“I Should Have Seen This Coming.” There’s a Tool for That.

Does this story ring any bells for you?

Tony* came to me after a reorganization that had gone sideways in almost every direction.

The intention behind it was sound. His sales and marketing teams were operating in silos — not coordinating, not communicating, and sometimes working at cross-purposes without even realizing it. Something had to change.

So the decision was made. A new org chart was drawn up. It looked clean, logical, even elegant on paper.

And then reality showed up.

The subject matter experts on the marketing side kept working in their bubble. The sales team kept making promises they couldn’t keep without marketing’s buy-in. What did change was that feelings got hurt, team leaders became more territorial than before, and everyone felt threatened by a reorganization that made sense structurally but hadn’t accounted for the human beings inside it.

When Tony and I sat down together, he said something that stuck with me:

“I should have seen this coming.”

He was right. And the frustrating part? He could have.

The Question Leaders Forget to Ask

Most of us approach big decisions by thinking forward. We build the case for why something will work. We focus on the upside. We create the plan.

What we rarely do is deliberately imagine failure before it happens.

This is the basis of a technique called the pre-mortem, developed by cognitive psychologist Gary Klein. In a traditional post-mortem, you examine what went wrong after the fact. The pre-mortem flips the timeline: before you commit to a decision, you project yourself into the future and assume the decision has already failed.

Then you ask: “What went wrong?”

It sounds simple. It is simple. But it’s surprisingly hard to make yourself do it when you’re excited about a plan, when you’ve already invested in it emotionally, or when the pressure to move forward is building.

Sound familiar? If you’ve been following this series, you’ll recognize those as exactly the conditions where bias tends to take hold.

Why It Works

The pre-mortem is effective for a few reasons — and there’s research to back it up. A 1989 study from researchers at Wharton, the University of Colorado, and Cornell found that mentally transporting yourself to a future failure increased the ability to accurately forecast risks by 30%. The simple act of assuming failure, rather than just imagining it as a possibility, sharpens thinking in ways that ordinary planning sessions don’t.

First, it gives people permission to voice concerns they might otherwise swallow. In Tony’s case, there were people on both teams who had doubts. But the momentum behind the reorg — and the HIPPO effect (Highest Paid Person’s Opinion) — kept those doubts quiet. A structured pre-mortem creates a legitimate space to say: “Here’s what worries me.”

Second, it counteracts the planning fallacy — our tendency to underestimate how long, costly, or complicated something will be. When Tony imagined the reorg failing, the answers surfaced quickly: the cultural dynamics between the teams, the lack of a change management plan, the absence of any real process shifts behind the pretty new chart.

None of that was hidden information. It was just never directly examined.

Third, it shifts the mindset from defending a decision to stress-testing it. That’s a subtle but important difference. You’re not trying to kill the idea. You’re trying to make it stronger — or catch it before it costs you.

Putting It Into Practice

Before your next significant decision, try this:

• Assemble the right people. Include voices that represent different perspectives — not just the ones who are already bought in.
• Set the scene. Tell the group: “It’s one year from now. We made this decision, and it failed. What happened?”
• Write independently first. Ask everyone to write down their failure scenarios before the group discusses. This prevents the HIPPO effect from dominating the room before the ideas are even on the table.
• Look for patterns. The concerns that come up repeatedly — especially from people who don’t usually agree with each other — deserve your closest attention.
• Then decide. You may still move forward. But now you move forward with your eyes open, having addressed the risks you can control and accepted the ones you can’t.

Tony told me that if he had run even an informal version of this exercise, he would have slowed down, invested more in the change management side of the transition, and brought both team leaders into the process much earlier. The reorg might have looked different. Or it might have looked the same — but landed differently.

That’s the point. The pre-mortem doesn’t guarantee a perfect outcome. It just makes an avoidable failure a lot harder to miss.

As Tony put it: “I should have seen this coming.”

With a pre-mortem, maybe he would have.

P.S. This is Part 4 in my series on decision-making. Catch up on the full series here.

* Client names and identifying details are always changed to protect their privacy.