Red teaming, our bi-annual session

Insights through sabotage

Story category: red teaming

Story tags: red team, strategy, assumptions, workshop

We have just concluded our bi-annual Decision Support Red Teaming workshop. Thirty participants from different positions in management, office, and operational teams joined the workshop. Following below is a short summary of the session and the things we did during the session.


The workshop started by looking inwards; not on team level but on individual level. We zoomed in on different cognitive biases.


A few of the biases that were covered were:


Framing effect; how we receive information based on how its framed.


Anchoring; how the first piece of information sets the bar.


Confirmation bias; how our brain resists alternative ideas.


Sunk cost fallacy; how investment in money, time, and ego traps us in the chosen trajectory.


Availability heuristic; how our brains recollect information based on frequency, recency, extremes, etc.




After we were warmed up by looking at our biased brains, we moved on to looking at our “EGO”. Our EGO loves us to death and influences our perception, decisions, actions, and interactions with others.


Next on the agenda was how we act within groups and which mechanisms lead to group think and how to deal with groupthink through structured techniques designed to mitigate these issues.


Once we were done with the awareness part of the workshop, we moved on to practical exercises designed to test and strengthen the organizational vision and supporting strategy. 


As plans are about the future, and the future is uncertain, plans and strategies contain lots of assumptions about what the future looks like, but also the plan we have made to have the vision succeed within that future. The first assignment was for teams to discover and visualize the assumptions that are at the foundation of the strategy. Assumptions were identified, vulnerable assumptions marked, and shaping and hedging actions were developed in order to strengthen the assumptions and cushion the blow in case assumptions break.


Armed with knowledge of the assumptions that have to be true in order for the strategy to work we tried to imagine what failure looks like. This time we decided to not use the pre-mortem (which is a great tool), but something a bit spicier and fun; the sabotage game. 


The exercise:


-Imagine that you are about to be fired, and you are pissed-off with management.


-Come up with ways to sabotage the company strategy.


It was great to see how much creativity this exercise unleashed, and how many new risks were identified that people never thought about before. A change in perspective and a pinch of creativity really brought about a slew of new insights. Some people were shocked to see what they are capable of coming up with to sabotage the strategy, others about risks that jumped onto the radar for the first time; insight and awareness accompanied by many “wow” moments. We had fun and came out of the session with new perspectives. Looking forward to the next session!

Copyright © 2020 ONP-Vietnam. All rights reserved.