The Hunt for Grey Swans — Top 15 Methods & Frameworks — #11 Red Teaming
Chasing Possibilities, Wild Cards and Extremes by Poking Holes in the Established View
Author: Sean Moffitt, Grey Swan Guild Founder and CEO, Cygnus Ventures
“Playing devil’s advocate isn’t about negativity; it’s about seeing a perspective that others might miss.”
Futures are always disputable — that’s what makes them so interesting, we know they could always turn out differently. They should not be considered sacrosanct as some of their authors seem to suggest, and even worse, as some of the prognosticating keynote speakers carry themselves above tough examination. However, if you want to strengthen an idea, any idea, subject it to the harshest scrutiny — play the devil’s advocate. This is the power of red teams.
Imagine if Jeffrey Katzenberg had red teamed Quibi before its launch. Imagine if Adam Neumann had overcome his ego for just a moment to red team WeWork before massively expanding. Imagine if Silicon Valley Bank had red teamed its risk profile before 2023. These are the high profile situations that blew up, but big decisions go unchecked everyday inside companies that draw down value on a company’s top and bottom line.
Red Teaming + Futures
Perhaps it was my imagination but I expected to see a lot more literature on the application of red teams and foresights, futures and forecasts. There was actually very little. Red teams have their roots in military preparation, cybersecurity and corporate risk defence, but the idea of bringing an external group to challenge assumptions, strategies, plans and tactics is equally valuable across a full range of future-minded activities, verticals and disciplines.
I was going to call this framework Orange Teaming to be distinctive about red team use within a broader set of executive circles, but why? If it quacks like a duck, looks like a duck, just call it a duck. So it’s Red Teams.
Although within its military roots, red teams, wargaming and simulations are very structured for armed force readiness, the needs, parallels and benefits mimic other areas too. The whole idea of bringing an external red team in to combat existing or internal thinking isn’t destruction — it’s actual enlightenment. They make you aware of your vulnerabilities before others do and these exercises done well usually walk away with the defending side saying “I would have never thought of that.”
Poking the Holes in Established Views — Red Teaming
Whenever you invite even the most well-intentioned critique, ground rules need to be followed so organizational feelings and actions don’t get crushed.
On behalf of member of the inside company team (also known as blue or white team), they need to:
- Listen actively to the constructive criticism — don’t go immediately into defence mode, repeat or rephrase what you heard from the red team as critique for confirmation, internalize any real gaps in thinking
- Control your emotions — when facing red team observations, take a deep breath and pause to think before responding, and make responses and actions that reflect your real intentions not reactionary whimsy
- Don’t take constructive criticism personally — chill … criticism is at the heart of the Red Team exercise, and it’s centred on the thinking about the work, not about the personalities and qualifications of the original authors
- Eye on the real prize, it’s a learning opportunity — red teaming can be a great forum for identifying areas of improvement, which at the end of the day is the goal of most firms
- Think the best of the critic — part of this is you have to respect the red team members as credible (so invite the right people in), and value the time and energy they have expended on your business and situation
On behalf of the external group (the red team), they also must practice behaviours ideally sought.
As much as I love the film The Dirty Dozen, Lee Marvin’s rag tag platoon of criminals and psychopaths are not the best role model, red teamers. Red teamers have a responsibility to the sponsoring company and exercise to exhibit:
- High integrity – commitment to ethics, confidentiality and transparency, as red teams are frequently exposed to sensitive information
- Empathy for the company team — understand the real challenges the blue team faces everyday in operating and enabling a plan, they will end up doing the heavy lifting of your work
- Broad scope awareness —your expert role is based on an awareness of potential repercussions across a wave of actions and reactions within an expansive environment and system, go deep AND wide
- Adversarial mindset, with a caveat — you need the ability to think like a devil’s advocate, a competitor, a critic, deeply understanding competing motives, tactics, and persistence — without carrying the antagonistic arrogance or hostility — it’s a delicate balancing act
- Credible evidence — tap into the ability to see things others can’t see by keenly understanding facts, research, patterns, complexities and systems, versus merely stating opinion or expressing it emotionally, in order to get companies to consider what they might not rather consider, they need the goods
“The red team’s value is in preventing groupthink, forcing companies to confront uncomfortable possibilities.”
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.
“A red team tests not to destroy but to reveal the cracks in certainty.”
Method #11: Red Teaming
Our Red Teaming tool has been oriented to an organizations’ need for a devil’s advocacy view. Formulating better and broader thinking, assessment, communication, analysis and documentation is core to the exercise. The best red team foresight exercises can operate at a very high “advanced, big alternative” focus and also ground itself in understanding “edge, counter-intuitive or non-traditional” basics and tactics. One of the key benefits of red teaming is its wide application across expected environments, plans and operational tactics (we have profiled ten key ones in the visual above).
“Red teaming is about learning to become the wolf when you’ve spent your whole life as the shepherd.”
Invented by: The Prussian military developed the earliest concept of Red Teaming to help officers better understand their enemy’s next moves in realistic war game scenarios. Subsequently, it was adopted by other military organizations worldwide. The use of red teaming in corporate scenarios began with RAND in the 1960s and have flourished within cybersecurity and civil defence since. White hat or ethical hacking, wargaming, simulation and murder boarding are also terms used in the space.
Category: Risk mitigation, strategic planning exercise, external futures audit, first principles review, resilience and vulnerability testing, and foresight anticipation.
Why we Love It as a Grey Swan Tool: Foresight Red Teaming taps into benefits that are uniquely practiced by external consultants and Grey Swan experts — exposing clients to worlds, concepts and tactics they did not know about, too easily dismissed, or had seen the same thing, but interpreted it in a different way.
Overcomes the sin of: Red Teaming does a better job than most of other fourteen tools we are profiling in breaking strategy sleep walking — doing what we always have done +/- 15%. It does it by the power of fresh eyes — involving people (internal, external or hybrid) that are not part of the normal strategic planning or deevlopment process to identify blindspots. Successful Red Teams also combat the emotional attachment and biased commitment to ideas that have been developed and sacred cows that resist being altered.
“Red teaming reveals the faults we fail to see in the systems we think we know best.”
Red Teaming Work Preceded By:
- Planning and Scoping — determine what specific areas (future assumptions, strategies, plans, or processes) need Red Teaming; identify the right authors, affected stakeholders and red team members as well as rules of engagement that establish boundaries, ingoing motivations and aims of the exercise.
- Reconnaissance & Intelligence Sharing — provide the proposed ingoing draft plan (or recommendation) with support; gather publicly available and internal information about the organization (as it relates to the red team focus), and gather intelligence to map out potential vulnerabilities and alternative perspectives.
The Heart of the Red Teaming Work:
- Red Team Simulation and Exploitation — test for misguided assumptions, interacting systems, competing forces and reactions, human factors/biases and missed or incorrect future signals/headwinds/tailwinds — present established and competing views.
- White Team Panel Review — have an independent, non-vested jury evaluate the effectiveness of the Red Team poking and internal Blue Team defence.
- Go Deeper — create scenarios and simulations based on the higher questionable or risky areas of the propsoed plan, with expected evolutions and impacts.
- Reporting — document full exercise findings by ranking key vulnerabilities, attached consequences, detailed evidence to support, steps taken/not taken, techniques used and actionable recommendations.
- Debrief and Collaboration — come together to encourage enhanced knowledge sharing, executive summary of the exercise, agreed recommendations and longer term, follow-up work required.
- Workshops with the Internal Teams (Blue and or White Team): Review tactics and encourage knowledge sharing to improve defence, and areas for improvement in future exercises.
Red Teaming Work followed by:
- Remediation and Retesting — implement fixes to address top vulnerabilities and retest to verify fixes are effective and no new vulnerabilities were introduced.
- Continuous Improvement and Monitoring: conduct regular red team audits, adapt to new opportunities or threats, optimize planning and red team processes, and rotate in red team personnel to keep external objectivity.
Additional Commentary on Red Teaming:
“The ability to withstand scrutiny (and actively invite it in) is the sign of a mature, successful organization. As much as we are used to seeing sober second thought applied to governance items like financial reporting, security measures or compensation competitiveness, how often do companies apply it to executive level strategic planning or their predictions of the future? Oftentimes, it is a shadowy black box process made worse by outsourcing its development to external consultants. Red Teaming provides a structured way to sharpen focus, expand viewpoints and confront uncomfortable possibilities by defending itself to expert questions.” — Sean Moffitt
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.
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