The Hunt for Grey Swans — Top 15 Methods & Frameworks — #10 Possibility Premortems
Chasing Possibilities, Wild Cards and Extremes by Backcasting the Future
Author: Sean Moffitt, Grey Swan Guild Founder and CEO, Cygnus Ventures
“The real trick in life is to turn hindsight into foresight that reveals insight.” Robin Sharma
That will never happen. When pigs fly. You are dreaming in technicolor. When hell freezes over. If you believe that, then (insert dig here). When the rivers run dry. Not even in your next life. That has a snowballs chance in hell. Maybe on days that don’t end in Y. When fish climb up poplars. When those peas shuck themselves. Are you high/drunk/insane again? If you believe that, you might be working at the wrong company. Resistance to that lone voice in the wilderness can be rampant.
The Power of Established Thinking
When looking into the unknown, many organizations cling to the safety of established thinking. Grey Swan ideas — those unlikely yet possible events — often get laughed off as madness. They’re called deranged, heretical. Old sayings get tossed around, shutting down visions of the unimaginable. But how often do we hear those same voices admit they were wrong when the “impossible” finally happens? Let’s be real — it’s rare as flying pigs.
A Sports Parallel
Sports are a perfect stage for this kind of thinking. Endless debates, fueled by pundits and experts, give us the illusion of predictability. There’s a mountain of podcasts, websites, radio talk, all churning out predictions, hot takes, and over-the-top reactions. Armchair quarterbacks, Monday morning overreactions — sports fans know these phrases well. And the thing is, in sports, you get to see the truth soon enough. You’re either right or wrong, and there’s no hiding.
The Power Rankings Test
One Sunday, I looked through the past three years of ESPN’s NFL pre-season Power Rankings. This panel of 80 insiders — writers, editors, TV faces — ranks the 32 pro football teams before each season. They come armed with data, analysis, and confidence you’d think came from on high. But looking at how those ranks held up? Not so godly. On average, the panel missed badly on 11 teams per season. That’s over a third of their predictions, way off the mark.
Here’s a taste of the biggest misses:
- 2023: Houston Texans were slotted at 31st, finished 10th.
- 2022: Los Angeles Rams, predicted 3rd, fell to 28th.
- 2021: Cincinnati Bengals were pegged for 28th, ended up 10th.
These aren’t minor misses. They’re swings that shake the foundation of expert prediction. In sports, the results are plain and trackable. There’s no veil. But ask yourself: how often do we bury the idea of unpredictable futures in our organizations, governments, or institutions?
Embracing the Unseen — Possibility Premortems
With that in mind, let’s talk about facing the unknown without being hypnotized by history. The work ahead is to consider futures from every angle — the known, the possible, and the almost unthinkable.
It’s with this in mind we tackle how we can consider the possible futures without fthe hypnotic allure of history. Let’s explore and backcast with Possibility Premortems.
“The beauty of hindsight is that it turns missteps into stepping stones.” — Unknown
A reminder of the area our continuing Grey Swan series is covering:
Grey Swan Definition: Grey Swans are those unlikely but conceivable forces, capable of being thought about, prepared for, with impacts big enough to shake the world, for better or worse.
“The best way to protect your dream is to confront every possible nightmare.”
Method #10: Possibility Premortems
Our Possibility Premortems tool was made to cut through our attachment to the past and the comfort of the present. Unlike postmortems — those exercises in hindsight where we lay out our failures and assign blame — premortems work before the fact. They help us see problems coming, the risks we overlook, the edges we don’t see. With Possibility Premortems, decision-makers and stakeholders know we’ve mapped out the whole field, considered every likely risk and possible outcome. Trust grows when people see you’ve thought things through.
“A wise man sees failure from afar and builds a bridge to success before he even starts the journey.” — Adapted from an old proverb
Invented by: In 2007, Gary Klein, a respected mind in management and psychology, created premortems to break through the fog of overconfidence and cognitive bias. His idea was simple: ask what might go wrong. It’s a tool used now by many executives, managers, and startup teams to avoid the blind spots that often come with big decisions. Too often, junior members feel the unspoken pressure to hold back doubts, fearing it might upset the team’s momentum. With enough reprogramming, the team loses the ability to even consider big pitfalls. Klein’s method began as a way to imagine project failures in advance; we now use it as Possibility Premortems to uncover blind spots in anticipating future landscapes.
Category: Scenario development, smart decision-making, risk analysis and mitigation, strategic force analysis, spotting weaknesses, critical thinking, and audit.
Why we Love It as a Grey Swan Tool: Possibility Premortems take away the stigma of exploring unlikely scenarios — that’s the whole point. It’s an exercise where team members, no matter their rank, can talk openly about risk. It means resources are better allocated, and there’s less panic and pressure in the eleventh hour if and when things err.
Overcomes the sin of: Possibility Premortems break the “ready, fire, aim” culture by working backwards, mapping out future scenarios and making room for those wild-card discussions. Take the Shaw Festival as a case in point: foreseeing the unexpected, they took out extra insurance in 2017. When the pandemic hit, that forethought kept 500 people employed.
“Planning for failure is not pessimism; it’s wisdom wrapped in foresight.”
Possibility Premortems Work Preceded By:
- Define the Future Expected Environment and Implications
Start by setting the scene. Brief the team on what’s expected — the future environment, key objectives, and essential background. Make sure everyone knows the lay of the land. - Gather Key Stakeholders
Bring in everyone with a stake in the game. From team members to decision-makers, make sure each voice that matters is in the room. - Assume Our Prediction of The Future Has Failed
Tell the team to imagine the current prediction for the future has fallen apart. No blame, no sabotage — just focus on where the cracks might show, the reasons we might be wrong. - Colorfully Describe Different Futures
Draw out a vivid picture of a “new future.” What does it look like if the world takes an unexpected turn? Think through what might cause a crisis or trigger vulnerability. Imagine new worlds within a clear time frame.
The Heart of the Possibility Premortem Work:
- Independent Factor Development
Each team member comes up with their own reasons for the unexpected future, solo. Groupthink has no place here. - Consider Multiple Gaps and Blindspots
All team members dig into what might go wrong, especially the scenarios we might not want to see. - Scrutinize Inquiry
Ask the right questions: “What shifts might shape or break this future?” and “How can we catch the signs if we’re headed the wrong way?” - Group Dialogue
Encourage open talk. Discuss each potential future, even the ones that seem way off. Let the team weigh in, validate, or challenge every concern. - Categorize and Rank Risks
Spot the common gaps and themes. Organize them by how likely they are and how much damage they could do. - Prevention Options
Once the gaps are clear, take ownership. Lay out actions, run analysis, and prepare for the possibilities with contingencies.
Possibility Premortem Work followed by:
- Document Action Items
Turn each gap into a set of action steps. Monitor, scrutinize, and prepare reactions. Decide whether each should be woven into the main view of the future. - Contingency Planning
For the big ones — high-impact risks and Grey Swans — outline plans to keep us from getting lost. Have responses ready to protect against damage. - Author a Possibility Premortem Report
Write down every gap, every prioritized risk, solution, and plan. Make this the reference, an ongoing document that’s revisited and refined. Build wisdom, strengthen the future.
Additional Commentary on Possibility Premortems:
“Veer too far off course in most organizations, and you’ll get hammered back in line. Even the boldest, most open leaders hesitate to allow critiques that seem at odds with the company’s purpose and vision. Possibility Premortems are built differently — they draw out the edge opinions, the fringe ideas, the contrarian voices, even the ones not fully believed. At the very least, this exercise is armor against tomorrow’s backlash. At best, it’s a place to lay a stronger, more thoughtful foundation for the future — for your market, your workplace, and your culture.— Sean Moffitt
Grey Swans — A Month of Specialty Posts:
This is number ten of a set of fifteen posts on different methods and frameworks for chasing Grey Swans. but we have so much other commentary on this valuable but often overlooked chase for the non-obvious:
- I — Grey Swan Week and defining Grey Swans
- II — Our 2023 Report Card of Grey Swans (last year’s review and performance)
- III — Fifteen Ways to Hunt for Grey Swans (methods and frameworks) — #1 CIPHER,
- #2 SCAMPER
- #3 SUPERCAFFEINATED U
- #4 FUTURES WHEEL
- #5 CONE OF POSSIBILITIES
- #6 WEAK SIGNALS
- #7 SWAN SOURCING
- #8 SCENARIO ARCHETYPES
- #9 OUTSIDE-IN COLLISIONS
- #10 POSSIBILITY PREMORTEMS
- #11 RED TEAMING
- #12 WHAT IF … EXPLORATION
- #13 ADOR EDGES
- #14 CRITICAL UNCERTAINTIES
- #15 MULTI-VIEW SCENARIOS
- IV — Fifty Grey Swan Wild Card Influences in 2025 (ranking the categories)
- V — Twelve Grey Swans Revealed (<25%) — Cloudy Swans
- VI — Twelve Grey Swans Revealed (<5%) — Stormy Swans
- VII — Twelve Grey Swans Revealed (<1%) — Shadow Swans
Stay tuned with us here, as well as on our website for all the rundowns.
Participate in our Hunt for Grey Swans
Don’t worry it’s a humane hunt. We have already invited some of our regular contributors to provide us the seeds of what will be our authoritative list of one hundred 2024 Grey Swans.
These are the improbable, disruptive and remote developments that decision makers better keep at least one eye peeled open for so they don’t blindside them. Perhaps you have some you’ve considered yourself.
Be among the most talented and wide-eyed observers. Let us know your Grey Swan additions and we will add them to our annual collection with our 2024 Grey Swan Guild Submission Form. Other benefits and collabroations may follow.
Grey Swan Guild — Making Sense of the World and Next Grey Swans=
We are the Guild whose mission it is to make sense of the world and next Grey Swans (wild cards, scenarios, early signals).
How we do this is guided by our four values of: aspiration, collaboration, curiosity and purpose.
We bring this to life through four facets of our world-leading Guild experience:
- Intelligence, Content and Publications
- Events, Experiences and Learning Forums
- Global Community and Network
- Experiments and Ventures
Here’s what you can do in the Guild:
Learn about the Guild: https://www.greyswanguild.org/
Read our Content: https://greyswanguild.medium.com/
Attend our Events: https://www.greyswanguild.org/calendar
Become an Official Guild Member: https://bit.ly/gsgsmemberform
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Now past our 4th year of our Guild, we have built twelve ventures designed to create value and tap our enormous reservoir of talent found inside the Guild.
To get directly involved in any one of our Cygnus Ventures , including two venture efforts focused on research and intelligence efforts called Weathervanes (current focused) and The Radar Collection (future-focused).
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