Every senior executive has confronted the same uncomfortable realization: the decision-making playbook that got them to the C-suite is no longer sufficient. Careful analysis, broad consensus, and staged commitment now collide with a reality where AI capabilities shift in months, and a single regulatory announcement can reshape an industry overnight.
This isn’t a call for recklessness. It’s a recognition that the nature of executive decision-making has changed.
Distinguish reversible from irreversible
Jeff Bezos’s distinction between “one-way doors” and “two-way doors” has aged well. Most decisions are reversible—piloting an AI tool, entering a market, restructuring a team—and should be made quickly, with imperfect information, by the people closest to the work. The irreversible decisions—acquisitions, balance-sheet bets, multi-year platform commitments—deserve the deliberation that once characterized all executive choices.
The trap is applying the same heavyweight process to both categories, producing paralysis on small bets and insufficient rigor on the ones that actually matter. While you’re convening another steering committee on a $50,000 pilot, your competitor has run three experiments and learned something you haven’t.
Plan in scenarios, not forecasts
Single-point forecasts have always been somewhat fictional, but they’re now actively dangerous. No one knows whether the cost of intelligence will drop by a factor of ten or a hundred in the next eighteen months, or how the next election cycle will reshape industrial policy. Building a strategy that depends on a specific future is building on quicksand.
The discipline worth cultivating is scenario planning—not as an annual offsite exercise, but as an ongoing habit. What three meaningfully different futures could we face in twenty-four months? Which current commitments work in all three? This reframing often reveals that bold strategic bets are actually concentrated wagers on a particular future. Robustness beats optimization when you don’t know which world you’re operating in.
Build optionality into commitments
The most sophisticated executives structure decisions so that information arrives before full commitment is required: staged investments with clear go/no-go milestones, partnerships with exit clauses, and technology choices that preserve the ability to switch vendors.
Optionality has a cost—it’s almost always cheaper in the short run to commit fully. But in a volatile environment, that premium is the price of being able to course-correct. The executives who locked in long-term software contracts in 2022 are watching peers with modular AI stacks move three times faster.
Treat dissent as infrastructure
In high-uncertainty environments, the worst failure mode isn’t being wrong—it’s being wrong together. Teams that prize alignment above all else systematically underweight the scenarios that would have been obvious to a dissenting voice. When everyone agrees the AI strategy is sound, that’s the moment to ask who in the organization would disagree, and why they’re not at the table.
Red teams, pre-mortems, designated skeptics—the specific mechanism matters less than the cultural commitment to taking disagreement seriously.
What great looks like
Great decision-making in this climate isn’t characterized by certainty or speed alone. It’s characterized by an honest accounting of what you don’t know, calibrated bets that match the reversibility of the choice, and a willingness to update visibly when new information arrives.
The executives who do this well aren’t the ones who predict the future correctly. They’re the ones who build organizations that can thrive across many possible futures—and who model, every day, that changing your mind in light of new evidence is a sign of strength rather than weakness.
The ground will keep moving. The question is whether your decision-making process is built for that reality or still quietly assuming it isn’t.
Chris Lee is Managing Director at Empirical, where he works with executive teams on strategic planning, decison-making, AI strategy, and more. He’s all ears if you want to talk about your current opportunities and challenges. Reach him at clee@thinkempirical.com or (610) 994-1139.
