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How to Connect with Donors

Thomas Wolf


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Acclaim for
How to Connect with Donors and Double the Money You Raise

“Story by story, this book is brimming with wisdom. Inspiring but practical, rooted in long experience but immediately applicable, it proves Tom’s point: that fundraising is all about building relationships.”

            - Rushworth M. Kidder, President
            Institute for Global Ethics
            Trustee, Charles Stewart Mott Foundation

“Tom Wolf focuses on the relationship side of fundraising, and therefore provides welcome relief as the craft becomes increasingly metric-oriented – the number of calls, meetings, asks. He provides great encouragement to use more imagination, time, and care in connecting to people.”

            - Christine W. Letts, Senior Associate Dean
            Rita E. Hauser Senior Lecturer in the Practice of Philanthropy and Nonprofit Leadership
            Harvard Kennedy School

“How to Connect with Donors provides us with the insights we all need to be at our best and at our most effective. Tom gives us his best with a light and humorous touch.”

- Tony Woodcock, President
            New England Conservatory

“With colorful and provocative stories Tom Wolf reminds us that fundraising is an art not a science. It is about people, not about institutions. When did you last enjoy a book about asking people for money?”            

- Michael Marsicano, President and CEO
            Foundation for the Carolinas

“The stories in How to Connect with Donors and Double the Money You Raise vividly provide examples of what makes for a successful fundraising effort and a successful fundraiser.      

  - Jeffrey P. Bonner, Ph.D
            Dana Brown President & CEO
            Saint Louis Zoo

“Tom Wolf addresses the practical and ethical dilemmas and unexpected joys of fundraising with candor and wit.”

- Paul Brest, President, William and Flora Hewlett Foundation
Dean Emeritus, Stanford Law School

“Tom Wolf compresses decades of experience into a very salient and easily read presentation. It’s particularly valuable for the volunteers who are the foundation of fundraising for most not-for-profit organizations.” 

  - David F. Hales, President
            College of the Atlantic

“Fundraising is always about two things: relationships and storytelling. Tom Wolf understands both, and he has the skill as a storyteller to put the importance of relationship into just the right narrative context.”

- Maxwell King, Former President of The Heinz Endowments and Chair of the Board of The Council             on Foundations

“Practical, funny, clear, innovative – Tom Wolf’s book is all these things and more. His real world experiences demystify the art of asking for money and remind us that giving always starts with the heart.”  

           - Lee W. Salter,  President & CEO
            The McConnell Foundation


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Interview with Thomas Wolf

In essence, your book is about cultivating donors. Other than sending the obligatory birthday card and special event invitation, what’s involved?

For my most important donors, I’m aware of the shape of their lives -- their states of health and that of their spouses, when a child will be graduating from school, when a donor has been honored with an award that merits a congratulatory call. I sometimes make condolence calls and attend memorial services.

Not every donor receives this level of attention. It’s all about getting to know people and learning what will make a difference to them. Then it’s calibrating the level of effort to the likely level of support.

The biggest misperception people have about donor cultivation is …?

That it’s like pushing the right button to get the desired result. I think of the riddle of the three doors. If you choose the right one, you get the wish of your dreams; open one of the wrong doors and you’re doomed. Donor cultivation is often thought of that way – if I only say or do the right thing at the right time, the money will flow. If I say the wrong thing, all is lost. But cultivation is about relationship building and even if you start off on the wrong foot or say the wrong thing (as I’ve done often), time and effort will often pay off, literally and figuratively.

Is there a difference between cultivating and schmoozing?

I love to schmooze and it’s part of the process. For example, one thing I almost always ask people is where they’re from. I’ve travelled a good deal so even an innocuous question like that can lead to something. Yesterday I learned that an individual I’d just met was from a small town in Wyoming famous for its proximity to a great fly fishing river. At some point I asked whether he’d ever done any fly fishing and it turned out that as a young man, he’d been a fishing guide and it had been a formative experience. We spoke for almost half an hour about something that was tremendously important to him. Is schmoozing important? You bet. But it’s only the beginning of a much longer process of relationship building.  


OF RELATED INTEREST: A watershed book, The 11 Questions Every Donor Asks prepares you for the tough questions you’ll inevitably face from prospective donors. Harvey McKinnon identifies 11 such questions, ranging from “Why me?” to “Will my gift make a difference?” to “Will I have a say over how you use my gift?” And the suggested answers are illuminating. Whether you’re a board member, volunteer, or staff, your ability to respond to these 11 questions will largely determine your fundraising success.

A lot of board members think they can sort of “quick-cultivate” a prospect – you know, bring a wealthy person on board as their campaign heats up and then ask for a sizable gift. Does that ever work?

I won’t say “never.” I have seen new prospects come to an event or activity – especially one that may involve kids or needy individuals – witness some transformational experience, and write a check on the spot. But most major donors are more deliberate and careful. They want to get to know an organization, and especially the people within it, before giving anything significant. With endowment gifts, the level of scrutiny will be even greater. After all, such gifts presuppose a healthy and thriving organization for a very, very long time.

A cynical person might say that donor cultivation is a manipulative ploy to snare money.

That’s an attitude I’ve never understood. I like people. I like getting to know them whether they have money or turn out to be donors. Invariably, our relating makes them feel good and makes me feel good -- especially when we strike a bond or find common interests. Why should there be an invisible barrier just because someone is a potential supporter? 

You say that if you were to choose one potential donor you’d like to make friends with, it would be the wealthy individual who says (or implies) that he or she doesn’t want to talk about money and doesn’t want to be solicited. That sounds counter-intuitive.

There are many wealthy people who don’t want to talk about money and others who tell you they don’t want to be solicited. It’s a challenge, certainly, but it can be overcome. One of my mentors was just such a person. He didn’t like talking about his personal giving but he did love to talk about what was going on with the organization. And more than anything, he liked to give advice. I asked for it frequently. Sometimes he would become especially interested in an idea and would ask, “How much would it take to do that?”  And that would usually lead to a nice check.

Can you be too close to someone to ask them for money? And, if so, what’s Plan B?

Absolutely. There are people I won’t solicit because the relationship is too close. But I’ll help others develop a plan of action and I don’t mind opening the door for other fundraisers, making the introduction. One of my boyhood friends – a man with quite a lot of money -- is someone I finally decided I could solicit. But I asked him first if he’d mind or would he rather be solicited by someone else. We had a good laugh, went off for a beer, and I came away with a contribution.

As for donor relations, what’s the worst mistake a fundraiser can make?

If there’s one mistake I’ve made all too often, it’s not paying attention to donors’ children. They’re the ones, after all, who will someday come into the family wealth. And once they do, it’s too late to cultivate a relationship. Because kids like to strike out on their own and usually don’t want to mimic their parents’ philanthropy, I try to find activities and programs for them that are completely different from the ones their mothers and fathers are supporting.

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Excerpt: Coping with Repellent Donors

This article is excerpted from Thomas Wolf's How to Connect with Donors and Double the Money You Raise. ©Emerson & Church, Publishers. To obtain reprint permission, call 508-359-0019 or email kbrennan@emersonandchurch.com.

There was no question Stephen had money – lots of money.

The way he threw it around when he came to town, there was no mistaking the fact that he was going to use his largesse to establish his clout. I had little to do with him until one day he phoned. He’d heard about the work of our organization and had an idea. He thought it would be very worth my while to meet with him.

Since Stephen was the talk of our small town, I mentioned to a few people that I was going to see him and the response was always the same, “Be careful.” But I wasn’t especially worried.

Being relatively young in my fundraising career, I had the overconfidence that comes with lack of experience. I was simply going to meet Stephen, have a tour of his renovated house, and hear him out. That was all. I knew how to deal with people like him and I knew how to say “no.”

I visited Stephen and was impressed with his house, one of the most historic in town. But once he started talking about himself, discomfort set in. He spent a lot of time telling me about his seven homes, his private plane, his two sailboats each with its own crew. He told me the prices he paid for each work of art on the wall and about how many so-called art connoisseurs were “idiots.” He was the kind of fellow to whom I take an instant dislike … but he had money, and he was making it clear that if I played my cards right I could have some.

In retrospect, I cringe at my behavior. I was friendly, feigned interest, and expressed admiration where the cues were obvious. Later I professed friendship and went to his house when summoned. In the end, my organization received his money, one of our largest gifts ever. I was cautiously pleased and so were my trustees.

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But no sooner did we get his gift than I got a lot else besides. Phone calls came at unexpected hours filled with advice, much of it impractical or downright crazy. Conversations were often spiced with derogatory comments about friends and associates I respected. I wanted to rebut Stephen but felt awkward, and then even worse about my cowardice for not doing so. At the end of the year, he offered even more money, and I had to make a decision. Was it really worth it? I went to some valued trustees to seek their advice.

Interestingly, the board was split. One of my trustees, old and wise, said we should take the money and not worry about it. “So you have to put up with some bizarre behavior. It’s part of your job.” He recalled a similar situation on another board where the headmaster came to him complaining about a donor whose money was gained in a shady manner. “It’s tainted money,” said the headmaster, “and it doesn’t feel right.” My board member shot back: “The only tainted money is the money we taint got.”

But the majority of my trustees felt differently. They saw how uncomfortable I was. More importantly, there was growing talk in the community and among other donors that this wasn’t a good situation for us. Stephen had a checkered reputation. They urged me to walk away and in the end I did so, leaving a large sum on the table.

My experience with Stephen points to a dilemma about our relationships with some of our donors. Good fundraisers have to be willing to be friends with their donors and to build strong relationships. But should we play nice with people we really can’t stand? How authentic are we if our “friends” include people like Stephen? Or should we simply admit that these efforts are manipulative ploys to secure money and not worry about it? What is our responsibility to our organizations, to the donors, and most importantly to ourselves?

Most wealthy people have learned to be cautious about those of us who profess to be their friends.  When we behave inexplicably, as I did with Stephen, they can only suspect one thing – it IS all about the money.

As one donor who I asked to join my table at a fundraiser said out of the blue, “My husband told me tonight, ‘Watch out, they’re just after your money. They’ll pretend to be your friend but just know what they are after.’ He says that to me all the time and I wish he wasn’t right about it so often.”

Sitting next to her I felt odd. Sure we wanted her money. But I thought the evening was fun for both of us and we were having a good time. Should I have felt guilty?

Everyone is suspicious of the sycophant who lavishes praise in advance of asking for money. But what of the fundraiser who goes about the process subtly and skillfully? Should we be even more on our guard? Is there any way to tell when people are being authentic?

This, perhaps, is the crux of the issue. When we’re inauthentic, donors can tell. But the opposite is true as well. When we act with integrity, it comes across, especially as donors come to know us.

My friend, Andrea Kihlstedt, an exceptional fundraiser in her own right, makes an interesting and important distinction. “We can be kind and gracious in the face of challenging behavior. That’s okay.  But we shouldn’t try to become everyone’s friend or pretend we enjoy working with donors who are troublesome. In the end, maintaining our integrity may be the most important thing that keeps us from growing cynical.”

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About the Author

Dr. Thomas Wolf’s career encompasses the fields of philanthropy, nonprofit management, education, and the arts.

After serving as the founding Director of the New England Foundation for the Arts for seven years, he established a consulting firm in 1983 (now called WolfBrown) to assist nonprofit organizations and the philanthropic sector. 

Helping his clients increase fundraising results and improve management practices, he also assisted 10 of the 50 largest U.S. foundations and various government agencies with their grants programs. 
At the same time, his workshops and convocations for trustees, administrators, and volunteers have earned him national recognition.

Wolf holds a doctorate in education from Harvard, and has taught at Harvard and Boston Universities. He is the author of the definitive textbook on nonprofit management that has been in print for over a quarter century (now titled Managing a Nonprofit Organization in the 21st Century) and he has written numerous other books and articles.

A professional flutist whose career included touring with the Goldovsky Opera Theatre and founding Bay Chamber Concerts in Maine, he is currently listed in the International Who’s Who of Music.

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Table of Contents


  1. I’d love to get to know you better
  2. Enough about me!
  3. What’s wrong with talking about money?
  4. It’s the donor’s ballgame
  5. Thank you. Thank you. Thank you!
  6. Remember the children
  7. Can you be too close to ask?
  8. Why isn’t he giving?!
  9. When donors disappoint
  10. Recovering from a fumble
  11. But I can’t stand the fellow!
  12. Whose friend are you anyway?
  13. We honor his memory
  14. Grantmakers need attention too        


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