Top 8 Nonprofit Major Gift Asking Blunders

A blunder is a careless mistake. It happens when you don’t 100% have a handle on what you’re doing, so taking good care becomes challenging. Have you ever blundered into disaster asking for a major gift? Let's review the top eight blunders I have encountered.

1. Not Finding Time to Visit Personally

There’s no substitute for face-to-face contact. Whether you physically get out of the office or meet across a screen, your advantage with a visit is being able to check in with each other’s energy and body language. Smile as you talk. Maintain eye contact. Lean forward. Let your passion shine through. Passion is contagious — and you want your donor to catch it! 

Also, be alert to when the donor’s energy shifts. If it suddenly turns positive, ask more about how they’re feeling now. If they seem bored about a topic, switch to a new one. Ask open-ended questions. What keeps them up at night? Is there something your organization does that can help? Help donors feel part of the solution as they take greater ownership of the problem.

2. Not Asking About Philanthropic Interests Sooner

Often a “No” means “No.” Put the topic of philanthropy on the table early to give ample time to discover donor passions. Don’t waste your entire meeting talking about something that doesn’t interest your donor. Find out what they care about most! Don’t begin with “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.” That way, when it’s time to ask, you can ask for a gift for that purpose.

There are many directions to take a proposal you create as a jumping off place for discussion. For example, if it’s a hospital capital campaign, and you’ve ascertained the donor cares about children’s issues, discuss a range of needs for a children’s wing and related programs. See if their eyes light up with the mention of cutting-edge treatments, research, volunteer services, parent support, education or something else. Then begin penciling in ideas and offer to get back to the donor with more details and associated costs at a future visit.

3. Not Asking for a Specific Amount for a Specific Purpose

A “No” may mean “No,” “Not this amount” or “No, not absent a specific aspect of the project.” Some major donors will give where most needed, especially for single-issue charities, but many want to be able to visualize how their money is used to help. Asking for something specific makes it real.

Putting the decision in stark, black-and-white terms can help donors reach a decision more easily than a giving proposition that’s simply: “Add more money to the pot to help us with the mission.” In this way, they draw themselves into one of your charity’s most compelling stories, making themselves a hero who gives the story a happy ending. You can then report back throughout the year, keeping this story alive and reminding the donor of the joy they felt upon making the gift.

4. Not Cutting to the Chase

Go into the meeting knowing your purpose and making this purpose clear to your donor. Be clear that you plan to ask for feedback and advice, and/or discuss their philanthropic interests. I prefer to let the donor know we’re going to touch on both of these things. You don’t want to get into the realm of bait and switch where you say you’re coming just for advice and then unexpectedly ask for a gift. 

Similarly, you don’t want a donor expecting an ask that never comes to feel you’ve wasted their time or, worse, they were important — or rich — enough to ask. A little small talk is swell, but remember your purpose: to secure a major gift! When you don’t meet donor expectations, they’ll feel betrayed — and you can say farewell to the trust you’ve been building over months of cultivation.

5. Not Staying Silent After Asking

Once asked, donors need time to reflect. I recommend my own 17-second rule. 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! Make your ask; count quietly under your breath to 17 seconds. Ninety-nine 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?” There is an unspoken rule in sales: Whoever speaks first loses.

6. Not Having the Right People in the Room

Include whoever will make the donor feel comfortable. Generally, two people can help them relax though sometimes a single person plays both of these roles:

1. The most authoritative person who can be trusted to spend the donor’s philanthropy effectively
2. The person with whom the donor has the best relationship (e.g., director of development or major gifts officer; board member or friend; doctor who saved the donor’s daughter; or trusted teacher).

If a board member can make a comfortable introduction, that’s a good place to begin. Board members play a powerful, almost magical role in offering social proof testimony. Make sure askers have already made a stretch gift themselves. It doesn’t have to be a tit for tat, but when they can testify “this is the largest philanthropic gift I’ve ever made,” that goes a long way toward vouching for your charity’s merit.

On the donor side, always ask if there’s someone they’d like to have join them. It could be a spouse, adult child or caregiver. Sometimes it will be a financial, legal or philanthropic adviser. The point is you’re 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 it again.

7. Not Closing by Keeping the Ball in Your Court

Have a plan for next steps, and make yourself a primary next actor. You might say, “Thanks for this great feedback. I’m going to get our program staff members’ thoughts and put some numbers to these ideas. When is a good time for me to get back to you next week?” Whatever you do, don’t walk out the door having not secured something (a gift, pledge to consider a gift, commitment to a subsequent meeting or permission to be sent additional information). Take responsibility to recap the next steps. If the donor has asked for time to consult with significant others, ask them for a timeframe and promise to check in with them on a specific date.

8. Not Following Up — Both ASAP and Beyond

Whether the donor said “yes,” “no” or “maybe,” thank them for their time. If you were on Zoom, immediately send them an email. Follow up with a handwritten note. If you met with them in their home, go outside and 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. 

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

Humans make mistakes. That’s OK as long as you learn from them. Hopefully, you’ll move forward with grace and great success. The good news is we can learn from mistakes.