From the Battlefield to the Boardroom: My Journey with Fear-Setting

That’s when I stumbled onto fear-setting—a tool that fundamentally changed the way I approach big decisions, both as a person and as a leader. This wasn’t something I picked up in an offsite workshop or found in the pages of a bestselling business book. It was a real-world, hands-on practice that asked me to do something counterintuitive: make fear an ally instead of an enemy. Over time, it’s become my go-to strategy when everything’s on the line.

And it turns out I’m not alone. So many veterans face this same fog of uncertainty and self-doubt when they step into new careers. According to the Department of Labor, those who use structured decision-making tools like fear-setting report higher confidence and adapt more smoothly to new environments.

What is Fear-Setting? A Framework for High-Stakes Decisions

At its core, fear-setting is about clarity—the kind that gets painfully specific about what’s holding you back. Tim Ferriss brought the practice into the spotlight, but at heart it’s simple: name your fears, plan your response if they happen, and weigh what it might cost you to do nothing at all. Traditional risk assessment stays analytical; fear-setting demands you face down the emotional weight behind your hesitation.

Fear-setting has a few things in common with frameworks like SWOT analysis or risk matrices, but what sets it apart is its focus on emotion—the hidden assumptions and quiet anxieties that can freeze us in place.

And this isn’t just personal experience talking. Research in psychology shows that reflective practices like fear-setting help leaders build resilience and well-being. By naming and examining your fears head-on, you sharpen your ability to make decisions—and bounce back from setbacks.

The Fear-Setting Playbook for Engineering Leaders

Think of fear-setting as a mental ‘pre-mortem.’ Picture a project failing—now rewind and ask yourself what went wrong, how you’d shore things up, and what you’d do differently next time. This kind of thinking brings not only technical risks into focus but also exposes team dynamics and blind spots.

So how do you actually use fear-setting in a world where outages, failed deployments, and bold redesigns can keep even seasoned leaders up at night?

1. Define the Fear, Not Just the Risk

   Too often, engineering teams stop at “What if production breaks?” That’s surface-level anxiety. Fear-setting demands specifics. Does ‘break’ mean five minutes of downtime or a full-day crisis? Who’s affected—customers or internal users? What’s the real consequence?

   Here’s why it matters: vague anxieties thrive in the dark; clear fears are problems you can solve.

   For instance, imagine a CTO about to approve a database migration. Instead of dreading “downtime,” get specific: “If we migrate this database and hit downtime, our SLA breaches could mean lost revenue and damaged reputation.” Suddenly, you know what needs shoring up.

   I’ll never forget mapping out my own worst-case scenario after leaving the military. Once I wrote it down, I realized even my biggest fears weren’t fatal—just tough setbacks I could recover from.

2. Diagnose Failure Modes and Mitigation Steps

   Once you’ve named your fears, break them down further. If your deployment goes sideways, what’s next? Can you catch issues quickly? Roll back changes? Communicate clearly?

   Tools like Failure Mode and Effects Analysis (FMEA) are invaluable here—they help you systematically spot breakdown points and prioritize fixes by likelihood and severity.

   But let’s be honest: the goal isn’t zero risk (that’s wishful thinking in engineering); it’s resilience. When you map out responses ahead of time, your team acts with purpose instead of panic.

   If you’re seeking ways to build this kind of resilience into your culture, the Change Resilience Playbook for engineering leaders offers practical strategies for guiding teams through transition without losing momentum.

3. Forecast the Upside—even Partial Success

   Fear-setting isn’t just about avoiding disaster; it also forces you to look at what you stand to gain if things go right—or even mostly right. Will you speed up development cycles? Improve reliability? Boost morale?

   Try giving rough probabilities to outcomes—even estimates count. Saying “We think there’s an 80% chance this improves throughput” is far more actionable than vague optimism.

   Don’t skip this step—it’s where perspective often shifts. If you let small-probability fears eclipse real gains, you’re shortchanging your team (and yourself).

   Scenario planning helps here too: outline not just best- and worst-case outcomes but also some middle-of-the-road ones so your strategy covers all bases.

   If fostering innovation amid ambiguity is a priority for your team, embracing uncertainty is key to driving breakthroughs. Learning how to lean into smart risk-taking can unlock new opportunities.

4. Quantify the Cost of Inaction

   There’s comfort in sticking with what you know—but sometimes that’s where real risk hides. Hanging onto outdated systems or clunky processes might feel safer than change, but what are you actually losing by staying put? Time? Talent? Competitive edge?

   Kodak learned this lesson the hard way—their refusal to move from film to digital cost them dearly.

   Make sure “do nothing” is one of your options when weighing risks. Inertia can be just as dangerous as bold moves.

   From my own experience—and after talking with other leaders—it helps to bring mentors or trusted peers into this step. Sometimes an outside voice makes it painfully clear when standing still is your riskiest choice.

5. Communicate the Whole Picture

   Leadership isn’t just about getting clarity for yourself—it’s about making sure your team feels confident too. Walk everyone through Plans A, B, and C—not to scare them but to show you’ve thought through every angle.

   When people see risks named out loud and plans exist for setbacks, anxiety drops and trust grows.

   Open risk communication builds a learning culture: regular postmortems and blameless retrospectives let teams digest lessons from both wins and mistakes—and make psychological safety real instead of just another buzzword.

   Building self-awareness, leaning on support networks, blending gut instinct with analysis—all these help leaders steer through pressure with clarity instead of denial.

   If you’re working on developing credibility as a leader during challenging times, owning your faults and backing words with action is crucial to inspiring teams to follow your lead.

Turning Fear into Fuel: Real-World Engineering Examples

Let’s make this concrete. Suppose you’re considering a major infrastructure overhaul—switching cloud providers or rebuilding a core service from scratch. The stakes are high; failure could mean downtime or customers walking away.

I’ve led teams through exactly these waters using fear-setting as our compass. On one particularly fraught system migration project, our first discussions revolved around every nightmare scenario: data loss, slowdowns, unhappy users—you name it.

• We broke each specific fear into events we could prepare for: “What if data sync fails?” “How fast can we roll back if performance tanks?”
• We mapped out mitigation steps: automated backups, staged rollouts, clear escalation paths—each ‘what if’ got its own action plan or early warning system.
• We forecasted upside too: If we pulled this off—even partially—we’d ship faster and boost morale across the board. Running some quick probability estimates helped set realistic expectations with leadership.
• Finally, we looked at the cost of doing nothing: If we didn’t modernize now, we risked higher costs down the road and losing talented engineers tired of legacy headaches.

This process didn’t just help us avoid disaster; it gave us conviction to move forward with eyes wide open.

Netflix’s move to the cloud is a classic industry example of fear-setting in action: leaders walked through every failure scenario up front, built roll-back plans for each one, then staged migrations so setbacks never spiraled out of control.

In every case—whether mine or industry-wide—naming fears openly transformed paralysis into progress.

Why Fear-Setting Matters: The Leadership Mindset Shift

At its heart, fear-setting is responsible risk-taking—the hallmark of resilient leadership in engineering organizations. It shifts your thinking from “What if everything falls apart?” to “How will we respond if it does—and what might we gain if things go right?”

This shift closely mirrors growth mindset thinking: setbacks become lessons instead of dead ends.

By making space for honest conversations about risk and reward—not just covering fears with false optimism—you foster psychological safety: the foundation for innovation and high performance on technical teams. When your team sees you naming risks (and preparing for them), trust deepens and people feel safe raising concerns early.

Research backs this up: psychologically safe software teams outperform because they talk openly about quality problems, admit mistakes early, help each other solve tough issues, and take initiative for continuous improvement—all traits that grow when leaders model fear-setting.

“We use [past mistakes] as examples…we discuss them and strive to avoid similar mistakes next time.” In high-trust teams, speaking up isn’t just okay—it’s expected.

This clarity is contagious. When people know both downside plans and upside opportunities are on the table, they’re far more likely to buy into ambitious projects instead of quietly resisting out of fear.

Adopting Fear-Setting in Your Leadership Practice

If you’re ready to bring fear-setting into your leadership toolkit, here are prompts I return to before every big decision:

• What am I really afraid of here? Get specific—write down each concrete outcome that worries you.
• What would I do if each feared scenario happened? Who would help? What could be fixed or reversed?
• What good things might happen if this mostly works out? How likely are those?
• If I do nothing, what might slowly get worse—team morale, technical debt, user happiness?
• How can I include my team in this process—discussing risks openly instead of pretending we have all the answers?

A simple way to put this into practice is with a worksheet divided into three columns: one for naming fears; one for preventative actions; one for how you’d repair things if those fears came true. This approach gets everyone thinking systematically about each decision point.

Many organizations now weave fear-setting into project kickoffs or regular risk reviews using shared templates so everyone owns both risks and solutions together.

Try formalizing this process with worksheets or digital templates during retrospectives or project launches. The goal isn’t erasing all uncertainty—it’s replacing vague worry with deliberate leadership.

If you’re looking for a more systematic approach to launching projects as an engineering leader, the Leader’s Kickoff Playbook offers proven ways to create alignment from day one.

The more you practice fear-setting, the less paralyzing uncertainty becomes—and the more progress feels possible. You’ll also model a culture where courage means facing fear head-on with strategy and support—not pretending it doesn’t exist.

Fear-setting for engineering leaders isn’t just another framework—it’s a fundamental mindset shift that turns uncertainty from an obstacle into fertile ground for growth and resilience.

Embracing fear-setting empowers you—and your team—to treat uncertainty as fuel for progress. By naming what holds you back (and inviting others into that conversation), you strengthen your own leadership—and set the stage for collective success. Next time uncertainty looms large, let it serve as your prompt: clarity and resilience begin with asking better questions.