In this episode, I was thrilled to sit down with military historian and decision-game master Bruce Ivar Gudmundsson to unpack how leaders actually develop judgment under pressure, through deliberate exposure to friction, incomplete information, and the emotional stakes of real decisions.

Bruce explains his signature tool: decision-forcing case studies (also called decision games), where participants are placed in historical scenarios as the protagonist (”You are Napoleon... what do you do?”). The goal in these decision-forcing cases is raw practice in orientation, reflection, and commitment under uncertainty.

Key threads:

* Why “cookbook doctrine” (rigid recipes) betrays people when reality shifts, while philosophical doctrine (how to think amid surprises) builds adaptability.

* The paradox of military systems: They demand loyalty/discipline and flexibility—yet often punish the experimentation needed for the latter.

* How friction is the environment where judgment grows. Ignoring it creates brittle leaders who feel “betrayed” by reality.

* Transferability far beyond the battlefield: Corporate teams, activist groups, creative collaborations, resistance networks—anywhere dynamic problems meet punished errors, orientation drifts, and decisions collapse.

* Practical starts: Read memoirs actively (pause at dilemmas: “What would I do?”), normalize truth-telling in high-trust cultures, and practice metacognition without identity risk.

If you’ve ever watched a “great on paper” leader freeze when conditions change, or felt your own organization quietly select out adaptive thinkers, this episode names the mechanism and points to the antidote.

Why listen? This is a framework for spotting systemic failures that kill initiative—and actionable ways to counter them in your world. Whether you’re building teams, running ops, or resisting entropy, understanding how judgment perishes (and revives) changes the game.

You can find Bruce’s most excellent Substack at The Tactical Notebook, where you can also get started if you’d like to join in on the decision games.

Subscribe to The Shepard Scale on Substack for more on orientation drift, counterintelligence psychology, and building antifragile human systems.

Get full access to The Shepard Scale at shepardscale.substack.com/subscribe

Change the Game Ep. 3: Decision Games, Friction, and Why Judgment Can't Be Taught by PowerPoint

Change the Game Podcast