How a Pre-Mortem Can Improve Strategic Planning in Uncertain Times

There's something about the current business environment that makes the usual approach to planning feel increasingly inadequate. Tariffs shifting overnight, inflation that won't quite settle, consumer confidence moving in ways that are hard to read, and a general sense that the assumptions you built your strategy on in January might not hold by March. Most CEOs are navigating genuine uncertainty right now, not the comfortable kind where you know roughly what's coming and you're just managing the timing, but the unsettling kind where the ground keeps moving slightly beneath you and the usual planning tools don't quite account for it.

Which is exactly why the pre-mortem deserves more attention than it gets.

The pre-mortem was developed by cognitive psychologist Gary Klein, who published it properly in the Harvard Business Review back in 2007, and the idea is disarmingly simple. Instead of asking your team to approve a plan, you ask them to imagine it's already failed, to stand a year from now looking back at the wreckage, and to explain what went wrong. That one shift in framing changes everything about who speaks and what gets said, because nobody is being asked to criticise the plan directly, which means nobody has to be the person who throws cold water on something the leader is clearly invested in. They're just explaining a failure that's already happened, and the risks that people are too polite to raise in a normal planning meeting tend to come out almost effortlessly as a result.

Research from Wharton, the University of Colorado and Cornell found that this approach to prospective hindsight, mentally placing yourself in the future before working backwards, increased the ability to accurately forecast risks by around 30%. Daniel Kahneman, who championed the technique in Thinking, Fast and Slow, understood why it works at a psychological level, because when we imagine ourselves already in a future situation we're able to look at it from a more objective outside view, rather than the inside view that makes us defend our own decisions before they've even been tested.

And this matters more right now than it did when Klein first wrote about it, because the conditions that make planning assumptions fail are more present than they've been in years. When the environment is relatively stable, a planning process that's essentially a polished version of asking for agreement will probably hold up well enough, because the risks you didn't name were unlikely to materialise anyway. But in a climate where the variables are genuinely shifting, where a policy change or a supply chain disruption or a sudden movement in consumer sentiment can unsettle a strategy that looked completely solid six months ago, the cost of going into a plan without properly surfacing what could break it is much higher than most leaders are accounting for.

The harder discipline, though, and the part most leaders quietly skip, is being genuinely prepared to act on what the pre-mortem tells you. It's relatively easy to run the exercise, nod thoughtfully at the risks that surface, and then carry on exactly as planned. The real test comes later, when the warning signs you identified at the start actually begin to appear, and you have to decide whether you're willing to stop or change course, or whether you're going to push on regardless because of how much has already been invested. Kahneman's work on sunk cost bias explains exactly why this is so hard, because the more conviction it took to start something, the more stopping it tends to feel like a verdict on your own judgement rather than simply a rational response to new information. But treating those early warning signs as data rather than as a personal challenge is precisely what separates the leaders who get genuine value from a pre-mortem from the ones for whom it turned out to be theatre.

There's also something worth naming about the kind of leader who finds starting easy but stopping almost impossible. Most ambitious CEOs fall into this category to some degree, and it isn't a flaw exactly, the same drive that makes someone back an idea with real conviction is usually the same drive that makes them build something worth having. But a leader who can only start things ends up running a business cluttered with half-finished initiatives, each one quietly draining energy and attention from whatever would actually move things forward. Before you launch the next thing, it's worth asking not just what could go wrong, but what you are genuinely prepared to stop if it does.

In a world where the conditions are shifting as fast as they currently are, that question isn't a nice extra to add to your planning process. It might be the most important one on the agenda.

What's a plan you're currently committed to that has never been properly stress tested against the thing most likely to break it?

Nicola Gunstone is an executive coach working with CEOs and MDs of growing businesses. If this struck a chord, you can connect with her and follow the conversation on Nicola Gunstone, PCC | LinkedIn.