A wise investment of time: Practicing the ask

One of the most universally applicable statements is: Practice makes perfect.

Ask any athlete, performer, or highly skilled professional, and they’ll tell you their success is based on rehearsal, preparation, and practice ad nauseam. Maybe, they won’t achieve perfection, but they certainly will improve, become more polished, and more confident in their respective crafts.

Malcolm Gladwell in Outliers popularized the “10,000-hour rule” which is the idea that it takes 10,000 hours of intensive practice to achieve mastery of complex skills and become world-class at something.

I’m not calling for 10,000 hours, but it sets them up for failure when so many of our nonprofit leaders, board members, and volunteers are sent out to raise money without any training or exposure to what a genuine solicitation looks like.

The primary reason that so many non-profit leaders are terrified of asking in person is because they’ve never observed or even experienced a genuine solicitation themselves. They are afraid of the unknown, which is another universal truth.

It doesn’t need to be this way. As professional fundraisers, our job is to demystify the art and science of fundraising for management, board, campaign committee members, and others partnering in developing resources. Staff will also benefit greatly from practice, especially as they work together with board members and volunteers on cultivating and soliciting prospects.

The first step in the training process is having new board members experience a first-rate solicitation themselves as part of their onboarding. They should be rated like prospects, and leadership such as the board chair, development chair, CEO or director of development should meet with them privately and ask for an annual gift at a stretch but realistic level. This will not only bring in important dollars but provide a great introduction to a proper ask.

I wince when I hear about such solicitations being made during a board meeting or even right before or after it. All gift solicitations should be conducted in private settings and allow ample time.

Before going any further, I need to emphasize there’s a big difference between “getting” and “asking for” gifts.

In getting a gift, the donor entirely determines the timing, amount, and purpose. In asking for gifts, the nonprofit proposes the timing, amount, and purpose and much more directly determines the outcome.

Too many nonprofit leaders are only familiar with the passive act of getting gifts.

Every nonprofit should commit time to training its board and volunteers about fundraising principles, strategies, and best practices. This starts by emphasizing that they can contribute mightily to success without ever asking for gifts themselves and play meaningful roles in the discovery, cultivation, and especially stewardship of donors. When the time is right, staff or other board members can step in to ask for the gift.

Training should also open with a frank discussion among board members and volunteers that it is perfectly normal to be afraid of asking. Most people are. They are far from being alone. It is very instructive to hear from peers how they overcame such fears.

Nonprofits need to highlight role-playing exercises during their meetings. If management and board leadership don’t feel they can lead the training themselves, it might make sense to bring in an outside consultant to lend third-party credibility.

Role-playing the ask can even be fun when you come up with scenarios and donor personalities that mimic the probable prospect pool, such as corporate leaders, successful entrepreneurs, and other affluent members of your community.

Role-playing exercises can help you with the following elements:

1. Explain the gift evaluation rationale based on capacity, philanthropic nature, and affinity for the cause.

2. Simulate teams typically combining board and staff members. I strongly recommend that there should never be more than twice the number of solicitors as prospects in a meeting.

3. Rather than word-for-word scripts, come up with simple talking points that each board member or volunteer can personalize. At a minimum, it needs to be very specific on who makes the ask and when to make it during the meeting.

4. It’s important to address the time management challenges that arise with solicitations. Here is an effective formula for a 45-minute meeting:

• Five minutes (maximum): Opening pleasantries
• Five minutes: Presentation of the problem or challenge being addressed
• Five minutes: Compelling arguments on how the request responds to the problem/challenge
• Two minutes: The ask
• 20 minutes: Responding to questions/concerns 
• Five minutes: Wrap up/next steps

5. Make sure your ask itself isn’t complicated. Ask for a specific amount for a specific purpose, then remain silent. Too many asks are compromised by nervous solicitors who break the silence, and worse yet, lower the amount requested.

6. Prepare for possible questions or concerns from your donor prospect. These can and should be anticipated. Typically, they center around four areas:

• The organization
• The project
• The amount
• The timing

It’s far from a death blow to tell the donor you need a little time to research their question(s). This provides a natural basis for a follow-up meeting and bringing the ask to closure.

7. Utilize sample question-and-answer guides as a smart resource to prepare for your donor prospect meeting.

8. Take advantage of virtual asks, done primarily through video conferencing and chats, which grew in popularity because of the coronavirus (COVID-19) pandemic and the need for social distancing. They worked well with donor prospects already familiar with the nonprofit’s mission. However, meeting virtually can be more exhausting for everyone involved. In general, virtual meetings should be planned for two-thirds the length of a live meeting.

9. Remember to take charge of the agenda and pace of the meeting while giving your donor prospect the majority of talking time. This is commonly referred to as “active listening.”

10. Know that most solicitations don’t culminate in an immediate result right out of the gate. Prospects ask for more time, especially with major gifts, to discuss the request with family members, financial advisors, and others. It is crucial to set a specific date and time to get back together.

Ideal follow-ups consist of both a brief email summarizing the ask and next steps, plus—my personal favorite—a handwritten thank you note sent via snail mail that really helps you stand out.

Group critiques of role-playing will help board and staff members learn from each other and be better prepared.

There are huge returns on devoting time and energy to rehearsing asks. Frankly, I can’t understand how nonprofits can send board members and volunteers on fundraising calls without strong preparation.

Of course, the best practice comes from real solicitation experiences. Board members who haven’t asked yet can learn much by accompanying an experienced staff or board member during a solicitation.

There is nothing like getting a few actual solicitations under your belt. Asking for gifts is the ultimate continuous improvement cycle, and you learn something every time, whether the response is yes, no, or “I need more time to think about it.”