The “Ask” Doesn’t Need to be Scary

“Asking” That Feels Wrong

I still remember my early days as the head of an independent school. Part of my responsibility was raising funds for the annual fund, and like many new fundraisers, I dreaded “the ask.”

In those first attempts, I’d reach out to people to grab coffee and “catch up.” But sitting there across the table, I always knew what was in my bag, a neat little annual fund brochure I planned to pull out when the time felt right. I’d rehearse transitions in my head, wondering how to pivot the conversation toward financial support for the school. Every time, it felt awkward. Even a little wrong. Because, of course, they didn’t know that’s why we were meeting.

Over time, I learned that how you set up the meeting determines how the “ask” will feel. So I started being clear upfront. Sometimes I reached out just to truly reconnect. Other times, I said plainly that I wanted to talk about their financial partnership with the school. And something surprising happened: honesty didn’t push people away; it built trust.

“Asking” That Feels Right

There was a couple I had known for several years before our capital campaign began. They were deeply woven into the life of the school. They were thoughtful, generous people who cared about the kind of learning environment we wanted to create for students. When we began a visioning and strategic planning process (which also included a feasibility study for a campaign), they volunteered immediately. I remember watching them light up as we discussed not just buildings and budgets, but also the outcomes we wanted for students: thoughtful thinkers, servant leaders, and engaged citizens. 

Over time, our conversations kept circling back to that vision. Sometimes it was at a school event, other times just in passing, sharing ideas about what was possible. There was never any talk of fundraising then, but we were building a shared sense of ownership over where the school was heading.

When the campaign began to take shape, it felt natural to reach out. I called and said something like, “We’ve developed a case for the campaign that outlines the vision you helped create through our planning process. It outlines how our community can come together to bring it to life. Would you be open to meeting to discuss the case and begin to talk about how you could participate financially?”

They said yes immediately. Not a hesitant yes, an eager one. Because it wasn’t a cold call or a surprise, it was the next chapter of a story we’d been writing together for years.

Before the meeting, I looked over notes from our past conversations and the feasibility study they’d participated in. I knew what mattered to them, what they valued, and roughly where their capacity was. I practiced walking through the case document out loud, not to memorize it, but to think about how I wanted to engage them conversationally, so it would feel like the kind of dialogue we always had.

When the day came, we met for lunch. The atmosphere was relaxed–laughter, easy conversation, talk about their kids and recent travels. Then, naturally, we turned to the campaign. I pulled out the case document, which they knew we’d be discussing, and their eyes lit up. They had given feedback on an earlier draft during the feasibility study, and this new version reflected some of their suggestions. They weren’t being pitched to; they were seeing something they had helped design.

We walked through the vision together, discussing the new facilities, the student experiences, and the broader possibilities for the school’s future. They were curious and engaged, leaning in as we talked. When I reached the end of the document, I paused and said, “We’ve prepared a giving plan that outlines ways families can support this campaign. I’d like to ask if you’d consider a three-year pledge in this range.” I pointed to the part of the plan that reflected a six-figure level of commitment. Then I stopped talking and let the moment breathe.

They looked at each other, then back at me, and smiled. “Yes,” they said. And then, unexpectedly, they thanked me.

“Thank you for presenting an opportunity that aligns so closely with our values and what matters to us,” they said. “We’re grateful to be part of it.”

That moment wasn’t about pressure or persuasion. It was about relationship and partnership, and the creation of a shared vision that had been taking shape for years. The meeting wasn’t the beginning of something; it was the culmination of trust, listening, and building a shared vision.

Within 24 hours, I followed up with another thank you and a written summary of their commitment. I made sure it was clear and specific. It wasn’t about formality; it was about honoring the relationship we’d built with clarity. That clarity made everything that followed —such as the thank-yous, updates, and even the pledge reminders —feel natural.

They became some of our strongest advocates for the campaign, joining me in meetings with others, sharing their story and enthusiasm. Their involvement was never transactional; it was transformative for them, for the school, and for me.

I walked away from that experience with a lesson that’s stayed with me: when the vision is genuine and shared, when an authentic relationship has been nurtured, when the invitation is clear, the “ask” doesn’t feel scary; it feels like continuing a conversation.