Empathy-Driven Legacy Fundraising

Legacy fundraising is all about fostering deep, meaningful connections with donors. However, traditional fundraising methods often focus on a linear approach — presenting information, making a case for support, and hoping donors respond. But what if we approached legacy fundraising through the lens of design thinking? This human-centered, iterative process can help fundraisers create more engaging, donor-focused experiences that lead to increased legacy commitments.

What is Design Thinking?

Design thinking is a problem-solving methodology that prioritizes empathy, creativity, and iterative learning. It consists of five key stages:

1. Empathize – Understand the donor’s motivations, fears, and desires.
2. Define – Identify the key challenges and opportunities in legacy giving.
3. Ideate – Brainstorm creative solutions to make legacy giving more accessible and meaningful.
4. Prototype – Develop low-risk, small-scale initiatives to test new approaches.
5. Test – Gather feedback, refine strategies, and continuously improve engagement efforts.

By applying design thinking, fundraisers can move beyond assumptions and create a legacy fundraising experience that truly resonates with donors.

Step 1: Empathize – Understanding Your Donors

Legacy donors are making one of the most personal and emotional philanthropic decisions of their lives. To create an effective legacy fundraising strategy, fundraisers must step into the donor’s shoes.

• Conduct in-depth interviews with existing and prospective legacy donors to understand their motivations and concerns.
• Use surveys to explore how different donor segments perceive legacy giving.
• Host focus groups to uncover emotional triggers and barriers to making a legacy gift.

By gaining deeper insights into donor behaviour and thought processes, fundraisers can craft messages and experiences that align with their values and aspirations.

Step 2: Define – Identifying Key Challenges

Once you’ve gathered insights, the next step is defining the core challenges that hinder legacy giving. Some of the most common barriers or objections include:

• Lack of awareness – Many donors don’t realize how easy it is to leave a legacy gift (we have to show how simple it is).
• Fear of discussing mortality – Some donors avoid estate planning conversations due to discomfort (it’s about life!).
• Perceived complexity – The legal and financial aspects of legacy giving can feel overwhelming (talk about what the world would look like through their generous legacy).

Defining these challenges allows fundraisers to design targeted strategies that remove friction from the donor journey.

Step 3: Ideate – Brainstorming Solutions

With challenges clearly defined, it’s time to brainstorm creative ways to engage donors. Involve diverse perspectives—including fundraisers, financial planners, and legacy donors—to generate ideas such as:

• Storytelling campaigns that highlight real donors who have left legacy gifts.
• Interactive digital tools to simplify the process of considering and planning a legacy gift.
• Legacy visioning workshops where donors can explore what kind of impact they want to leave behind.

The key is to generate a wide range of ideas without judgment, then refine them based on feasibility and donor feedback.

Step 4: Prototype – Testing Small-Scale Initiatives

Rather than launching a full-scale legacy campaign immediately, test small-scale initiatives to gauge donor response. Examples include:

• Creating a mini-series of donor impact videos to see which stories resonate most.
• Piloting a legacy ambassador program where current legacy donors share their experiences with others.
• Developing a one-page legacy giving guide to simplify the process.

By testing ideas on a small scale, fundraisers can refine their approach before committing significant resources.

Step 5: Test – Gathering Feedback & Refining Strategies

Once prototypes are in place, actively collect donor feedback. Did they find the process easy? Did a particular story or resource inspire them to take action? Use:

• Follow-up surveys to assess donor sentiment.
• One-on-one conversations to dive deeper into their experience.
• Data analysis to track engagement and conversion rates.

Then, refine and iterate. Design thinking is a continuous process, ensuring that legacy fundraising remains dynamic and responsive to donor needs.

Conclusion: A Human-Centered Approach to Legacy Giving

Applying design thinking to legacy fundraising fosters a more empathetic, innovative and donor-informed approach. By understanding donor motivations, identifying key barriers, brainstorming creative solutions, testing ideas, and continuously refining strategies, fundraisers can build a legacy pipeline that is both effective and deeply meaningful.

Final Thought: Legacy giving isn’t just about raising funds—it’s about helping donors leave their mark on the world in a way that feels personal and fulfilling. By embracing design thinking, fundraisers can transform the way donors engage with organizations and legacy giving, making it an inspiring and accessible journey for all.