How to Overcome The Fear of Making a Major Gift Ask

The fear of asking for a major gift -- it's REAL. When I was just staring out as a major gift officer, I would think, how am I going to ask this person for a gift? What if it ruins my relationship with them? What if it ruins their relationship with my organization? What if they get mad at me? What if they say no? What will I do? How absolutely awkward and cringe-tacular will that be?

The internal monologue was incessant. The questions were valid and the only time that internal monologue actually shut down was after two things happened. First, I got my first "no." And guess what? I survived!  My relationship with the prospect remained intact, she still cared deeply about the organization I worked for, she still took my calls and visits, and she ultimately ended up making a $25,000 gift. The world didn’t end that day when she turned me down. Was there some embarrassment on my part? Yes, but it was only in my mind. She was lovely and graceful, and it ended up being a timing issue.

I get the fear, believe me. I understand when my major gift coaching clients tell me that they don’t want to pick up the phone, and that they just want to cultivate and pray to the philanthropy gods that a major gift arrives at their office one day. (By the way, that doesn’t happen.) Yes, fear can be debilitating, but here are some tips and tricks to get you past the fear and build your confidence.

Change Your Mindset About Asking for Major Gifts

First is to change your mindset. Most people think that asking for a gift is a withdrawal in the emotional bank account. It isn’t! Change that thinking. You are making a deposit. You are offering them an opportunity to help change the world and realize their philanthropic vision. Your organization might be the only one that can help them do that. Believe me, it’s a deposit, not a withdrawal.

The other mindset that is prevalent in our culture is that talking about money is taboo. We view financial matters as very private and discussing money can cause friction or tension.  When people begin talking about money, we start to hear the voices of our parents saying things like inappropriate, impolite, and insensitive. Here’s my take: you’re not asking your prospects about their wealth. You’re not asking your prospect how much money they make. You’re not asking your prospect how they invest their assets. You’re not asking how much they paid for their home.  You’re asking for their investment in a better world. They can work out the finances and how they will fund the gift.

Once you get past that asking for a major gift is a bad thing – whether it is going to hurt the relationship, make a withdrawal in the emotional bank account, or be impolite because it has to do with money, you’re getting closer to being the fierce major gift fundraiser I know that you are. We’ve covered a couple mindset shifts, now let’s talk about cultivation tactics.

Preparing Your Prospect For a Major Gift Ask

You need to prepare your prospect for the ask, and this is done during multiple cultivation visits. Before you ask for a gift, you need to know several things about your prospect. You need to know why they care about your organization and its mission.  You need to know what program or project gets them the most excited. You also need to know what their vision is for a better world and match that to your mission. You need to know their favorite memory with your organization. You need to know if your organization is in their top three charities. All of this knowledge will equip you to make the most compelling, personalized ask, and it will be easy for them to say yes!

These conversations are deep and meaningful, and they will happen over time. These conversations develop trust between you and the prospect. That trust will also serve you well when you go to ask for a gift. Here is a link to download my favorite 15 questions you must ask during cultivation. The answers to these questions will give you the roadmap for building and deepening the relationship and get you closer to the ask.

Knowing When It Is The Right Time to Ask for a Major Gift

Another issue that comes up with solicitation and I hear this question all the time…. How do I know it’s time to ask for a major gift? The answer is easy. When you’ve received permission to ask for a gift. I strongly believe in permission-based fundraising where you agree to next steps with your prospect at every meeting, on every call, in every conversation.

Here’s what I mean by permission-based fundraising. Before you end any phone call or meeting, you ask for next steps. For example, “Whitney, this coffee date has been so much fun. Would it be okay for me to call you next week to set up a tour of our new facility?” Or “George, this phone call was such a day-maker, could I give you a call in a couple weeks and set up lunch?” Or “Cheryl, the next time we meet, I’d like to talk to you about a gift to support the cardiac expansion. Could I call you next week to get it set up?”

The beautiful thing about permission-based fundraising is that you’re building and agreeing to next steps together. Everyone is on the same page. There’s no confusion. And, when you go to ask for a major gift, it won’t be a surprise, which is a good thing. 

Turning a No into a Maybe and a Maybe Into a Yes

First of all, if you’ve done all the things we’ve discussed, your chances of a 'no' are slim. You understand what makes that donor tick and what is important to them, you’re going to match your programs to the change they want to make in the world, you’ve built a sense of trust, they knew an ask was coming and agreed to the meeting. That’s perfect. However, if you get in the room, make the ask, and the prospect is non-committal, there are a few questions you can keep in your back pocket. These should be framed as open-ended questions that a prospect cannot answer with a yes or no answer.

The first example is to inquire if the program you pitched is the program that speaks most closely to their heart.  You can say, “Tim I know we’ve spent a lot of time talking about the enhancements to our after-school programming. Is this still the program you care most about or is there another area of our organization you’d like to support?” This will help you understand if you’re asking for the right program or project. It will also help you understand what is giving your prospect pause.

The second example is to inquire about the timing and amount of the gift. It might be phrased as “Mrs. Rodriquez, I thought $25,000 - $35,000 was a good range based on your past giving and passion for the new garden at the Church. Is my thinking correct?” Or you could phrase it like “Mrs. Rodriguez, we often have donors pledge their gift over 2-3 years, would that be helpful for you?”

The third way to understand why the prospect isn’t committing is to ask if there is someone else they’d like to chat with. You might say, “Dale and Tracy, I know you are dear friends with our board chair, David. Would it be helpful to have a meeting with you, me and him to talk through some options?” or “Dale and Tracy, I understand you might have some questions about the engineering program. Would it be helpful to set up lunch with Holly, our program expert, so you can ask more questions and make your decision?”

My hope is that these questions will serve you well when your prospect is teetering. I’ve used these questions hundreds of times and it helped me understand what the hang ups were and how to remedy them. These questions have helped me close millions of dollars, so please use them. They’ll also help take the fear away. These questions should completely shut down that nagging fear of being turned down. Because now, you can handle objections.