7 Lessons I Learned From Raising Three 7-Figure Gifts

by Bryn George | August 19, 2026

Over the past 12 months, I raised three 7-figure gifts.

There were three different donors, three different relationships and three different paths to a yes.

Along the way, I came away with seven lessons that I think are useful for anyone raising major gifts.

1. Make an “ask to ask.”

You don’t always have to jump directly from cultivation to solicitation.

Before one significant request, I asked a trusted contact whether we could ask the larger family to consider a special investment.

The answer was yes.

That permission created an opportunity to begin discussing a potential gift range before the formal solicitation. It helped us understand what might be possible and ultimately prepare a stronger request.

Sometimes the first ask isn’t for money.

It’s permission to have the conversation.

2. Keep virtual solicitations simple.

Sometimes you simply can’t get everyone in the same room.

For one solicitation, geography meant we had to make our request virtually.

Rather than putting a traditional case for support on the screen, I stripped the presentation down. Very few words. Strong visuals. A clear visual representation of the request.

Then, immediately after the conversation, I sent the supporting materials.

Virtual meetings can make it harder to read body language and gauge reactions. Don’t compensate by putting more information on the screen.

Keep it simple. Be confident. Listen carefully. Answer questions. And let your follow-up materials carry the details.

3. Protect annual giving when discussing transformational giving.

A major campaign commitment shouldn’t automatically replace a donor’s annual support.

When we prepared one multi-year request, we also included the donor’s existing annual commitment.

The donor understood immediately.

This is an important reminder: don’t assume donors see annual and special giving as interchangeable.

Help them understand the role each investment plays.

4. Prepare your leadership to make the ask.

Senior leaders can bring tremendous weight to an important donor conversation—but only if we prepare them well.

Before a solicitation, I like to brief leadership thoroughly.

Who is saying what?

What does this donor care about?

What should we listen for?

Who will make the invitation?

What amount are we requesting?

What happens after the number is said?

When possible, I like the senior leader in the room to make the actual ask, including saying the amount. Then I can step back in to discuss timing, structure and next steps.

Don’t simply bring your CEO into the meeting.

Tee them up for success.

5. Invite donors to come and see.

Not every solicitation ends with an immediate yes.

Sometimes the best answer you can hear is: I’d like to see it.

When someone wants to experience your mission firsthand, make that happen quickly.

There’s something a proposal, presentation or meeting simply can’t replicate about seeing the work in action.

When donors can meet the people, walk through the space and experience the mission for themselves, the opportunity becomes tangible.

Never underestimate the power of “come and see.”

6. Go to your donors.

Fundraising is increasingly virtual, and that’s opened up wonderful opportunities for relationship building.

But face-to-face still matters.

For significant relationships and significant asks, consider whether you should be the one making the effort.

Take the trip. Have lunch. Sit across the table. Spend unhurried time together.

Showing up demonstrates that the relationship matters.

7. Think about the whole family.

A gift can be the beginning of a relationship rather than the culmination of one.

One of my favorite moments from this year came when donors wanted to bring the next generation of their family into their philanthropy.

We welcomed the opportunity.

For families with children or grandchildren who are beginning to participate in charitable decisions, nonprofits have a wonderful opportunity to help make generosity meaningful.

Don’t think only about the donor sitting across from you today.

When appropriate, think about the family and the legacy of generosity they’re building together.

The Thread Through All Seven Lessons

When I look at these three gifts, I don’t see one fundraising formula.

I see relationships. Preparation. Listening. Thoughtful invitations.

And a willingness to adapt to the donor in front of us.

That’s one of the reasons I love major gift fundraising. The fundamentals may remain consistent, but the path is rarely exactly the same.

Our job isn’t to force every donor through the same process.

It’s to know our donors well enough to recognize the right next step—and confidently invite them to take it.