The HeadScratcher Post - The Power of the Pre-Mortem: Thinking Backwards to Move Forward

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June 28/29

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Imagine this: your project has completely failed.

Dead in the water. Budget blown, timelines missed, objectives unmet. Now ask yourself

—

what went wrong?

That

’

s the essence of a pre-mortem.

While post-mortems examine what failed after the fact, a pre-mortem flips the script.

You assume failure before you begin, then work backward to explore what could cause it. And in doing so, you identify risks and blind spots you might otherwise overlook.

It may sound counterproductive

—

who wants to start off by imagining doom? But counterintuitive thinking is often where the smartest insights come from. In fact, research by psychologist Gary Klein, who popularized the technique, shows that teams who use pre-mortems surface significantly more potential problems than those who don't.

Here

’

s how it works:

Step 1: Assume Failure

Begin by telling your team (or yourself):

“

It

’

s six months from now, and this project has failed spectacularly. What happened?

”

Encourage everyone to write down the reasons they believe things went wrong

—

without filters or politeness.

Step 2: Share and Group Ideas

Have participants share their imagined causes of failure. Group similar ideas. Don

’

t debate or defend. This is about surfacing concerns, not solving them (yet).

Step 3: Identify the Real Risks

Look for patterns. Are there process weaknesses? Overly optimistic assumptions? Dependencies that haven

’

t been accounted for? Often, the pre-mortem reveals issues people were hesitant to bring up until they were

“

safe

”

to speak about in the hypothetical future.

Step 4: Strengthen the Plan

Now that you

’

ve seen the possible future, adjust your course. Build in safeguards. Clarify ambiguous steps. Reassign roles. Or, in some cases, decide that the project shouldn

’

t move forward at all

—

an equally valuable outcome.

Why It Works

Most planning exercises are rooted in optimism

—

How will we succeed? A pre-mortem, by contrast, invites skepticism: How might we fail? That switch opens the door to honest thinking. It liberates people from the pressure to sound supportive or enthusiastic, especially in group settings where criticism feels risky.

It also beats overconfidence.

When teams skip this step, they often fall prey to

“

planning fallacy

”—

underestimating costs, complexity, and time. A pre-mortem inserts a layer of reality that makes overconfidence harder to sustain.

And it

’

s not just for big projects

. You can do a solo pre-mortem on anything

—

a job transition, a startup idea, even a vacation. Asking,

“

If this doesn

’

t go well, why not?

”

can make your thinking sharper and your results stronger.

Headscratcher Takeaway

Next time you

’

re excited about a plan, try this: Pause. Pretend it failed. Then ask why.

What you learn in that uncomfortable moment could save months of work, thousands of dollars, or your reputation.Thinking backward might just be the most forward-thinking move you make.

The Power of the Pre-Mortem: Thinking Backwards to Move Forward

Check out our free preview of our on-line self paced Critical Thinking Course

Next Critical Thinking Open Enrollment One day workshop in two half days, June 28/29

Imagine this: your project has completely failed.

Dead in the water. Budget blown, timelines missed, objectives unmet. Now ask yourself

—

what went wrong?

That

’

s the essence of a pre-mortem.

While post-mortems examine what failed after the fact, a pre-mortem flips the script.

You assume failure before you begin, then work backward to explore what could cause it. And in doing so, you identify risks and blind spots you might otherwise overlook.

It may sound counterproductive

—

Here

’

s how it works:

Step 1: Assume Failure

Begin by telling your team (or yourself):

“

It

’

s six months from now, and this project has failed spectacularly. What happened?

”

Encourage everyone to write down the reasons they believe things went wrong

—

without filters or politeness.

Step 2: Share and Group Ideas

Have participants share their imagined causes of failure. Group similar ideas. Don

’

t debate or defend. This is about surfacing concerns, not solving them (yet).

Step 3: Identify the Real Risks

Look for patterns. Are there process weaknesses? Overly optimistic assumptions? Dependencies that haven

’

t been accounted for? Often, the pre-mortem reveals issues people were hesitant to bring up until they were

“

safe

”

to speak about in the hypothetical future.

Step 4: Strengthen the Plan

Now that you

’

ve seen the possible future, adjust your course. Build in safeguards. Clarify ambiguous steps. Reassign roles. Or, in some cases, decide that the project shouldn

’

t move forward at all

—

an equally valuable outcome.

Why It Works

Most planning exercises are rooted in optimism

—

How will we succeed? A pre-mortem, by contrast, invites skepticism: How might we fail? That switch opens the door to honest thinking. It liberates people from the pressure to sound supportive or enthusiastic, especially in group settings where criticism feels risky.

It also beats overconfidence.

When teams skip this step, they often fall prey to

“

planning fallacy

”—

underestimating costs, complexity, and time. A pre-mortem inserts a layer of reality that makes overconfidence harder to sustain.

And it

’

s not just for big projects

. You can do a solo pre-mortem on anything

—

a job transition, a startup idea, even a vacation. Asking,

“

If this doesn

’

t go well, why not?

”

can make your thinking sharper and your results stronger.

Headscratcher Takeaway

Next time you

’

re excited about a plan, try this: Pause. Pretend it failed. Then ask why.

What you learn in that uncomfortable moment could save months of work, thousands of dollars, or your reputation.Thinking backward might just be the most forward-thinking move you make.

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June 28/29

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Previous versions of The HeadScratcher Post

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