Category Fundraising

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)

Combines three earlier posts: “Common Threads: Donor Acquisition” (LinkedIn, December 12, 2014), “Making the case for acquisition mail” (LinkedIn, August 14, 2015) and “Retention or Acquisition? Maximizing your ROI.” (knowgood.ca, September 11, 2023)

Updated September 2026

Some years ago, over coffee, a colleague told me their charity had dropped mail acquisition entirely and gone all-digital. I understood the appeal. I also knew their donor file was about to get older and smaller.

Every charity loses donors. People move, retire, change priorities and, eventually, pass away. So every charity needs to keep finding new ones – which brings us to the question I still hear most often: is direct mail still worth it?

My answer is yes, for most Canadian charities, with a plan for when the mail stops.

Mail still works, with a backup plan

Direct mail still works, especially for donors over 65. In 2022, nearly half of every dollar donated in Canada came from that group. It has also become riskier. Postal strikes in late 2024 and fall 2025 hit charities during their busiest giving months, and Canada Post is moving through a major federal overhaul, including a shift away from door-to-door delivery.

Keep mailing, and build campaigns that can survive a disruption:

1. Tell the same story in several places. Mail, email, social and your website should carry one message to the same audiences at the same time.
2. Make online giving fast. A donor should be able to give from their phone in about a minute. Test it yourself.
3. Have a backup plan. Know in advance how you will reach mail donors if the mail stops – a phone call, an email, a text.
4. Test your mix. The right split between print and digital depends on your donors. Your own results will tell you more than any rule of thumb.

Keep the donors you have, and keep finding new ones

It costs less to keep a donor than to find one. That has been true for my whole career. But retention alone won’t hold your revenue steady anymore.

The number of people giving keeps falling. The Fundraising Effectiveness Project, which tracks giving across thousands of US charities and is the closest thing we have to a North American benchmark, reported that donor counts fell again in 2025 – by 3.6%. Overall retention sits around 43%. And turning a first gift into a second one remains, in their words, the most consequential unsolved problem in the donor pipeline.

So plan for both:

1. Fund retention first. Thank people well, report back on what their gifts made possible and invite them to give again.
2. Fund acquisition every year. Treat it as an investment in next year’s base, with its own budget line and its own targets.
3. Plan the second gift before the first one arrives. The welcome journey for a new donor – the thank-you, the first update, the second invitation – is where acquisition pays off.

Introduce yourself the way you’d want to be introduced

Years ago, someone told me that if I could make a person cry, I had a new donor. I’ve also taken calls that tried to guilt me into giving – “You care about kids with cancer, right?” – from someone who couldn’t tell me who they represented. I hung up.

A first contact is an introduction. It works best when it is warm, clear and generous. When I built acquisition campaigns, the pieces that did best followed a simple shape:

1. A bold opening that makes the reader stop and think.
2. A few clear facts about what your community has already achieved together.
3. An invitation to join people like them.
4. The difference their gift can make.
5. A way to learn more and a simple way to give.

When I was with the Missing Children Society of Canada, we talked about the children who came home. We showed people what their community was already making possible and invited them to be part of it. That message built donors who stayed.

A few things I include in every acquisition piece:

1. Some urgency, with no guilt. Giving should feel good.
2. The hopeful outcome. Show the result your work produces.
3. An easy way to ask questions. Assume a new reader has some. Give them a phone number and a web address.
4. A consistent way to give – online, by phone or by mail.
5. The word “please.”

Try this

Pull your list of first-time donors from last year. How many gave a second time? Now look at what each of them received from you between the first gift and the second ask. That gap is where your next dollar of investment belongs.

Be well.

Sources

1. Association of Fundraising Professionals, Fundraising Effectiveness Project Q4 2025 report (April 2026) – https://afpglobal.org/news/fundraising-effectiveness-project-reports-strongest-revenue-growth-five-years-even-fewer
2. Future of Good, Charities to stick with direct mail fundraising for older donors after Canada Post disruption – https://futureofgood.co/charities-to-stick-with-direct-mail-fundraising-for-older-donors-after-canada-post-disruption/
3. ITIF, Reforming Canada Post for a Lower-Volume Era (April 2026) – https://itif.org/publications/2026/04/01/reforming-canada-post-for-a-lower-volume-era/

Since about 2013 or 2014, Conor has been sharing ideas, thoughts, and experiences on LinkedIn. Some of his pieces are well-written articles, while others more closely resemble stream of thought pieces.

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