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How one Japanese insurance behemoth future-proofed its leadership pipeline
Published December 2, 2025 in Talent • 9 min read • 
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Japanese insurance holding company, Tokio Marine Holdings, took a novel, immersive, and “surprising” approach to developing ambidex and aligned future leaders. Here are five talent development lessons they can share with organizations looking to future-proof their succession plans.
Imagine traveling from the Far East to the West for the first time. Taking a plane from Tokyo to Zurich, by way of Hong Kong, or from the coasts and plains of the US, with a stop in London, traveling for the best part of 24 hours and crossing eight time zones. Now imagine how you might feel on arrival: jet-lagged for sure, probably a little dazed. Making your way to Lucerne, you might start feeling slightly discombobulated – hurtling through the unfamiliar Swiss countryside on your way to spend five intensive days working with 25 people you have never met in your life. Next, imagine your arrival. You’ve made it to base, you’ve introduced yourself to 25 leaders of your organization’s other subsidiaries, and you’re just starting to make some sense of your surroundings when you find yourself face to face with a Swiss Army officer barking instructions at you.
Sounds disconcerting, right?
And yet this is precisely the kind of experience your leadership might need. This kind of experience can accelerate building the ambidexterity that organizations absolutely need to safeguard core business profitability today while simultaneously reimagining their operating and business models to leverage the new possibilities of tomorrow. Because when you are plucked so far out of your comfort zone that everything is new and strange and unfamiliar – when you are thrust into an environment peopled by strangers from diverse cultures, challenged to collaborate and obliged to do so in a boot camp setting – you really have just one option: to perform AND transform. This is precisely what your organization needs you to do.
This is what happened to the leadership team from insurance behemoth Tokio Marine Holdings.
Tokio Marine Holdings: From insular to ambidex by way of the discomfort zone
In the last 20 or so years, Tokio Marine Holdings has grown from a predominantly domestic organization to a global enterprise with a market cap of $81bn and more than 70% overseas profits. A sequence of successful mergers and acquisitions has created a successful, highly decentralized holding. During this time, risks have proliferated: floods and landslides, disasters like the 2011 Tsunami and the Fukushima meltdown, COVID-19, earthquakes, the fire in Maui, competition – all while the company’s home base is becoming increasingly challenging, its insurance market mature, its population aging and shrinking.
Meanwhile, fortifying the succession pipeline with international talent is a key opportunity. Even as Tokio Marine Holdings expanded internationally, successive generations of Japanese managers were becoming increasingly reluctant to leave home and gain exposure to foreign economies and cultures. Today, there is a growing trend for Japanese students and younger employees to pursue their careers domestically, leading to a dearth of the kinds of expanded mindset, flexibility, resilience, and range capabilities – ambidex leadership skills – that multinationals need to compete and innovate. Broadening the range of future leaders was therefore essential if they were to transform the business.
Finding foreign talent to lead a multinational company with its HQ in Tokyo hasn’t been easy either. The popularity of Japan as a tourist destination has soared in the last few years – a function of its many cultural attractions and a low yen – but working conditions are not yet a major drawcard for international talent. Workplace culture, with its strict adherence to hierarchy, risk aversion, and rigid corporate practices and behaviors, can feel very different to the leaner, faster-moving, and more flexible approaches elsewhere, potentially making Japan a less attractive target for ambitious leaders from the West.
Drawing on research on ambidex leadership and our work with executives from all over the world, IMD, together with Tokio Marine Holdings’ CHRO and his team, co-created a highly experimental range of bold and daring measures to shake up ideas and mindsets, shift assumptions, and build bonds of trust and cooperation between diverse leaders.
Here are five things that we did that had a significant impact on these leaders, as well as on their thinking and mindsets – ideas that you might want to think about as you ponder the kind of training or learning intervention it will take to future-proof your business.
“Something that worked well for us was utilizing the element of surprise to simulate preparing these leaders for unknown futures.”
Five lessons from a leadership bootcamp
1 – The element of surprise
What we call ambidex leadership at IMD is the ability to lead simultaneously for today while planning for tomorrow. It’s a bit like a captain navigating the immediacy of a near-shore squall while keeping an eye on the constantly changing weather systems in the open sea ahead. Most accomplished leaders will have shown that they can generate profits from their assets in the here and now, but the same leaders may struggle to generate innovative ideas about future business opportunities. Today’s leaders need both. They need to expand their range and adopt an ambidex mindset.
Something that worked well for us was utilizing the element of surprise to simulate preparing these leaders for unknown futures. How did we do this? Simply put, we initially didn’t tell them what was in store. Instead of spelling out the program curriculum and calendar at the outset, we kept them in the dark about half of the content we’d prepared for them. They were told in advance to think about the kinds of things that keep them awake at night: geopolitics, nonmarket strategy, AI, customer-centricity, and strategy execution. What they didn’t know was that they’d have to collaborate closely with peers they had never met before and devise novel approaches to these issues through trust-based teamwork. They were caught off guard, yet through the uncertainty, they fashioned responses that were different, innovative, some left-field, and many of them also… surprising.
2 – Dropping into an alternate reality
We didn’t give these leaders much time to adapt to a new setting or time zone. Flying them into Switzerland from Japan, the US and the UK, Hawaii, and Singapore, we allowed for only the shortest respite to tackle the worst of the jetlag or culture shock, before dropping everyone into a starkly new and unfamiliar setting. Our participants were promptly whisked off to the barracks of the Swiss Armed Forces for a swift immersion in how the Swiss Army responds to geopolitical, technological, and stakeholder crises. Here they were challenged to take on decision-making roles in an alternate and extremely high-pressure reality; an experience that called for initiative, ingenuity, creative and original thinking, and no small measure of courage.
Typical executive education programs expose participants to a few hours of debate and discussion, a case study, or a simulation.
3 – Enduring under duress
Not only did we literally and physically drop these leaders into an alternate reality – a kind of non-comfort zone where they had to deploy new ways of thinking and working – we also left them there, literally. Typical executive education programs expose participants to a few hours of debate and discussion, a case study, or a simulation. Here, our leaders were immersed for 60 hours with the Swiss Army – a bootcamp exposure to pressure and duress – in a profoundly unfamiliar context. The reason we did this, and the reason it worked? The realism and intensity of the experience, the lack of comfort, fatigue, and heightened stress created a real-time need for innovative approaches, inventiveness, and ingenuity as well as collaboration, joint action, and teamwork. Thrown into a situation – albeit controlled, safe, and with medics and support staff on hand – and left to struggle together for three days, these leaders break habits, challenge assumptions, experiment with new ways of doing and thinking, and forge tight bonds on the hoof.
4 – Continuous rotation
Another condition we implemented was frequent role rotation, meaning that none of our leaders were allowed to settle into a fixed position or perspective – or get too comfortable at any given task. Rotating roles meant that each individual was obliged to continuously adapt to new demands and new situations; a shared experience of discomfort and relentless modification and adjustment that also helped our leaders build fast trust, to forge bonds of mutual support, and to interchange experience and perspective to solve problems faster.
An experience as visceral and demanding as our Swiss Army leadership bootcamp has an immediate and profound physical and psychic effect.
5 – Follow-up coaching
An experience as visceral and demanding as our Swiss Army leadership bootcamp has an immediate and profound physical and psychic effect. Our leaders were thrown in at the deep end and left with minimal resources to figure things out, find answers, build solutions, and to do so with people they did not previously know or trust. Coming out of this experience, the challenge was to process the impact and embed all the learning in a way that will continue to drive ambidex leadership and alignment. We supported this through intense coaching and strategic leadership assessment tools: helping these leaders to pinpoint the cognitive and behavioral skills and the range that they must continue to grow and prioritize to sustain today’s mature business and seed tomorrow’s opportunities.
The power of the cohort
The future prosperity of any organization hinges on the future resilience of its leadership. For large, multinational corporations, the challenge is developing leaders who can run today’s businesses effectively while innovating tirelessly for the business opportunities of tomorrow – and to align those leaders around current needs and future exigencies, come what may. With Tokio Marine Holdings, we found that throwing key decision makers into a live and high-pressure situation together, quite literally plucking them from their comfort zone, subjecting them to surprise, alternate reality, duress, rotation, and then intensive coaching led to interesting outcomes for the organization. Not only have these leaders come back to us reporting that they are better at the ambidex thinking and doing that future-resilient leadership requires, they also forged the kinds of cohorts that endured long after the bootcamp finished.
Among these leaders, not all will ascend to overall leadership of the holding organization. Yet, the experience of being part of one team that came together under pressure is likely to create support for those who eventually do make it to the very top. Those who get to the highest rung of the leadership ladder will know they are part of a team. It’s less likely they will suffer the freezing solitude that usually sits at the summit.
For organizations, building this kind of support cohort should enhance succession decision-making while creating a more mutually empowering environment for all involved. The stronger the cohort, I believe, the easier the succession. When leaders can be first among friends, it is more likely that the organization will enjoy greater productivity, innovation, and alignment – the kind of forward-thinking connectedness that will fortify organizations against uncertainty today and tomorrow.
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