Demystifying the Major Gifts Process: Part 4 – How to Ask for a Major Gift

advice communications fundraising major gifts Nov 01, 2021

This is part three of a four-part series I am doing on major gift fundraising.

  1. Working with major gift officers or consultants
  2. The foundations of why major donors give and how to talk with them
  3. How to identify major donors for your small to mid-sized nonprofit
  4. How to do the major gift ask (according to major donors who have been solicited hundreds of times)


Demystifying the Major Gifts Process: Part 4 –How to Ask for a Major Gift


Learn from My Mistake

I was wrapping up a large capital campaign. We were so tight on our goal, and I seriously thought that I might miss my target for the first time on a capital campaign. I was losing sleep, had a constant knot in my stomach, and my anxiety was physically taking its toll on my body. I was almost through my “backup plan” asks – that’s how bad this situation was. I can still remember when I got up in the middle of the night to pull up my excel spreadsheet of emergency ask opportunities.

Some of these people were donors who said “no” on the first round, but I thought they would give outside of the lead gift phase or who would love to be the ones who would seal the deal and meet the goal. There were some personal relationships that I might be able to call in a favor. There were some total shots in the dark.

I penned a handwritten note to one of the philanthropists to drop off with an Edible Arrangement in the morning.

I got the appointment; I got it the same day. I went in well prepared, and I gave a kickass presentation (if I say so myself). The answer was a HARD PASS. It was, in fact, the hardest I had ever been rejected. But, what I learned at that meeting changed my approach to major donors and capital campaigns forever.

Here is what the philanthropist said to me: “I was very enthralled at your letter – you made me feel like I could change the world. You found out that I ate healthily and used that to impress me into meeting with you last minute. You’re charismatic. You’re convincing. Your messaging is great. Your case for support is compelling. But I will not give today, nor will I ever support this organization. I do NOT give to your mission. You came in here guns blazing, and I know you are under a tight deadline for this campaign. But you started your meeting with what you need. You never asked me what I needed. You read it on the internet, but it’s not public knowledge, and so you made the mistake of not asking me what motivates me to give.”

Long story short, his wife died about ten years ago, and his son died the following year at only eleven years old. He dedicated the rest of his life to leave a legacy for them. When you read it online, the description is vague and could apply to many things. But he was right. I never formed that relationship. The timeline was tight, but I could have afforded 30 minutes. I should have talked less about what we were raising money for and more about what the donation could mean for the philanthropist.

This fundraising failure is one of the most significant moments of learning in my life. I am incredibly humbled that this gentleman took the time to explain to me how I could do better. I was also very blessed to be at a point in this campaign where I was humbled enough to listen and not just take this as a rejection and move on to the next ask.

I have done hundreds of millions of dollars of major gift asks in my career. I have been ill-prepared, rejected, surprised, and humbled. As my career expanded into coaching fundraising professionals, I have been given a unique ability to talk to philanthropists following the ask I coached clients through. I hear what the fundraiser heard, see how they interpreted it, muse at their blind spots, help them form an ask based on the information available, listen in on the ask, and then have a private one-on-one with the philanthropists (some who said yes and some who said no). This has given me such a unique perspective on the major gift ask process.

There are several questions I ask every multi-millionaire philanthropist that I meet. One of them is “how do you like to be approached for a gift”, and surprisingly an overwhelming majority say just about the same thing.

It is no secret that these donors have money or that they give it. But at the end of the day, major donors are people too. Humans are relationship-driven people. There is nothing more irritating to a major donor than to be treated like an ATM. I hear all kinds of things that the world’s wealthiest people hear in their asks. From the presumption that they will support to being referred to as “people like you.” Almost all of the wealthy philanthropists I’ve spoken to told me it’s rare to be approached for a gift as a genuine partnership, even though that’s the most effective way to earn their support. 

The #1 key to getting a major gift from a philanthropist is to have a personal relationship.

Here are some pro-tips:

  • Acknowledge that this person is a philanthropist and ask them how they got their money, how they determine where they give it, how an organization would get on their radar, and how they like to be approached for a gift.
  • Invite them to dinner without an ask! Let them know there is no ask in advance. Or invite them to some donor-only events.
  • The advice model works well with some (not all) major donors. Bring them an idea in the early stages. Let them know it’s a concept that you’re developing and you would like their advice. Ask what they or other philanthropists on their situation would want to know, what questions they would ask.
  • Let the philanthropist know that the meeting is an ask. If you must sneak around and spring it on them, the relationship isn’t there, and you haven’t told them enough about your organization.
  • Have a unique communication plan for major donors that differs from your other communications. That does not mean you downplay smaller gifts—your overall communication strategy should treat every gift as a major gift after it is given. However, fostering a major gift requires more personalized communication leading up to the ask and following up with the gift.

But you can over-do the focus on the donor or the “let’s talk about you.” Some fundraisers have an entire meal with potential donors. Drinks, appetizers, soup and salad, main course, dessert, coffee, and pay the bill. THEN, as they are about to leave, they spring the ask. That’s not helping the relationship either. Imagine how uncomfortable that is for the major donor. Major donors are people too, and they just want to be treated as a person, not an ATM. 

The #2 key to getting major gifts from a philanthropist is to choose who you ask and who you do NOT ask.

Here are some pro-tips:

  • Your research and relationship building should naturally result in a choice NOT to ask.
  • Organizations need to build a major gift funnel that allows them to feel confident in meeting their funding goals without relying on specific gifts from specific givers.
  • The discipline of asking only well-aligned givers who are aligned with your mission will result in more predictable results and happier development staff.
The #3 key to getting major gifts from a philanthropist is to remain focused on the WHY and make the donor the superhero.

Here are some pro-tips:

  • As mentioned in Part 1 of this series, we need to change our mindset and attitudes from “why wouldn’t someone support us?” to “why would someone support this cause?”
  • Remind the philanthropist what impact they will secure with their gift and make sure that impact is meaningful to them
  • Tell the philanthropist how you plan on reporting to them the impact of the gift during the ask, so they are confident that the impact of their contribution is secure.


Final Thought:

How you thank a donor for a gift is just as important as how you ask for it in the first place. Follow the thank you process I teach in the Fundraising Framework if you want to ask the donor for another gift in the future.