In 2016, the profile of a successful insurance leader was relatively clear. Deep technical expertise, long tenure, a strong command of risk, and the ability to optimise mature business models in complex but largely stable environments were widely seen as the markers of leadership excellence.
Many of those qualities still matter. What has changed is the environment in which they are expected to perform. As we move toward 2026, the operating context for insurance leaders has shifted so fundamentally that success can no longer be defined by experience alone. The leaders who will thrive over the next decade will not simply be more modern versions of their predecessors. They will think differently, prioritise differently, and in many cases arrive at the top through very different paths.
For boards and executive teams, this raises a difficult but necessary question:
are we still hiring for the leaders who succeeded in the past, or the leaders equipped to navigate what comes next?
The World Changed Faster Than Leadership Models Did
Leadership models evolve slowly. Risk, technology, and market dynamics do not.
In 2016, insurance operated in an environment where risk was more compartmentalised, technological change was incremental, and leadership experience remained a reliable predictor of future performance. Transformation existed, but it was often linear and contained. That stability has disappeared.
Today’s insurance leaders operate amid converging pressures: accelerating climate volatility, rising cyber exposure, rapid AI adoption, skills shortages driven by obsolescence rather than scale, and heightened scrutiny from regulators, customers, and employees alike. These forces do not emerge one at a time. They compound.
This shift is reflected in how boards are redefining risk. According to the Allianz Risk Barometer 2025, cyber incidents ranked as the number-one global business risk for the fourth year in a row, cited by 38% of respondents, ahead of business interruption (31%) and natural catastrophes (29%).
What this tells us is not simply that risk has increased, but that it has become more interconnected. Leadership effectiveness is no longer measured by how well someone manages a known system, but by how confidently they can navigate uncertainty across multiple dimensions at once.
From Managing Risk to Navigating Systems of Risk
Insurance has always been about risk. What has changed is the shape it now takes.
A decade ago, many leaders could think about risk in functional terms. Underwriting risk, operational risk, technology risk and reputational risk were often addressed in parallel, if not entirely separately. That approach is no longer viable.
A cyber incident today can trigger regulatory action, operational disruption, reputational damage and customer attrition simultaneously. A climate-driven loss event can ripple through pricing, reinsurance availability, capital adequacy and public policy debate within a single reporting cycle.
The scale of this shift is visible in the data. Swiss Re estimates that global insured losses from natural catastrophes reached USD 137 billion in 2024, and projects that annual losses could reach USD 145 billion in 2025 if current trends persist.
In response, boards are no longer looking for leaders who are simply good custodians of risk frameworks. They are looking for leaders who can understand second- and third-order impacts, make decisions with incomplete information, and clearly communicate trade-offs to regulators, investors, and customers.
The strongest insurance leaders in 2026 are not necessarily more cautious than their predecessors. In many cases, they are more decisive. The difference is that their decisions are informed by systems thinking rather than siloed expertise.
AI Is No Longer a Project. It Is a Leadership Responsibility.
In 2016, digital transformation was often treated as a programme. Leaders sponsored it, technology teams delivered it, and success was measured largely through efficiency gains.
That distinction has disappeared.
Artificial intelligence is now embedded across underwriting, pricing, claims, fraud detection, customer experience and compliance. Its impact extends beyond productivity into fairness, explain ability, trust, and regulatory accountability.
The pace of adoption is striking. McKinsey’s State of AI 2025 report found that 71% of organisations now regularly use generative AI in at least one business function, up from just 33% two years earlier.
In insurance, this has prompted regulators to sharpen their focus. The International Association of Insurance Supervisors (IAIS) has explicitly identified AI governance, model risk and accountability as supervisory priorities, signalling that responsibility ultimately sits with senior leadership, not technology teams.
As a result, boards are increasingly holding leaders directly accountable for AI outcomes. Not because they expect them to write code, but because they expect them to ask the right questions: where AI is creating value, where it introduces risk, how decisions can be explained, and what AI adoption means for skills and culture.
Leaders who still view AI as something to be “handled by IT” are already falling behind.
Talent Is No Longer a Hiring Problem. It Is a Skills Problem.
Few issues concern boards more than talent, yet the challenge they face today is fundamentally different from a decade ago.
In 2016, leadership teams could plan around stable role definitions and predictable career paths. Skills evolved, but slowly. Experience accumulated over time.
In 2026, skills depreciate faster than organisations can replace them.
According to the World Economic Forum’s Future of Jobs Report, nearly 44% of workers’ core skills are expected to change by 2030, driven largely by AI adoption and digital transformation.
At the same time, AI is already embedded in day-to-day work. PwC’s Global Workforce Hopes & Fears Survey found that 54% of workers have used AI in the past year, with 14% using generative AI daily.
The leaders who perform best in this environment understand that talent strategy is no longer about filling roles. It is about designing organisations that can continuously adapt, reskill and redeploy capability.
That requires moving away from static job descriptions, encouraging cross-functional collaboration, and valuing learning agility as highly as tenure or experience.
Trust and Legitimacy Have Become Commercial Issues
Insurance has always been a trust-based industry. What has changed is how fragile that trust has become.
Customers expect transparency around pricing and claims decisions. Employees expect ethical leadership and clarity about how technology is used. Regulators expect proactive governance rather than reactive compliance.
The erosion of trust is measurable. The Edelman Trust Barometer reports that trust in institutions remains under pressure globally, with growing expectations that business leaders take responsibility for societal and ethical outcomes, not just financial performance.
In this environment, leadership behaviours once considered “soft” now have hard commercial consequences. Decisions around AI, pricing or claims handling may need to be defended publicly, not just internally.
The best insurance leaders in 2026 are those who can lead through scrutiny, explain complexity clearly, and build confidence even when decisions are unpopular.
From Authority to Credibility
Another subtle but significant shift is how authority itself operates.
In 2016, seniority, title and tenure carried significant weight. Leaders were often trusted by default. However, in 2026, credibility must be earned continuously.
Highly skilled teams expect leaders to understand their world. Regulators expect informed engagement. Boards expect leaders who can challenge assumptions rather than simply provide reassurance.
As a result, the strongest leaders today tend to combine confidence with humility. They ask better questions, listen carefully, and are comfortable acknowledging what they do not know while surrounding themselves with people who do.
Far from weakening leadership authority, this approach strengthens it.
What Boards Are Actually Hiring For Now
Across the global insurance market, hiring briefs have evolved.
Technical expertise and market knowledge remain essential, but boards are increasingly prioritising broader leadership capabilities: systems thinking across risk and capital, decision-making under uncertainty, fluency in AI-enabled operating models, strong stakeholder presence, learning agility and emotional resilience.
These traits are not always obvious on a CV. They require deeper assessment, more nuanced referencing and a willingness to challenge familiar leadership archetypes.
Crucially, this does not mean boards are simply looking for younger leaders or external disruptors. They are looking for leaders who have evolved with the role.
