Turning chaos into triumph: How to win big in times of crisis and uncertainty
Over the past decades, I have had the privilege of advising and working alongside some of the world’s most successful business leaders—from Fortune 500 CEOs to billionaire entrepreneurs and family business owners across continents. There is one pattern I have observed repeatedly: The greatest fortunes—and the greatest strategic leaps—are made in times of uncertainty.
Because every crisis carries within it the seeds of extraordinary opportunity—if you know how to position yourself. Bloomberg has called me an “expert in managing change, times of uncertainty and crisis.” During COVID, our clients who followed our structured crisis strategies actually outperformed competitors significantly.
Yet most leaders get this moment completely wrong. Today’s environment is a perfect storm: geopolitical conflicts, supply chain disruptions, surging energy prices and economic instability across multiple regions. For many, this feels like a time to retreat, to wait, or to simply “ride it out.” That is precisely the mistake.
Step one: Face reality—don’t hide from it
Core Principle: You cannot win in a crisis you refuse to acknowledge. Leaders must clearly recognize three simultaneous truths—This is a crisis. This is a period of uncertainty. This is a massive opportunity.
The first move sounds obvious, but it is astonishing how many leaders still fail to do it. You must stop and acknowledge the situation for what it is: a crisis, a period of uncertainty and an opportunity. All three at once.
The worst thing you can do is put your head in the sand and wait for it to be over. That is the most dangerous posture in business. Why? Because while you are waiting, the market is moving. Competitors are repositioning. Customer needs are changing. Costs are shifting. New vulnerabilities are appearing. New profit pools are opening.
Step two: Build scenario-based contingency plans
With our clients, we often run what I call a Crisis Opportunity Planning Session—a focused strategic planning session in which we examine the major scenarios that could emerge from a volatile environment. We ask: What if supply chains are disrupted for longer than expected? What if a war drags on? What if energy shortages intensify? What if a key commodity spikes? What if regional instability creates demand shifts or distribution bottlenecks?
Most leaders underestimate duration. Wars, in particular, almost never go as planned. They usually last longer than expected and produce second- and third-order consequences that few people model properly at the beginning. History makes that point again and again.
So instead of building strategy on a single assumption, you build several scenarios. For each one, you examine the likely impact on your business—negative and positive. That last part matters enormously. Most companies only think about the downside. Serious leaders also look for upside.
For each scenario, define: Potential risks and damage. Mitigation strategies. Potential upside opportunities.
Step three: Actively hunt for an opportunity
Every major disruption creates losers and winners. The difference is rarely luck. It is usually preparation and perspective. When you work through different scenarios, you must ask two questions. First: How do we soften the negative impact? Second: How do we profit from what is happening?
That profit opportunity can take different forms. It may be a smart twist on your existing business model. It may be an add-on solution that suddenly becomes highly valuable in the new environment. It may be an adjacent line of business. It may be a side business. Or it may simply be a sharper way of exploiting opportunity within your core business while others are distracted.
This is fundamental. Most people see change only as a threat. But every major change creates dislocation and dislocation creates openings. Business history is full of companies born in adversity. Microsoft is one of many examples often cited to remind us that great businesses are not only built in boom times. They are often built in downturns, recessions and moments of upheaval. The opportunity is there. The question is whether you are strategic enough to see it.
Step four: Replace emotion with strategic foresight
Precision beats panic. In a crisis, most organizations fall into one of two traps. The first is inertia. They do too little. They wait. They hope. They postpone difficult decisions and tell themselves that caution is wisdom.
The second is what I sometimes think of as conquistador-of-chaos mode. Lots of motion, lots of meetings, lots of urgency, lots of frantic activity—but no real strategic clarity. It exhausts the team and burns resources while producing very little advantage.
Why both fail: Inertia = missed opportunities + delayed response. Chaos = wasted resources + strategic confusion. What works is planned, strategic, focused action with foresight. And foresight does not come from vague optimism. It comes from disciplined trend analysis. It comes from studying the forces shaping your market. It comes from plotting multiple scenarios.
It comes from calmly asking, “If this happens, what will we do next? And where is the advantage if it does?”
This is where experienced external advisers can make an enormous difference. If you bring in people you trust—people who have helped organizations through this kind of exercise before—you dramatically improve the quality of your thinking. In a crisis, outside perspective is often one of the fastest ways to create clarity.
Step five: Install checkpoints to track reality in real time
A scenario plan is not a document you write and then admire. It is a living operating tool. That means you need checkpoints—specific moments at which you assess which scenario is actually beginning to materialize, and what your next move should be.
This is one of the great differences between amateurs and masters. Napoleon did not rely on a single linear script. He planned campaigns in detail, including contingencies and multiple possible turns in the battle. That preparation gave him speed and flexibility in execution because he had already thought through the alternatives.
Five to thrive
1. Face reality relentlessly. Do not deny the crisis. See it clearly—and see the opportunity inside it.
2. Plan for multiple futures. Use scenario thinking, contingency plans and checkpoints. The winners are rarely those who predict best. They are those who prepare best.
3. Get expert advice to see all opportunities: If you bring in experts you trust—people who have helped organizations through this kind of exercise before—you dramatically improve the quality of your thinking. In a crisis, outside perspective is often one of the fastest ways to create clarity.
4. Bet small to win big: Protect the core, then place carefully chosen bets with limited downside and exceptional upside.
5. Install checkpoints: Specific moments at which you assess which scenario is actually beginning to materialize, and what your next move should be.
Tom Oliver, a “global management guru” (Bloomberg), is the chair of The Tom Oliver Group, the trusted advisor and counselor to many of the world’s most influential family businesses, medium-sized enterprises, market leaders and global conglomerates. For more information and inquiries: TomOliverGroup.com or email Tom.Oliver@inquirer.com.ph.
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