5 Major Gift Meeting Mistakes to Avoid Before You Make the Ask

A successful major gift solicitation rarely begins when you ask for a gift. It begins well before that — with whom you invite to meet, how you prepare, what you learn about the donor, and the kind of relationship you establish.

Get these things wrong, and even the most compelling case for support can fall flat. Get them right, and you create the conditions for a conversation that feels less like a fundraising pitch and more like an opportunity to explore what you might accomplish together.

Before we get to the five mistakes, I’d like you to try a quick visualization exercise. Think of a donor you’ve been hoping to meet with about a major gift.

Imagine Yourself in the Room with a Donor

Picture the two of you together. What would make this meeting feel comfortable, engaging, and worthwhile for both of you?

So let’s get curious. I’m going to ask you to close your eyes for a minute and imagine a donor you’ve been hoping to meet with about a major gift. Picture the two of you together. Where are you meeting? In your office? At the donor’s home? Over coffee? Or perhaps on a Zoom screen? Choose a setting that feels comfortable and where you could realistically see this meeting taking place in the next month or so.

Okay, do you have your donor and meeting place in mind? Excellent!

Now, before opening your eyes, imagine these four things:

1. You’re in the room together.
2. You smile. They smile back.
3. Someone else is there with you. Imagine you’ve invited this person to join you. Who are they, and how does it feel to have them there to support you?
4. Bolstered by the smiles and good company, what do you say to open the conversation?

SELF-EXERCISE: Ready? Close your eyes and picture your donor, your meeting space, the additional person supporting you, and how you’ll open the conversation. What are you saying? What might the donor say in response? Don’t think in terms of pitching what they can do for you, but of promising what you can do together. Play out the scenario just a bit, until you reach a place of comfort — or discomfort. Then open your eyes.

What did that feel like?

What felt comfortable? Uncomfortable? Did it feel more pleasant than you imagined? Smiling people, committed to the same cause, spending time together in a comfortable space… from such a space can come many good things.

• What did you say to open the conversation?
• How did that feel?
• If it felt good, why?
• If it didn’t, why?
• What might feel better?
• Do you think it might feel better to the donor, too?

REFLECT AND JOURNAL: Take a few minutes to jot down your answers. Whatever comes to mind first is fine; don’t overthink it. This simple exercise can help you shift the energy you bring to your next donor meeting — in real time.

A Mistake is Just a Misjudgment

It’s not fatal; you can correct it. But first you have to recognize it happened!

Many mistakes in major donor conversations arise because you don’t know enough about the donor — or the donor doesn’t know enough about you. That’s why it’s important to understand which of two kinds of visits you’re planning:

1. The “Getting to Know You” Visit
2. The “I’ll Make You an Offer You Won’t Want to Refuse” Visit

Know going in which kind of visit you’re intending to have.

This helps you set appropriate expectations for both yourself and the donor. If you’re there to explore your mutual interests in the organization and cause, make that clear. The goal is for both of you to leave feeling you’ve had a worthwhile, energizing conversation.

Of course, conversations don’t always follow a script. A fact-finding and relationship-building visit may evolve into an opportunity to discuss a gift. That’s fine. Just be prepared. If the donor signals they’re ready to talk about making a commitment, you should know what you’d like to ask for.

Five Common Mistakes to Avoid Before the Ask

There’s much to learn to become an effective major gift fundraiser, but it’s not as hard as you might think. Most of us simply aren’t taught how to do it. Unless we’re lucky enough to learn from a good mentor, we often figure things out through trial and error.

I’m sharing five common mistakes so you won’t have to make them yourself — or find yourself in an uncomfortable situation before you’ve even gotten to the ask. And remember: mistakes aren’t fatal. You can learn from them, correct course, and do better next time.

Let’s get started!

1. Mistake: Not Asking to Meet

People are largely social creatures. They welcome human contact, especially around an issue of interest to them. Generally you won’t be calling major donor prospects cold. You’ve likely identified them because you already know something about them. They’re aware of what you do, interested in what you do, possibly actively engaged (e.g. as a volunteer, parent, patient, member, ticket buyer, newsletter subscriber, etc.) and even invested as a mid-level or major donor. Your goal is to learn more about them, discover what matters to them, and begin building a human relationship. Donors are people first, donors second. The more they feel a human bond with you, the more likely they are to be receptive to a philanthropic solicitation.

You want to meet personally because there’s no substitute for face-to-face contact. This used to absolutely mean getting out of the office for a visit. Yet post-pandemic we’ve learned meeting face-to-face across a screen can also work surprisingly well. If this is your choice, make sure you both turn your cameras and microphones on. You want to be able to check in with the donor’s energy and body language. And they yours. You can’t do this through an avatar. Smile as you talk. Lean forward. Let your passion shine through. Passion is contagious – and you want your donor to catch it!  Also be alert to the places where the donor’s energy flags or shifts. If they seem bored about a topic, switch to a new one.

Ask open-ended questions about what’s really troubling them in your area of work right now?  Ask if they can imagine possibilities for improvement? If their energy suddenly turns positive and energetic, ask them more about how they’re feeling now. Help them to feel part of the solution as they take greater ownership of the problem.

2. Mistake: Having the Wrong Philanthropy Facilitator in the Room

Donors must feel comfortable in order to trust this meeting will be worth their while. Sometimes you’ll want to invite another person, or even persons, to join you. Generally, there are two people who can make them relax:

(1) The person with the greatest authority and credibility, who can be trusted to use the donor’s philanthropy effectively to get the job done; and and

(2) The person with whom the donor has the best relationship.

Sometimes these two roles can be played by a single person. Consider your options, and use your judgement so you don’t overwhelm your prospect. Board members, for example, play a powerful, almost magical role in offering “social proof” testimony. Other donors and volunteers can do the same. Similarly, the doctor who saved the donor’s daughter, or the teacher who was instrumental in the donor’s career, can join you as an admired VIP.

A board member who is close to your donor, and can make a comfortable introduction to you or your E.D., is a good place to begin.  If you do bring in a board member, other donor or volunteer, make sure they’ve already made a stretch gift themselves. It doesn’t have to be a million dollar gift to ask for a million dollar gift. But, for this volunteer, it must be equivalent  in meaning as the size gift you’re asking for from the donor. When they can testify this is the “largest philanthropic gift I’ve ever made,” that goes a long way towards vouching for your charity’s worth.

An admired VIP who is trusted by the donor is an excellent choice. When the donor feels gratitude, or has already built a positive relationship, these are traits upon which to build ongoing and deeper connections. And, yes, sometimes it’s the director of development or major gifts officer who has already built a relationship with the donor.

3. Mistake: Having the Wrong Donor or Donor Representative in the Room

When arranging the meeting, ask the donor whether there’s someone else they’d like to have join them. 

It just makes sense for everyone involved to hear the same information and have an opportunity to participate. Otherwise you’re likely going to have to go back and do this again.

Often the added donor representative will be a spouse, adult child or other significant family member or friend. Sometimes it will be a caregiver or a financial, legal or philanthropic advisor.

4. Mistake: Beating Around the Bush

Go into the meeting knowing your purpose and making this purpose clear to your donor as well.

If you’re going to be asking for feedback and advice, make this clear in your invitation. If you’ll be wanting to discuss their philanthropic interests, also make this clear. I prefer to let the donor know we’re going to touch on both of these things. Donors know what these visits are all about, and you don’t want to get into the realm of “bait and switch” where you say you’re coming just for advice and rush immediately to asking them for a gift. They’ll feel betrayed in such a case – and you can say farewell to all the trust you’ve been building over months of cultivation.

Once you’re there, and have chit-chatted for a minute or two, introduce the primary subject of your meeting. If you don’t do this, they’ll feel one or more of the following:

• I’m anxious. I thought they wanted my advice… is this about something else?

• I’m anxious, I thought they would ask me for a gift. Am I not important enough?

• I’m annoyed. All they’re doing is talking about their needs; they don’t seem to care about what I think.

• My time is being wasted… I’m getting annoyed.

5. Mistake: Not Asking about Philanthropic Interests Sooner Rather Than Later

Again, the donor knows what this is all about.

Your job is to meet their expectations, yet to do so in a manner that is enjoyable beyond their wildest expectations. Rather than say “It’s time for me to hit you up for a gift this year,” instead try “I’m wondering what your philanthropic priorities are this year.” Let the donor lead you towards their area of greatest concern and passion. That way you’ll know specifically what most floats their boat – so, when it’s time to ask, you can ask for a gift for that purpose.

Putting the topic of philanthropy out on the table early also gives you ample time to discuss it and answer donor questions. Let’s say you have a draft proposal and plan to use it as a jumping off place for discussion. There are many directions to take this. For example, if you’re asking for a gift for your hospital capital campaign, and you’ve ascertained the donor really cares about children’s issues, you can then talk about a whole range of needs for your new children’s wing and programs.  See if their eyes light up at the talk of cutting-edge treatments, research, volunteer services, parent support, publicity, recruitment, education or whatever else captures their imagination.  After that, you can begin penciling in some ideas around things that may be needed, offering to get back to the donor at a future visit with more details and associated costs. 

Before You Make the Ask, Build the Relationship

A major gift meeting isn’t just an opportunity to present your organization’s needs. It’s an opportunity to understand what matters to the donor, discover where your interests intersect, and begin imagining what you might accomplish together.

When you’ve established that common ground, you’re in a much stronger position to move toward a solicitation. But making the ask brings its own challenges.

In Part 2, we’ll look at five mistakes that can trip you up when it’s time to actually ask for the gift — and how to avoid them.

Welcome to the Certification Course for Major Gift Fundraisers

I’m again partnering up with The Veritus Group to offer you this amazing online course — 8 modules over 13 weeks, and after that you’ll never look back.

This is the best way to avoid all the frustrating trial and error that comes from not having the best teachers in the business from the ‘get go.’  You’ll get more than you can imagine in a combination of readings, podcasts, webinars, live phone-in calls, peer group conversations, individual check-ins and even a free data assessment if you wish. Plus, at completion, you’ll receive a major gifts certification + 29 CFRE credits.

Email me at claire@clairification.com with any questions. I’ll respond personally with honest answers. I hope you’ll join us! This course is worth it, and you’re worth it!  Thanks for all you do to create a better and more caring world,

Claire

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