The Trustee Who Said She'd Make Calls
Margaret Whitfield-Day is sixty-seven, retired partner at a regional law firm, and she has been on the board of a small environmental nonprofit in the Hudson Valley for nine years. In March, in the conference room above the bakery on Main Street, she said the sentence she has said, in some form, in every March of those nine years. I'd love to make some calls for you, Priya. Send me a list. Priya, the executive director, thirty-four, two kids under five, wrote it in her notebook with a small star next to it. She believed Margaret. Margaret believed Margaret.
Priya sent the list on March 19th. It had eleven names on it. She drafted the email on a Wednesday night in her kitchen, after the kids were down, and it took her an hour and forty minutes to write because she wanted Margaret to want to call them. The list had a paragraph about each prospect. It had suggested phone times. It had a one-sentence intro Margaret could borrow.
Margaret read the email on her phone on a Saturday morning in the parking lot of a CVS. She thought, I will sit down with this on Sunday. She did not sit down with it on Sunday. She did not sit down with it the Sunday after.
On June 4th, in a meeting in the same conference room above the bakery, Margaret looked across the table at Priya and said, very kindly, Honey, I'm so sorry. I just got buried. Send it to me again?
We've been thinking about Margaret a lot lately.
The board is not the gap you think it is
There is a folklore in small-shop fundraising that the board is the broken part. If only our trustees would give. If only our trustees would ask. If only our trustees would do the thing they said they would do at the March retreat. Whole consulting careers have been built on the premise that the development director's job, secretly, is to fix the board.
This is mostly wrong, and the wrongness costs us a generation of trustees.
Margaret is not a bad board member. Margaret donated $9,000 last fiscal year. Margaret reads the financials. Margaret showed up to the gala in February in a navy dress and stayed until the end and helped fold the chairs. Margaret loves the mission of this organization the way you love a thing you have given nine years of evenings to.
What Margaret is, is busy. And what Margaret is not, is a development professional. The job we have been quietly asking her to do — find prospects, qualify them, write personal outreach, follow up on a calendar she does not keep — is the job we hire a thirty-four-year-old with a master's degree and a Bloomerang seat to do, full-time, and we still complain it takes her too long.
The board did not break. The job we keep handing the board is the wrong shape.
What give-get-or-get-off was trying to say
The blunt old slogan — give, get, or get off — has been embarrassing the field for forty years. It survived because the alternative, in most rooms, was nothing.
But the slogan has the right verb count and the wrong verbs. Trustees are not, on average, going to get you a gift. Most of them have never asked a person for money in their adult life. The verb terrifies them. The verb is in the wrong language. The verb belongs to a stranger in a suit and not to the woman who shows up on Tuesday to read the financials.
What trustees will do, in our experience, is much smaller and much more useful. They will:
- Open a door. A two-sentence email — Priya is the executive director of an organization I love. I think you two would have an interesting conversation — sent to a peer the trustee already knows, on a Tuesday morning, costs the trustee nine minutes. It generates a meeting Priya could not, alone, have generated in nine months.
- Vouch. In the second half of a tour, when a prospect turns to the trustee in the hallway and says honestly, what do you think of them, the trustee says one warm true sentence and the gift moves twelve months forward.
- Be in the room. The presence of a known, respected community member at a small lunch — saying almost nothing — moves the room more than any case statement ever could.
None of these are getting. All three of them are the actual mechanism by which boards have moved money for two hundred years. We have been training our trustees to do the rarest job in fundraising while neglecting the three jobs only they can do.
The list of eleven was the wrong ask
When Priya sent Margaret the list on March 19th, she sent her a project. Eleven names, each with a paragraph, each requiring Margaret to read, sort, decide, draft, schedule, follow up, and report back. The cognitive load of that email was, conservatively, two hours of focused attention on a Sunday afternoon Margaret was going to spend at her granddaughter's recital instead.
Margaret didn't say no. Margaret said I'll get to it. And then Margaret didn't get to it, because getting to it meant building a small parallel job on top of the seven volunteer commitments she already had.
The right ask, in our experience, looks almost embarrassingly small.
It is one name. It is one sentence about why. It is a four-line draft email Margaret can copy, paste her own name into, and send in under ninety seconds from her phone in the CVS parking lot.
Margaret — Would you be willing to forward the email below to Anne Lacoste? You served with her on the watershed council in 2019. We'd love an intro. No reply needed if it's not the right moment.
Margaret will forward it. Of course she will forward it. Margaret has been wanting to help for nine years. Nobody ever made it easy enough.
The four-line email is the whole product
We keep coming back to a small idea about board cultivation. The job of the development office is not to motivate trustees. Motivation is not the bottleneck. The trustee is already motivated; that's why she's on the board.
The bottleneck is latency. It is the seventy hours between the trustee thinking I should do something this week and the trustee opening a blank email at her kitchen table and trying to remember the prospect's name.
Cut the seventy hours. Hand the trustee, on the morning of the day she has fifteen free minutes, a draft she can send in two. Make the friction so low that not sending it would feel like effort.
The four-line draft email is the product. The list of eleven was the failure mode. The retreat speech about give, get, or get off was the symptom of having no better idea.
Boards do not need to be motivated. They need to be served — gently, briefly, and with one warm specific name at a time.
What the trustee needs to know that you do not have time to tell her
There is a quiet asymmetry that almost no small shop addresses.
Priya knows everything about Anne Lacoste. She knows Anne's giving history at three peer organizations, the year Anne's husband died, the foundation Anne chairs, the policy Anne testified on in Albany in 2022, the daughter who works at a community land trust upstate. She knows this because she spent two evenings building the file before she put Anne on the list.
Margaret knows none of it. Margaret remembers serving with Anne on a council seven years ago and thinking she was sharp. That is the entire file Margaret has access to. The introduction Margaret is supposed to make is, from her side of the table, an email to a vaguely-remembered acquaintance about an unspecified prospective conversation.
No wonder she stalls.
The honest thing the development office owes the trustee, before the ask, is context. A short, sourced, eight-sentence note about who Anne is now — what she's been giving to, what's mattered to her this decade, what to mention in the email, what not to mention. Not a dossier. Not a CRM dump. A note Margaret can read in ninety seconds while the kettle boils.
When the trustee has the same context the development director has, the trustee stops feeling like a polite generalist being asked to do an awkward favor. She starts feeling like a colleague being asked to do the one thing only she can do — say my name to a friend, warmly, on a Tuesday morning.
That is a job a trustee can do all day. That is a job a trustee will, in fact, ask you for more of.
The retreat we keep having and shouldn't
Most small shops, every spring, run a board retreat at which somebody — a consultant, the chair, the development director — tries, again, to get the board engaged in fundraising. There is a worksheet. There are name-storming exercises on flip-chart paper. Everyone leaves with a list of three to five people they will think about.
Sixty days later, nothing has moved.
This is not a board problem. This is a workflow problem dressed up as a culture problem, and the consultants have been selling us the wrong solution for thirty years.
The fix is not another retreat. The fix is not another speech. The fix is not a guilt trip and it is, very emphatically, not a give-or-get policy that drives the busiest, most well-connected trustees off the board with a quiet I just don't have time for this anymore.
The fix is the four-line email, on the right Tuesday morning, with one warm name in it.
The retreat is for vision. The Tuesday morning is for the gift.
What we want from a tool
Rōmy's job, in our heads, is not to write the four-line email to Anne. The four-line email is Margaret's, in her own voice, with her own small joke about the watershed council in it. There is no version of the world where software should be inside that introduction.
What a tool can do is make sure that the four-line draft is in Margaret's inbox on the right Tuesday — the Tuesday Anne's foundation just announced a new program area, the Tuesday Anne was quoted in the Times Union, the Tuesday the algorithm of opportunity briefly turned the lights on in the right room. It can hold the cross-reference between the eleven names on the list and the nine trustees on the board, and quietly surface the one introduction that has the highest odds of landing this week.
It can give Margaret the eight-sentence context note about Anne so the forward feels personal and informed and not like a favor she's doing on autopilot. It can keep the list of warm doors organized, freshly dated, and easy enough to act on from a phone in a CVS parking lot.
The pen is still Margaret's. The relationship, when it lands, is still Margaret's. The institution should remember everything that lets her be the trustee she has been quietly wanting to be for nine years.
The boring revolution, again
We keep arriving at the same picture. The future of board cultivation does not look like a louder retreat, a tougher policy, or a guilt-laden one-on-one with the chair. It looks like a sixty-seven-year-old retired lawyer in a CVS parking lot on a Saturday morning forwarding a four-line email to a friend, and feeling, for the first time in months, like she did the thing she joined the board to do.
Loud revolutions break things and call it transformation. The boring one lets Margaret help.
A small assignment, with love ♡
This week, take down the list of eleven names you sent your trustees in March.
Open it. Cross out nine of them.
For the two that are left, write — for each one — a four-line draft email a trustee could send in ninety seconds from her phone. Hi Anne — I wanted to introduce you to Priya, who runs an organization I've loved for years. She'll be in your part of the world the week of June 14th, and I think the two of you would have an interesting conversation. No reply needed if the timing isn't right. — Margaret
Then pick one trustee. Not the chair. Not the loudest one. The one you suspect has been quietly wanting to help and has not been given the right shape of help.
Send her the draft, with one paragraph of warm context about Anne underneath it. Tell her: No pressure, no follow-up needed. If you forward this on Tuesday, that's the whole thing. I'll take it from there.
Watch what happens. The first time will surprise you. The second time will not, because you will already know what this work was supposed to be all along.
The board did not need a retreat. The board needed an inbox they could actually act from. Build that — and the gift, the door, the meeting in the room above the bakery on a warm afternoon in late June, all of it tends to follow.