What should you do when research uncovers something uncomfortable about a major donor?
Don’t bury it — and don’t sensationalize it either. Most philanthropic due diligence situations aren’t clean yes-or-no decisions. They live in the gray area, and they require organizations to have honest, structured conversations about risk, values, and what it means to stand behind a gift.
Key Takeaways
- Discomfort is a reliable indicator that something important needs to be examined — not avoided
- Most due diligence situations live in the gray area; context matters as much as the finding itself
- The Braver Leadership framework — clarity, candor, courageous follow-through — gives teams a structure for hard conversations
- When presenting uncomfortable information, researchers should stick to facts, provide context, and offer pathways — not ultimatums
- Uncomfortable information isn’t usually the problem; it’s whether organizations are willing to have the conversation at all
Evelyn Chen, Partner at Russell Philanthropies, knows what happens when due diligence reveals an uncomfortable truth and why the worst move is to ignore it.
After more than 20 years as a fundraiser, she’s learned that discomfort is a reliable signal that there’s something important to learn. That philosophy shapes how she approaches one of the most challenging parts of the work: philanthropic due diligence.
Why does discomfort matter in due diligence?
Evelyn Chen was spotlighted in the AFP Global Newsletter for naming discomfort as her favorite word. She’s learned over time that when something feels unsettling, there’s always a reason. And if you take the time to examine it rather than push it away, you’ll often find a conflict to resolve, a gap to address, or something important to learn.
That philosophy shapes how she approaches philanthropic due diligence. It’s one of the areas where researchers and fundraisers most often encounter information that nobody quite knows what to do with.
What is the real question behind a due diligence red flag?
Philanthropic due diligence rarely produces a clean yes or no. It’s less about catching bad actors and more about navigating uncertainty. Organizations often don’t know if a red flag is a solid no, or an uncomfortable fact that needs to be considered.
Evelyn took these thoughts further and indicated that when researchers uncover uncomfortable information, their first job is to name what the flag actually is. Was it an allegation or a conviction? Did it happen ten years ago or last month? Context matters.
“When a fundraiser or a board member raises a flag, they’re not just asking about that particular incident,” Evelyn said. “They’re asking whether partnering with this donor aligns with your organization’s values.”
That’s the real question underneath: can the team stand next to this donor and this gift, publicly, and feel good about it?
At Russell Philanthropies, Evelyn uses a framework called Braver Leadership to navigate these moments, built on clarity, candor, and courageous follow-through. Naming the real tension, being willing to talk about it directly, and making a values-aligned decision even when it isn’t a perfect one.
“There’s very rarely a clean, perfect answer,” she said. “But if you have courageous follow-through and stand with your principles, you’ll either say yes, maybe with some guardrails, or you’ll say no, and you’ll be able to explain why.”
How should researchers present uncomfortable information?
Researchers are often the first to surface these issues and how they present findings matters as much as what they find. Evelyn’s advice:
- Stick to facts. Say what you know, note what you don’t, and resist filling in gaps or extrapolating.
- Provide context for why it matters. Help name the real concern — risk, alignment, optics — so the team can have the right conversation.
- Offer pathways, not ultimatums. Frame the implications and options: monitor it, address it with the donor, or escalate to leadership for a decision before proceeding.
Listen to the full episode to hear Evelyn’s story about the eight-figure gift she ultimately couldn’t stand behind, and what that experience taught her about how organizations handle, or avoid, hard conversations.
Resources Mentioned
- Connect with Evelyn Chen: LinkedIn
- Russell Philanthropies: Enews Subscribe
- Getting Started and Getting Serious about Due Diligence with Courtney Cutler
- Workshop | Due Diligence: Practice to Policy?