How Good Can This Get? What if that was the question we began with?

Somewhere along the way, the default opening question in most planning rooms became: “What could go wrong?” We call it due diligence. We call it risk management. We call it being responsible stewards of the mission.

And it is those things. But it’s also a posture. And posture shapes everything that follows.

What if we flipped it? What if, before we mapped the risks and braced for the obstacles, we asked: “How good can this get?”

Two Questions. Two Very Different Rooms.

“What could go wrong?” is a defensive crouch. It optimizes for survival. It builds strategy around fear, around the edges of failure, around protecting what already exists. It’s not without value—but it is fundamentally a contracting question. It makes the room smaller.

“How good can this get?” is an act of imagination before it’s a plan. It assumes possibility as the starting condition rather than something that has to be earned or proven first. It invites people into expansion instead of bracing them against collapse. The room gets bigger. People lean forward instead of sitting back.

In fundraising, I’ve seen this play out thousands of times. Donors don’t give to organizations that are managing risk. They give to people and visions that make them believe something extraordinary is possible. The question “how good can this get” is essentially the emotional architecture of every great campaign I’ve ever been part of. It’s the question underneath the question in every meaningful donor conversation—the one that unlocks generosity when everything else has only unlocked caution.

You Can’t Answer It Alone

Here’s what I find most compelling about this reframe: it’s fundamentally relational.

When you ask “what could go wrong,” you’re often asking it alone, or in a room full of caution—people protecting their turf, hedging their bets, quietly calculating what they stand to lose. The question isolates.

But when you ask “how good can this get,” you almost can’t answer it without other people. It pulls people toward each other. It requires shared imagination. You need someone else’s vision to expand your own. You need the person across the table to dream out loud so you can dream louder. The question is inherently collaborative, and that collaboration—that leaning in together toward something better—is itself a form of relationship-building. It’s belonging before the ask.

This is why I’ve always believed that the best fundraising conversations aren’t pitches—they’re co-creations. When a donor sits with you inside the question of how good something can get, they’re no longer a prospect. They’re a partner.

The Antidote to the Algorithm

There’s another reason this question matters so much right now. Our sector is awash in tools designed to tell us what could go wrong—predictive analytics, donor scoring models, AI-generated risk flags. These tools have their place. But they are exceptionally good at measuring what has already happened and extrapolating cautiously from it. They are not built to dream.

“How good can this get?” is a question no algorithm can fully answer, because the answer lives in human relationship, human trust, and human generosity—none of which can be reduced to a data point. It is, in the best possible way, irreducibly human.

In a moment when so much of our sector is chasing efficiency and automation, I’d argue that this question is an act of resistance. It insists that the most important work we do cannot be optimized into a workflow. It can only be tended—person to person, conversation to conversation, relationship by relationship.

Start There

The next time you walk into a campaign planning session, a team retreat, a board meeting, or a donor conversation—try beginning there. Before the risk register. Before the feasibility analysis. Before the contingency plans.

Ask: “How good can this get?”

Then listen. Really listen. Because what people say in answer to that question—what lights up in their face, what they reach for, what they can barely bring themselves to hope out loud—that’s your campaign. That’s your case for support. That’s the relationship waiting to be built.

The tools will catch up with the risks. They always do. What they can’t do is begin with wonder.

— Sterrin Bird, Founder, Wingspan Philanthropy