Why Planning Matters More Than the Plan
Created at: September 22, 2025
Plans are worthless, but planning is everything. — Dwight D. Eisenhower
From Quip to Strategic Principle
Dwight D. Eisenhower’s remark captures a paradox: we must plan rigorously even though any single plan will likely be wrong. He framed this view not as cynicism but as discipline, emphasizing that the act of planning sharpens judgment, clarifies priorities, and exposes assumptions long before pressure mounts. The line traces to his remarks to the National Defense Executive Reserve (Nov. 14, 1957), where he argued that adaptability is born from preparation, not from clinging to documents. Thus, the aphorism becomes a strategic principle: planning creates a shared mental model that survives contact with reality even when the plan itself does not.
D-Day: Flexible Planning Under Fire
Eisenhower’s own experience at Normandy illustrates the point. Operation Overlord demanded exhaustive logistics and rehearsals, yet the decisive move was a last-minute shift driven by weather forecasts from James Stagg that forced a delay from June 5 to June 6, 1944. Eisenhower even drafted a contingency note on June 5 (misdated July 5) accepting full responsibility if the landings failed—evidence that he planned for reversal as much as success. The thousands of pages of orders mattered, but their true value lay in the commanders’ shared understanding, which enabled rapid adjustments to tides, cloud cover, and enemy response.
Planning as Cognitive Rehearsal
From this historical grounding, the idea extends to decision science: planning functions as cognitive rehearsal. By envisioning multiple futures, leaders build mental readiness for surprise. Shell’s scenario planning in the early 1970s—pioneered by Pierre Wack—anticipated oil shocks and helped the firm outmaneuver rivals (Harvard Business Review, 1985). Likewise, Gary Klein’s research on recognition-primed decisions shows that mental simulation equips experts to act swiftly under uncertainty (Sources of Power, 1998). In both cases, the activity of planning improves intuition, so when conditions shift, teams are already halfway to the answer.
From War Rooms to Boardrooms
Carrying this logic forward, modern strategy favors cycles over scripts. John Boyd’s OODA loop (observe–orient–decide–act) and W. Edwards Deming’s PDCA cycle institutionalize learning under change. Agile management echoes the same rhythm: iterate, test, adapt. NASA’s Apollo 13 mission (1970) showed how relentless simulation and contingency planning let flight controllers improvise a lifesaving CO2 scrubber—creativity that looked effortless only because practice had already mapped the option space. Thus, planning creates the conditions for improvisation to succeed, turning surprises into solvable puzzles rather than paralyzing shocks.
Risk, Checklists, and Resilience
However, adaptability requires scaffolding. Risk registers, decision trees, and checklists transform planning into operational resilience. Atul Gawande’s The Checklist Manifesto (2009) shows how structured pre-briefs and cross-checks reduce complexity-induced errors in surgery and aviation. Similarly, the Incident Command System in wildfire response assigns roles and common vocabulary so disparate teams can mesh quickly. These tools do not predict exactly what will happen; they ensure that when the unexpected arrives, people coordinate seamlessly, escalate wisely, and keep critical information flowing.
How to Plan When Plans Will Change
Finally, turning principle into practice means planning for pivots. Run pre-mortems to imagine failure and trace plausible causes (Gary Klein, 2007; echoed by Daniel Kahneman, 2011). Wargame adversarial moves and red-team assumptions (U.S. Army Red Team Handbook, 2013). Define decision points and triggers in advance, link them to data, and rehearse the handoffs. Then, update the plan continuously as feedback arrives. In this way, the plan becomes a living hypothesis—and the planning process, a habit of collective sensemaking. That enduring habit is what Eisenhower deemed indispensable.