The Hunt for Grey Swans — Top 15 Methods & Frameworks — #12 What If … Exploration

15 min readNov 1, 2024

Chasing Possibilities, Wild Cards and Extremes by Unshackling What’s Now

Author: Sean Moffitt, Grey Swan Guild Founder and CEO, Cygnus Ventures

“A prudent question is one half of wisdom.” — Francis Bacon

When we ask good questions, we supercharge the part of our brain that is in charge of creativity. Brain scans of healthy people show that their hippocampus is pivotal to imagination and is engaged even more when they imagine the future than when they summoned the past. When we’re asked a question our whole brain is stimulated, serotonin is released causing the brain to relax and creating a rush of dopamine triggering our reward mechanism. We are chemically motivated to go in search of the answers. A good question posed will trigger a cognitive reflex called instinctive elaboration hijacking our mental bandwidth so we can’t contemplate anything else. And one of the best questions to elicit this reaction is “what if….?”

The Qualities of A Good Future-Savvy Question

Many people have a difficult time imagining a future that is radically different than the present. Recent discoveries suggest that the area of the brain (DMN) that evaluates things also envisions them. Strange irony that many people suggest silencing their inner critic when futuring, rather than perhaps integrating them.

The questions that start with what if (or closely related to cousin prompts how could we and what would happen if…) are stimulating launch pads for breakthroughs because they are:

Future-Oriented Curiosity-Driven — Prompting a digging deeper for consideration of possibilities, trends, or “what if” scenarios.
Open-Ended — Alloings for a variety of responses without judgment, rather than a simple “yes” or “no.”
Engages the Mind— Grabbinbg attention and holding interest, making people want to respond.
Challenging — Pushing people to think outside of their comfort zones or typical thoughts.
Thought-Provoking — Encouraging the responder to consider new perspectives, hidden opportunities or wider possibilities.
Multidimensional Critical Thinking — Allowing exploration of various facets of a topic, comparisons, evaluations and creative solutions.
Emotionally Resonant — Appealing to feelings or values that the audience cares about.

”When you ask ‘what if,’ you open yourself to innovation, creativity, and new ways of seeing.”

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 Full Collection of Grey Swan Methods & Frameworks

“The power to question is the basis of all human progress.” — Indira Gandhi

Method #12: What If… Expoloration?

Our What If tool is a straightforward approach to getting at creatvity about the future. By asking ‘What If?’ questions, we open ourselves up to new possibilities and hopefully identify the emotion behind them. The idea behind the approach is to tackle problems from a fresh perspective.

Unlike Scenario Archetypes (profiled as tool #8) you can use What If …Exploration as quick ways to understand new developments, tap future sources of interest, spot new opportunities, and rethink efforts, without applying a probability component. When executed well, What If … sessions overcome fear of failure or embarassment, empower all participants, and get at outputs quickly with less experts or special resources required thna our other tools profiled.

“The most serious mistakes are not being made as a result of wrong answers. The true dangerous thing is asking the wrong question.” — Peter Drucker

Invented by: There are many people who have conducted What If approaches and facilitation. They tend to fall into two groups: sensitivity analysis and scenario analysis. Sensitivity analysis addresses changes in one key variable, and has its toots in mathematics and uncertainty, and as chapter 1 of our book Uncertainty suggests has many early contrubutors. Scenario analysis addresses multiple shifts or variables and stems back to Hemran Karn and his work with the US Military in the 1950s. The open ended What if approaches takes learnings from DeBono’s Six Hats effort from 1970s and 1980s that considered responses widely both positive/negative, feelings/facts, and big pictures/new ideas amongst its participants.

Category: Scenario Development, Creative Imagination, Trend Analysis, Horizon Scanning, Systems Thinking, Visioning & Strategic Planning Ethics

Why we Love It as a Grey Swan Tool: Foresight What Ifs … allow even stiff companies to be receptive to unconventional or unexpected futures. the exercise addresses the top and rising leadership skills of the 2020s — adaptability — being able to mentally adjust thinking in light of future uncertainties; and empathy — understanding how scenarios affect stakeholders.

Overcomes the sin of: Ignoring the corporate elephants in the room - those things beyond some of our preconceived notions, usual frameworks, initial assessments and conformist opinions that prevail as unquestioned beliefs inside. What If … Exploration provides a space and forum for dissenting views that could overcome planning fallacies.

“What if, instead of being afraid of failure, we began to embrace possibility?”

What If… Exploration Work Preceded By:

Define Your Focused Challenge or Goal: Provide a clear focus that will help you generate relevant ‘What If’ questions around a specific big decision(s), debated strategy(s), or a future scenario(s).
Create an Even Playing Field of Creative Contributors: do not provide a preference for responses across senior/junior levels, talent — external/internal or with certain disciplines — ensure some of the right brained planets of your organizational solar system get invited in however.
Establish the Standard of Response: frequently the straight arrows of the bunch will provide linear responses to even great what if questions, point out to other situations where what if situations created the bold, imaginative type of responses you are expecting.

The Heart of the What If… Exploration Work:

Ask Provocative What If … Challenging Questions: Challenge conventional thinking by asking bold and thought-provoking ‘What If?’ questions that spawn radical ideas and possible scenarios. We have provided seven areas to explore (visualized above) and a list of 100 provocative questions (below). Get participants to add cultural trends, economic conditions, technology, or regulations that can provide what if responses more context and possibility.
Put Yourself in Others’ Shoes: After first general responses, ask participants to answer what ifs from a future customer, employee, investor, regulator, media or other key stakeholder standpoint; ask them to consider both the rational and emotional impact of the what if scenarios.
Prompt The Edges: Tease out the far unknowns and barely imaginables by taking the what if questions further; get people open to exploring uncharted territories. Map out short- and long-term consequences.
Combine Ideas: Intersect responses from within and across what if question exercises and turn them into scenarios and concepts about the future.
Summarize into Future Conditions and Actions: Define colourfully what the future looks like and what actions that could feasibly addressed now to rise to that level and type of future.
Prototype and Test: Screen, Validate conditions, prototypes and test actions among the best potential and fringe responses.

What If…Exploration Work followed by:

Headline, Prototype and Test: Make work digestible through headlines, visuals and narrative. Screen, validate conditions, prototype and test actions among the best potential and fringe responses — both conditions and actions.
Crowdsource: Extend the perimeter of contribution on the best what if questions to external audiences.

Additional Commentary on What If … Exploration:

“What if questions are the lubricants for right-brain thinking among organizations and teams. Ask some of the best entrepreneurs what kept them going through the dark times and most will tell you it was a passion to address a big question or unresolved challenge. This is what ‘what ifs’ do Just look at a person’s eyes when you ask them a what if question and you can tell you are invoking a different part of their brain and adjusting their mindsets in the moment, maybe even ongoing. Foresights come out of open-ended what if curiosity that take into account the emotional and rational sides of the future.” — Sean Moffitt

One-Hundred (100) What if Questions

Purpose/Focus What ifs:

#1 What if we could create greater meaning in our work?
#2 What makes you most wonder about the reasoning behind all of this company’s vision and purposeful efforts?
#3 What if our core purpose were to change to meet new societal needs?
#4 What if our purpose were driven entirely by customer needs rather than internal goals?
#5 What if we eliminated or redefined all non-essential purposes in our organization?
#6 What if we shifted our focus from short-term gains to long-term impacts?
#7 What if we redirected our focus based on the latest industry trends?
#8 What if we envisioned a future where our products were entirely digital?
#9 What if we adopted a decentralized structure instead of a hierarchical one?
#10 What if our strategy included a commitment to total transparency with stakeholders?
#11 What if our purpose, focus, and vision aimed to solve a single global issue?
#12 What if we introduced a strategy to pivot annually to stay adaptable?
#13 What if our vision led us to enter a completely new industry or market?
#14 What if we reversed our purpose to focus on the most underserved or “unprofitable” segments of the market?
#15 What if we shifted our focus entirely from production to education, helping competitors and consumers understand the industry?
#16 What if we envisioned an entirely different future where our industry no longer existed, and prepared for that outcome?
#17 What if we used our strategy to actively encourage customer “hacks”, adds and modifications to our products?
#18 What if our purpose was to make our own company obsolete within a decade?
#19 What if we focused on only the 1% most controversial product ideas that we’ve previously dismissed as “impossible” or “too risky”?
#20 What if we pursued a “leak everything” strategy, where all product plans and updates are made public in real time?

Blindspot What ifs:

#21 What if we could leap ahead, what’s missing from our view now?
#22 What’s not being talked about or overlooked here?
#23 What if the biggest risk to our business is something we haven’t even considered?
#24 What if a small competitor or new entrant disrupts our industry in ways we never anticipated?
#25 What if an unlikely but impactful global Grey Swan event (like a pandemic or climate disaster) changes everything overnight?
#26 What if we’re missing out on a breakthrough innovation because it doesn’t fit within our current priorities?
#27 What if we’re ignoring potential collaboration with an industry we don’t traditionally consider relevant?
#28 What if our past successes are preventing us from taking necessary risks now — what if smart 23 years old ran our company?
#28 What if a major social movement or demographic shift renders our products or services irrelevant?
#29 What if a global shift toward sustainability forces us to rethink our entire supply chain or product design?
#30 What if our most profitable product suddenly becomes illegal or publicly shunned overnight?
#31 What if a rogue insider publicly exposes all of our hidden weaknesses or trade secrets?
#32 What if we’re so focused on looking good publicly that we avoid hard but necessary truths?
#33 What if artificial intelligence replaces half our workforce, and we haven’t prepared for it — how do we catch up?
#34 What if every person, instead of purchasing products, could instantly “manifest” whatever they wanted ?

Bias What Ifs:

#35 What’s if we questioned alll current sacred cows/rules?
#36 What’s a key giverning assumption that should be challenged?
#37 What if we’re too risk-averse, leading us to overlook bold moves that could redefine our industry?
#38 What if our hiring practices unconsciously prioritize cultural “fit” over cultural “add”?
#39 What if our diversity programs focus more on metrics than on truly inclusive mindsets?
#40 What if our recruitment is biased by specific educational backgrounds, missing out on diverse skills?
#41 What if our company vision is so focused on our core market that we miss adjacent opportunities?
#42 What if our entire strategy assumes that our current business model is infallible, creating tunnel vision?
#43 What if our leaders prioritize looking competent over actually learning, hiding their mistakes from the team?
#44 What if we really are jealous of our competitor X vs. dismissive of them?
#45 What if our hiring is biased toward people who feel “safe” rather than those who might shake things up?
#46 What if our “collaborative culture” actually punishes people for working independently or challenging ideas?
#47 What if our commitment to our founding mission is outdated and now holding us back from innovating?
#48 What if our strategy revolves around what’s easiest to measure rather than what the market truly values?
#49 What if we our blind to talent who are content with working for us but not happy?
#50 What if we reverse engineer bad ideas in the hopes that good lives on the other side?

Aspiration What Ifs:

#51 What if we could unlock the key to our runaway success?
#52 What’s the next level thinking we should apply here?
#53 What if our ambition shifted to prioritizing employee happiness as our top goal instead of profit?
#54 What if we aimed to be a completely remote organization — how would that transform our culture and operations?
#55 What if we abandoned quantitative metrics altogether in favor of qualitative feedback from customers?
#56 What if our success was determined by our ability to adapt to change — how would we measure that?
#57 What if we set a metric to gauge the level of innovation within our organization rather than just revenue growth?
#58 What if we aligned our amvitions with UN’s Development Goals — what new objectives would emerge?
#59 What if our primary ambition was to foster a culture of failure, encouraging risk-taking — how would that reshape our organization
#60 What if we aimed to become a thought leader in our field — what metrics would we use to measure that influence?
#61 What if our ambition was to create a completely decentralized organization — what metrics would help us gauge success?
#62 What if our ambition was to disrupt not just our industry but the entire economy — what radical strategies would we pursue?
#63 What if we aspired to be the most controversial brand in our sector — what would that look like, and how would we embrace it?
#64 What if we embraced failure as a badge of honor and created a public “failure wall” to celebrate it — how would that change perceptions?

Future What Ifs:

#65 What if we acted now on something not relevant in 10 years?
#66 What’s emerging fast and potentially relevant here?
#67 What if a significant economic downturn lasted for the next decade— what strategies should we put in place to mitigate its impact?
#68 What if regulatory changes drastically alter our industry landscape — what proactive steps should we take?
#69 What if a new startup emerges with a disruptive business model that challenges our traditional practices — how would we pivot?
#70 What if the global supply chain faces unprecedented disruptions — what contingency plans should we develop?
#71 What if younger generations prioritize different values in their purchasing decisions — how can we adapt our branding?
#73 What if geopolitical tensions affect our international markets — how should we diversify our risk?
#74 What if public trust in corporations declines significantly — what steps can we take to rebuild our reputation?
#75 What if consumer sentiment shifts to favor local businesses — how can we leverage our local presence to gain a competitive advantage
#76 What if a celebrity or influencer starts a rival brand that resonates more with our target market — what radical moves would we need to make?
#77 What if climate change forces our company to relocate entirely — how would we handle logistics and employee transitions?
#78 What if virtual reality becomes the dominant form of consumer interaction — how would we pivot our marketing strategies?
#79 What if consumers turn to DIY solutions instead of our products — how can we pivot to support this trend while retaining relevance?

Customer What Ifs:

#80 What if we could get customers to spend more time with us?
#81 What could delight customers with the unexpected?
#82 What if future customers reject all forms of advertising and rely solely on peer recommendations — how would we adapt?
#83 What if future customers demand complete control over their data — how would we build trust and transparency in our practices?
#84 What if customers become frustrated with automation and demand authentic human interactions — how would we balance efficiency with personalization?
#85 What if future consumers were increasingly influenced by virtual influencers rather than traditional celebrities — how would we adjust?
#87 What if customers expect instant gratification, with no tolerance for delays — how would we streamline our operations to meet these demands?
#88 What if future customers view brands as extensions of their identities — how can we align our messaging to resonate deeply with them?
#89 What if our marketing campaigns must now be delivered as “truths” rather than promotions — how do we adapt our campaigns?

Industry What Ifs:

#90 What if we could change the unquestioned rules our industry operates on?
#91 How can we create our very own industry in the future?
#93 What if our entire industry shifted to a subscription model, even for products traditionally sold outright — how would we adjust?
#94 What if our competitors began offering lifetime warranties — how would we respond to remain competitive?
#95 What if we pivoted to a model that focuses on selling experiences instead of products — how do we create immersive customer journeys?
#96 What if our company was run by our biggest competitor or future threat — how would they run our company?
#97 What if a new technology emerges that allows consumers to 3D-print our products at home — how would we adapt our supply chain and distribution?
#98 What if a major environmental crisis forces our industry to adopt a circular economy model — how would we redesign our products and processes?
#99 What if we started collaborating with competitors to create industry standards — how would that change the competitive landscape?
#100 What if we had to operate in a world with no patents, leading to rampant innovation and copying — how would we protect our I.P.?

Grey Swans — A Month of Specialty Posts:

This is number eleven 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 Submission Form: https://bit.ly/2024greyswan

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).

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