Nine Expedition Rules That Every Leader Needs Right Now

Every senior executive I speak to at the moment is navigating the same sensation: they have been asked to lead their organisation into genuinely unknown territory, with an incomplete map, changing conditions underfoot, and no guarantee of a safe return. That sensation has a name. It's called an expedition.

Artificial intelligence, geopolitical instability and societal change has made expeditioners of us all. And that, it turns out, is something I know a little about.

Over the years I have trekked through Nepal's Kali Gandaki gorge, climbed Kilimanjaro, walked over 3,500 kilometres on the Camino de Santiago, and played a support role in the Shackleton Epic expedition in Antarctica in 2013. I have also spent 25 years advising organisations on strategy, transformation and culture — and before that, as a CEO and investor, building, buying, selling and occasionally burying businesses of my own.

A few years ago I compared notes with Justin Jones — Jonesy — the professional adventurer who walked 2,275 kilometres from the edge of Antarctica to the South Pole and back in 89 days, and before that paddled 3,318 kilometres across the Tasman Sea without assistance. Between us we found that the lessons from extreme expeditions and the lessons from extreme business situations were, with striking frequency, the same lessons.

Here is what we came up with. I think they apply more urgently now than ever.

Why the parallel holds

Expeditioners set out to do something genuinely difficult and original. They need financial backing while putting their own futures on the line. They are managing risk while adapting in real time to obstacles they did not anticipate. And they are learning — about the environment, about their limits, about what they're made of — the entire time.

Senior leaders navigating transformation are doing exactly the same thing. The ones who succeed are, without exception, learning faster than those around them.

Nine rules for expeditioners and executives alike

1. Get clear on your true purpose. When things get hard — and they will — it's your why that carries you through. It's also what your team, your board and your backers need to believe in. You can't fake your why. People can tell.

2. Commit completely. No one will follow a leader who is hedging. You have to go first, visibly and without reservation, before you can expect anyone else to follow. Half-hearted AI pilots with no executive sponsorship fail at the same rate as half-hearted summit attempts.

3. Be willing to adapt. Hold your outcomes firm and your methods loosely. Intelligent improvisation in the face of obstacles — tinkering, controlled experimentation, willingness to change course — is not weak strategy. It's how expeditions actually succeed.

4. Don't sit still. A CEO I admire used to say: losers mistake hope for action. Movement in any direction beats paralysis dressed up as prudence. There is no failure in retreating from a peak that cannot be safely descended. There is enormous failure in waiting at base camp for the perfect moment that never comes.

5. Maintain your composure. In your own company, perhaps you can lose it occasionally. In front of your team, your clients and your board — don't let them see you sweat. Your calm, clear-headed self is the most useful person in a crisis. The other version is not.

6. Prepare relentlessly. War-gaming everything that can go wrong is not pessimism — it's professionalism. Understanding your risk environment and building genuine resilience into your plans is often the difference between coming home and not. This applies as much to an AI transformation programme as it does to a Southern Ocean crossing.

7. Beware the compound failure. Expeditions rarely fail because of a single catastrophic event. They fail because several individually manageable problems accumulate into a system-wide collapse. Data governance gaps, regulatory uncertainty, capability shortfalls and cultural resistance each look manageable in isolation. Together, they become the black swan. Build redundancy into your people, processes and technology before you need it.

8. Hold on to your big ideas. You can usually only execute one major thing at a time. But the ideas waiting in reserve are the fuel for what comes next. Keep them alive.

9. Know your gaps and fill them. You will never have every skill the moment demands. Be honest about your edges. Find people who think and act differently, who will cover your blind spots and tell you the truth. The best expeditions — and the best leadership teams — are built on complementary strengths, not cloned agreement.

In the face of scarce resources, fierce competition and an environment that keeps changing faster than the map can be redrawn, success is always hard won at considerable personal cost.

The question I ask every senior leader I work with right now is simple: how would you approach this challenge if your life depended on the outcome of it?

The expedition has already begun. The only question is how well prepared you are to lead it.