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The Courage of the Lead Gift: A Demonstration of and Commitment to Core Values

There’s a special breed of donor, possessing courage, commitment and vision, who is capable of a lead gift in a major campaign. Most donors are not.

Often when asked for a major gift, the prospect responds with a question: “Who else has given?”

It’s a logical request from the prospect’s point of view. There’s a cascade of implicit questions behind the one we’re asked. Who among her/his peers is leading this campaign? Who else thinks that this is such a good idea that they’re putting good money into it? How many others are on this particular bandwagon? Is this some pet project of a Board member, or does it really have a chance of success? Is this the idea of somebody I really don’t like?

Many questions similar to these run through the minds of prospective donors –especially those slated for pre-campaign or early campaign leadership gifts.

I have often experienced a sense of insecurity among those titans of the business world and community when, early on in a campaign, they are asked for large sums of money — to become the lead donors in a worthwhile cause.

No one wants to be taken for a fool, or give money to a sinking ship. Even more, few want to be first on board whatever the circumstance.

Case statements, bank statements, peer solicitation, organization charts, testimonials, plans and tales of previous successes all play a role in convincing leadership to sign on. However, the largest motivator is always the list of those already signed on.

That’s why it’s so very important to embark on long-term development of the courageous few around each cluster of values represented by an institution.

Motivating those to lead, to put their name at the top of the list, to influence and directly ask others to support the cause, just doesn’t happen. This set of uncommon behaviors, even for wealthy people — especially for wealthy people, is one of the highest functions of the development officer and the head of the organization seeking support.

Often the signals given by the potential lead givers are subtle. The extra question, or the too long lingering over a minor point, or the lifted brow during a conversation may be actual signals of interest.

Sometimes the signals are blatant, but the first person to step up and offer to lead in a dramatic way may not be the right person.

Distinguishing between those on a charitable journey and those on an ego trip are also parts of the function of the major gifts person and those volunteers and staff close in.

I remember another kind of signal given. When asked by a new prospect, “How much to get my name on that wall?” I immediately saw red flags, big red flags and, they turned out to be a true and significant warning. The question didn’t stop me, but led to a series of activities and probes that determined the consistency of the original message.

The question I love to hear from a major gift prospect is “How can I help make this happen?”

That may lead to a progression of activities, of familiarizing the person with the project, of cultivation, of seasoning, of engaging in a long-term development with each person like this. The more we can do with this type of donor, the more we will ensure the future charitable leadership of the organization.

The idea of a quick fix for leadership usually doesn’t work. I remember going to a very wealthy person whom we thought “should” be interested in leading our campaign. He listened politely to our Board Chair, then matter-of-factly told us that if we elected him to our Board and awarded him an honorary doctorate, he would “consider” a gift.

Few good things happen quickly in leadership development if that leadership is to last.

Some may think that we left this gentleman just at the time we should have dug in and probed. After all, this was the first time we had talked to him. Perhaps they’re right, although, in this case, the ego trip manifested into blackmail.

It was a case, not of appropriate exchange of important values, but of “bid for my gift.”

There’s a big difference between cultivation and exploitation — either by the prospect or of the prospect. The difference tests and defines the professionalism and the ethical behavior of the development officer.

Courageous gifting doesn’t come easily; it is developed over many years and, very often, works out to be the right gift from the right person at the right time. To do this means planning, time, research, cultivation, involvement, and relationships with those capable of stepping up significantly.

The process again points out the long-term nature of the concept of “development.”

Often we are pushed to the expedient and the convenient, always to our detriment. It is so very important for us to understand that leadership is not a given, but often a contextual, situational, time-related function. Understanding this and then using the information over the long term will allow for the steady stream of leadership gifts required for significant success in our work.


Jim Toscano

About the Contributor: Jim Toscano

James V. Toscano

Jim Toscano is a principal in the consulting firm, Toscano Advisors, LLC, and an adjunct professor at the School of Business, Hamline University. Recently retired as president of the Minneapolis Heart Institute Foundation, the cardiovascular research and education center of Abbott Northwestern Hospital in Minneapolis, he is a past chair of the Minnesota Charities Review Council and board member of Minnesota Council of Nonprofits. Mr. Toscano served as chair and co-chair of the committees that produced the two editions of MCN’s Principles and Practices for Nonprofit Excellence, and is serving in the same capacity for the third edition in 2014.
With 50 years experience in nonprofit management, Toscano has served as consultant to hundreds of nonprofit organizations and served on over 50 nonprofit boards and commissions, many as chair. He has served as Executive Director of the World Press Institute, President of the Minnesota Museum of American Art and as Executive Vice President of the Park Nicollet Foundation. See his essays on many nonprofit and philanthropy topics at He is a graduate of Rutgers College and Yale University.

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