Decisions Under Fire

1. The most intense moment when a decision had to be made immediately

People often ask me to point to the most intense moment of my career, and the honest answer is that the ones that stay with you aren’t always the ones that look most dramatic on paper. The one I come back to most often is the evacuation of the Canadian embassy in Libya, which I led during the Tripoli War and involved eighteen military personnel and four diplomats.

In that moment, we faced a hostile environment outside the wire, with militias moving freely, communications half-functional, and a shrinking window by the hour. The information I had was fragmented, partial intel from the ground, and conflicting reports on which routes were still passable, all from people whose lives depended on me getting it right. The information I didn’t have was just as critical: I couldn’t verify which checkpoints would hold, I couldn’t guarantee the border crossing window, and I couldn’t see around the next corner.

That wasn’t an isolated experience. On 11 September 2012, as Benghazi went up in flames, I was getting a German oil crew out of the city and through safehouses to Tripoli while the city around us was on fire. More recently, I coordinated the extraction of 220 people from Israel as the situation deteriorated. Different geographies, different threats, same problem: act now and act with what you’ve got.

How did I decide? I went back to first principles. Mission first: get our people out alive. Then I worked the problem in front of me, asking what I control, what I influence, and what I ignore. I didn’t try to solve the whole crisis. I solved the next ten minutes, then the ten after that. That’s how Tier 1 operators are wired.

2. Why many leaders freeze or hesitate in chaotic situations

Most leaders freeze for one of three reasons, and I’ve seen all of them in boardrooms and in operations.

The first is fear of being wrong. They’ve built their career on being right, so the idea of making a call that fails publicly feels worse than making no call at all. The irony is that no decision is itself a decision, and it’s usually the worst one available.

The second is that they’ve never been there before. They’re trying to think their way through a problem they’ve never trained for. In the military, we say you don’t rise to the occasion; you fall to the level of your training. If you haven’t put yourself under stress in rehearsal, you’ll find out the hard way that you can’t access your own thinking when it actually counts.

The third is information addiction. They keep asking for more data, another meeting, another model, another opinion. They confuse motion with progress. By the time they’re ready to act, the window has closed. In Benghazi that night, the window was measured in hours. There was no version of the operation in which I sat back and waited for clarity.

3. Frameworks and mental models that helped me decide in high-stakes environments

I keep my mental models simple because complicated frameworks fall apart the moment things get loud. A few I use constantly:

• OODA — Observe, Orient, Decide, Act. The team that cycles through this loop faster wins, whether in a fight, in a market, or in a crisis. The aim isn’t to be the smartest in the room; it’s to out-cycle the problem.
• The 70% rule. If you have about 70% of the information you’d like, decide and move. Waiting for 100% means you’re late. Waiting for 50% is reckless. 70% is the sweet spot in almost every environment I’ve worked in.
• Mission, Threat, Resources. Before any move, I ask: what is the actual mission, what’s threatening it, and what do I have available right now? That keeps ego, politics, and noise out of the decision.
• Commander’s intent. You don’t need every detail planned. You need everyone to understand the required outcome. If comms drop or the plan breaks, your team can still make good decisions because they know the ‘why’. On the Canadian embassy job, comms were unreliable; intent kept the team aligned when the radio wasn’t.
• Worst-case rehearsal. Before any operation, we war-game what could go wrong. Not to be pessimistic, but to make sure that when it does go wrong, no one sees it for the first time.

4. How to determine what actually matters in the middle of chaos

When everything is screaming for your attention, the discipline is to ignore most of it. The questions I ask myself, in order, are simple:

• What kills the mission in the next sixty seconds? Solve that first.
• What can wait? Park it. Don’t pretend it doesn’t exist  just shelve it.
• What’s noise pretending to be signal? In a crisis, you’ll have ten people offering opinions and one person offering ground truth. Find that person.
• Am I solving the problem in front of me or the problem I wish I had?

In Israel, with 220 people to move and conditions changing by the hour, that filter was everything. Half the inbound traffic was emotional, political, or speculative, and none of it would get a single person across a border. Good-enough prioritization, executed quickly, beats perfect prioritization delivered late every time.

5. The role of preparation and training in fast decision-making

Elite teams don’t make better decisions because they’re smarter. They make better decisions because they’ve already made them hundreds of times in training.

In special forces selection and beyond, you’re subjected to physical exhaustion, sleep deprivation, sensory overload, and time pressure, then asked to make tactical decisions. The point is to fail in training so you don’t fail in real operations. By the time you’re on a real operation, your nervous system has been there before. You’re not deciding cold, you’re recognizing a pattern.

This is the part most businesses skip entirely. They run strategy offsites, but they never stress-test their leaders. No one rehearses the press release for a data breach, the call to the family of an executive kidnapped abroad, or the decision to pull a product line that just hurt someone. Then the day arrives, and people are improvising their first response on national television. Train it. Rehearse it. Pressure-test it. The decision in the moment becomes muscle memory rather than guesswork. 

6. How leaders can avoid analysis paralysis when information is incomplete

The mindset shift is accepting that uncertainty is the environment, not an obstacle. You will never have full information. Once you accept that, the question shifts from ‘how do I get certain?’ to ‘what’s the best move I can make right now with what I’ve got, knowing I’ll adjust?’

The risks of waiting too long are usually worse than the risks of acting on partial intel. In an evacuation, the road that was open at 0900 is closed by 1000. In a market, the window your competitor is hesitating in is the one you take. Hesitation has a cost, and most leaders don’t account for it. They only see the cost of being wrong, never the cost of being slow.

My rule is to act on principle when you can, on probability when you must, but always act.

7. What happens after a decision is made, especially if it turns out to be wrong

Elite teams have one trait that separates them from everyone else. They don’t fall in love with their plan. They’ll execute it with full commitment, but the moment the ground tells them it’s not working, they adjust without ego. In Benghazi, the original route through the city wasn’t viable. We adapted, used safehouses, and stopped moving to gather accurate information and swap out drivers due to tribal influence and potential exposure. The plan changed three or four times that night. The mission didn’t.

After-action reviews are sacred in our world. We’re honest, sometimes brutally so. What worked? What didn’t work? What would we do differently? Rank doesn’t matter in that room. The most junior soldier can call out the team leader. That’s how you learn fast.

In business, most ‘lessons learned’ exercises are theater. People protect themselves, blame the market, and blame the team below them. That’s how organizations make the same mistake three times. If you want elite decision-making, build a culture where being wrong fast and adjusting publicly is rewarded more than being right slowly.

8. Communicating decisions during high-pressure moments

Under pressure, communication has to be clear, calm, and confident, even when you’re not feeling any of them.

Clear means short sentences, specific verbs, and no hedging. ‘We’re moving in two minutes. You’re with me. He’s on rear security.’ That’s a sentence. Compare that to ‘So I think probably what we should maybe consider doing is…’ That’s a leader who’s lost the room before they’ve even started.

Calm doesn’t mean unfeeling. It means your voice doesn’t betray panic, because the team takes its emotional cue from you. If you tighten up, they do too. If you’re steady, they are. The four diplomats and eighteen military personnel I moved out of the Canadian embassy didn’t need a speech. They needed someone to look them in the eye and tell them exactly what would happen next.

Confident doesn’t mean certain. It means committed. You can absolutely say, ‘I don’t have all the information. Here’s what we’re doing and why. We’ll adjust as we go.’ That kind of honesty under fire builds more trust than false certainty ever will.

9. How these lessons translate to business leadership

The principles port directly. The variables change. Bullets become balance sheets, evacuation routes become market exits, and hostile actors become activist investors, but the human dynamics under pressure are identical.

Speed of decision still wins. Clarity of intent still wins. Trained nervous systems still win. The leaders I coach who have come from sports, military, or front-line operational backgrounds usually adapt to executive pressure faster than those who have only ever lived inside the building. They’re used to consequences.

The key point is this. The executive who treats their leadership like a craft to be trained in physically, mentally, and decisively outperforms the one who treats it like a title.

10. Where executives struggle most with decision-making

Three patterns I regularly observe while working with senior leaders and family offices:

• They optimize for consensus instead of clarity. They want every stakeholder on board before they move, so they move late, or they water down the decision until it can’t fail and can’t succeed either.
• They confuse data with judgment. More dashboards, more reports, more analytics, and yet the call still has to be made by a human being. At some point, you have to put the deck down and decide.
• They don’t train for crisis. Their first real test is the test itself. No rehearsal, no scenario work, no stress inoculation. They’ve built businesses but never built themselves for the moment when the business is on the line.

11. The mindset shift leaders need to make

Stop trying to eliminate uncertainty. Start training to operate within it.

That single shift changes everything. You stop chasing perfect information and start building decision-making capacity. You stop fearing being wrong and start practicing adaptability. You stop relying on titles and start relying on craft.

The leaders I respect most, whether they wear a uniform, run a company, or race across a continent on a bike, all share one trait. They have made peace with the fact that the decision must be made by them, with what’s in front of them, now. That acceptance is freedom. And it’s the difference between leaders who survive pressure and those defined by it.

The information provided is for informational and educational purposes only and does not constitute investment advice, recommendations, or solicitation. Solyco Capital and/or its affiliates may have financial interests in companies discussed herein, which creates potential conflicts of interest. The views expressed are personal opinions and do not necessarily reflect official positions of Solyco Capital. Past performance does not guarantee future results. Forward-looking statements are subject to risks and uncertainties, and actual results may differ materially. Readers should conduct independent research and consult their own attorneys, accountants, and other professional advisors before making any investment decisions. The content herein should not be construed as a solicitation or offer to engage in any investment strategy, purchase of securities, or other transaction. All information is provided “as is” without warranty of any kind, express or implied.

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