What I Wish Every Fundraiser Knew, Part 2

When you listen, everything changes

In Part 1, I wrote about how I used to approach major gift fundraising: armed with a campaign plan, a proposal, and a sense of what I thought the donor should do. I didn't ask what their vision was. I determined that to be my job and decided for them.

But everything changed once I realized how backward that approach was—and started doing things differently.

Here's my story:

The meeting that changed everything

I was sitting down with a longtime couple who had given consistently for years but never at what we'd call a major gift level. I'd been tasked with moving them "up," and the expectation was clear: pitch a project and ask for a bigger gift.

But instead of launching into the proposal, I paused. Something gnawed at me to ask a simple question that I had never asked before:

"What do you hope our organization will accomplish in the next few years?”

I admit I was slightly startled by what came out of my mouth. What prompted me even to ask that question? Could their answer possibly change the direction of our organization? Was THAT possible, as if my organization would consider the notion?

I wasn't the only one startled by my question. The couple leaned back, surprised, and just stared at me. Apparently, no one had ever asked them that question before, either. The couple then looked at each other as if to seek permission. Slight nods were given as if to signal the floodgates to open. Then they started talking. And talking. And talking. They kept talking for 45 minutes.

While I don't remember all the details of their impromptu download, I do remember some of the more salient concerns. They told me why they first got involved and what had initially inspired them. Then, they shared what frustrated them over time, hoping for the leadership to "right the ship." Clearly, they had a vision of what they thought our organization COULD be. It was thoughtful, bold, and aligned with our mission in ways I hadn't expected. By the end of that conversation, I didn't just have more context—I had partners. I had people who wanted what our organization wanted, though we had missed some important steps along the way.

But who was I to orchestrate organizational change?

We didn’t talk about dollars that day. Instead, we spoke of possibility.

The gift came later. It was larger than I would have asked for, and more importantly, it was offered joyfully because the couple felt heard and that we would address their concerns. That's the moment I realized listening isn’t a strategy. It's a posture. It's a commitment to finding a shared purpose.

Why "Tell Me More" might be your most powerful tool.

Fundraisers are taught to craft compelling stories, articulate impact, and make the case. Those are important skills. But we're rarely taught to hold space for the donor's beliefs, hopes, or fears.

"Tell me more" is a humble invitation. It turns a one-sided pitch into a mutual exploration. It shows that we're not just looking for money—we're looking for alignment, shared investment, and vision that transcends any single campaign.

Sometimes, the most generous thing we can offer a donor is not a proposal—it's the chance to dream with us.

Letting the donor lead doesn't mean abdicating your role

Now, let's be clear. This isn't about handing over the reins or chasing dollars wherever they lead. Our role is to protect mission integrity, steward resources wisely, and move the organization forward. But we do that best when we treat our donors like partners, not prospects.

When you invite donors into conversations—not just about what they'll give, but why—you build trust. Trust is what sustains long-term generosity. It's what turns a gift into a partnership instead of a transaction.

Coming in Part 3:

Next time, I'll talk about internal alignment—how to bring your program staff, executive team, and board into a donor-centered approach without losing focus or momentum because it's one thing to shift your mindset. It's another to help your organization do the same.

Until then, remember that great fundraising isn't just about strategy. It's about sincerity, curiosity, and the courage to ask, "What do you see that we might be missing?” Asking this question may even require us as fundraisers to go back to our leadership and share our findings to help orchestrate internal change. Positive growth and partnerships come when we are unafraid to address these potential barriers.

That's how transformation and transformational giving begin.