Imagine your plan already failed

A pre-mortem is a planning exercise where you imagine your project has already failed, then list every reason it might have. Psychologist Gary Klein popularized it in Harvard Business Review in 2007, building on 1989 research showing that imagining an outcome as certain helps people come up with about 30% more reasons for it.

You've got a new plan. A launch, a new offer, a big hire, a marketing push. You're excited about it. So here's an exercise that might feel strange at first.

Imagine it's six months from now. The plan failed. Not a little. Completely.

Now: Why did it fail?

That question, asked in exactly that way, is one of the most useful planning tools I know. It's called a pre-mortem, and it works because of a quirk in how our brains think about the future.

The power of "it already happened"

In 1989, researchers Deborah Mitchell, J. Edward Russo, and Nancy Pennington studied something they called prospective hindsight: imagining that a future event has already happened.

They found that when people imagined an outcome as certain ("the project failed") instead of just possible ("the project might fail"), they came up with about 30% more reasons to explain it.

That sounds like a small wording change. It's not. "What could go wrong?" invites your optimistic brain to wave off concerns. "It failed. What did go wrong?" forces your brain to come up with an explanation, and suddenly the risks you were quietly ignoring start showing up.

Psychologist Gary Klein turned this into a practical tool for business teams and wrote about it in Harvard Business Review in 2007. He called it the pre-mortem: the opposite of a post-mortem. Instead of figuring out what killed a project after it's dead, you figure it out while you can still save it.

Why regular planning misses the risks

When we plan, we're in go mode. We're excited, we've already decided this is a good idea, and we mostly picture it working.

If you read my post on the planning fallacy, you know we're wildly optimistic about our own plans. We picture the steps going smoothly and forget about everything that usually gets in the way. There's a social piece, too. On a team, nobody wants to be the one raising doubts about the boss's exciting new plan. It feels negative. Disloyal, even.

Klein pointed out that the pre-mortem flips that. When the exercise is to find reasons for failure, raising concerns stops being negative. It's the assignment. The person who spots the biggest risk is suddenly the most helpful person in the room.

How to run a pre-mortem

This takes about 20 to 30 minutes. You can do it alone or with your team.

1. Describe the plan. Write down what you're planning to do and what success looks like.

2. Declare the failure. Say it out loud or write it at the top of the page: "It's [date]. This plan failed."

3. Write the reasons, independently. Everyone (or just you) takes five minutes to write every reason the plan might have failed. Don't filter. Obvious, embarrassing, and unlikely reasons all count. If you're doing this with a team, write alone first so people don't just agree with whoever speaks first.

4. Share and list them. Go around and collect every reason. Put them all on one list.

5. Pick the biggest threats. Which reasons are most likely, or most damaging? Circle the top three.

6. Change the plan. For each of the top three, decide what you'll do now to prevent it. Then update the plan.

What this could look like in practice

Let’s say you are getting ready to launch a group coaching program. While completing a pre-mortem, your list of reasons it failed may include: "I launched in December when everyone is distracted," "I only promoted it to my email list, which is small," and "I got sick of selling after week one and stopped."

None of those will be surprises once you write them down. But without this exercise, none of them would have come up in the planning phase either. Now you move the launch to late January, line up two podcast guest spots to reach new people, and schedule your promotion posts in advance so can’t quit early.

And your program fills up.

Do it alone, too

You don't need a team for this. Some of my favorite pre-mortems are solo ones, done in ten minutes with a notebook before a big decision.

Thinking about raising prices? Imagine it's a year from now and it was a disaster. Why? Maybe you lost your best clients. Maybe you explained it badly. Maybe you caved on the first pushback. Now you know exactly what to prepare for.

Plan for the failure, so you get the success

The pre-mortem isn't about being negative. It's about being honest early, while you can still do something about it. Because every plan has weak spots. The only question is whether you find them in a 20-minute exercise now, or six months from now when it's too late.

If you've got a big plan coming up and want someone to pressure-test it with you, let's run a pre-mortem together.

Sources to link: Klein (2007), "Performing a Project Premortem," Harvard Business Review · Mitchell, Russo & Pennington (1989), Journal of Behavioral Decision Making

Frequently asked questions

What is a pre-mortem?

A pre-mortem is the opposite of a post-mortem. Instead of figuring out why a project failed after the fact, you imagine it has already failed and work out why, while there's still time to change the plan.

How long does a pre-mortem take?

About 20 to 30 minutes. Describe the plan, declare that it failed, have everyone write reasons independently, combine the list, pick the top three threats, and update the plan.

Why does a pre-mortem work better than asking what could go wrong?

Imagining an outcome as certain ("it failed") rather than possible ("it might fail") makes it easier to generate reasons, a technique called prospective hindsight. It also makes raising concerns the assignment instead of a sign of disloyalty.