Experts here or on your favorite podcast app. If you need help writing donor stories, our experienced editors will interview your donors and write effective stories that you can share in your communications and on your website. Contact us for more information.

Teri Sullivan, Sharpe Group Vice President of MarketingTeri Sullivan is vice president of marketing for Sharpe Group and serves as co-producer of the podcast Sharpe Insights: Conversations With Your Planned Giving Experts. You can connect with Teri via email or on LinkedIn.

 

 

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