Turning turbulence into triumph: A guide to crisis breakthrough sessions
Bloomberg has called me an “expert in managing times of change, uncertainty and crisis.”
Across regions, cultures and continents, I’ve seen firsthand with our clients that there’s tremendous opportunity hidden within uncertainty and times of change—if you have a well-thought-out playbook.
I will guide you in structuring a strategic session to navigate crises. We’ll cover the core steps to uncover opportunities, manage emotional dynamics and leverage external facilitators to ensure clarity. By the end, you’ll have a practical framework to run a crisis-breakthrough session that turns challenges into strategic wins.
Leverage outside experts
When my team and I lead and facilitate sessions like these, we always see how little experience companies generally have with this. It is just not part of the common playbook.
And who can blame them? Who is prepared for the unexpected, the highly unusual, the thing no one could have seen coming in the last annual corporate planning session?
This is why it is so important to call on outside experts to facilitate sessions like these.
Select people who have a proven track record of being experts in managing change. They will have an unbiased and neutral and—most of all—expert view that will see opportunities in plain sight that your team may be missing. The low-hanging fruits that are obvious to a seasoned outside expert. They will see the forest, not just the trees.
I remember a strategy session with an Asian client where the whole board was present, together with several members of the owner’s family. I watched them going back and forth about a software product launch decision that was pivotal for their business but had been delayed because they could not reach an agreement. Any day this decision was delayed cost their business valuable market share because their competitors were already aggressively taking over clients.
I asked the owner how long this had been going on. He replied, “Six months.” And they still couldn’t make a decision!
When my team and I stepped in, we solved the issue in exactly 90 minutes. Done! Imagine how much money they could have saved if they had brought us in earlier?
Napoleon’s strategies to protect your core business
He was famous for not only being the greatest battle commander in history but also the best prepared. He went through every possible scenario before every battle. I always mention him because his mindset and approach is so vital for any business to this day.
Go through every possible scenario and map it out to be prepared. Then go to battle.
“Did any of your battles ever play out exactly as you had planned it?,” they asked Napoleon.
“No,” he replied. But he went on to say that going through all the scenarios in his mind prepared him for the battles so he could quickly switch between the different scenarios.
I remember when COVID-19 came. And we had just been advising one of the largest retail chains in the world on managing times of change and uncertainty and on innovation.
Guess what? They did a lot better than their competitors during the COVID-19 pandemic because they were prepared.
Did they suffer? Sure, they did. Like everyone in that category. But they recovered faster, lost less money and were able to pivot to online distribution and sales faster than any of their competitors.
I still remember their president coming to me at a dinner after COVID-19 was over and said: “Thank God, Tom, for how you prepared us because we were able to handle COVID with calm and readiness, making swift decisions. And we took a lot of market share from our biggest competitors—faster than we could have in normal times. So in hindsight, it was a blessing.”
This is the Napoleon battle-preparedness. You don’t know exactly what is going to happen, but you are prepared and can take swift action, and you are not stuck in inertia.

Your own ‘Strait of Hormuz’ checkpoints
Once you have made your plans, developed your contingency scenarios, mapped out all possible scenarios on how to protect your core business, you need to determine checkpoints: By when will you reassess what again with your team.
When you make your plans, you need to write down assumptions because every plan, like any battle, is built on assumptions. You need to watch if these assumptions play out and at which checkpoints you need to reassess your plans.
These are usually fork-in-the-road moments: Scenario A or B happens. If this happens, then we do X. If that happens, then we do Y.
In practice, these are usually a bit more complex because you have more options and usually more than one strategy alternative.
If you are diligent about assessing these checkpoints and then going back to the drawing board quickly to assess what your next moves are—based on the longer planning you did earlier—then you will be able to make fast decisions.
Place strategic bets with asymmetrical upside
There is another dimension to winning in uncertainty that many leaders neglect entirely: the investment side. Once you have mapped the scenarios, there will often be opportunities to place small strategic bets—moves that cost little relative to the size of your business, but that could create a very large upside if a particular scenario unfolds.
This is where a simplified version of Nassim Taleb’s barbell strategy is useful. (Nassim Taleb is the author of the book “Black Swan”, described by The Sunday Times as one of the 12 most influential books since World War II.)
In plain English, the idea is this: Keep the core of the business stable and protected, while using a small portion of your resources to make carefully chosen, high-upside bets.
You do not pivot the whole company. You do not gamble the balance sheet. You do not swing wildly into a completely new business.
You simply place a few intelligent bets where the downside is limited and the upside is unusually large. That is how you become more resilient—and potentially antifragile—in uncertainty.
Imagine, for example, that you operate in a small Southeast Asian country and one plausible scenario is a severe gasoline shortage. What small move could you make now that would become highly profitable if that scenario plays out? A partnership, an add-on service, an energy—efficient delivery solution, a logistics adjustment, a backup distribution capability—there are many possibilities depending on the industry.
The key is the structure of the bet. If it fails, it does not hurt you badly. If it works, it pays disproportionately well. That is a smart crisis strategy.
Your five to thrive
1. Remember that big change also brings great opportunity.
2. Leverage outside experts.
3. Use Napoleon’s strategies to protect your core business.
4. Establish clear checkpoints to reassess your plans.
5. Place strategic bets with asymmetrical upside.
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.
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: www.TomOliverGroup.com or email Tom.Oliver@inquirer.com.ph.

