When our team talks with fundraisers about technology, especially AI, we usually find people in one of two places.

Some are avoiding it almost entirely. It feels impersonal. It feels risky. They worry that using AI to draft a donor communication somehow makes the relationship less genuine. They care deeply about their donors and do not want anything to interfere with that relationship.

Others have moved just as strongly in the opposite direction. They are automating thank you letters, cultivation emails and stewardship updates almost completely. They are moving quickly. But something important is getting lost.

Neither of those approaches truly serves your donors.

The strongest major gift teams have found a middle ground. They use technology to help them draft communications. Thank you letters. Follow-up emails. Impact updates. These pieces take time to write thoughtfully, and a strong draft gives you a useful starting point.

But they never send that draft without reviewing it carefully.

They read every word. They ask themselves whether it sounds like a real person who actually knows this donor. They add the personal detail that only they would know. They adjust the tone so it feels natural and specific. They make sure it reflects the relationship, not just the transaction.

Major gift donors can tell the difference. They may not be able to explain exactly what feels off, but they can sense when a message sounds generic. They can just as easily feel when it is warm and personal.

Technology cannot sit across the table and notice when a donor hesitates. It cannot hear the change in someone’s voice when you begin to talk about a gift. And it cannot build trust over years of steady relationship.

That part of the work still belongs to you.

When technology is used wisely, it frees you to do more of the human work. It helps your team communicate more consistently. It helps you follow up more reliably. It reduces the time you spend staring at a blank page so you can spend more time having real conversations.

That is the balance you are looking for.

When All Five Gaps Are Closed

Over the past few weeks, we have talked about five hidden gaps that quietly weaken major gift programs.

We have talked about an unclear strategy. About portfolios that are either too large or poorly focused. About misalignment between leadership, board and development staff. About under asking. And now about using technology without intention.

When those gaps remain open, your team may still be working very hard. But the results feel uneven. Momentum comes and goes. Confidence rises and falls.

When those gaps are addressed intentionally, something steadier begins to take shape. Your team understands exactly who they are focused on and why. Your leadership and board are aligned around the same goals. Your fundraisers approach donor conversations with preparation and confidence. And your systems support the work instead of creating more noise.

That kind of program is not theoretical. We see it every year. And it is buildable with the right structure and guidance.

Before you move on, take a moment to consider your own organization. As you read through these five gaps, where did you feel a small nudge of recognition? Where did you think, “That sounds familiar?”

That awareness is not something to feel discouraged about. It means you care about getting this right. It means you are paying attention.

It may also mean you are ready for the next step.

Join The 2026 Major Gifts Intensive

The Major Gifts Intensive is where teams come together to close these gaps.

Over twelve weeks, Gail Perry and the Gail Perry Group consultant team work directly with you and your colleagues to strengthen your strategy, focus your portfolios, align your leadership and build confidence into your asking.

This year, Gail will personally lead live teaching sessions, including her Conversational Ask framework and a dedicated session on engaging and activating your board for major gifts. You will not just hear ideas. You will apply them to your own donors and build your plan as you go.

The 2026 cohort begins March 12, and registration closes March 10. Limited seating is available.

This program runs once each year. When enrollment closes, the next opportunity to join will not be until next year.

If you have been following this series and quietly recognizing your own program in these gaps, this may be the right moment to act.

Click here to find out more or send us an email and tell us a little about where your major gift program stands right now. We would be glad to discuss whether this cohort is the right next step for your team.

Start here to read the entire series in order.