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What initiatives deserve premortem insurance?

What initiatives deserve premortem insurance?

Anticipating points of failure can create more resilient business decisions.

Leary Gates
Mar 09, 2025
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Strategic CEO
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What initiatives deserve premortem insurance?
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THINK ON IT: What initiatives deserve premortem insurance?

We all know that, after a catastrophe, conducting a postmortem can be a terrific learning technique, keeping us from experiencing similar outcomes in the future.

But what if we were to do it before disaster strikes. What if we were to conduct a premortem before undertaking our most important strategic initiatives? 

Think back to that last less-than-ideal outcome you experienced. Imagine if you were able to travel back in time, before it unraveled. What might have you told yourself to be on the lookout for?

Could that information have better prepared you to recognize its coming? Could it have given you time to make viable contingency plans? And, could those plans have mitigated the catastrophe or lessened the cost to remedy it? 

Welcome to the power of a premortem.

Premortems are like jumping into a time machine and imagining a future where things don’t turn out the way you like. Think Luke Skywalker entering the Cave of Dagobah.

Few of us like to confront our future failures. We’d rather just keep the optimism for our initiatives in high gear, than deflate it with all the ways they can go bad.

So, while we might like the idea of a premortem as a good-to-have, kind of like insurance, it’s not a have-to-have. We’ll get by without them.

That is, until tragedy does strike and we wonder what just went wrong. And whether it could have been avoided had we conducted that premortem we thought we could do without.

The bottom line: The strategic initiatives you’re investing significant resources to achieve deserve the modest cost of some premortem insurance.

Go ahead. Step into the dark cave of your future. Look at all the ugly stuff that could happen to your most important projects.

And step away better prepared for it if it does.

Premium Subscribers, read on for how to create a premortem blueprint for your strategic initiatives. (Become a Premium Subscriber. Paid subscribers get access to nearly 100 tools and how-tos on implementing strategic topics, including a 7-part series to help leaders build their own strategic capacity.)


“Good intentions don’t work. Mechanisms do.”

— Jeff Bezos


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