When Leadership Blocks Your Pre-Mortem

TL;DR: The Pre-Mortem

Leadership resistance to your pre-mortem reveals whether your organization’s operating model prioritizes comfortable narratives over preventing failure. This article shows you how to diagnose cultural dysfunction and decide which battles to fight.

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The Magic Of Risk Mitigation Without Passing Blame

There’s a risk technique that takes 60 minutes, costs nothing, and surfaces problems other planning methods miss. It’s been field-tested for nearly two decades. Teams that use it catch catastrophic issues while there’s still time to act.

Most organizations never run one. When you try to introduce it, the people who complain loudest about projects failing are likely the same ones who will kill it in the meeting. The technique is the pre-mortem, and the resistance you hit tells you more about your organization than any risk register.

The Basics (In Case You Haven’t Run a Pre-Mortem)

Traditional risk planning asks “what might go wrong?” A pre-mortem flips it: Assume your initiative already failed. It’s six months from now, the project is a smoking crater, and you’re gathering the team to explain what happened.

That shift from “might fail” to “did fail” breaks something open. People stop hedging. The risks they’ve been too politically careful to mention in a typical planning session suddenly make it into the room: the technical debt everyone knows about, but nobody wants to raise, the stakeholder who will torpedo this in month four, the assumption the whole plan depends on that nobody has actually validated.

The pre-mortem technique is simple: In a 60-minute session, everyone first writes down their own reasons for failure. You cluster them, vote on the critical ones, then dig in:

• What does that failure actually look like?
• What early warnings would we see?
• What can we do this week to prevent it? What’s the backup plan?

You walk out with a shared understanding of what could kill this initiative and concrete actions you can take immediately. Not a document to file. Actual insight. My tip: Liberating Structures work very well in this context; think of TRIZ, for example.

Objectives from Leadership Level Against Pre-Mortems

Interestingly, the pre-mortem technique is not as popular as we think. On the contrary, any facilitator who suggests a pre-mortem may face serious opposition from leadership.

The top-three objections are:

1. “We Don’t Have Time for Another Workshop”

When you hear this, you’re not hearing a scheduling problem. You’re hearing a confession.

What they’re saying: Calendars are packed, we’re under pressure to deliver, and an hour spent imagining failure is an hour not spent building.

What they’re confessing: Planning in this organization is theater. We can’t tell the difference between looking busy and being effective. We have time for roadmap sessions and strategy off-sites that produce nothing but slide decks, but not for 60 minutes that might actually prevent failure.

Ask yourself: if you don’t have 60 minutes to pressure-test a significant initiative before you commit resources to it, what are you doing in all those other meetings? If you can’t spare an hour for thinking, you’re not planning but performing planning for an audience.

You always have time for what you actually value. This objection shows that the organization values the appearance of progress over its substance.

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2. “This Is Too Negative, It Will Demotivate People”

This one is my favorite because it’s pure magical thinking dressed up as leadership wisdom.

What they are saying: We need to project confidence. Dwelling on failure becomes self-fulfilling. Teams need positive energy.

What they are actually revealing: We have confused optimism with competence. We believe reality is negotiable, that if we just maintain the right attitude, the laws of physics, market dynamics, and technical constraints will join our efforts and make us successful.

The problem, of course, is that reality doesn’t care about your team’s morale. Your competitors aren’t checking your confidence level before they move. Technical debt doesn’t vanish because you chose not to discuss it.

I have watched this play out repeatedly. Teams that can only stay motivated by avoiding hard truths aren’t resilient; they’re brittle. The first time they hit a problem they didn’t prepare for, the whole structure collapses. Motivation built on denial shatters the moment you encounter reality.

The most motivated teams I have seen are those that know precisely what they are up against and have a plan to deal with it. And if that is not working, they can pivot rapidly to another plan. Confidence that survives contact with reality requires facing reality first.

3. “We Already Manage Risk”

This objection is the most revealing because it exposes a category error in the organization’s thinking.

What they are saying: The PMO maintains risk registers. We have governance processes. Project reviews happen. Therefore, a pre-mortem looks like duplication.

What they are missing: They have mistaken the artifact for the activity. Having a risk register is not the same as having risk awareness. It is the difference between owning a fire extinguisher and understanding how fires start.

Look at the risk registers in your organization. You will often see the same five entries on every project: “scope creep,” “resource constraints,” “stakeholder alignment,” “technical complexity,” and “timeline pressure.” Not wrong. Just useless. Too generic to act on, too obvious to provide insight, too abstract to prevent anything.

A pre-mortem asks different questions. It focuses on what will kill this particular initiative in this context. It uses collective intelligence from everyone who knows something critical about what could go wrong, not one person filling out a template alone, thereby creating alignment and a shared understanding of the risk situation. You are not duplicating risk management. You’re doing it for the first time.

Conclusion — What You Learn from a Pre-Mortem’s Rejection

When leadership blocks a pre-mortem with one of these objections, pay attention. You are learning more about the system you are operating in than about the technique.

The pattern is consistent: The organization prefers comfortable narratives to uncomfortable truths. It would rather maintain the fiction of control than develop the capability to handle what is coming.

No facilitation method fixes that. If leadership can’t spare 60 minutes for critical thinking, or believes acknowledging problems creates them, or thinks documentation equals understanding, you face a cultural dysfunction that runs deeper than your initiative’s risk profile.

You can still use that information. You can make better decisions about where to invest your energy, which battles are worth fighting, and whether this organization is serious about the outcomes it claims to want.

Sometimes, the most valuable thing a pre-mortem shows you is that nobody in charge actually wants to know why a project might fail.

📖 Pre-Mortem Related Posts

Why Agility Matters (And How to Break the Cycle When It Doesn’t)

AI Transformation Déjà Vu: Why Today’s Failures Look Uncannily Like Yesterday’s “Agile Transformations”

Why Leaders Believe the Product Operating Model Will Succeed Where Agile Initiatives Failed

AI Risks: Why Product Professionals Are Sleepwalking Into Strategic Irrelevance

👆 Stefan Wolpers: The Scrum Anti-Patterns Guide (Amazon advertisement.)

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