The Pre-Mortem

Embrace the Chaos: Harnessing Worst-Case Scenarios for Strategic Resilience

Regular readers know we typically encourage nuanced futures-thinking in this space. Just a few weeks ago, we were calling for an embrace of the messy middle, a prolonged exploration of the rich, syntopian gray area that requires us to actively resist the (totally understandable) inclination toward catastrophizing, constructing false-but-reassuring binaries, and generally thinking in extremes.

Today, we’ll have none of that. We’re going to really let the lizard brain run. But we’re going to intentionally leverage the deeply human capacity for envisioning worst-case scenarios as a means of improving strategy and increasing resilience via an approach known as the pre-mortem.

The pre-mortem isn’t new, and there are many frameworks (most commonly deployed in project management) for productively asking ourselves “What could go wrong?” and working with the answers. Here, I’m encouraging you to widen the aperture a bit and give yourself permission to consider the demise not only of a discrete project but of the organization itself—at least as you’ve known it. And just as it might be for individuals, a brush with death (even hypothetical death) can be a bracing and perspective-shifting thing for the organization as well.

To conduct the pre-mortem as a workshop, I recommend convening a fairly small group (e.g., 20 – 25) for a solid and structured block of time (45 – 60 min). Be sure to set the scope appropriately: While we can pretty easily discuss the “total” failure/death of a discrete, time-bounded project, it’s often more effective to frame the organizational failure/death somewhat more specifically. 

E.g., “In 3 years, we’ve gone from being the market leader to being a secondary or tertiary player…” or  “In 5 years, we’ll look back on our AI transformation journey as a failure…”  

It’s also often helpful to have already done some trend work so that assumptions about the broader environment of the future in question are clear—and shared. These will also likely come into play as we explore potential causes for the organization’s future failure.

After framing the failure, provide a few minutes for participants to quietly jot down all of the causes or reasons that could likely account for that failure—one per index card. 

Then, ask them to review each cause and rate it on dimensions of Criticality (How central would this cause/reason be to the ultimate failure? from 1 = Not Important to 5 = Essential) and Probability (How likely is this cause/reason to be part of the picture of failure? from 0% = Impossible to 100% = Inevitable). Allocate 10 min for this altogether.

At the end of this ideation and analysis round, each participant should have a set of index cards with potential causes of failure, and each cause should have a Criticality-score and a Probability-estimate. Time for a discussion. 

Ask the participants to share any causes/reasons that have a C-score of 4 or 5 and a P-estimate of at least 50%. Collect and cluster these on a whiteboard or similar in front of the room. You might also divide them between INTERNAL causes and EXTERNAL. Take note—especially—of causes/reasons that pop up repeatedly in the room and are highly rated by multiple participants. 

Now, you’re ready to lead a focused discussion (20 – 30 min) going cause by cause. You can take this in any number of directions, but there are some questions we’ve found particularly useful as you consider each of the highly-assessed causes of future failure for the org:

• If a reason/cause is EXTERNAL, is there anything you can do to mitigate risk, reduce exposure, or increase resilience against this thing?

• If a reason/cause is INTERNAL, is it something already in evidence? Is it already happening / being done / not being done within the org?

• If the reason is something already happening in the org: Why? What might be done to stop or mitigate it? And why wouldn’t we do that?

• If not yet happening, what leading indicators should we be watching? Are we tracking these things? How might we become more aware and responsive?⠀

At this point, you’ll already be generating and capturing a list of potentially viable next steps and valuable items for further exploration. But to prioritize the outputs, I also recommend asking the group to collectively identify (possibly with anonymized voting) the top three to five causes or reasons for failure must be meaningfully addressed. Capture these for a post-session report and follow-on discussion.

After running the pre-mortem, there will still be some very important questions of ownership and implementation to answer, but you should at least find that the brush with death has imparted a new sense perspective, clarity, and perhaps urgency as well. Now is the time to take concrete steps to make that catastrophic vision of the future less likely to become your organization’s reality. 

To repurpose the cliche: This is the first day of the rest of your (organization’s) life. Live well.

@Jeffrey