Pre-Mortems vs. Post-Mortems: The Anticipatory Executive Strategy Muscle

The fundamental flaw in waiting until after a crisis to figure out what went wrong screams at us. Something has already gone wrong.

Executive culture conditions us to rely on the post-mortem. Whether you face a failed initiative, an operational disaster, or a fractured governance dispute, the standard playbook dictates that you gather the team in a room, pull up a polished PowerPoint, and conduct an autopsy. But the standard post-mortem sets a trap. Survivor bias deeply infects it.

When we look back at an emergency or a project that was not entirely fatal to the organization, we naturally paint the response in a favorable light. We tell ourselves we did things mostly the right way and note a few minor tweaks for next time. This creates a dangerous illusion. It ignores the blind spots, the unknown unknowns, and the systemic vulnerabilities that we should have addressed before the crisis ever arrived.

If you want to build an organization that does not just survive crises but actively outmaneuvers them, you must stop conducting perfunctory autopsies. You need to build anticipatory muscle memory.

Imagine a standard HR disaster. You hire a problematic employee, their performance sours, you initiate an exit, and suddenly a massive lawsuit lands on your desk. Your legal team, your insurance carrier, and your HR director gather for a post-mortem. They conclude that you gave the employee good reviews in the past. When you finally separated from them, the employee used those four years of glowing reviews against you. The post-mortem merely tells you why you are currently writing a million-dollar settlement check.

If you take a Murphy’s Law approach, where anything that can happen will happen, you scrutinize your current performance review process before the employee ever fails. You identify the failure points and legally compromising habits before they become liabilities. When your team sanitizes a failing project or a massive operational pothole into a nice green checkmark on a polished PowerPoint, you lose the context you need to manage the system.

Anticipatory muscle memory allows you to see two or three steps ahead of an impending problem.

Most leaders believe that executive power means saying "yes" to new initiatives. True executive authority gives you the freedom to say "no" to things desperation would otherwise force you to accept. When you develop this anticipatory muscle, you discern which paths lead to a sub-optimal outcome. You anticipate the inevitability of events such as a new grant, a major acquisition, a natural disaster, or a funding shift.

Once you know an event approaches, you map out exactly how your organization will fail its way into that occurrence. When your culture ingrains this muscle memory, your team stops looking backward at how they avoided failure in the past. Instead, they look forward to preventing future failures.

The Pre-Mortem provides the antidote to the post-mortem trap. While I teach the granular, step-by-step mechanics of running this exercise within our private advisory forums, every executive must grasp the core philosophy immediately. You must learn to engineer failure on a quiet Tuesday.

A Pre-Mortem requires you to look at an upcoming quarter, assume your biggest project or impending challenge has catastrophically failed, and work backward. You do not ask your team if it will fail. You tell them it has failed.

Assuming failure right out of the gate shifts human nature. If you merely ask for a risk assessment, your staff naturally tries to package and sanitize bad news to protect themselves and please you. They throw generic, corporate filler language at you to soften the blow. But declaring the failure as a reality removes ego from the equation. Suddenly, your directors speak from their own zones of genius. Finance explains how the credit dried up. Operations explains how the supply chain broke.

People show remarkable creativity when figuring out how a system broke. They expose the soft underbelly of their own departments in ways they never attempt during a standard strategic planning meeting. You demand the unfiltered truth. Over time, this demand strips away the buzzwords and develops a cultural shorthand that remains blunt, honest, and highly efficient.

Anticipatory muscle memory offers cross-functional beauty. You use the exact same executive muscles to navigate a natural disaster, survive a toxic governance dispute, or overcome a sudden operational failure.

During my tenure as Mayor of Orting, we systematically built this anticipatory muscle. We did not just passively receive emergency response plans. My job as the executive required me to actively pierce those plans and look for the failure points before the water ever rose.

In January 2020, long before the World Health Organization declared COVID-19 a global disaster and while public health officials still downplayed the threat, my city clerk pointed out rising flu-like cases. Utilizing our anticipatory framework, we compared regional hospital bed capacity to historical flu trends. The math terrified us because the beds simply could not accommodate a large-scale outbreak.

The very next day, we held a tabletop exercise. We assumed a catastrophic virus. We assumed tens of thousands of cases required hospitalization in our region. We assumed people died, residents raged, and food and water supplies vanished. We looked at the board and asked what we did wrong to get here.

Assuming the worst, we immediately identified our critical vulnerabilities. While the rest of the world waited to see what would happen, we worked backward from failure. We produced tangible results. We secured water purification systems, procured tens of thousands of meals, and stockpiled PPE for our police officers well before the global shortage hit. We even quietly secured a refrigerated truck and staged it at our wastewater treatment plant to serve as a makeshift morgue. We anticipated the fundamental public safety breakdown that occurs when families cannot care for their deceased.

Engineering the failure on a whiteboard in January prevented us from flying blind. We executed a plan born from anticipatory clarity.

You translate that exact same methodology directly to a political or organizational crisis. Toward the end of my tenure, we faced a significant City Council revolt. The mechanics of surviving the revolt mirrored the mechanics of surviving the pandemic perfectly.

A political disaster, an HR scandal, or a loss of major funding acts fundamentally like a flood. Given enough time and enough variables, friction occurs. If you serve as a non-profit CEO answering to a volunteer board or a City Manager dealing with an activist council, you anticipate the gridlock.

Running an anticipatory exercise on a political failure prompts you to start vote-counting early. You anticipate the exact objections your board plans to throw at you. You identify the critical communication breakdowns that trigger a vote of no confidence. Casting forward into that failure gives you the leverage to disrupt the political theater before it paralyzes your agency. You learn when to build alignment and when you must take a bold, courageous step in the opposite direction of the room.

When executives hear about this process, they immediately ask for the meeting's physical artifact. They want an Excel spreadsheet, a Gantt chart, or a new binder.

A good friend of mine, a former Deputy Mayor, refers to standard strategic plans as "SPOTS," meaning Strategic Plans On The Shelf. This creates the worst-case scenario for an executive. You spend $100,000 on a consultant to build a matrix of tasks that no one culturally buys into. A strategic plan providing a checklist without shifting the organizational mindset proves less than useless. It actively drains your resources.

Anticipating failure certainly generates task lists like ours to procure PPE or secure lines of credit. But the true artifact of this work resides in the movement on culture. The real prize produces a team that naturally looks ahead and makes anticipatory risk management their daily way of doing business.

Introducing this framework to leaders consistently triggers two distinct types of resistance.

First, we meet the non-profit "Martyr Founder." In the non-profit sector, a singular, highly passionate founder frequently drives the organization and carries the entire operational weight. They resist looking at catastrophic failure because they feel they already figured everything out. The exercise feels like a distraction that fails to immediately remove items from their plate. But well-meaning boards and passionate teams fall short. To scale an organization beyond a martyr founder into a high-functioning governance body, leadership must institutionalize this anticipatory thinking.

Second, we encounter the ego-driven executive. In the municipal and corporate sectors, City Managers and CEOs often push back. They claim they already practice this concept and focus heavily on their post-mortems to change future behavior. I respond to them bluntly. A post-mortem shines the brightest light on the things you view with the most pride. Anticipating failure shines a light equally on all potentials for ruin.

Practicing this properly prevents the constant surprise of crises hitting your desk. It stops you from micromanaging a failing project simply because you react to sanitized information. Right now, you fly blind because you failed to build an organizational culture of anticipation.

Stop waiting for the disaster to reveal your weaknesses. Look at your calendar for next Tuesday, gather your directors, and assume you have already failed. Only then do you build the scaffold that ensures you never actually do.

You now understand the fatal flaw of the post-mortem. You know that survivor bias is a trap and that waiting for the disaster is a choice to fly blind. Knowing the philosophy is the start; execution is the barrier.

I have developed two ways to help you move from theory to operational resilience immediately:

Review the excerpt below from our Resilience Scaffold Strategic Playbook. A tangible, useful, and transformative approach to working with your team and building your culture of proactive leadership.

Direct support from someone who’s been in the trenches and worked the problems in real time - with the scar tissue to prove it. Book time with me to develop your executive leadership skills and start working the problems that hold you back.