Making The Big Ask, Part I: Preparation

Created By: Steve Orr
December 11, 2023

I have spent about half my career in business and half in philanthropy, and the two sectors have more in common than many would suppose. Both have smart, talented, and driven people who strive for a competitive edge through innovation and collaboration. Both sectors are constantly changing, and the leading players are the ones most capable of adaptation. Perhaps the most surprising overlap between business and nonprofits comes with the alchemy of investment. In business, investments are made in order to generate a financial return. In philanthropy, the return takes the form of impact, but an investment is still an investment.

To secure a big investment for big impact, you need to make a ‘Big Ask’. As the old 80-20 rule (20% of your donors are responsible for 80% of your campaign) shifts to 90-10 or even 95-5, it is all the more important to get the Big Ask right. In this two-part series, I offer tips for an endeavor that some may find intimidating but upon which nonprofits depend. These points mainly concern individual donors rather than foundation grant-making, but the lessons apply broadly.

The first tips below involve the work that goes into preparation.

Do the research.

The individual with the capacity to make a principal gift in your organization is just that—an individual with unique motives for giving and a distinct set of values that the potential investment expresses. A recent Forbes article on attracting venture capital investors makes a similar point: “By familiarizing yourself with their investment thesis, you can think as they do and are more likely to find the VC aligned with your goals.”  Wealth screens and other tools will help you understand the person on the other side of the table, including but not limited to the financial outlook. If possible, you will also want to conduct informal research by talking to a donor’s friends and associates. It’s even better if you can discover motives and values through a direct conversation. Take, for example, the alumna of a prep academy. What experiences defined her education? Maybe it was athletics or a particular teacher who became a mentor. Everything you learn will inform the type and timing of the donation you are soliciting. 

>>>Seven Ways To Make Your CRM Work For Your Organization

Make blended giving easy.

Just as there are many ways to structure a business deal, a philanthropic gift doesn’t have to take the form of a one-off financial transaction. Planned giving is a mutually beneficial tool for structuring philanthropy, allowing for that annual gift to be complemented by investments related to the individual’s estate plan. Once donors of any age contemplate your organization in the context of their legacies, you are well-positioned to secure repeated and, hopefully, ever-larger investments to further your mission. Orr Group’s team of experts works with client organizations to identify the most advantageous planned giving vehicles. Charitable Lead Trusts and Charitable Lead Annuity Trusts are often effective, but it all depends on the situation.

>>>Redefining Campaign Success: The Transformative Role of Planned Giving

Involve your board.

The people on your board of directors should be champions of your cause and constant allies in your quest for investment. The board should be emotionally and financially invested in your mission. (This is especially true when you launch a campaign. When the time comes to test the campaign’s viability—it will probably still be in the quiet phase—leadership gifts will set you up for success.) In some cases, there might be somebody on the board who personally knows the prospect or who has a significant second-degree connection and valuable insight into how much to ask for and when and how to ask.

Develop the relationship.

Wealthy people are like everyone else, in that they have a basic need to be seen and heard. Many, in fact, feel this need especially acutely because of all the salespeople, major gift officers, and “friends” who value them for only one thing. They have heard all the nonprofit pitches already. They know why you’re there. And yet, if you take time to get to know them as people before asking for money, you might just stand a chance of breaking through their defenses. If you ask their opinions about, for example, the education of young adults or the opportunities for mitigating climate change, you’ll develop a deeper relationship that might just open their minds to your organization’s theory of change—and you might learn something in the process.

>>>How Stewardship Can Increase The Short-Term Benefits Of Your Planned Giving Strategy

Now that you’ve prepared for the Big Ask, you’re ready to execute on it. Check out Part II of this series, out now.

Orr Group applies a business mindset to help our nonprofit partners develop and execute impactful fundraising strategies. Get in touch to learn how we can help you raise money more effectively.

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.