Why Smart Leaders Make Messy Decisions

Claire Monroe

Welcome to the show—Edwin, I want to start with a leadership behavior that gets rewarded constantly and probably shouldn’t: answering too fast. There’s this moment where a leader jumps in with, “Here’s what we’re doing,” and everyone thinks, okay, that’s decisiveness. But I’m starting to wonder if we’re just rewarding speed over actual thinking.

Edwin Carrington

That confusion happens a lot. Speed gets mistaken for certainty. Sometimes it is decisiveness, but often it’s just rushed judgment presented confidently. And because it sounds clean in the moment, nobody challenges it.

Claire Monroe

And that’s the expensive part. It looks like leadership in real time. Then three months later you realize nobody tested the assumptions, nobody named the trade-offs, and now the team is stuck executing a bad decision that felt good for about thirty seconds.

Edwin Carrington

Exactly. And the data on this is fairly sobering. McKinsey asked senior executives about strategic decisions, and seventy-two percent said bad decisions were about as frequent as good ones, or even the norm. That tells you this isn’t a fringe issue—it’s built into how many organizations operate.

Claire Monroe

Seventy-two percent is… uncomfortable. If that many leaders admit decision quality is inconsistent, then the issue probably isn’t intelligence. It’s something structural.

Edwin Carrington

Yes. Not intelligence—process. Smart people can still create very poor decision environments. Especially in unstructured meetings. One person dominates, someone introduces a late anecdote that shifts the direction, and then the leader calls it “alignment.” It isn’t alignment. It’s social pressure.

Claire Monroe

Social pressure with slides. That’s basically half of corporate decision-making right there. So when we say “slow down,” what does that actually mean? Because leaders hear that and assume it turns into more meetings and more overhead.

Edwin Carrington

It doesn’t require more meetings. Usually just a bit more discipline. First, define the decision in one sentence—not the topic, the actual decision. Second, separate facts, assumptions, and preferences. Those get blended constantly. Third, clarify roles: who recommends, who decides, who needs input, and who simply needs to be informed. That structure might add ten minutes, but it can prevent months of rework.

Claire Monroe

So the goal isn’t to make leaders slower. It’s to stop them from being fast in the wrong direction—like rushing toward an answer before the question is even clear.

Edwin Carrington

That’s exactly it. Good decision systems don’t eliminate speed. They protect it. They make sure the organization moves quickly after the logic is clear, not before.

Claire Monroe

This is where the McKinsey framework helps, right? Because not every decision needs the same level of structure. There are big-bet decisions, cross-cutting ones, delegated ones, and then the quick ad hoc calls.

Edwin Carrington

Yes, and problems start when leaders treat all four the same. A big-bet decision—like entering a new market or restructuring—needs rigor. More options, clearer assumptions, visible risks. Cross-cutting decisions fail because no one owns the seams between teams. Delegated decisions should stay close to the work. And ad hoc decisions need to stay lightweight, or they slow everything down.

Claire Monroe

The “seams” point is real. In cross-functional decisions, that’s exactly where things fall apart. Everyone assumes someone else owns the hard part.

Edwin Carrington

And that’s why decision rights matter. Who recommends, who decides, who can veto, who owns execution. Without that clarity, cross-functional work becomes performance rather than progress.

Claire Monroe

And none of these tools are particularly glamorous. Decision rights, an executive sponsor, a devil’s advocate, an assumption check… it’s not exciting, but it’s the difference between thinking and improvising.

Edwin Carrington

The devil’s advocate is especially important. Not someone who argues for the sake of it, but someone responsible for testing the logic. What would have to be true for this to fail? Which assumption carries the most risk? What evidence would actually change our minds?

Claire Monroe

That last one—what evidence would change our minds—that’s the line. Because once a team can’t answer that, they’re not deciding anymore. They’re defending.

Edwin Carrington

Exactly. And to make this repeatable, there’s a simple loop I find useful: Listen, Analyze, Act, Learn. Listen means gathering the right inputs, not just the loudest ones. Analyze means testing assumptions and alternatives. Act means making a clear decision with ownership. And Learn means coming back afterward to evaluate what happened. Most teams skip that last step, which is why they keep repeating the same mistakes.

Claire Monroe

Right—if you skip Listen, you’re blind. Skip Analyze, you’re impulsive. Skip Act, nothing happens. Skip Learn… you just keep thinking you’re getting better when you’re not.

Edwin Carrington

That’s a fair summary.

Claire Monroe

I saw this play out in a really ordinary way. A leadership team kept debating whether to centralize customer support. Weeks of models, cost analysis, service levels. And eventually someone realized the real decision wasn’t about structure—it was about what they were optimizing for. Consistency, speed, or customer intimacy. We never defined that upfront, so everything else was noise.

Edwin Carrington

That’s a classic case. Teams think they have a decision conflict, when in reality they have a question-definition problem. I’ve seen similar situations where entire discussions shifted once the real constraint was named. Until then, everyone is solving a slightly different problem.

Claire Monroe

Let’s talk about traps. Confirmation bias is obvious—falling in love with the first good story. But after a bad outcome, I see leaders swing the other way and start centralizing everything.

Edwin Carrington

Yes, a kind of overcorrection. One decision fails, and suddenly every decision needs senior approval. It feels responsible at first, but it quickly slows the organization and weakens accountability. People stop deciding and start escalating.

Claire Monroe

Which turns into an entire culture of forwarding problems upward instead of solving them.

Edwin Carrington

Exactly. Delegation only works if boundaries are clear. What you own, what level of risk you can take, when to escalate. Without that, people either freeze or escalate too early.

Claire Monroe

And on the cross-functional side, too many people in the room can actually make decisions worse. There’s this assumption that more perspectives automatically lead to better outcomes, but sometimes it just raises the social cost of saying the uncomfortable thing.

Edwin Carrington

Consensus is often confused with clarity. Consensus asks if everyone can accept the outcome. Clarity asks whether we understand who is deciding, why, and what success looks like. You can have perfect agreement and still have a very weak decision.

Claire Monroe

And avoiding that clarity usually comes from wanting harmony. But not naming the decision owner doesn’t remove conflict—it just delays it until execution, where it’s more expensive.

Edwin Carrington

Exactly. Delayed conflict tends to compound. This is why structure isn’t bureaucracy. Bureaucracy adds friction without improving thinking. Structure improves thinking so friction doesn’t spread later. It protects decision quality and, importantly, trust.

Claire Monroe

Because people can accept a tough decision if they understand how it was made. What erodes trust is when the process feels arbitrary or political.

Edwin Carrington

Yes. Once people believe decisions are arbitrary, they stop contributing their best thinking. At that point, decision quality declines even further.

Claire Monroe

So maybe the real question isn’t just whether a leader is fast or even whether the decision is right. It’s what they’re optimizing for—control, speed, certainty, or the long-term quality of decision-making across the organization.

Edwin Carrington

That’s the more useful question. And if you’re thinking about how to bring more structure into your own decision-making—without slowing everything down—you can test OAD’s tools, including behavioral frameworks, for free at o-a-d-dot-a-i. It’s a practical way to make decisions more consistent and more reliable.

Claire Monroe

Which, at the end of the day, is what people actually want. Not just fast decisions—but better ones.