Key Takeaways

The Sentence Most Fundraisers Never Say Out Loud

Forty minutes into a coaching call a few weeks ago, an executive director said the thing most fundraisers only think.

We had spent the hour walking through his portfolio. Eighty-some names. An ask amount next to each one. The whole thing adding up to a target in the high six figures, which was considerably more than he had ever personally raised. He had gone quiet for a stretch. Then this:

“A lot of these folks I have been working with, and you’re suggesting, at least for some of them, that they could give more, which I don’t doubt. And yet conversations I’ve had with them haven’t sort of led to that in the past. Sort of like, eh, this is where I’m at, type conversations. Or body language. So maybe this gets back to how good I am. Maybe I’m not good enough to really bump them up higher.”

I have handed a lot of leaders a portfolio with bigger numbers on it than they have ever raised. Some version of that sentence shows up almost every time. It rarely gets said.

He said it. That is the main reason I think his program is going to work.

What Is Actually Happening When the Number Looks Too High?

Something specific happens in the ninety seconds after a fundraiser sees a number they do not believe. It is worth slowing down and naming it, because what happens next determines whether the portfolio gets worked or quietly abandoned.

The Competence Verdict

Here is the move: a donor has given $2,500 a year for six years. The model says the ask is $10,000. The fundraiser looks at that and does not think

The model might be wrong. The fundraiser thinks I have had six years with this person, and I got $2,500, so the missing $7,500 is a measure of me.

That is the competence verdict. It is a fast, private, and almost entirely unexamined conclusion that the gap between what a donor gives and what a donor could give is a report card on the fundraiser.

I want to be careful here, because the instinct behind it is not stupid. It comes from taking the relationship seriously. People who don’t care about their donors don’t lie awake wondering whether they are good enough. The competence verdict is a professional’s disease, not an amateur’s.

But it is still wrong, and it is expensive. A fundraiser who has quietly decided the number is a judgment on them will do one of two things. They will avoid the donor, or they will go in apologetically. Both produce the same result, which is another year at $2,500, which confirms the verdict, which makes next year’s avoidance easier to justify.

What Your Past Conversations Actually Measured

So let us examine the evidence he was working from.

He remembered specific conversations. He remembered body language. He remembered the

Eh, this is where I’m at shrug.

That memory is real, and I do not want to talk anyone out of trusting their own read of a room. Reading people is most of this job.

But look carefully at what that memory is evidence of. It is evidence of how a particular donor responded, on a particular day, to a particular request, made by a person who at the time may not have known what that donor cared about, may not have had a specific project to attach the money to, may have led with organisational need instead of donor interest, and may have named a number that was itself anchored to the last gift.

That is a lot of variables. The donor’s shrug was a response to all of them at once. Attributing it entirely to your own skill is not humility. It is a measurement error.

A giving history is not a capacity study. It is a record of what has been asked and how it was asked. Change the ask, and you have changed the experiment.

Why Do Donors Sit Flat for Years?

In my experience, there are three reasons a donor gives the same amount for a long stretch, and only one of them has anything to do with the fundraiser’s talent.

1. Nobody ever asked for more: This is the most common and the least dramatic. The donor gave $2,500 the first year because $2,500 was on the reply card, or because that felt like a reasonable opening, or because someone suggested it. Every year since, the renewal has come in at the same level because nobody has ever proposed a different one. The donor is not signalling a ceiling. The donor is on autopilot, and autopilot is a setting somebody else chose.
2. The relationship plateaued before the giving did: A donor’s giving tends to track their proximity to the work. If proximity stops increasing, giving stops increasing, and it does not matter how well you write. This is the reason our post on how to turn a major donor into a partner matters more than most people think: the donors who are already offering advice, introductions, and time are telling you they want a bigger role, and a bigger role almost always precedes a bigger gift.
3. The donor genuinely is at their level with you: This happens. Some donors have found their number, and they are happy. A person can love your work and still have decided that you are a $2,500 organisation in a portfolio where somebody else is the $100,000 organisation.

Notice that the first two are conversation problems and the third is a fact. You cannot tell which one you are looking at from the giving history. You can only tell by having the conversation.

What Does the Work Actually Look Like?

Here is the approach I gave him, and it is the approach I would give you.

1. Separate the Estimate From the Verdict

An ask amount is a hypothesis. It is built from three inputs: capacity (what could this person do), affinity (how much do they care about you specifically), and history (what have they done). None of those three inputs is “how skilled is the fundraiser.” Your name is not in the formula.

Say it plainly to yourself before you make the first call. This number is a hypothesis about the donor. It is not a scorecard about me. If you cannot get there, the portfolio will sit.

When he asked me what he should actually expect to come in against a target that size, I told him the truth: there is no formula that converts an ask target into a landing number. The result is usually somewhere between the model and the history. Not at either end. Somewhere in between, and where in between depends almost entirely on the quality of the twelve months of work you are about to do.

2. Re-Enter the Relationship Before You Re-Enter the Ask

For any donor you have not spoken with in a while, the next conversation should not contain a number. It should contain a reintroduction.

He had a good instinct on this. His plan for the neglected names was to open with something like I want to introduce myself again, since we haven’t talked in a while. That is the right move, and if you have any legitimate news to hang it on, use it. A new program. A new strategic direction. A change in how you are working. Something that makes the outreach feel like an update rather than an apology.

The purpose of that meeting is not to soften anyone up. The purpose is to find out what changed. People’s lives move. A donor who was flat for six years may have sold a business, retired, lost a spouse, had a grandchild diagnosed with the thing your organisation exists to fight. You cannot know that from a giving screen.

If you have never run a meeting like this, our piece on how to run a first major donor meeting is the place to start. The short version is that you should be talking about twenty percent of the time.

3. Build the Ask Up From What You Learned

This is where most upgrade attempts fall apart. The fundraiser has a target. The target is uncomfortable. So the ask gets framed around the organisation’s need, because the organisation’s need is the thing generating the discomfort.

Donors can hear that. What they hear is:

You have a hole, and I am the shape of it.

Build the other direction. Take what the donor told you they care about, attach it to something real and specific your organisation is doing, and size the ask to the ambition of that thing rather than the size of your gap. A donor who was flat at $2,500 against general operating may not be flat at all against a specific, named, time-bound piece of work they told you they cared about.

And never move from a qualifying conversation straight to a proposal. There is a step in between, and skipping it is the single most common way good prospects go cold. We wrote about that in the blog: why you never skip from a qualifying call to a pitch.

4. Let the Number Be a Range You Test Across a Year

Do not treat the portfolio as eighty-some individual verdicts you have to survive. Treat it as a year-long experiment with eighty-some data points.

Set an activity number rather than an outcome number for the first two quarters. Six qualifying meetings a month is a reasonable target for a leader who is also running the organisation. Then look at what actually came back. Some donors will surprise you upward. Some will confirm the history. A handful will tell you plainly that they are done, which is also useful information and costs you nothing you were actually going to get.

At the end of twelve months, you will know something you cannot know today, which is what your donors will actually do when they are asked well.

How Do You Know If the Number Was Wrong?

Fairly. A model that overshoots on a third of a portfolio and undershoots on a tenth is a working model, not a broken one. Capacity screening is directional. It tells you where to spend your time, not what people will write.

The signal that a number was genuinely wrong is not a no. It is a specific no with a reason attached, which is: We give at this level because we have committed the rest to our family foundation. We are three years from retirement, and we are not increasing anything.

Those are real ceilings, and you should record them and adjust.

A vague no is not a ceiling.

Let me think about it is not a ceiling.

This is where I’m at right now is not a ceiling.

Those are responses to a moment, and the moment is something you influence over.

What About the Donors Nobody Has Ever Called?

There was a second moment on that call worth more than the first one, and it went by in about eight seconds.

We were looking at recurring gifts, and he scrolled, stopped, and said:

“I see this one. Donations come in very regularly, and it’s never a huge amount; I think it’s $100. And I don’t think we’ve ever reached out to him. So there may be more that he could give.”

Then we moved on.

Do not move on. That is the highest-return sentence anyone said in that hour.

A person who gives $100 every month without being asked, without being cultivated, without a single phone call, is not a small donor. They are an unqualified donor. Nobody has ever found out who they are. Reliable, self-initiating, quietly loyal givers are the single most under-worked asset in the sector, and they are under-worked precisely because they never cause a problem.

I have seen this play out at the far end of the timeline more times than I can count. A check arrives from an estate for a quarter million, half a million, a million dollars. Somebody looks the name up in the database and finds a person who gave $20 a month for forty years and never once got a phone call. The organisation had four decades of warning and read none of it.

Wills are not set and forgotten, either. People revise them every five or seven or ten years. If someone in their eighties stops hearing from you, you can be quietly removed and replaced by the organisation that kept showing up.

So the practical instruction is short. Pull a list of every donor who has given in each of the last three years, at any amount, without ever having been personally contacted. Sort by consecutive years, not by dollar value. Call the top twenty. Ask them why they give. Do not ask them for anything else on that call.

Some of them will be exactly what the screen says they are. Some of them will not.

Frequently Asked Questions

How much higher than the last gift should I ask?

There is no universal multiple, and anyone who gives you one is selling something. What I would say is that the size of the jump should track the size of the change in the relationship. If nothing has changed since last year, a large jump will read as arbitrary. If the donor has toured a site, met a beneficiary, joined a committee, or told you something new about what they care about, the jump can be substantial because the donor has moved, not just the number.

What if I ask for more and the donor gives less than they used to?

This is the fear underneath the competence verdict, and it is worth taking seriously rather than dismissing. In practice, a downgrade after a larger ask is rare, and when it happens it is rarely caused by the amount. It is caused by the ask feeling transactional, or arriving with no relationship behind it, or landing at a bad moment in the donor’s life. A well-built ask that is too large produces a counter-offer, not a retreat. That is the whole reason you name a specific number rather than leaving it open.

My board wants a forecast. How do I forecast a portfolio full of untested numbers?

Forecast the activity, not the outcome, for the first two quarters, and tell your board plainly that is what you are doing. Then forecast revenue from your top twenty relationships and your institutional pipeline, and treat the rest as rounding. Boards get nervous when a number changes. They get much less nervous when you told them in advance which numbers were estimates and when the estimates would firm up.

I only have a handful of hours a week for this. Where do I start?

Start with the donors who have already told you something. Anyone who has increased in the last two years, anyone who has responded to a personal email, anyone who has asked a question about the work. Warm and moving beats large and static. If you are the executive director and you are doing this alongside everything else, six real conversations a month is a good year. It is also more than most organisations manage.

Should I tell the donor I am asking for more than they have given before?

Yes, and be relaxed about it. Something close to: I want to talk with you about a bigger role than we have asked you to play before, because of X. Naming it removes the awkwardness for both of you, and it signals that the number is considered rather than random. What you should not do is apologise for it. An apology tells the donor the number is unreasonable, and then they have to agree with you.

Wrapping Up

The gap between what your donors give and what your donors could give is not a measure of you. It is a measure of the conversations that have not happened yet.

That is not a comforting thought, exactly. It would be easier if the problem were talent, because talent is fixed and you get to stop worrying about it. Conversations are not fixed. Conversations are work, and the work is in front of you, and nobody else is going to do it.

The executive director who said the hard sentence out loud is not less likely to succeed than the one who kept it to himself. He is more likely, because a thing you have named is a thing you can argue with.

So argue with it. Then make the calls.