Overthinking vs Scenario Planning: A Manager's Guide to Better Decisions

What feels like restless overthinking before a big decision may actually be something else entirely. For centuries, philosophers, soldiers, and strategists have treated this kind of preparation as an advantage, not a flaw.

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Overthinking vs Scenario Planning: A Manager's Guide to Better Decisions

Seeing the Future First

Since I was young, I felt like I constantly overthought things. Sleepless nights before sales meetings, fundraising pitches, even dates. I was always playing out not only the perfect outcome but every possible way things could go wrong. It gave me an edge, but it also made me feel almost guilty for being such an overthinker.

Since I read the book Clear Thinking by Shane Parrish, some things became clearer. It made me think back to a situation when I was 10 years old, a psychologist told me something very strange but explained a lot when I think of it today.

It was during a regional math competition, where you sit with a sheet of questions and solve problems against the clock. The quiet of pens on paper, complete silence in the room, only the sound of a ticking second hand. Before the test began, someone slipped in with a clipboard and passed around a questionnaire. I filled it out the way I did everything then, neat boxes, quick decisions, no commentary. At the end of that day, after the test was over, I was called into a small room where two psychologists were waiting. They talked to me about the questionnaire I had filled out earlier, and only then did I find out what the test was about. They told me I had achieved a perfect score, meaning I showed no signs of having any stage fright (or trema, as we say in Serbian).

"You got a perfect score," they said. "On a stage fright test. That's impossible."

At the time it didn't feel like anything. I liked competitions. I chose to be there. Why would I be nervous of something I signed up for?

Looking back, I think I misunderstood what was happening, both in the room and in my head. Before I walked into that classroom, I had already walked into that classroom. I'd tripped on a mid test question and felt my pulse spike, then heard it slow again on the next one. I'd lived the awkward quiet before results, both the thrill of hearing my name and the sinking feeling of not. By the time I took the test, the room felt familiar, as if I'd visited it the night before and left a light on.

Years later, the props changed, the test and pen became Powerpoint and Jira, the invigilator a partner at a fund or team of eager developers, the bell a calendar alert, but the habit stayed. On the elevator to a pitch, I rehearse the unsmiling hello, the HDMI handshake that fails, the first question that comes three slides too early. In a multi stakeholder sales call, I've already met procurement's skeptic and the CFO's pause at price. Even with my own team, before a roadmap review, I've felt the friction in advance: the estimate that masks a trap; the design that's right and late at the same time. I don't write any of this down. It plays by itself.

There's a cost. When you've seen the ending three ways, you have to resist steering a meeting toward the version in your head. I've found myself answering questions that weren't asked yet. I've rushed to a conclusion and missed a better one hiding behind someone else's uncertainty.

For a long time I called this overthinking. Then I found a better name.

This is an essay about that shift, from calling it overthinking to treating it as tradecraft.

The Quiet Advantage of Scenario Prep

Bad Outcome Practice Lowers Your Fear

Imagine walking into a sales meeting where you've already played out every awkward pause, every pricing objection, even the coffee spill before the projector starts. When you've mentally run the bad movie, the jump scare loses its power. Shane Parrish calls this the Bad Outcome Principle: failure often springs from a failure to imagine failure. By rehearsing the downside, you reduce panic and improve your ability to respond. Seneca put it simply: "The unexpected is what crushes us." Visualizing hardship beforehand makes it bearable when it comes.

Take the example of a founder preparing for a VC pitch. Instead of focusing only on the perfect delivery, she scripts the skeptical questions: What if the TAM is smaller than you say? What if customer acquisition costs triple? What if a competitor launches tomorrow? By rehearsing these moments, her calm response is almost muscle memory. The room feels like déjà vu, not ambush.

This technique shows up everywhere. Elite athletes don't just picture the winning shot, they picture the ball slipping, the stumble, the miss, and then the recovery. Pilots spend hours in simulators practicing engine failures, storms, and equipment glitches, not just smooth takeoffs. Stage actors rehearse their lines when the lights flicker, when the microphone cuts out, and even when another actor forgets a cue. The point is simple: when the failure is no longer unfamiliar, it stops being terrifying. Familiarity strips away surprise and replaces panic with practiced response. This is why athletes call it visualization, why the military calls it training under stress, and why leaders can call it scenario prep, it makes the mind comfortable with discomfort.

Premortem Catches Blind Spots

The premortem is essentially prospective hindsight. Gary Klein popularized it in Harvard Business Review (HBR): imagine the project has failed, then list the reasons why. In a roadmap session, it gives permission for someone to say, "We'll miss the launch if we underestimate integration time." Suddenly the hidden risks are safe to name.

Think of it as a license for candor. In most meetings, people hesitate to voice doubts, they don't want to sound negative. But when you frame it as "we're imagining failure that already happened", the psychology flips. Everyone is free to share. Teams that do this often discover subtle blockers early, an overlooked dependency, a missing compliance check, a budget assumption that won't hold. By catching them in rehearsal, you design detours before hitting the wall.

Amazon famously uses a version of this in new product proposals, where teams write a future press release and FAQ as if the launch already happened. By starting with prospective hindsight, they spot gaps in reasoning and execution before spending months building.

More Ways to Prepare: Analysis, Speed, and Scenarios

Reducing bias, not just risk

Intelligence analysts faced the same challenge of avoiding tunnel vision and overconfidence in a single explanation. Richards Heuer Jr. described Analysis of Competing Hypotheses (ACH) to prevent falling in love with a single storyline. By weighing evidence across multiple possible explanations, you weaken confirmation bias. In a business setting: is a sales slump caused by product market misfit, weak pipeline hygiene, or seasonal cycles? ACH forces you to test each, not just your favorite. Stories from the CIA illustrate this: analysts used ACH after the Bay of Pigs to check their assumptions, and later to dissect the flawed WMD assessments before the Iraq war. Both cases showed the danger of groupthink and how structured methods could surface contradictory evidence. Founders and managers can adapt the same logic when debating market signals or product hypotheses.

Gaining decision velocity

John Boyd's OODA loop (Observe, Orient, Decide, Act) was born in fighter pilot dogfights but translates cleanly to boardrooms. The pilot who orients faster dictates the engagement. For a founder, scenario prep sharpens orientation: you've already mapped what legal might ask, what procurement might stall on, what investors will probe. So when the question comes, your answer is quicker, calmer, and better aimed. As Boyd put it, "Machines don't fight wars, people do. And they use their minds."

Privileging robustness over precision.

Pierre Wack at Shell made scenario planning famous when forecasts kept breaking. Rather than bet on a single oil price future, Shell leaders prepared for a handful of plausible worlds. When one unfolded, they weren't right, they were ready. For a startup, this means you don't just model the perfect hockey stick; you model the flatline, the slow rise, and the sudden surge. Then you design moves that survive across them all. Arie de Geus later noted that Shell outperformed rivals not by predicting, but by preparing. For founders, the lesson is clear: fewer brittle bets, more resilient options.

Where This Habit Comes From

We didn't invent it in boardrooms. The Stoics practiced negative visualization to blunt life's shocks, Marcus Aurelius reminding himself each morning that difficult people awaited him, Seneca urging Lucilius to rehearse poverty and loss so fortune could not dominate him. Centuries later, military strategists refined the same habit: from Prussian general staff war games to the US Army's formalization of red teams tasked with thinking like the adversary. Intelligence services, faced with catastrophic surprises, built structured techniques like Richards Heuer Jr.'s Analysis of Competing Hypotheses (ACH) to discipline reasoning and avoid groupthink. Businesses, watching forecast after forecast collapse, turned to Pierre Wack's and Arie de Geus's scenario planning at Shell in the 1970s, which later became a template for corporate resilience.

Different domains, same instinct: prepare for impact so you can keep steering after it. What philosophy called premeditatio malorum, the military called red teaming, the CIA called ACH, and strategists called scenario planning. Authors like Gary Klein (Sources of Power), Bryce Hoffman (Red Teaming), and Nassim Nicholas Taleb (Antifragile) all circle the same lesson: systems and leaders thrive not by predicting perfectly, but by preparing broadly.

In Closing

That "impossible" test result from fourth grade makes sense to me now. I wasn't fearless—I was familiar. I had already walked through the room where things fall apart. The craft is in doing that on purpose, and then letting the real room—the one you're actually in—surprise you, correct you, and change your mind when it should.

Time box the rehearsal. Invite a critic. Decide. Set tripwires. Not overthinking, just refusing to be surprised.

Sources & Further Reading