The brief that keeps changing

By Hannah Baker

Dear Reader,

There’s a particular kind of exhaustion I keep hearing about.

It’s not burnout, exactly. It’s not being overworked. It’s something more specific, the feeling of being asked to plan something when the thing you’re planning for keeps shifting underneath you.

I’ve been hearing it a lot lately. And more and more, it has AI somewhere in the middle of it.

Here’s a version of a situation I keep encountering. Someone is working on two large projects that are probably going to merge, but nobody’s ready to have that conversation yet. In the meantime, both projects are moving. Decisions are being made. Workshops are being planned. A north star is being defined for something that might look completely different in six months.

When I ask “who owns the decision about whether these merge?”, the answer is usually some version of: " That’s a great question we’re working on."

So the work continues. Because it has to.

What I find interesting about this situation, and I see versions of it constantly right now, is that it’s not caused by laziness or bad leadership or people not caring. It’s caused by the pace of the technology itself.

Nobody knows what their AI strategy will look like in eight months. Nobody knows which of the three things their team is building will still be relevant. And yet the roadmap needs to exist. The workshop needs a goal. The decision needs to be made.

So people do what they can. They move. They plan. They build the track while the train is running over it.

And somewhere in all that movement, a quieter question gets lost.

Not what should we decide? But what kind of situation are we actually in?

What happens when you ask it

Most of the advice on decision-making under uncertainty assumes you have the authority to slow things down. Name the problem. Design better conditions. But a lot of the people I work with don’t have that authority. They’ve been handed the urgency and asked to build structure around it.

So what happens when someone in that position tries anyway, when they ask, out loud, “Do we actually know what we’re deciding here?”

Usually one of three things.

The first is silence. Or a topic change. The question lands and gets absorbed, the conversation moves on, and nobody acknowledges that it happened. Not because people are being deliberately evasive, but because nobody quite knows what to do with it either.

The second is a confident answer that, when you listen carefully, is actually a restatement of the solution rather than the problem. "We’re deciding whether to merge these two products." Yes, but why? By what criteria? What does a good outcome actually look like? The answer sounds like clarity, but it’s one layer above where the real uncertainty lives.

The third is the rarest and in some ways the hardest: an honest no. We don’t know. Followed by silence. Because naming it doesn’t automatically create a path forward. It just makes the gap visible.

What people do with this

Here’s the thing I’ve observed, and I think it’s worth saying plainly.

Most people don’t push back on any of these responses. They hear what they hear, they pivot, and they continue. The work goes on. The workshop is designed. The roadmap gets built.

And from the outside, that can look like avoidance. Like people not being brave enough to stop the train.

But I don’t think that’s what it is. I think it’s a rational response to not having power over the container. If you’re not the person who can change the deadline, extend the timeline, or redefine the brief, naming the problem out loud doesn’t solve it. It just makes you the person who complicates things.

So people absorb it. And they move.

Three moves that don’t require authority

This is where most advice stops being useful. Because the standard playbook, slow down, define the problem, align on criteria, assumes you have the standing to do that. And a lot of people don’t.

But there are a few moves that work even when you’re not in charge. None of them solves the uncertainty. They just create conditions where the right question can finally land with the people who actually own it.

Ask the smaller question.

Not “Do we know what we’re deciding?”, that’s too big, too abstract, and too easy to absorb and move past. Instead, find the one specific question that’s actually blocking everything else and ask only that.

In the situation I described earlier, the two projects that might merge, the question isn’t “Should these merge?” That’s the whole conversation nobody’s ready to have. The smaller question is: "Are these two things fundamentally the same, or not?

That’s it. One question. Ninety minutes. The right people in the room. Everything else stacks up behind that answer, and until it’s answered, everything else is guesswork anyway.

The smaller the question, the harder it is to defer.

Get the decision-makers in the room, just for a conversation.

There’s a difference between a working session designed to produce alignment and a short, contained conversation where someone has to say out loud what’s actually true. The second one is much easier to get on a calendar. And it’s often more useful.

Not an agenda. Not a Miro board. Just here’s the question, here are the people who own it, ninety minutes, someone has to say something by the end.

The goal isn’t a decision. It’s making the absence of one visible enough that it can’t stay comfortable.

Make the ambiguity visible with an artifact.

This is the one I keep coming back to. When you can show someone, visually, concretely, the current state of a system, where the pieces connect, where the gaps are, and where the unresolved decision sits in the middle of it all, it becomes very hard for a senior leader to say “we’re not ready to have that conversation yet” while looking directly at the gap.

A map. A diagram. Something that makes the shape of the problem impossible to look away from.

You’re not making the decision for them. You’re making the cost of not deciding visible. Which is a very different kind of leverage than asking the question out loud, and it works even when you’re not the most senior person in the room.

None of this resolves the deeper problem though

Because even if you ask the smaller question, get the right people in a room, and make the ambiguity visible, the deadline is still tomorrow.

The one move I’ve seen make even a small difference is what happened in a recent conversation with someone trying to figure out the right workshop to run for their team.

We spent most of the session realising they didn’t yet know what problem they were actually trying to solve. The workshop idea wasn’t wrong; it was just premature. And naming that was genuinely useful.

But here’s the uncomfortable truth: that kind of clarity doesn’t help if the deadline is tomorrow. You can slow down, talk to more people, map more of the system, and the calendar still doesn’t care.

So maybe the reframe isn’t about how to make better decisions under uncertainty. Maybe it’s about what we think a good decision even means right now.

Because I think a lot of the exhaustion I keep hearing isn’t just from the pace or the ambiguity. It’s from the gap between how decisions are supposed to work, defined problem, clear criteria, confident choice, and how they actually have to work right now.

And when the decision turns out to be wrong, or incomplete, or needs to change six weeks later, people treat that as evidence that they did something wrong.

But in conditions like these, that’s not failure. That’s just what it looks like to make a decision before the full picture exists, which is often the only option available.

Moving forward without full clarity isn’t the same as moving blindly.

Revising a decision isn’t the same as having made a bad one. And being open about uncertainty, before the workshop, before the roadmap, even just to yourself, isn’t a weakness. It’s probably the most honest thing you can do.

The goal isn’t a perfect decision. It’s a movable one.

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Until next time!

Hannah Baker ​Facilitator & Co-Founder ​The Fountain Institute

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