Unlikely Things Take Root in Premortem Soil

wmjclarke
May 15
4 min read

Let’s play a leadership game, the kind most organizations don’t realize they’re in until it’s too late.

You’re about to launch a bold initiative: maybe it’s a brand-new advisory program at a high school, a redesign of how your university hires and supports adjunct professors, or a plan to "revolutionize" professional development for program leaders in your organization. The energy is high. The slides look clean. The vision statement fits on a poster.

WOULD YOU RATHER…

A) Run a premortem: Before anything happens, before the first email goes out or the first meeting is scheduled, you gather the team and say:"Let’s pretend it’s six months from now. The project has failed spectacularly. It’s a cautionary tale. What went wrong?"

You get uncomfortable. You pull apart your assumptions. You name the hidden risks. You surface what’s brittle, what’s naive, what’s invisible. Then—critically—you design around it.

B) Wait for the postmortem: The initiative has launched. It didn't go well. It fizzled, or it bombed, or it blew up in ways no one had ‘modeled’ in the project plan. Now you assemble your debrief team. You write the final report. You do the "lessons learned" exercise. You circle the calendar for a "refinement" phase. You carry the bruises—and maybe you lose the momentum, the trust, or the people you needed most.

Postmortems are valuable, but they are reactive. They are the organizational equivalent of saying, "Well, at least we learned something" as the building smolders behind you.

Why We Avoid Premortems (and Why That’s a Mistake)

Here’s the thing: premortems feel wrong because they force us to imagine failure on purpose. In organizations (especially schools, universities, nonprofits), there’s an ingrained bias toward optimism. New initiatives are launched under banners like "student-centered innovation" or "transformational leadership models." Failure is not in the marketing brochure.

A premortem feels disloyal to the dream. It feels like inviting the critics into the room before you’ve had a chance to build anything worth criticizing. But that discomfort is exactly the point. Premortems allow you to fail imaginatively instead of operationally. They create a space for constructive pessimism—the kind that saves you from destructive realities later.

In a premortem, the goal is not to find reasons not to act. It’s to find the cracks while they're small enough to patch.

Here’s an example:A nonprofit working to expand mental health access in rural communities launched a mobile counseling unit designed to reach underserved populations without the need for brick-and-mortar clinics. The idea was simple and high-impact: bring licensed therapists directly to communities using retrofitted vans—convenient, private, and localized.

They were driven by urgency and conviction. The need was obvious. The funding was secured. The vans were wrapped with hopeful slogans and parked in high-traffic areas like grocery store lots, churches, and community centers.

But they didn’t run a premortem. They didn’t ask what might go wrong. Instead, they moved straight to execution.

In the postmortem three months later, the picture was painfully clear:

Utilization was low. Many community members were reluctant to approach the vans, unsure if the services were truly confidential or meant for "someone like them."
Stigma hadn’t been accounted for. Parking a therapy van outside a Walmart created visibility—but not necessarily safety. People didn’t want to be seen walking in.
Local buy-in had been skipped. Community leaders hadn’t been involved early, so they didn’t promote the service. In some cases, they openly questioned it.
Staff burnout was high. Clinicians in the van felt isolated and unsupported. Infrastructure for debriefing and self-care was insufficient.

All of these issues were predictable—but they weren’t predicted.

Why It Matters for Organizations

In most organizations, time and energy are precious, perishable resources. So is stakeholder trust. You often get one window to launch something new before resistance calcifies.

Running a premortem is not about being negative. It’s about being strategically imaginative. It’s the practical expression of an innovation mindset: designing for failure points, not merely reacting to them.

It’s also an act of respect—for the work, for the people doing it, and for the future you're trying to build.

If You Need a Starting Point for Premortems…

Here’s a simple structure we use with teams (works for K-12 schools, universities, nonprofits, startups, anyone tackling a complex rollout):

Frame the Premortem: "Imagine it’s X months from now. The project has failed dramatically. Tell me the story. What happened?"
Create Categories of Failure:
- Operational (logistics, timing, execution)
- Communication (messaging, perception, stakeholder engagement)
- Technical (tech, tools, platforms)
- Behavioral (culture, adoption, resistance)
Gather Brutal Honesty:Let everyone contribute. No sacred cows. No defensive posturing.
Prioritize Risks:Not every imagined failure needs an action plan. Focus on high-impact, high-likelihood threats first.
Design Pre-emptive Moves:Build scaffolds, create response plans, install early warning systems.