What Climbing Kilimanjaro Did to Our Leadership Team - A CEO's Perspective

I'll tell you the exact moment I knew the expedition had worked.

It was day seven. Summit night. Approximately 1am. We were at around 5,200 metres, somewhere above Crater Camp, below Stella Point, and one of our senior directors was struggling badly. Altitude headache, severe nausea, questioning everything. I was watching from twenty metres back, wondering if we were going to have to make the call.

Before I could say anything, three of his peers had formed a quiet circle around him. No drama. No management-speak. Just presence. Someone took his pack. Someone told him a story about their own worst moment on the mountain two days earlier, different camp, same feeling. Someone else just walked beside him in silence for forty minutes.

He reached the summit at 6:17am, as the sun came up over the crater rim, and cried for reasons that none of us needed to explain to each other.

That circle, that instinctive, unscripted act of collective leadership had never happened in our offices. The mountain made it happen. And I have been watching its afterglow in the way our leadership team operates ever since.

What We Were Looking For

We'd had a good two years commercially but a difficult eighteen months culturally. Rapid growth had fractured what had once been a tight team. Silos had formed. Communication had become functional rather than genuine. The leadership team met regularly and performed well in those meetings, but the trust that makes a leadership team more than the sum of its parts had slowly eroded.

I had tried the standard interventions. External facilitation, 360-degree feedback, a two-day off-site with a very good consultant and a very expensive lunch. All of it helped at the margins. None of it went deep enough.

I chose Kilimanjaro on the advice of a peer CEO who had taken her team two years earlier and described it, unprompted, unsolicited, over a completely unrelated dinner, as the single most significant investment she had ever made in her leadership team. I trusted her judgment. I booked within the week.

Eight Days: What Actually Happened

Days 1–2: The Masks Come Off

Within forty-eight hours, professional personas had dissolved. This happened faster than I expected and was more complete than I thought possible. There is something about sustained physical effort in extraordinary landscape that makes the performance of confidence feel not just unnecessary but actively exhausting. By the second evening at camp, my leadership team was talking to each other with a directness and a vulnerability that I had not heard from them in years.

The guide from Vertical Sky, Zizu, who has been on this mountain more than I can count, had a quiet gift for creating the conditions for this. He spoke about the mountain with a kind of reverence that made everyone want to be worthy of it. And he seemed to understand, intuitively, that his job was not just to get us to the summit but to get us there as a better group than the one that arrived at the gate.

Days 3–5: The Altitude Test

By day three, altitude had begun to level the hierarchy completely. When you are exhausted and your head aches and your appetite has vanished, the size of your title means nothing. What matters is whether the person next to you is honest about how they're feeling, whether they ask for help when they need it, and whether they give it before they're asked.

My most senior director , a man who in twelve years I have never seen ask for anything, asked for help on day four. He simply said, to no one in particular, 'I'm struggling.' The response from the team was immediate and generous. I watched from behind and thought: this is worth more than any coaching programme I could buy. This is the real version.

Summit Night

I won't try to describe what standing at 5,895 metres at sunrise feels like. The attempt always falls short. What I will say is that the sixteen hours from departure to return, the darkness, the cold, the doubt, the summit, the descent compressed something into all of us that normally takes years of shared experience to build. We arrived at the summit as colleagues. We descended as something closer to a tribe.

What Changed When We Got Home

The changes I observed in the six months after Kilimanjaro were not dramatic. They were not the subject of a post-expedition debrief or a culture initiative. They were simply present, quietly, in the way the team operated.

• Meetings changed. Not the format. The quality of listening. The willingness to say 'I don't know' or 'I got that wrong'. The reduction in performance.

• Conflict resolution changed. Two team members who had been in a slow professional cold war for eighteen months resolved it, without my involvement, within three weeks of returning. I still don't know exactly what they said to each other on the mountain. I don't need to.

• Recruitment conversations changed. The expedition became part of how we talked about our company in hiring conversations. Several strong candidates told us it was a meaningful signal about our culture. One accepted a role at lower compensation than a competitor offer specifically because of it.

• Resilience changed. When a significant business challenge arrived four months after the expedition, I watched my leadership team handle it with a steadiness I had not seen before. The mountain had given them a reference point for difficulty. Office challenges, however real, existed on a different scale.

What I Would Tell Another CEO

Don't wait for a cultural crisis to justify this investment. The ROI is higher when your team is already functioning well, because the expedition amplifies what's there rather than repairing what's broken.

Trust the mountain. It will do things to your team that no amount of facilitation can manufacture, because it is not manufactured. It is real. The cold is real. The altitude is real. The choice at 5,500 metres is real. And the relationships formed in response to real things are real in a way that nothing artificial can replicate.

And trust Vertical Sky. The quality of the operation, the preparation programme, the guides, the camp setup, meant that from the moment we landed in Tanzania to the moment we flew home, my only job was to climb and to watch my team discover what they were made of. That is exactly the right amount of responsibility for a CEO to have on a mountain.

"The sixteen hours from base camp to summit and back compressed something into all of us that normally takes years of shared experience to build."

🏢  Bring your leadership team to the mountain. Plan your Kilimanjaro expedition at www.vertical-sky.com

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