The Courage of the Lead Gift

The Courage of the Lead Gift

  Post by James  V. Toscano

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 someone 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.

Major Donor Insecurity

I have often experienced a sense of insecurity among  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 for a worthwhile cause.

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

Case statements, bank statements, peer solicitations, organizational 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 on board.

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,  doesn’t just 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 giver are subtle. The extra questions, or the too-long lingering over a minor point, or the lifted brow during a conversations may be the actual signal of interest.

Sometimes the signal is blatant. 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 part of the functions 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 warming. The questions didn’t stop me, but led to a series of activities and probes that determined the motivation of the original question.

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  long-term cultivation of 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.

Quick Fixes?

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 a honarary 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 not the first time we had talked to him. Perhaps they are right, although, in this case, the ego trip resembled 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 ethical behavior of the development officer.


Courageous gifts don’t come easily; they are developed over many years and, very often, work 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 out work.
Copyright 2011, The Good Counsel, division of Toscano Advisors, LLC. May be duplicated with citation.

  1. […] 6.   Lead gift. One, better more than one, lead gifts should be secured before launching the organized effort. (See my posting “The Courage of the Lead Gift”) […]

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