The Skill Mill
Dr. Wendell Loop / Switchback Press / 2024-01-16

Discover the premortem technique used by surgeons and planners to identify potential failures before they occur.

The Premortem Technique: How to Catch Problems Before They Happen

Imagine this: You've made a decision. You're going to start exercising four times a week. Or you're going to finish that project. Or you're going to stop checking email after 6 PM. You feel good about the plan. You're committed. And then, three weeks in, the whole thing falls apart.

You know how this story ends. You've lived it before.

There's a technique used in operating rooms and flight planning that could have saved you the heartbreak. It's called a premortem. And it works backward from failure instead of forward from hope.

What Is a Premortem, and Why Does It Work?

A premortem is a planning tool that asks you to imagine your plan has already failed. Not that it might fail. That it has failed. You're looking back from the future at what went wrong.

This matters because of how human brains work. When we're optimistic about a new plan, we tend to imagine best-case scenarios. We underestimate obstacles. We overestimate our own follow-through. It's not delusion. It's a quirk of how prediction works when we're emotionally invested in an outcome.

But when you flip the perspective--when you imagine failure as already happened--your brain switches into a different mode. You stop defending the plan. You stop assuming things will go smoothly. Instead, you get curious about what actually went wrong. And that curiosity generates useful information.

Research on premortems shows that teams who run them before implementing a project identify significantly more potential problems than teams who use other planning methods. The technique is now standard in medical settings and in project management precisely because it works.

The beauty of it is that it's not complicated. It's just a shift in perspective.

How to Run Your Own Premortem

Start with a decision or plan you're about to commit to. The bigger the change, the more useful a premortem becomes. Habit change, relationship decisions, career moves, major purchases. These are the kinds of things where a premortem can actually save you months of wasted effort.

Now imagine it's six months in the future. Your plan didn't work out. The habit you intended to build didn't stick. The project you started fizzled. The change you committed to didn't happen.

You're not asking "What could go wrong?" You're stating as fact: "It went wrong. Now tell me why."

Write down everything that happened. Don't filter. Don't worry about whether it's realistic or fair. Your brain is in fault-finding mode, and that's exactly what you want. What got in the way? What did you underestimate? What did you want to happen that didn't? What did you not anticipate?

You might write things like:

Don't censor yourself. The specificity is what makes this work.

From Prediction to Prevention

Once you've identified the ways your plan is likely to fail, you have actual material to work with. You can now design your plan to account for these failure points.

If you predicted that you'd get busy and let the routine slip, you can build in a buffer or a minimum viable version of the habit. Not four workouts a week. Maybe two, scheduled in concrete. The standard is less important than the continuity.

If you predicted you didn't have a plan for disruptions, you can create one now. What will you do if you travel? If you're sick? If work gets demanding? What's the tiniest version of the habit you'll commit to in those circumstances?

If you realized you were relying on willpower, you can redesign the environment instead. Remove friction from the desired behavior. Add friction to the undesired one.

If you flagged that you didn't have accountability, you can build it in. A check-in with someone. A tracking system. Something that makes the behavior visible.

The premortem isn't about being pessimistic. It's about being realistic. And then it's about building a plan that actually works in reality instead of in the best-case scenario.

Common Failure Points People Miss

In habit change specifically, premortems consistently reveal the same categories of failure points that people don't naturally account for:

First, environmental friction. People plan to change a behavior but don't change the environment where the old behavior lives. You can't decide to eat healthier without looking at what's in your kitchen. You can't decide to stop mindless scrolling without changing notification settings.

Second, reward deficit. People eliminate the old behavior but don't replace it with something that meets the same need. The old habit was probably filling a gap: stress relief, boredom relief, comfort, connection. If you remove it without replacement, you're fighting the need itself.

Third, inconsistent conditions. You can do something when everything is perfect. But life isn't perfect. Your plan needs to account for disruptions, travel, illness, schedule changes, emotional stress. If it only works under ideal conditions, it will fail.

Fourth, motivation decline. You're excited now. That's the beginning of the habit loop. But excitement fades. You need to build something that works when motivation isn't carrying you. Systems, environments, and accountability matter more at week four than they do at week one.

Fifth, perfectionism. You miss one day and tell yourself you've failed. You're looking for an all-or-nothing restart instead of just resuming. The premortem helps you predict this pattern and decide in advance: What does "getting back on track" actually look like?

The Premortem as a Change Agent

The premortem is useful for more than just avoiding failure. It's also genuinely useful for understanding yourself. When you ask "What will cause me to quit?" you're asking "What am I up against?" And the answer is almost never "I'm lazy" or "I don't have willpower."

The answer is usually something like: "I underestimated how much this would disrupt my evening." Or "I didn't realize I'd feel deprived." Or "I wasn't ready for how much I'd miss the old routine." These are useful pieces of information. They're not failures. They're data.

Once you have the data, you can design differently. Not perfectly. Just more thoughtfully.

Conclusion

Plans fail not because they're ambitious but because they don't account for reality. The premortem is a way of importing reality into your planning before you commit to something.

You're not trying to predict the future perfectly. You're trying to identify the most likely ways your good intentions will collide with how you actually live. Then you build around those collisions instead of hoping they won't happen.

Take 20 minutes before your next major change. Write down how it will fail. Then design your plan to account for those failures. That's the difference between a plan that looks good and a plan that actually works.

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The Past Is the Future (and the Future Is the Past) goes deeper with the full step-by-step framework.