What is Business Wargaming with Nick Drage

What if the businesses that survive a crisis aren't the ones with the best plans but the ones who've already lived through the toughest days they could face? In this episode, Nick Drage tells me about business wargaming - rehearsal, role-play and the surprisingly serious business of play.

A toolbox borrowed from military history and modern games that create structured experiments. Teams step into scenarios, play out mergers from the target's point of view, or simulate cyberattacks to see how they might make decisions on the fly.

Listen to hear how the boardroom becomes a battlefield: leaders wrestle with the instinct to ‘pull the plug’ during an attack, internal teams are asked to play the hacker, and simulations demonstrate that real life rarely behaves like a textbook drill. Nick seeks to provoke hard conversations that prepare us to be better in the moment. From cyber red-team work to the simple, humane lesson of having a will, he explains why being prepared isn’t negative or morbid; it’s caring for the future.

Listen to this episode if you want to find out:

• Why this kind of play is serious
• What a preparing for cybersecurity is like a fire drill - but the fire fights back
• Why the most useful thing leaders can do with an acquisition target is pretend to be them
• How making it "safe-to-fail" lets people make catastrophic mistakes on purpose, before it matters
• Why VCs almost never stress-test founders the way a good war game would — but they should
• What making a will has to do with surviving a cyberattack

Links:

Nick Drage / Path Dependence:
https://www.pathdependence.co.uk/about/

The Handbook of Cyber War Games by John Curry & Nick Drage
https://amzn.to/4yYi0yS (Affiliate Link)

Random: How to Thrive in an Unpredictable World by Matt Ballentine & Nick Drage
https://securityblendbooks.com/products/random

UK Resilience Academy white paper, "Wargaming in a Resilience Context"
https://ukresilienceacademy.org/wp-content/uploads/2026/07/UKRA-Wargaming-Insight-Paper.pdf

Stone Paper Scissors:
https://www.stonepaperscissors.co.uk/

Chapters:

• 0:00:49 — What is a business war game (and why the name is wrong)
• 0:04:53 — The master question: how a session actually gets built
• 0:09:15 — The fire drill where the fire fights back
• 0:10:45 — Giving your own staff permission to be evil
• 0:12:08 — The pen-test that made him unpopular in the office
• 0:13:11 — What separates a real war game from a strategy away-day
• 0:17:06 — Playing the enemy: what happens when leaders role-play a takeover
• 0:19:32 — Designing for disagreement, on purpose
• 0:21:06 — What his father's death taught him about planning and preparation
• 0:25:21 — Should VCs war-game founders before they invest?
• 0:28:45 — How to try this yourself, on a small scale

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Thanks for listening.

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