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Brazen Solutions · Leadership

The executive director is carrying all the fundraising alone. Nobody ever decided that.

Every funder relationship runs through one calendar, and nobody planned it that way — it accreted, one reasonable decision at a time. What that costs the organization, why the development hire never arrives, and the first move out.

August 2026 · 7 min read

She's writing the out-of-office note.

Two weeks in August, the first real two weeks since 2022, and she wants to leave things clean, so she opens a document for the office manager. If someone calls, here's what to say.

It starts as a paragraph. It ends up four pages, and eleven of the entries finish the same way: this one will have to wait until I'm back.

She reads it over on a Tuesday night with the house quiet. Somewhere on page three she stops reading it as a coverage note. It's an inventory of what the organization loses access to for fourteen days, and every item on it is a person who will only pick up for her.

Nobody sat down and decided this

Be precise about how it happens. The precision is what lets you off the hook.

She wrote the first grant because there was no one else in the building to write it. She met the first major donor because the founder brought her to a lunch in 2016, and then the founder retired. Someone had to phone the family foundation in October, and she knew the program officer's daughter's name, so it was faster if she did it.

Every one of those was the right call on the day it got made. None of them was a decision about how the organization should be built.

Then it holds, for a reason that has almost nothing to do with control. Handing off a donor is slower than keeping one — every time, for at least a year. Passing Bill Rhodes to your program director means three meetings, a debrief, and six months of Bill replying to you anyway because you're who he knows. Keeping Bill means one coffee in the spring. When you're behind, and she is permanently behind, that math picks itself.

The board doesn't push on it because she's good at it. That's the part that stings. Boards defer to competence, and when the ED is the strongest fundraiser in the room, the most natural thing eleven volunteers can do is get out of her way and let her work. They experience that as respect. She experiences it as being alone with the number.

The hire that never arrives

"We'll bring on a development person when we can afford it."

Follow the loop around. The money to fund the position has to be raised, and the only person who can raise it at that level is the ED, whose hours are already spoken for by the fundraising that meets payroll. The role gets funded out of growth that requires the role.

The version where they do hire is often worse. A junior at fifty-eight thousand, because that's what the budget allowed. No onboarding — her calendar was full that month. No warm handoff, because those introduction meetings kept getting bumped for something on fire. Eighteen months later the junior leaves, and the organization owns a story it will repeat for years: we tried a development person and it didn't work.

That story costs more than the salary did.

The risk your board has never priced

Your board reads the audit. They review the insurance renewal every year, and somebody always asks about the reserve.

Here's the question that has never been asked out loud in that room. If the ED gave notice on Friday, how much of next year's revenue walks out the door with her?

Not the files. The files are fine. The database has addresses and gift histories and a note from 2021. I mean the thing that actually produces gifts, which is eleven years of one woman knowing that Bill's wife had a stroke in March, that the family foundation's program officer will not be cc'd on anything, that the Hendersons always give in November and nobody ever wrote down why.

A relationship is not an organizational asset until a second person is standing in it.

In any other kind of business a board would call this concentration and put a dated plan against it. One customer, sixty percent of revenue — that's a governance conversation. When it's the executive director and the donor file, the same board calls it dedication and gives her flowers at the AGM.

It surfaces hardest in campaign planning. Build a capital campaign gift table with real names, add a column for who makes each introduction, and watch one name appear twenty times down the page.

"The board should help more" stopped working three years ago

She's already said it. At the retreat, in the strategic plan, and in a one-on-one last spring where a good man nodded a lot and then didn't do anything. If saying it were going to work, it would have worked by now.

There's a real conversation to have with the board here, and I've written the long version — what board members mean when they won't fundraise is usually that nobody has handed them a job small enough to say yes to on a Tuesday. Worth fixing, and it takes about two years, because board terms are long and culture is slow.

She needs something that changes the structure inside the next thirty days.

One relationship, in writing, with the introduction made

Here it is, and it's smaller than you want it to be.

Pick one donor. Not your largest — your largest is the one you're most frightened to let go of, and fear makes a terrible first repetition. Pick someone mid-level and long-standing and genuinely warm, who'd take a call from anyone at the organization and be pleased about it.

Name a second person. An actual human being with an actual name — your program director, your finance lead, the board member who keeps asking what she can do and means it. Write it down where other people can see it. In the file. In the board package.

Then make the introduction yourself, in the room, out loud, in front of the donor. Denise is going to be part of this with me from here on. She runs the program you fund, and she can tell you things I can't.

Then leave it alone for a quarter. That's the entire assignment.

It will feel like nothing. One donor out of two hundred. What it does is create the first relationship in your organization's history that survives your departure, and teach everyone watching that a handoff is an ordinary Wednesday rather than a crisis.

Do it again next quarter. Four a year. Three years in, twelve relationships have two people in them and your file is no longer one calendar deep. That's slow. It's also the only version I've watched hold.

The written part matters more than it sounds. A verbal handoff evaporates in about six weeks — everyone means it, nobody schedules it. What holds is a document with names in it that somebody reviews once a year, which is exactly what the board charter piece does for a board.

What she gets wrong about herself

Almost every ED I have this conversation with has landed on a private explanation for why she's carrying all of it, and it's always some version of a personal defect. She's bad at delegating. She's a perfectionist. The ED at the larger organization across town seems to manage.

This is a design problem, and she has spent four years auditing her character for it.

The organization was built with one fundraiser in it. It has hired to that design and budgeted to that design for a decade, and every reasonable person along the way made a reasonable decision. She didn't choose it, and she can't fix it by being more disciplined on Sunday nights.

Which is the good news, honestly. Design problems have moves in them. You can't self-improve your way out of being the only person alive who knows Bill Rhodes. You can put a second name beside his, this month, for the price of one coffee and one paragraph in a file.

Back to the four-page document

She took the two weeks. Most of the document never got used — August is quiet, and the things that could wait, waited.

What changed was that it existed on paper. In September she brought it to the board — not as a complaint, as an agenda item — and read three of the eleven entries out loud. Then she asked something she hadn't asked in eight years: who is the second person on each of these?

The room went quiet in the way rooms do when a question has been sitting there a long time unasked.

If you're not certain this is the layer holding your organization, the free organizational diagnostic takes fifteen minutes and names the pattern you're in. The system for redistributing the work — who owns which relationship, written down, reviewed — is what we build inside the Organizational Resilience Charter. And if the hardest part is having nobody to say this to out loud, Brazen Connections is a free gathering every two weeks where fundraisers and EDs doing this work sit together for an hour. No cost, no pitch. If you'd rather talk one to one, book a discovery call.

Open your donor file tonight and find the one you'd hand over first.

Write a second name beside it.

Wondering whether your organization could carry a capital campaign? The free readiness assessment scores you across the eight areas that decide it.

Take the free readiness assessment

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