The Fundraising Executive

FALSE ASSUMPTIONS: Even Long-time Pros Can, and Do, Make Consequential Mistakes

Grant Whitney joined Harvard University’s Faculty of Arts & Sciences and served there for over 20 years, leading the university’s largest planned gift recognition effort—responsible for enrolling more than 1,000 alumni and friends as new members of the John Harvard Society over the course of the university’s $9.2 billion campaign (2018).

Grant joined Massachusetts General Hospital in October 2022 and now provides vision and leadership for a team of 11 professionals across the full range of planned giving activities. He earned his J.D. from Albany Law School of Union University and his undergraduate degree from Cornell University. I’ve known Grant for years and had the privilege of serving with him on the Board of Directors for the National Association of Charitable Gift Planners.

Even the most seasoned gift-planning professionals can make mistakes with donors based on assumptions about what others, with longer and more entrenched relationships, should have done. “That’s no excuse,” Grant is quick to add. “Gift planners should make sure that donors’ best interests are achieved, but sometimes where that line is, isn’t as clear as one thinks.” The following story is repeated here with Grant’s permission.

My question: In every Industry Icons online interview, I ask: “Looking back over your 20+ year career and all the donors with whom you’ve worked, was there a fundamental mistake you made, and if so, what did you learn from it?”

Grant’s reply: “There is one oversight with a donor that was so significant, I tell this story every chance I get; with a colleague, in every seminar and presentation to gift-planning professionals, major donors and volunteers. I always offer it up as a cautionary tale, even though ultimately, it ended positively and as far as I know, the donor remains connected with the University to this day.


Grant Whitney: I was working with a prospect who was new to philanthropy. It was a completely foreign world to him. He had multiple degrees from Harvard—undergraduate, Law School, and the Kennedy School of Government. He practiced international law, served in the U.S. State Department and in industry. This potential donor was a person of great influence, a person who was highly respected in his field.

The donor decided to make a $1 million gift as his first foray into charitable giving. It wasn’t a planned gift per se but an outright gift commitment. Because of his time in the State Department, we had a signing ceremony analogous to what sovereign nations might arrange to solemnize a treaty. It was important that his first major-gift experience be positive as a catalyst to nurturing a relationship with the institution for the long term.

It was important that his first major-gift experience be positive as a catalyst to nurturing a relationship with the institution for the long term.

The $1 million pledge was payable over five years. The first installment was received in six months; the second, not due for another year, was received six months later. The third installment was received at the 18-month mark. In terms of his gift commitment, he was “way ahead of the game.”

His first major gift was a demonstration of his integrity, his commitment to its purpose, as well as his philanthropy. He was a poster child for a committed donor. There was a lot to celebrate about our enthusiastic donor.

Until suddenly it wasn’t.

At the time, the donor was working for a large, cloud-based software company. Most of his assets were stocks and negotiable securities. He had bankers and brokers at institutions and firms too big to fail. At the $600,000 mark, again, well ahead of the payment schedule, my phone rang. I answered, recognized his voice, and then couldn’t get a word in edgewise for another 45 minutes.

I was “raked over the coals” as the donor confronted me over what he saw as a failure of my responsibility to him. The donor revealed that he had been selling significantly appreciated stock to fulfill his commitments to Harvard. The cost to the donor in capital gains tax alone could have approached six figures.

Despite having a cadre of advisors, presumably some with fiduciary status in relationships going back years that this donor looked to for financial advice, they were either unaware of his gifts to charity or “asleep at the wheel.” Was it my job to involve myself with the donor’s financial advisors and instruct them what made the most sense for him to give? It should not have been, but that didn’t matter. The optics of a gift made ineffectively taxwise, didn’t paint gift planning in a favorable light or sweeten his experience in this inaugural foray — at scale — into philanthropy.
Though it was not my fault—at least not technically—it was my responsibility. Once he agreed to the pledge amount, I could have thanked him and then asked whether he had given thought to how he would satisfy it. That question might have opened the door to a conversation about the value of giving long-term appreciated securities over cash. I should have outlined and confirmed his understanding of the most effective giving strategy. Though this incident happened years ago, I tell the story at every alumni event or to every new member of my gift-planning team.

I should have outlined and confirmed his understanding of the most effective giving strategy.

Years later I was making a presentation to a group of Harvard donors and volunteers at the Harvard Club in New York City. It has a classic old-style décor; rooms of dark mahogany complete with animal heads mounted on the wall. It’s quintessential Harvard, reflecting the institution’s 388-year tradition.

I shared the story of this $1 million donation gone awry. I got to the moment of that phone call and asked the attendees why I might have been on the receiving end of the donor’s anger.
That question hung in the air for what seemed a long time.

Eventually, a brave soul asked, “Did he sell the stock and give you the cash?” A collective groan accompanied this revelation.

After my talk, I was scheduled to have lunch with a donor/volunteer who attended. I found him in the crowd and confirmed that we were still on. But I noticed he was distracted, and looked positively green, like one about to faint. “Are you okay?” I asked. “Do you want to reschedule?” I asked.

“Grant, I’m fine,” he said though not very convincingly, shaking his head. “I just realized in the last installment I made towards my scholarship fund, I used cash. What was I thinking?”

Postscript for the curious. The story of this donor who taught me a valuable lesson of never making assumptions has a happy ending. Not only did he complete his pledge in record time – tax effectively, not long thereafter he included the College in his estate plan, becoming a John Harvard Society member too.

Grant’s consequential mistake serves as a poignant reminder of the pitfalls of false assumptions, even among seasoned professionals. As gift planners, our job is to navigate the intersection of philanthropy, financial planning, and donor relations, which can only be achieved through communication and proactive engagement. Grant has reminded me that while missteps may be unavoidable, how we respond and adapt is what shapes the trajectory of our charitable giving relationships.

Eddie Thompson, Ed.D., FCEP
Founder and CEO
Thompson & Associates

“If we merely aim for the industry standard, then our goal is mediocrity. Emulating the average nonprofit, we are destined to live with all the problems the average nonprofit faces. So, we suggest you aim to be exceptional in your approach to fund development.”  —Eddie Thompson