Strategy & Decision-Making
Vickrey Auction (Second-Price Auction)
A single-item auction where the highest bidder wins and pays the highest competing bid, with truthful bidding weakly dominant under standard private-value assumptions.
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Strategy & Decision-Making
War of Attrition (Who Quits First)
A contest where participants incur costs while waiting for others to concede, trading future expense against the chance of winning.
Game TheoryStrategy & Decision-Making
Appeasement
The strategy of making concessions to an adversary to avoid conflict—most historically associated with Chamberlain's concessions to Hitler at Munich
Military StrategyStrategy & Decision-Making
Asymmetric Warfare
Military conflict between parties with dramatically different resource levels—where the weaker party uses unconventional strategies to offset the stronger party's advantages
Military StrategyStrategy & Decision-Making
Attrition warfare
The strategy of wearing down an opponent through sustained losses in personnel, resources, and morale rather than through decisive battles or maneuvers
Military StrategyStrategy & Decision-Making
Beachhead
Military strategy adapted to business: establish a small, defensible foothold in a new market before expanding
Military StrategyStrategy & Decision-Making
Boots on the Ground
The military principle that strategic objectives ultimately require physical presence and sustained commitment—air power, technology, and remote influence can support but not replace direct engagement
Military StrategyStrategy & Decision-Making
Containment
George Kennan's Cold War strategy of preventing the expansion of a threat without attempting to eliminate it directly—accepting that the adversary exists but limiting its spread through consistent, patient counter-pressu…
Military StrategyStrategy & Decision-Making
Counterinsurgency
The strategy of defeating an insurgency not by direct military force (which often strengthens the insurgency) but by winning the support of the population the insurgency operates within
Military StrategyStrategy & Decision-Making
Empty Fort Strategy
From the Chinese Thirty-Six Stratagems: when weak, display confidence and openness to make the enemy believe you're stronger than you are—turning vulnerability into apparent strength
Military StrategyStrategy & Decision-Making
Exit Strategy
A pre-planned method for ending an engagement—selling a business, leaving a relationship, withdrawing from a market, or terminating a project—designed before or during the engagement rather than after things go wrong
Military StrategyStrategy & Decision-Making
Fighting the Last War
The military and strategic error of preparing for the previous conflict rather than the next one—assuming the next challenge will resemble the last
Military StrategyStrategy & Decision-Making
Flypaper Theory
The military strategy of deliberately engaging the enemy in one location to fix them in place—drawing their resources and attention to a chosen battleground so they can't deploy elsewhere
Military StrategyStrategy & Decision-Making
Guerrilla Warfare
The strategy of a weaker force using unconventional tactics—hit-and-run attacks, local knowledge, speed, and flexibility—to offset a stronger opponent's advantages in resources and conventional power
Military StrategyStrategy & Decision-Making
Mission Command (Auftragstaktik)
The German military doctrine of telling subordinates WHAT to achieve but not HOW to achieve it—giving clear objectives, boundaries, and intent while leaving tactical execution to the person closest to the situation
Military StrategyStrategy & Decision-Making
Mutually Assured Destruction
The Cold War nuclear deterrence doctrine where both sides possess sufficient retaliatory capability to destroy the other even after absorbing a first strike—making first-strike impossible because it guarantees your own d…
Military StrategyStrategy & Decision-Making
Rumsfeld’s Rule
The epistemological framework distinguishing four categories of knowledge: known knowns (things we know we know), known unknowns (things we know we don't know), unknown unknowns (things we don't know we don't know), and…
Military StrategyStrategy & Decision-Making
Seeing the Front
The military principle (emphasized by leaders from Napoleon to Rommel) that commanders must personally observe front-line conditions rather than relying solely on reports, data, and subordinate summaries
Military StrategyStrategy & Decision-Making
Trojan Horse
A strategy of disguising your true objective inside something the target willingly accepts—gaining access through apparent gift or cooperation rather than through direct confrontation
Military StrategyStrategy & Decision-Making
Two-Front War
The strategic principle that fighting on two fronts simultaneously divides resources, attention, and energy—dramatically reducing effectiveness on both
Military StrategyStrategy & Decision-Making
Winning Hearts and Minds
The strategic principle (from counterinsurgency doctrine) that lasting influence comes not from coercion but from genuine engagement with the concerns, values, and needs of the people you're trying to influence
Military StrategyStrategy & Decision-Making
Winning a Battle but Losing the War
The strategic error of optimizing for short-term tactical victories at the expense of long-term strategic objectives—winning individual engagements while losing the overall campaign
Military StrategyStrategy & Decision-Making
Alternative Dispute Resolution (ADR)
A family of conflict resolution methods—mediation, arbitration, negotiation, collaborative law—that resolve disputes outside traditional litigation
Strategic ThinkingStrategy & Decision-Making
BCG Matrix (Growth-Share Matrix)
Boston Consulting Group's portfolio analysis tool that classifies business units by market growth rate and relative market share into four quadrants: Stars (high growth, high share), Cash Cows (low growth, high share), Q…
Strategic ThinkingStrategy & Decision-Making
Barbell Strategy
Taleb's strategy of combining extreme safety with extreme risk-taking while avoiding the middle
Strategic ThinkingStrategy & Decision-Making
BATNA (Best Alternative to Negotiated Agreement)
Roger Fisher and William Ury's concept from 'Getting to Yes': your best option if the current negotiation fails
Strategic ThinkingStrategy & Decision-Making
Betting Thinking (Expressing Confidence as Odds)
Annie Duke's technique of forcing yourself to express beliefs as probabilities or wager amounts rather than verbal labels like 'I think' or 'probably.' When you say 'I'd bet $100 at 3:1 odds that...,' you're forced to ca…
Strategic ThinkingStrategy & Decision-Making
Business Case
A structured justification for a proposed investment or initiative, including expected costs, benefits, risks, and alternatives
Strategic ThinkingStrategy & Decision-Making
Cessation (Knowing When to Stop)
The underappreciated skill of knowing when to stop pursuing a goal, project, or strategy
Strategic ThinkingStrategy & Decision-Making
Chesterton's Fence
G.K
Strategic ThinkingStrategy & Decision-Making
Conflict Resolution (Force, Power, Negotiation)
The three fundamental approaches to resolving disputes: force (coercion, threat, or violence), power (using positional, informational, or relational leverage), and negotiation (finding mutually acceptable solutions)
Strategic ThinkingStrategy & Decision-Making
Consequence-Conviction Matrix
A framework for matching decision-making approach to the situation: high-conviction/low-consequence decisions should be made quickly by individuals; high-conviction/high-consequence decisions deserve rapid execution with…
Strategic ThinkingStrategy & Decision-Making
Decision Groups / Backcasting
Backcasting starts with a desired future outcome and works backward to identify the steps needed to reach it—the inverse of forecasting (which projects forward from the present)
Strategic ThinkingStrategy & Decision-Making
Dragonfly Eye (Aggregating Perspectives)
A metacognitive strategy from Philip Tetlock's superforecasting research: like a dragonfly's compound eye that integrates thousands of lenses into a single image, excellent forecasters aggregate multiple analytical persp…
Strategic ThinkingStrategy & Decision-Making
Foxes vs Hedgehogs
Isaiah Berlin's distinction, operationalized by Philip Tetlock: hedgehogs know one big thing and apply their master framework to everything, while foxes know many things and draw on multiple frameworks
Strategic ThinkingStrategy & Decision-Making
Game Theory
The mathematical study of strategic interaction between rational decision-makers
Strategic ThinkingStrategy & Decision-Making
Hail Mary Pass
A high-risk, low-probability strategy employed when conventional approaches have failed or are unavailable—named after the desperation football play
Strategic ThinkingStrategy & Decision-Making
Intuition
Rapid, unconscious pattern recognition based on accumulated experience—what Gary Klein calls 'the power of thinking without thinking.' Intuition works by matching current situations to patterns stored in memory from thou…
Strategic ThinkingStrategy & Decision-Making
Local vs Global Optimum
The distinction between the best solution in your immediate neighborhood of the search space (local optimum) and the best solution overall (global optimum)
Strategic ThinkingStrategy & Decision-Making
Morphological Box
Fritz Zwicky's systematic creativity technique: decompose a problem into independent dimensions, list possible values for each dimension, then systematically explore combinations
Strategic ThinkingStrategy & Decision-Making
OODA Loop
John Boyd's decision cycle: Observe → Orient → Decide → Act
Strategic ThinkingStrategy & Decision-Making
Optionality (Convex Tinkering)
Nassim Taleb's principle of structuring your life and portfolio to benefit from uncertainty—creating situations with limited downside and unlimited upside (positive convexity)
Strategic ThinkingStrategy & Decision-Making
Outcome Fielding (Skill vs Luck Attribution)
Michael Mauboussin's framework for determining how much of an outcome was driven by skill versus luck
Strategic ThinkingStrategy & Decision-Making
Outside View vs Inside View
Daniel Kahneman and Amos Tversky's distinction between estimating based on the specific details of your situation (inside view) and estimating based on how similar situations typically turn out (outside view/reference cl…
Strategic ThinkingStrategy & Decision-Making
Perpetual Beta (Always Updating)
The mindset of treating your beliefs, strategies, products, and self-concept as permanently provisional—always subject to revision with new evidence
Strategic ThinkingStrategy & Decision-Making
Positive-Sum Thinking
The recognition that many interactions can increase total value rather than merely redistributing a fixed amount
Strategic ThinkingStrategy & Decision-Making
Precautionary Principle
The principle that when an action carries the potential for SEVERE, IRREVERSIBLE harm, the burden of proof falls on those proposing the action to demonstrate SAFETY—rather than on opponents to demonstrate danger
Strategic ThinkingStrategy & Decision-Making
Premortem (Prospective Hindsight)
Gary Klein's technique: before launching a plan, imagine it has already failed spectacularly, then work backward to identify what caused the failure
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