Spy's
Guide
Thinking
Taking Risks
Strategy
DADA

Endgame Reasoning: A Spy's Strategic Thinking Framework

By John Braddock, former CIA case officer and author of the Spy's Guide series

Endgame Reasoning is a strategic thinking method where you identify what each side wants the situation to look like when it's over, then reason backward from that end state to determine what moves make sense now. Instead of asking 'what should I do next?' you ask 'what does each side want this to look like when it's done?'

How It Works

Every strategic situation has an endgame — the desired end state. The Endgame has three elements: people, place, and things.

You identify the endgame first, then reason backward step by step to your current position. This reveals what moves are logical and what moves are noise.

Most people think forward: 'What should I do next?' Endgame reasoning inverts this. You think backward: 'Where does each side want to end up?' Once you know the Endgame, the moves become obvious.

This works on negotiations, geopolitics, career decisions, competitive strategy — any situation where multiple sides have different objectives.

Example From the Field

In A Spy's Guide to Strategy, Braddock describes an airport security incident. His shoes test positive for explosives. Security converges. His endgame: get on the plane without revealing he's CIA. He reasons backward from that endgame — what story is plausible? What explanation lets him board without triggering a deeper investigation? He builds the backward chain from the desired end state to his current position, then executes forward.

The power of the method is that it eliminates irrelevant options. Once you know the endgame, most possible actions fall away. You're left with the moves that actually lead where you need to go.

How to Apply It

  1. Identify your endgame: What do you want this situation to look like when it's over? Be specific — people, place, and things.
  2. Identify the other side's endgame: What do they want it to look like when it's over? This is the most important step most people skip.
  3. Reason backward from both endgames: What steps lead from the current state to each endgame? Where do the paths conflict? Where do they align?
  4. Identify the next logical move: Based on the backward chain, what is the one move that advances your endgame while accounting for theirs?
  5. After each move, reassess: Has the endgame changed? Has the other side revealed new information about what they want?

Related Frameworks

About the Author

John Braddock was a case officer at the CIA. He developed, recruited, and handled sources on weapons proliferation, counter-terrorism, and political-military issues.

Endgame Reasoning is the central framework in A Spy's Guide to Strategy.

Apply these frameworks to your specific situation with The Operative — a strategic analysis service built on Braddock's CIA frameworks.