The Readiness is all: Preparing for Tough Questions from Major Gift Prospects

William J. Acton William J. Acton, Senior Partner at Advancement Partners

Over the past few days, I have met with three separate major gift prospects for three different schools, asking each about their interest in providing major gift support. Each person offered enthusiastic support for the school…but also shared a number of serious and complex questions.

I am a proud long-ago graduate of a small(ish) New England liberal arts college who majored in English. It's a rather quaint academic background, which, while valued, has offered me little in the way of practical, professional application in my years as a fundraising consultant. Sure, it helped a little in my first few years out of college when I taught high school English in an all-boys Catholic school. But even in those years as a teacher, it would have been more helpful to have had training in things like mob mentality and adolescent hygiene.

But every now and then something practical pops into my brain that I learned in college. Most recently, something Professor Callahan offered up in one of his scintillating lectures on Hamlet has cut through the fog of my college brain. I'll spare the reader all of Professor Callahan's brilliant insights, but rather hone in on one foundational theme of that Shakespearean classic. It is this:

There comes a time in all of our lives where we realize we just have to get on with it. That there is nothing we can do to control the actions of others, or the fate that God has ordained for us. But we can control ourselves. We can be prepared. We must be prepared!

"The readiness is all," Hamlet says to his good buddy Horatio. That’s what matters.

So too in the business of advancement and major gifts these days.

There is no way to control the actions, questions or concerns of others. The only thing we can control is being ready to answer those questions, handle those concerns.

It used to be simple to anticipate the questions prospects would want answered before they agreed to sign a pledge form:

  • What's the money for?
  • Who decided that?
  • What's your timeline for implementing these projects?
  • When do you need a decision on a gift from me?

But now, like an undergraduate degree in English literature these days, those kinds of questions seem rather dated and quaint. Over the past few days, I have met with three separate major gift prospects for three different schools, asking each about their interest in providing major gift support. Each person offered enthusiastic support for the school…but also shared a number of serious and complex questions. Questions they needed answered before they would begin discerning a pledge amount/decision. One even arrived with 8 questions in writing! A sampling of the questions that were proffered:

  1. What funding plans have been established to handle the increased operating costs this new facility will have on school operations?
  2. What plans are in place to cap projected building costs so we avoid the typical project “scope creep”?
  3. With local feeder school enrollments shrinking, what is the strategy to recruit more public school students and sustain our enrollment?
  4. With steadily increasing demand for tuition assistance, what is the five-year funding model for school operations?
  5. How will we attract and retain the best faculty? How will we pay them while maintaining affordable tuition pricing?

These days, we like to use the word investment instead of gift or pledge when we visit with prospects. Indeed, the questions prospects ask today – the issues and concerns that are on their minds – reflect the mindset of a prospective investor. They need to understand and then believe in the bigger picture, the vision, the plan. Often they need details, financials, contingencies that will support the plan. Yes, the case for support must be compelling and inspiring. But it also has to be grounded in factual, common sense planning. It has to be grounded in reality.

Back in the day, churches passed a basket during services and people tossed in their gift. So much for a case for support! Hard to ask a basket questions, right? Collection success was absolutely dependent on trust. Occasionally, churches would outline or buttress their case for support with an article in the church bulletin. Sometimes an inspiring speaker would deliver an oral appeal (and the case for support) from the pulpit before the basket was passed. I don't recall any opportunity for the congregants to raise their hands during any such presentation and ask a question, though.

My favorite church case for support was posted on a bulletin board I noticed as I entered the church for Saturday evening Mass. This Catholic church was located in a vacation locale, with the majority of the parishioners being seasonal cabin owners/renters. “The more you pay, the less I say,” the posting said. That evening Mass I attended clocked out at 27 minutes. The collection baskets were noticeably overflowing.

Trust is still an essential component of the major donor-school relationship. But it is not enough, it seems. In many ways, the element that works follows the mode of the old Russian proverb, made famous years ago by President Ronald Reagan: "trust , but verify."

A philanthropic decision still leans on emotion – things like trust, and faith and love for the institution. But with so many not-for-profits seeking support, donors are much more sophisticated, discerning and cautious in making their investment decisions.

"There's no loyalty anymore," one head of school recently said to me. I'm not sure that's true, but I do know this: if you're depending on loyalty to sustain your advancement operations, well, you're going to be out of luck. It's true that many people give back to a school out of loyalty and gratitude – appreciation for what the school did for them. And certainly that is wonderful and important! Let's all realize that the most important alumni cultivation that ever happened in a school took place years prior when those alums were students.

But transformational philanthropy comes from those who give forward. They may – probably do – already have those feelings of loyalty and gratitude. But before they move the decimal point on a pledge decision, they want a better understanding of the future. They have a few questions they want to clear up. Yes, they want to verify.

So preparation is all – before you ask! That used to mean making sure to have the case statement printed or the collection basket ready to go. But the kind of preparation required today is much deeper, requires more mindful forward thinking. Prospects are not being aggressive or "stalling" or avoiding commitment by asking these questions. They are doing all of us a favor by forcing us to be better planners and stewards.

Posted on: September 18, 2023

William J. Acton

William J. Acton

Senior Partner

A graduate of Loyola Academy (Wilmette, IL) and the College of Holy Cross (Worcester, MA), Bill has over 30 years of hands-on experience in organizational advancement, strategic planning, board training and capital campaign management. Prior to beginning his consulting career in 1993, he worked in development for Loyola Academy (running its alumni and annual giving programs) and then for Cardinal Bernardin at the Archdiocese of Chicago, as the first Director of Development for archdiocese’s four-school seminary system and then as the first Director of the Cardinal's Annual Appeal.

Over the past 22 years, Bill has specialized in capital campaign management, major gift solicitation, strategic planning and development operation re-engineering. Partnering with school leaders, he has personally engaged in over 4,500 major gift solicitation calls ranging from $5,000 to $10,000,000.

Bill lives in Elmhurst, IL with his wife Sheila. They are members of Old St. Patrick’s Church (Chicago, IL) and the proud parents of two adult daughters, Mary Alice – a development director at a Chicago Catholic grade school – and Margy, a Chicago-based sports physical therapist.