The Art of Strategic Decision Making
Every leader faces a constant stream of decisions. Some are routine; others shape the trajectory of careers and organizations. The difference between good and great leaders often comes down to decision-making quality.
Here's how to make better decisions, faster.
The Two Types of Decisions
Jeff Bezos distinguishes between Type 1 and Type 2 decisions:
Type 1 (Irreversible): One-way doors. Major commitments that are hard to undo—acquisitions, key hires, strategic pivots.
Type 2 (Reversible): Two-way doors. Decisions you can walk back if they don't work—most daily choices.
Most leaders over-deliberate on Type 2 decisions and under-analyze Type 1 decisions. Flip that pattern.
The OODA Loop
Developed by military strategist John Boyd, OODA provides a framework for rapid decision-making:
Observe: Gather relevant information. What's actually happening?
Orient: Analyze and synthesize. What does this information mean in context?
Decide: Choose a course of action based on your analysis.
Act: Execute the decision.
Then loop back: observe the results, and continue the cycle.
The speed of this loop often matters more than perfectionism at any stage.
The Eisenhower Matrix for Prioritization
Not all decisions deserve equal attention. Use the urgency-importance matrix:
| | Urgent | Not Urgent |
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| Important | Do first | Schedule |
| Not Important | Delegate | Eliminate |
Most people spend too much time on urgent-but-unimportant tasks. Great leaders protect time for important-but-not-urgent strategic thinking.
Decision-Making Under Uncertainty
Real decisions rarely come with complete information. Here's how to proceed:
Determine what you'd need to know: What information would change your decision? If no available information would change it, decide now.
Set a decision deadline: Parkinson's Law applies—decisions expand to fill the time available. Force a choice.
Make reversible bets: When uncertain, take small steps that generate information.
Prepare for multiple scenarios: Don't predict the future; prepare for several possible futures.
Avoiding Common Traps
Confirmation bias: We seek information that confirms what we already believe. Actively seek disconfirming evidence.
Sunk cost fallacy: Past investments shouldn't drive future decisions. Ask: "If I were starting fresh, would I make this choice?"
Analysis paralysis: More information isn't always better. Know when you have enough to decide.
Groupthink: Homogeneous teams make worse decisions. Cultivate dissent and diverse perspectives.
The Pre-Mortem Technique
Before finalizing a major decision, imagine it failed spectacularly. Ask: "It's one year from now, and this decision was a disaster. What went wrong?"
This surfaces hidden risks and blind spots that optimism obscures.
Building Decision-Making Muscle
Like any skill, decision-making improves with practice and reflection.
Keep a decision journal: Record major decisions, your reasoning, and later results. Review periodically.
Conduct post-mortems: When decisions don't work out, analyze why without blame.
Study others' decisions: Read case studies and biographies. How did successful leaders handle similar situations?
The Courage to Decide
The biggest decision-making failure is indecision. A good decision made quickly usually beats a perfect decision made too late.
Trust your judgment, gather appropriate input, decide, and commit. You can always course-correct.
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