The Question Underneath the Question

This next series of The Load is about the kind of problems that have already been “fixed” once… or twice… and are somehow back again. It’s not for lack of caring or effort. Usually the opposite. Smart teams, real exertion, good intentions… and still, the same issue finds its way back into the room. At some point, it stops being about the problem itself and starts being about what’s underneath it.

That’s where we’ll spend our time. Looking at what pressure is revealing, where things are quietly straining, and what actually has to change so the fix sticks.

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It’s a meeting just about every leader is familiar with. The problem on the table isn't new. It might have been around for months, maybe longer. The people in the room are experienced, they care, and they understand that it’s important to fix the issue. But somewhere in the middle of the discussion, you can feel the conversation start to circle. Someone suggests a fix that was tried before. Someone else raises the same objection that was raised before.

The meeting ends with an action item or two, everyone leaves with good intentions, but a couple months later the problem is back.

The issue isn’t bad leadership. It happens in good organizations, with capable people and real urgency. It's that the questions being answered in that room aren’t the questions that actually needs answering.

Most organizations are legit great at solving problems they can see. A team is missing deadlines, so you add an interim project manager. Customer complaints are climbing, so you add a quality check. Two departments keep clashing, so you get everyone to do teamwork exercises together. These are reasonable responses to real symptoms. And they often can work for a while. But if the problem keeps coming back, if the team works around the project manager rather than with them, if the same two departments are at each other's throats six months after the alignment session, chances are good that something else is wrong. 

Over the past couple decades of strategic work, I’ve found that this ‘something else’ is almost always structural, specific, and traceable. The way the organization is built produces the problem, the same way a sloped floor will roll a ball to the same corner no matter how many times you pick it up and set it somewhere else. You can keep picking up the ball, or you can start looking at the floor more closely.

The hard part is that this is genuinely difficult to see from the inside. When you're in it - responsible for outcomes and managing real pressure - the visible problem is huge and unmissable. And responding directly feels right, because doing nothing means the problem will continue. It’s hard to stop before getting to work and ask whether you're solving the right problem in the first place.

Let’s game it out. A company is growing at a consistent pace. More customers, more products, more moving parts. The teams that built the place were small and fast. Decisions happened in hallways. Everyone knew what mattered and who to call. But as the organization got bigger, something started to slow down. Approvals that used to take a day now take two weeks. Simple projects require sign-off from four teams. Meetings multiply. People start talking about ‘red tape’, the term people use when the coordination overhead stops feeling worth it.

Leaders respond the way good leaders do. They cut meetings. They push decisions down. They streamline the approval process. Some of it helps. None of it for very long.

The question everyone's trying to answer in that situation is "how do we move faster?" That's reasonable. But it's aimed at the symptom. The question underneath it, the one that leads somewhere useful, is "what is the organization actually doing when it slows down, and why is it doing that now when it didn't before?"

The answer is almost always about pressure. The organization grew. The demands on it increased. And the way it was built, which worked well enough when things were simpler, started to show strain when more was being asked of it. The slowdowns aren't a sign that people stopped caring or that leadership lost its edge. They're the system doing exactly what it's designed to do, just now under conditions it wasn't designed for.

That shift, from "we have a problem" to "our structure is producing this under pressure," changes what you look for and where you look for it. It's the shift this newsletter is built around.

Over the coming issues, we'll work through a set of questions designed to get below the visible problem to the structural layer underneath it. None of the questions are complicated. But they do require slowing down, which is exactly what pressure makes hard. I am to give you tools to help you see what's already in front of you, the patterns you've been living with, the problems that keep returning, in a way that makes the lasting right move more obvious.

The place to start is with repetition. If something keeps happening despite real effort to stop it, that pattern is worth investigating. It suggests that your system has been refined to deliver that outcome. You can’t change the result until you modify the system that consistently delivers it.

That's where we'll start next time: what keeps repeating, and what does that actually tell us about how we're built?

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