Key Takeaways

The Call I Had This Week

An executive director I work with had just come through two of the worst weeks of a long career. A Termination that went badly. A threatened lawsuit. Board members opening their inboxes to find petitions from a former employee.

We spent four minutes on that. Then the real problem surfaced, and it had nothing to do with the lawsuit.

“How do I find them? I think that’s the biggest challenge for me. Who are the donors that I’m calling and asking to meet with? That’s what I don’t have.”

And then, a beat later, the sentence underneath the sentence: there is no way to cold call the chief executive of a Fortune 100 company.

No. There is not. Nobody can do that. It is not a personal failing, and it is not really a fundraise problem. It is a starting-point problem, and almost every leader I work with has some version of it.

Here is the short answer, and then I will spend the rest of this piece on how to actually do it. You do not need an introduction to the biggest name in your region to fundraise effectively. You need six low-stakes meetings in the next sixty days with people who will absolutely take your call, and you need to keep going until asking stops feeling like a performance.

What Is Actually Happening When a Board Cannot Open Doors?

The board handbook says board members give, get, or get off. In a direct-service organisation with a budget between $1 million and $20 million, reality is usually different, and the gap between the two is where many executive directors quietly lose a year.

The Board You Have Is Not the Board in the Handbook

Listen to how this leader described the actual composition of the room:

“The people who are our donors, you know, they’re teachers, they’re people from the not-for-profit world, they’re not the big money people. And I do need to find people to introduce me to the big money people, because our board is really not made up of wealthy people.”

That describes most direct-service boards in this country. They were recruited for program credibility, for lived experience, for professional expertise, for representation of the community being served. Those are good reasons. They are the right reasons. They are also completely unrelated to whether a person has a personal network of high-capacity donors.

You did not build a bad board. You built a board for governance and you are now asking it to perform a function nobody recruited it to perform.

The Executive Director Problem

Then there is the part that almost nobody says out loud, and this leader said it in one breath:

“And the ones who are on our board, many of them are executive directors like myself. And they’re obligated to do their own fundraising. So I can’t mine them for contacts, because they’ve got to keep their own contacts.”

Read that again, because I think it is the single most useful sentence in this whole article.

If a third of your board runs other nonprofits, a third of your board has a fiduciary obligation to a different balance sheet. Every name they could give you is a name they need. Asking them for introductions is asking them to fundraise against themselves.

They will not say that to you. They will say they will think about it. Then nothing will happen, and you will privately conclude that your board is disengaged. Your board is not disengaged. Your board is doing math.

Why Does the Introduction Never Actually Come?

I have watched this stall out in the same two places for twenty years.

The Rolodex Ask

The standard board exercise to fundraise is a name-storming session. You put a list of local companies and foundations on the wall and ask everyone to mark who they know. It feels productive. It generates a spreadsheet. It produces almost nothing.

The reason is that you asked for a category and not a task. “Who do you know?” is an open-ended request for a person’s entire professional identity, delivered in a room full of their peers, with no defined limit and no defined ask. The rational response to that question is vagueness.

Compare it to what I told this leader to do instead:

“We reach out to the policy champions we have, we reach out to the guy that runs the trade association for all the office parks. We slowly start asking, and we’re not asking them for their whole Rolodex. We’re asking for two or three connections.”

Two or three. A number small enough that a busy person can say yes on the spot and actually deliver by Friday.

The Permission Gap

The second stall is quieter. A lot of executive directors are waiting for a moment that feels safe enough to begin. They want the case for support finished. They want the new one-pager. They want the impact numbers from last quarter. They want the personnel situation resolved.

There is always one more thing to fix first.

Our post on how to communicate with your major donors during uncertain times makes a version of this argument from the donor’s side. Preparation feels like progress because it produces artifacts. Meetings feel like exposure because they produce a verdict.

But you cannot learn your way out of this. I got asked recently what our firm has been saying publicly about fundraise anxiety, and the honest summary is one line: the way out of it is to do it. There is no reading list that gets you there. There is no workshop that gets you there. You do your way out.

What Should You Actually Do Instead?

Here is the practice. Five moves, in order.

1. Start Where the Stakes Are Low

This is the part that made the executive director on my call visibly relax.

“Let’s go meet with the big-box retailer that has a store in your county. Let’s go meet with the home improvement chain. Those are nice and easy, low-stakes ones. Let’s just build the muscle up through doing it. And we’ll find the next ones and the next ones, and we’ll keep going.”

Local corporate giving programs are the beginner slope of major gifts. The store manager or the regional community relations lead will take your meeting. The dollar amounts are modest. The rejection, if it comes, costs you nothing, because you had no relationship to protect. And the conversation itself is nearly identical in shape to the conversation you will have two years from now with a family foundation.

You are not doing this for the money. You are doing this for the repetitions.

An executive director who has had fourteen corporate conversations is a fundamentally different person in a major donor meeting than one who has had none. Not because the fourteen taught them anything they could not have read. Because the fourteen took the adrenaline out of it.

2. Ask for Two Names, Not the List

Every time you ask someone for introductions, name the number.

“You know this world better than I do. Would you be willing to think of two or three people I should be talking to, and make an email introduction to whichever one feels most natural?”

Two or three. An email introduction, which is a defined action with a clear end point. Whichever one feels most natural, which gives them an exit if the others are complicated.

I have rarely seen that version of the ask fail. I have watched the open-ended version fail hundreds of times.

3. Go to Your Champions Before You Go to Your Board

If your board cannot open doors, stop treating your board as the door.

Make a list of everyone who has publicly advocated for your organisation in the last three years and is not a board member. Policy champions who went to bat for your fundraise. Association executives whose members benefit from your work. Former staff who left on good terms and now sit somewhere interesting. Vendors and partners with their own networks. The lobbyist or consultant who used to be a colleague.

These people are frequently more useful than trustees, for a reason that is a little uncomfortable: they have no fiduciary duty to you, which means they carry none of the anxiety about whether helping you constitutes a conflict. They can just help.

This is also where a non-fundraising cultivation event earns its keep. The leader on my call has around eighty people coming to an appreciation day next week. A genuinely mixed bag: people who used the programs years ago, people who wrote letters of support during a hard stretch, and a handful of business leaders who have expressed interest without ever being asked for anything.

That is not an event to fundraise, and it should not become one. But it is eighty people standing on site watching the staff do the work, and every one of them is now a person you have permission to follow up with.

I told this leader not to ask at that event. I also told them to let the need be known, which is a completely different thing. Name what you are working on. Say that you will be seeking support from the business community this autumn. Invite anyone who wants to talk further to say so. Then follow up the following week, individually, by name.

4. Treat Your Time Goal as a Destination

There is a moment in this call I keep thinking about.

We had put a proposal in front of this executive director recommending that they spend fifty percent of their time on the fundraise process. They read it, thought about it, and came back with something better than agreement:

“I think that 50% of my time is a goal, but it’s not the starting point. Maybe to start, until some of these personnel issues are completely behind me, it’s probably going to be 20%.”

That is right. That is exactly right, and it is the response of a leader who intends to actually do it rather than to nod at it.

Fifty percent is a destination. Twenty percent is a starting line. Twenty percent of a working week is roughly eight hours, which is four donor meetings and the preparation and follow-up around them. Four meetings a week, sustained, will change an organisation.

Zero percent, dressed up as fifty percent because fifty percent was in the plan, will change nothing. Ambitious targets that ignore the operational reality of the person carrying them are not ambitious. They are decorative.

Set the destination. Then set the starting line honestly, and put the increase on a calendar with a date attached.

5. Put the Reps on the Calendar Before You Feel Ready

Then somebody has to make sure the meetings happen.

For the client on this call, that meant two working sessions a month where we build the list together and go through it name by name, plus a colleague on the inside with enough proximity to notice when a week goes by without a donor conversation.

This is the least glamorous part of the entire method, and it is the part that determines the outcome. Fundraising does not fail at the strategy layer. It fails on Thursday at 2 pm when the meeting you scheduled three weeks ago collides with a payroll question and the meeting loses.

Somebody has to be watching the calendar. If that person cannot be you, it has to be someone else. Our post on creating a nonprofit funding strategy that actually works goes deeper on how to structure that accountability without turning it into surveillance.

What About the Email Appeal That Did Not Work?

Before any of the above came up, this leader reported on a three-message email campaign we had written.

“We did the three messages that you guys had written for us, and we did not get a good return on them. A few thousand dollars came in, but nothing of substance.”

I told the truth, which is that the result sounded about right to me.

This matters, so I want to be plain about it. Three emails to a modest house file of teachers, program alumni, and community supporters is not a major gift strategy. It was never going to be. It produced a few thousand dollars and, more usefully, converted a handful of occasional donors into sustaining monthly donors at low levels.

That is a completely reasonable outcome, and treating it as a failure would be the actual mistake. The sector-wide numbers from the Fundraising Effectiveness Project, the long-running research collaboration founded by the Association of Fundraising Professionals and the Urban Institute, put overall donor retention in the low forties and first-time donor retention closer to twenty percent. Against that backdrop, an email series that moves people from occasional to recurring is doing something structurally valuable, even when the topline number is small.

The mistake is expecting broad-based digital appeals to solve a problem that is fundamentally about proximity. Email scales attention. It does not manufacture relationships you do not have. The relationships get built one meeting at a time, which brings us back to the calendar.

What Does This Look Like Six Months In?

Not dramatic. That is the honest answer.

Six months in, you have had somewhere between twenty and forty conversations. Most of them produced nothing you can put on a board report. Four or five produced a first gift in the low thousands. Two produced introductions you would not have gotten any other way. One person you met in month two has turned into someone who now brings you names without being asked.

And the thing that has changed most is not on the balance sheet. It is that asking has stopped costing you anything emotionally. You do it the way you do any other part of the job.

That is the whole return on the low-stakes reps. Everything else compounds from there.

Frequently Asked Questions

My board members signed a give-or-get policy. Should I enforce it?

Enforce the give. Be careful with the get. A give expectation is a clean, binary commitment that a board member can meet regardless of their network, and it is a reasonable condition of service. A get expectation assumes a resource that many good trustees simply do not possess, and enforcing it tends to produce resignations from exactly the people whose program expertise you most need in the room. If you want a board that can get, you have to recruit for it deliberately over several cycles, and you should be honest with yourself that this means trading something else away.

Is it worth recruiting wealthy board members just for their networks?

Sometimes, and less often than people assume. A high-capacity trustee who is not genuinely committed to the work will attend two meetings, make one introduction, and disengage. A high-capacity trustee who is committed will change your organisation. The predictor is not net worth, it is whether the person has already demonstrated interest in what you do. Look at your own donor file before you look at anyone else’s board. The person who has given quietly for six years and has never been asked to serve is a far better prospect than a stranger with a good balance sheet.

How do I ask a policy champion or association contact for help without seeming transactional?

Ask them a question rather than for a favour. “Who should we be talking to in the business community this fall, and how would you go about it?” invites expertise rather than resources. Most people who have advocated for you enjoy being consulted, and the introductions tend to follow naturally from the advice. If they do not, you can come back later with the smaller, specific ask for two names.

What if I genuinely do not have time for four donor meetings a week?

Then start with two, and be honest with your board about the trade. What you cannot do is carry a fundraise target that assumes four while doing zero. The gap between the plan and the practice is where most executive directors accumulate a year of quiet guilt and no additional revenue. Name the real number, put it in writing, and revisit it when the operational fire that is currently consuming you is actually out.

Should I hire a development director instead of doing this myself?

Eventually, yes. Not first. A development director hired into an organisation where the chief executive has never done the work will spend their first year translating rather than to fundraise, and the good ones leave. Build the muscle yourself for two or three quarters, learn what the job actually requires, and then hire someone into a function you can supervise honestly. Our piece on the nonprofit CEO’s guide to fundraising covers what that supervision looks like in practice.

We are in a slow season, and nobody is around. Should I wait?

Wait a couple of weeks if your region genuinely empties. Do not wait a season. Use the quiet time to build the list, draft the outreach, and get the first three meetings on the calendar for the week things restart. The leaders who use August to prepare are having conversations in the first week of September. The ones who use August to wait are still building the list in October.

Wrapping Up

Your board cannot introduce you to money. Fine. Almost nobody’s board can.

The pipeline does not come from a name-storming session. It comes from a leader who decided that four uncomfortable conversations a week were worth more than another month of preparation, and who started with the easiest possible call rather than the most important one.

You are not going to cold call the chief executive of a Fortune 100 company. You are going to call the regional community relations manager at the retailer twenty minutes from your office, and you are going to do it on Tuesday.

Make the easy call first. Then make the next one.

Is Your Fundraise Strategy Built for the Board You Actually Have?