A Pre-Mortem for Your Strategic Plan

by Braden Kelley and Art Inteligencia

Picture the meeting. It’s eighteen months from now, and the strategy your team spent the autumn building has not worked. The numbers are down, the board is asking pointed questions, and somebody at the far end of the table says what everyone is now thinking: “We saw this coming, didn’t we?”

Here’s the uncomfortable part. Somebody probably did. Somewhere in your organization, a person noticed the weak assumption, the dependency that wouldn’t hold or the signal that didn’t fit the story. They just didn’t say so, because the plan was in motion, the leader was invested and speaking up would have felt like sabotage.

A pre-mortem is a way of getting that person to speak, while there’s still time to change the plan.

What a pre-mortem is

You’ve heard of a post-mortem, the review you hold after something has died. A pre-mortem flips the timing. You gather the team before the plan is final, and you ask them to imagine that it has already failed, badly, and to write down why.

The technique is associated with psychologist Gary Klein, who described it in The Power of Intuition and in a 2007 Harvard Business Review article, “Performing a Project Premortem.” It rests on earlier research on what’s called prospective hindsight. A 1989 study by Deborah Mitchell, Jay Russo and Nancy Pennington found that imagining an event has already happened increases people’s ability to correctly identify reasons for future outcomes by about 30%.

That’s a striking result for such a simple change. Asking “what might go wrong?” produces polite, vague answers. Saying “it has gone wrong, so what happened?” produces specific, vivid ones.

Why strategy teams need it more than project teams

Pre-mortems are most often used on projects, but I’d argue they matter even more for strategy, for three reasons.

• Strategy is built on assumptions nobody has tested. A strategic plan quietly assumes things about customers, competitors, regulation, technology and your own organization’s ability to execute. Most of those assumptions are never written down, so they’re never challenged.
• The cost of being wrong is higher. A failed project wastes a budget. A failed strategy can waste a year of the organization’s attention and commit capital in the wrong direction.
• Dissent is harder. By the time a strategy reaches a leadership team, it carries weight: the CEO’s endorsement, months of analysis, sunk effort. Raising doubts feels disloyal. A pre-mortem changes the social rules. Finding a flaw becomes the assignment, not an act of rebellion.

How to run one on your plan

You can run a strategic pre-mortem in about an hour. Here’s the structure I’d use.

1. Set the scene. Gather the people who will shape or carry out the plan, plus a few who don’t have a stake in defending it. Tell them the strategy is close to final. Then say: “Imagine it’s eighteen months from now. This strategy has failed. Not underperformed. Failed. Write down every reason you can think of.”
2. Write silently first. Give everyone several minutes to write their own list, alone, without talking. This step matters. If people share out loud first, the most senior voice anchors the conversation and everyone else adjusts. Silent writing gets you the independent views.
3. Collect one at a time. Go around the room, each person offering one reason per turn, and record them where everyone can see. Keep going until every concern is on the board. No debate, no defending. The only job at this stage is to surface.
4. Cluster and rank. Group related items. Then ask the room to rank them by two measures: how likely the failure is, and how badly it would hurt if it happened.
5. Change the plan. Take the top few risks and decide what you’ll do about each. Sometimes that means a change to the strategy itself. Sometimes it means a safeguard, a test, a contingency or a tripwire. The exercise is worthless if the plan comes out unchanged.
6. Revisit it. Schedule a review every few months. Some failure stories will fade. New ones will appear.

Prompts that make it work for strategy

A generic “imagine it failed” works, but a strategy pre-mortem gets richer when you steer the imagination into the places strategic plans usually break. Try asking:

• Which assumption turned out to be wrong? Make the team name the specific belief about the customer, the market or the competition that didn’t hold.
• What did we not see coming? Not what we got wrong, but what was simply outside our view.
• What did a competitor do? Strategies often fail because someone else moved in a way the plan didn’t allow for.
• Where did we fail to execute? The strategy was sound but the organization couldn’t deliver it: not enough capacity, capability or alignment.
• What did we know and ignore? This one stings, and it’s usually the most productive. Which warning signs were visible?

Where foresight makes a pre-mortem sharper

This is the part I find most useful, and it’s where the pre-mortem connects to the rest of the work I do.

A pre-mortem is only as good as the imagination feeding it. If your team has no structured view of how the world might change, the failure stories tend to be about internal execution: we didn’t hire fast enough, the launch slipped. Those are real, but they’re the failures people can already picture. The more dangerous ones come from outside, from a shift nobody was watching.

That’s where a foresight process pays off. If you’ve collected signals about what’s changing, grouped them into trends and built a set of possible futures, as the [FutureHacking™](https://bradenkelley.com/offerings/futurehacking/) approach does, you can run the pre-mortem against each of those futures, not only against the one you hope for. Ask: “It’s eighteen months out and we’re in this future. Why did our plan fail?” A plan that survives one future and collapses in another has just shown you where it’s fragile.

Your signals also give the pre-mortem evidence. When someone says “a competitor might disrupt us,” you can point to what you’ve actually seen. And the failure causes you find become your tripwires: the specific, observable events that tell you a risk is turning real, so you aren’t the last to know.

Mistakes to avoid

1. Running it after the decision is made. If the plan is already approved and funded, nobody will change it. Hold the pre-mortem while the answer is still open.

2. Letting the boss go first. Silent writing exists for a reason. Don’t undo it.

3. Turning it into a pessimism session. The goal isn’t to kill the strategy. It’s to make it stronger. Frame it that way, and end by deciding what to do, not just what to worry about.

4. Defending the plan. The author of the strategy will feel an urge to rebut each failure story. Ask them to listen instead, and to write down what they hear.

5. Doing it once. Conditions change. A strategy that survived a pre-mortem in October may need another in March.

A way to get started

If you haven’t yet built the evidence base for your plan, start with signals. The free FutureHacking Signal Picker helps you identify and prioritize the signals worth watching, and a good list of signals makes your pre-mortem far less abstract.

I’m also finishing the FutureCanvas Picker, which takes planners through the whole arc: from signals to trends, to a set of possible futures, to your most probable future, and then to the path toward the future you’d prefer. It pairs naturally with a pre-mortem, because once you’ve mapped the futures you can test your plan against each of them. I’m opening early access to a select group first: CSOs, strategic planners and leaders running a planning process right now who can tell me honestly what works under real deadline pressure. If that’s you, reach out and let me know and I’ll follow up personally with the select few who get in first.

The meeting you’d rather have now

Back to that table, eighteen months from now, with someone saying “we saw this coming.” The point of a pre-mortem is to have that conversation this autumn, when it costs you an hour and a few uncomfortable minutes, instead of next year, when it costs a great deal more.

Imagine the plan has failed. Then ask what happened, and fix it before it does.

Sources

• Klein, Gary. “Performing a Project Premortem.” Harvard Business Review, 2007
• Pre-Mortem Analysis summary (Philadelphia Health Foundation resource archive)

Image Credits: Pexels

Content Authenticity Statement: The topic area, key elements to focus on, etc. were decisions made by Braden Kelley, with a little help from Claude to clean up the article.

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