The Judgment Calls We Make Alone

Issue #51
3-minute read

Hi Reader,

There’s a category of decision in this work that doesn’t have a good home.

Not the strategic calls. Those we can think through with our CEO and our leadership team.

Not the operational calls. Those live inside our systems and our staff.

I’m talking about the judgment calls. The ones that require a read on people and pipeline that only someone sitting in our seat can make. And the ones where being wrong has real consequences.

I make those calls alone. So do you.

The Staff Performance Question

I want to trust my team. I want them to trust that I believe in their success. Those two things are not in tension until I’m sitting with a performance question I genuinely can’t resolve.

Big gifts, individual or institutional, take time. It’s the nature of the work. Relationships mature slowly. Asks get delayed. Portfolios don’t move on a schedule that neatly aligns with fiscal years.

But there’s a line somewhere between “this is how it works” and “this person isn’t performing.” And I’m the one who has to find it.

I sit across from someone in a one-on-one, listening, wanting to believe them — and I’m not always sure I should. That moment doesn’t get easier just because I’ve been doing this a long time.

Without a peer running a comparable operation who can tell me: yes, that’s what I’m seeing too — or no, that’s a performance issue — I’m calibrating alone.

My CEO is above this. My team is inside it.

The check on my judgment doesn’t exist in any structured way.

The Market Feedback Problem

The other version: a fundraiser tells me the environment is driving poor results. The economy is soft. Donors are cautious. Timelines are extending.

And I’m reading headlines about nine-figure commitments to children’s hospitals. Corporate gifts. Individual transformational gifts. Major philanthropy is moving visibly into our space.

So which is it? Is my fundraiser right, and are those gifts outliers I’m overweighing? Or is something else going on, and I’m being managed rather than informed?

I don’t always know.

What This Has To Do With Trust

Last week, I wrote about trust being the whole job. I meant it in terms of the relationships above us, with CEOs, boards, and donors.

But trust runs inside our teams too. And the hardest part of building it isn’t the culture work, the one-on-ones, or the vision conversations.

It’s the judgment calls we make about people. We do that quietly, alone, with real consequences for the trust we’re trying to build.

If you know a Chief Fundraiser who's been making these calls alone, forward this to them. We're in this together.

Your Turn

I'll be honest, this is something I've been looking for myself.

A small, confidential space where Chief Fundraisers can bring exactly these questions about people, about pipeline, about whether your read is right. No consultants. No vendors. Just peers who hold the same seat.

I haven't found it. Does it exist somewhere I haven't looked?

And if it doesn't, would you want to build it with me?

Reply and tell me. One sentence is enough.

Coming Next Week

Growth is supposed to make things better. Sometimes it makes things harder. Next Sunday: the complexity that scaling creates and the operational drag nobody warns you about.

Cheers,
Christine

PS — Fifty-one issues in, I'm thinking about what comes next for Chief Fundraiser Weekly. If you have thoughts on what would make this more useful to you — content, format, something else entirely — I'd love to hear that too. I respond to every message.

I’m Christine Bork, Chief Development Officer at the American Academy of Pediatrics. I write Chief Fundraiser Weekly to share what I’m learning as I lead a growing team and try to do the work in a way that’s sustainable and thoughtful.

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