10 Common Nonprofit Major Gift Asking Mistakes to Avoid

When you’re not aware you’re making a mistake, it’s hard to avoid it.

So let’s get curious. I’m going to ask you to close your eyes for a minute to imagine a donor you’ve been wanting to ask for a major gift. I’m going to ask you to visualize a space where you’re meeting. Put them in your office, their home, a café or even a Zoom screen. Choose what’s comfortable, and where you think you’d be most likely to meet with this donor within the next month or so.

Okay… do you have your donor and your meeting space in mind? Excellent!

Now, before closing your eyes, commit to visualizing these four things:

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

SELF-EXERCISE: Okay, are you ready to close your eyes? Even if this feels a little weird, why not give it a try? (1) Pick your donor… (2) your meeting space… (3) your additional person supporting you in the room… and (4) open the conversation. What are you saying to them? What are they saying back? Don’t think in terms of pitching what they can do for you, but in terms of promising what you can do together. Play this scenario out just a bit, until you get to a place of comfort or discomfort. Then open your eyes.

What did that feel like?

What felt comfortable to you? Uncomfortable? Did it feel more comfortable and pleasant than you may have imagined?  Smiling people, committed to the same cause, hanging out in a comfortable space together…. 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 feel good, why?
• What might feel better?
• Do you think it might feel better to the donor too?

REFLECT and JOURNAL: Take a few minutes to quickly journal some answers to the questions posed above. Whatever comes to mind first is great; don’t overthink this. I guarantee this will help you shift the energy for the next time you move into this space – in real time – with a donor.

A Mistake is Just a Misjudgment

It’s not fatal; you can correct it. But first you have to recognize it happened! Mistakes in major donor conversations generally arise when you don’t know enough about the donor, or vice-versa. That’s why there are two kinds of major donor visits:

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 visit you’re intending to have so you can avoid some of the most common mistakes. If both you and the donor know going into the conversation that your underlying purpose is to discuss the mutual love you have for your organization and cause, there’s no reason you shouldn’t both emerge from the encounter feeling joyful and purposeful. Note, however, sometimes things will evolve rapidly and you may find you’ll want to make an ask when you thought you were just on a fact-find and relationship-building mission. That’s okay. Just be prepared to know what you’ll ask for should this situation arise.

Don’t Make the Mistake of Underestimating the Value of Asking for Major Gifts

The lion’s share of philanthropy comes from major gifts. So before you read further in this article, don’t make the one overarching lapse in judgment that will assure you raise significantly less than you could. If you think your organization is too new, small, unknown or unpopular to attract major gift philanthropy, disabuse yourself of this mistaken notion right now!

If you’re doing important work, and people are relying on you, you have the responsibility — and the privilege — to do what you can to generate funding that will move your mission forward. Even a few new gifts, or a few current major donor upgrades, can make a BIG difference to your bottom line.

There’s no more cost-effective fundraising strategy. You’ll find it’s so much easier than putting on an event (which are challenging at best right now), or sending a ‘shot in the dark’ grant proposal, or trying to raise an extra $100,000 by asking for $1 from 100,000 people! Plus it’s way more efficient in terms of dollars and energy spent. If you know how to generate these gifts, you’ll be in high demand throughout your nonprofit career. No matter what your role or job description, it’s going to help you to know the skills of identifying, qualifying, cultivating, soliciting and stewarding major gift donors.

Common Major Gift Asking Mistakes to Avoid

There’s much to learn to become an effective major gift fundraiser, but it’s not hard. I mean it! It’s just not something most of us are taught. Unless we’re super lucky to fall in with a good mentor, we learn from trial and error. I’m listing some errors below so you won’t have to try them and find yourself in an uncomfortable place. Of course, if you do make a mistake, it’s not the end of the world. There are plenty of ways to pick yourself up and start all over again. 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 and begin to build 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 VIP, most authoritative person, who can be trusted to spend the donor’s philanthropy effectively to get the job done, 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

Always ask the donor at the outset if there’s someone else they’d like to have join them. The point is that you’ll be putting on a bit of a dog and pony show; it just makes sense to perform the show simultaneously for everyone in the audience. 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 they’re eyes light up at the talk of cutting-edge treatments, research, volunteer services, parent support, publicity, recruitment, education or whatever else floats their boat.  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.

6. Mistake: Not Asking for a Specific Amount for a Specific Purpose.

In my experience, at least a majority of major donors prefer having a place to hang their hat. Some will give “where most needed,” especially for single issue charities, but many others want to be able to visualize how their money is used to help. In this way, they draw themselves into one of your charity’s most compelling stories and make themselves a hero who gives the story a happy ending. You can then report back to them throughout the year, keeping this story alive and reminding the donor of the joy they felt upon making the gift.

Asking for something specific is it makes it real. It brings the donor to the precipice of saying “Yes I’ll help so this will happen” or “No I won’t help so this won’t happen.” Putting the decision in stark black and white terms can help donors reach a decision point more easily than a giving proposition that’s simply: “Add more money to the pot to help us with the mission.” Note that any amount you ask for should be tailored to the donor’s giving history, capacity and existing linkages with your organization.

7. Mistake: Not Staying Silent after Asking for a Specific Gift

Donors need time to reflect; I recommend my own 17 second rule.  Somewhere in my career I learned that, at least in American culture, most people are uncomfortable after 17 seconds of silence. We’ll try to jump in to break that silence – at all costs.  Don’t!

There is an unspoken rule in sales: “Them who speaks first loses.” Make your ask; count quietly under your breath to get to 17 seconds. 99 times out of 100 your donor will speak before you do.  This is much better than jumping in prematurely with “Oh, if that’s too much, would you give less?” 

8. Mistake: Not Maintaining Eye Contact

It’s handy to bring a video, brochure or case statement as a prop. They can work, but only if you show them briefly and spend the majority of your time together chatting face-to-face. The last thing you want to do is read to your donor or stand behind the back of their head while they view your video on a computer screen. They can read to themselves! They can watch a video on their own too!

Connect with the donor the entire time you’re together. Leave the props as a take-away gift when you leave. This gives you an excuse to call again and find out what they thought about the materials. Hopefully do this eye-to-eye. If you’re phoning, use Zoom, GoogleMeet, FaceTime or Skype.

9. Mistake: Not Closing By Keeping Ball in Your Court

Have a plan for next steps and make it easy for the donor to join you. You might say “Thanks for all this great feedback. I’m going to go back to our program staff and get their thoughts, and also try to put some numbers to these ideas. When’s a good time for me to get back to you next week? Would Tuesday or Thursday this same time work?”

Whatever you do, don’t simply walk out the door having not secured a gift, a pledge to consider a gift, or a commitment to a subsequent meeting. Everyone in the room should have absolute clarity on what’s happening next, and you never want to be in the position of waiting by the phone. Take responsibility to recap next steps. Make yourself a primary next actor.

10. Mistake: Not Following Up, Both ASAP and Beyond

Whether the donor said yes, no or maybe, you need to thank them for their time. Don’t even give them five minutes to wonder if you enjoyed the visit. If you were on Zoom, immediately send them an email. Follow it with a handwritten note. If you met with them in their home, go outside and take a moment to write a quick handwritten thank you to drop in their mailbox. If you met with them at your office or a café, go back to your desk or car and dash off a quick email or text. These are just for starters.

Next you’ll want to send a quick email summarizing your discussion and outlining next steps. For donors who don’t read email, you can send a letter. Or even a text. Ask them their communication preferences. This follow-up piece shows the donor you were paying attention, and definitely want to keep the conversation going.

Continue to follow up on anything your promised. Talk to others on your team, get the donor’s questions answered, and make sure everyone within your organization is on board for whatever the next steps in the solicitation will bring. Get back to the donor to fill them in and facilitate the next meeting. If the donor had asked for time to consult with significant others, ask them for a timeframe and promise to get back to them on a specific date to check in.

Closing:

Humans make mistakes. That’s okay, as long as you learn from them. Now that you know these 10 major gift fundraising mistakes to look out for, hopefully you’ll move forward with grace and great success. Still… if you’re at all like me you may prefer to avoid mistakes by learning from mentors who’ve already been down that road.

Welcome to the Certification Course for Major Gift Fundraisers

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.’  I’m 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. 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 as a “Veritus Scholar” + 36 CFRE credits. If you want your E.D., Finance Officer or other program director to take this with you, there’s a companion Certification Course for Managers and Executives that will be running simultaneously. You can mix/match and register for both simultaneously to qualify for a group discount.

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Email me right away at claire@clairification.com for the group discount code or 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