Before You Ask, Look for Connection

Combines two earlier LinkedIn posts: “The most critical factor in fundraising” (December 5, 2014) and “The Upside. Understanding Philanthropic Motivation” (January 19, 2015)

Updated September 2026

Early in my fundraising career, I went looking for major gifts. I wanted to prove myself, so I found a list of Canada’s wealthiest people and set out to connect with them.

I had some success – gifts I was proud and humbled to receive. But mostly, I spun my wheels. When the campaign wrapped up, I walked a few board members through what I’d been doing. One asked to hear my pitch. I shared it, and he wrote a cheque on the spot equal to my average gift for the entire year.

I’d been chasing the people with the most wealth. The board member had something they didn’t: a connection to the cause.

Connection comes first

Major gift fundraisers often talk about three things: linkage (a connection to you), ability (the capacity to give) and interest (a passion for your cause). All three matter. Capacity is real – it shapes how large a gift can be.

But passion decides whether there’s a gift at all. Without it, no amount of wealth or sales skill will get you there. With it, people find ways to give that surprise you. I’ve seen a donor whose own giving capacity was around $500 raise $100,000 from their network in a few short months.

So look for your next major gift prospects close to home: your volunteers, monthly donors, event guests, sponsors and board. Put the rich list down and look through your database.

Understand what moves people

Donors meet with you because they want to do good. Their reasons vary. In 1994, Russ Alan Prince and Karen Maru File described seven common motivations in The Seven Faces of Philanthropy: the Communitarian, the Devout, the Investor, the Socialite, the Altruist, the Repayer and the Dynast. It’s an older model, and people rarely fit one box. It’s still a useful lens for listening.

Tailor the conversation to what you hear. A Repayer may want to give back to the community where they found success. An Investor wants leadership and tangible results. Whatever the motivation, anchor every conversation in your mission and the good the donor can do.

Ask, share, ask again

1. Ask. “What experience do you have with our cause, personally or through your giving?” Some experience is a head start. None is an opportunity to inform.
2. Share. Tell the real, human impact of your work, and why you do it. Lead with hope. When I was with the Missing Children Society of Canada, I talked about the children who came home. At Canadian Blood Services, I talked about my wife, Annie, a blood recipient.
3. Ask again. If there was no passion before: “Would you like to learn more about how people are making a difference here?” If there was: “Is this something you’d like to have an impact on?”

If the answer is no, thank them and stay in touch. Keep sharing updates. Welcome them at events and gifts at whatever level fits. And give your major gift time to the donors who are saying yes.

Before you make the ask

1. Can you deliver? If a donor wants to fund something specific, are you equipped to do it, and can you spend the gift on the timeline you’re promising?
2. What does the donor want in return? Ask early how they’d like to be recognized, before any number comes up.
3. Who should ask? Sometimes a passionate donor connects better with someone else – a board member, a program lead, a peer. Bring the right person in, and step back if that serves the donor best.

A fundraiser’s job is to help donors reach their philanthropic goals. There’s no room for pressure or dishonesty, and endless room for relationships that do lasting good.

Try this

Pull a list of your ten most engaged volunteers and monthly donors. For each one, write down what you know about why they care. Where the answer is blank, that’s your next coffee.

Be well.

Sources

1. Russ Alan Prince and Karen Maru File, The Seven Faces of Philanthropy: A New Approach to Cultivating Major Donors (Jossey-Bass, 1994)