Making The Big Ask, Part II: Execution

Created By: Steve Orr
December 18, 2023

Your organization’s mission is important, and the more money you raise, the more you can do to advance that mission. Ambitious plans can’t happen on the scale they need to without the Big Ask.

The Big Ask is a science and an art. The science involves proven development strategies such as moves management, engaging events, and a solid case for support. The art calls upon people skills that develop with years of experience. It’s a sixth sense that enables you to be on the same wavelength as the donor. Early in your career, asking for money without providing a good or service in return will probably feel awkward, but make no mistake, donors are getting something for their money, and over time, you will come to recognize the look on the face of “satisfied customers” who get to see the impact of their generosity.

The first installment in this two-part series addressed preparation for the Big Ask. Here the focus is on flawless execution.

Make the ask in person.

We’re all busy, and it might be tempting to agree to a phone call or Zoom rather than an in-person meeting, but there’s no substitute for looking someone in the eyes. When you make the effort to show up at your donor’s office or at a nearby restaurant, you’re demonstrating your respect and appreciation. You’re also eliminating unwanted distractions and making space for small talk that helps to establish a personal connection. (Of course, small talk itself is an art, and if you’re not careful, it can veer into uncomfortable territory such as politics or world affairs.) The human factor is critical if the discussion turns to whether a donation is targeted to a specific program or can be used for general operations. Their emotional investment in your organization makes it more likely that they will want to support the people behind the work, the building they work in, and so on.

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Make it a conversation.

A Harvard Business Review article on making a great investment pitch observes, “The more senior your audience, we learned, the less you should rely on your deck and the more you should expect your pitch to be a conversation, showing your team’s authentic passion for the challenge or problem and their resilience for solving it creatively, together.” The same goes for the Big Ask. Both sides should have an equal share of the conversation. When possible, you might bring along an industry peer (from the board or beyond) who has made a substantial gift. Their endorsement of your “product” will carry more weight than anything you, as executive director or chief development officer, can do or say.

Ask for more than they’re expecting you to.

In my experience, donors are never offended when you ask for twice or three times as much as the research says they’re capable of. Instead, it helps them see a more ambitious picture of themselves as philanthropists. It might lead to aspirational naming opportunities that they hadn’t previously considered. Saying a higher number than they’ve ever heard before opens the door for further conversations about their philanthropic priorities and who they consider their peers to be. The prospect of blended giving puts these stretch donations within the realm of possibility.

Socialize the ask.

When you sit down with the donor, don’t “pop the question” too soon. As the prospect becomes more engaged with your mission, you might want to ease your way into the Big Ask by socializing the amount. Say something along the lines of, “We see you in the range of $5 million”—and then note the reaction without pursuing the matter further right away. We find consultants or other trusted intermediaries can be effective at the step of socializing the size of the gift, but no matter who’s doing the asking, they shouldn’t expect a yes or no right away.

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Stay in touch.

No matter how the Big Ask goes, don’t disappear after making it. When you stay in touch throughout the year and not just when it’s time for them to fulfill their annual commitment, you build trust and reassure them they matter as something more than a piggy bank. Mission-related communications as well as informal check-ins about family, business, or any common interest deepen the relationships that drive the business of philanthropy.

Mastering the art and science of the Big Ask takes experience and collaboration among your team and with trusted advisors. Orr Group stands ready to partner with nonprofit organizations to realize ambitious plans.

Steve Orr is the Co-Founder and Managing Partner of Orr Group. Steve draws from his investment banking and finance background to bring a problem-solving approach, a focus on metrics, and an outcomes-driven perspective to the nonprofit sector.