You Can Replace a Position. Can You Replace the Knowledge?

The insurance industry has a people problem, but describing it simply as a talent shortage misses something important. Experienced professionals are retiring, taking decades of technical expertise and institutional knowledge with them. At the same time, insurers are competing for people with capabilities in data, technology, analytics, digital operations, and other areas that are becoming increasingly important to the industry’s future.

That means insurers aren’t simply trying to replace the people who leave. They’re trying to preserve what those people know while developing a workforce capable of doing work that continues to change.

Deloitte’s 2026 insurance outlook describes this as a significant workforce challenge. Veteran employees are steadily exiting the industry while recruiting has struggled to keep pace, creating pressure to preserve legacy knowledge, attract new talent, and reskill existing employees. At the same time, insurers are reconsidering how people and technology should work together. In Deloitte’s research, 90% of surveyed insurance executives agreed on the urgency of reinventing the employee value proposition for human-machine collaboration, but only 25% had taken tangible action to elevate human skills.

The question for insurance leaders, then, isn’t simply who will fill the open positions?

It’s what knowledge and capability does the organization need to make sure it doesn’t lose?

When Someone Retires, More Than a Position Can Leave

Insurance is an industry built on accumulated expertise. Experienced underwriters, claims professionals, actuaries, agents, brokers, risk professionals, and leaders develop judgment over years of working through situations that don’t always fit neatly into a manual or data set.

Some of that expertise can be documented. Much of it is harder to capture.

It can be knowing which questions to ask when something doesn’t look quite right. Understanding why a process exists because you remember what happened before it did. Recognizing patterns in a claim or account because you’ve encountered something similar before. Knowing which relationships matter, where exceptions tend to occur, or how a decision that looks reasonable on paper might actually play out.

Global Finance, examining the insurance workforce challenge, cites industry research in which 66% of property and casualty professionals identified the loss of institutional knowledge as the biggest impact of the industry’s retirement wave. The article argues that what insurance is experiencing may be better understood as workforce reconfiguration than a straightforward talent shortage. (gfmag.com)

That distinction matters. Hiring someone into an empty seat replaces the employee count. It doesn’t automatically replace what the previous employee knew.

The Industry Needs New Skills Without Losing the Old Ones

Preserving institutional knowledge cannot mean preserving the workforce exactly as it exists today.

The insurance business itself is changing. Data and analytics are influencing underwriting and pricing. Technology is changing claims, distribution, customer service, and operations. New risks require different expertise. Employees are increasingly expected to work across functions and use tools that may not have existed when many experienced professionals began their careers.

Insurers therefore face two workforce challenges simultaneously: retain and transfer the expertise that remains valuable while developing the capabilities that will be valuable next.

Those goals can easily be treated as competing priorities. Organizations can focus so heavily on recruiting a new generation of talent that they underestimate the knowledge leaving with experienced employees. Or they can become so protective of established ways of working that they fail to develop people for how the industry is changing.

Neither creates a strong Roster.

The better question is not whether insurance needs experienced professionals or new capabilities. It needs both.

Knowledge Transfer Has to Be Intentional

Institutional knowledge doesn’t automatically move from one generation of employees to the next simply because people work in the same organization.

It has to be transferred.

That can happen through mentoring, coaching, job shadowing, cross-functional assignments, succession planning, documentation, apprenticeships, collaborative decision-making, and opportunities for less-experienced employees to learn how experienced professionals think—not simply what they do.

That last distinction is important. A procedure can tell someone which steps to follow. Developing judgment requires helping them understand why those steps matter, when the standard approach may not fit, and what factors an experienced professional considers before making a decision.

Organizations that wait until a longtime employee announces a retirement may already be too late. Knowledge transfer works better when developing the next person is treated as part of the job rather than something that begins during the final few months of someone’s career.

Leaders Have to Develop People for Who They Can Become

Walter Bond teaches that one of the responsibilities of leadership is to become a coach. Strong coaches don’t simply evaluate people based on their current performance. They recruit, develop, and retain talent while learning to see people based on who they can become, not only who they are today.

That philosophy has particular relevance to insurance’s workforce challenge.

If the industry needs capabilities that its current workforce doesn’t fully possess, hiring cannot be the only answer. Leaders also have to identify people already inside the organization who can grow into new responsibilities, learn new technologies, deepen their expertise, and eventually carry knowledge that currently resides with someone else.

That requires more than training programs. It requires leaders who know their people well enough to recognize potential, provide meaningful feedback, create development opportunities, and hold employees accountable for growth.

A Roster doesn’t become stronger simply because new names are added to it. It becomes stronger when the people on it continually become more capable.

Technology Changes What People Need to Be Good At

As technology assumes more routine work, the value of human expertise doesn’t necessarily disappear. In many roles, it changes.

Employees may spend less time gathering information and more time interpreting it. Automated systems may surface anomalies, but someone still needs to understand whether they matter. Technology can accelerate a claims process, but complex situations can still require judgment and communication. Analytics can improve underwriting decisions, but experienced professionals may need to recognize when an unusual circumstance falls outside the patterns represented in the data.

This makes the human side of workforce development more important, not less. Technical proficiency matters, but so do judgment, communication, curiosity, critical thinking, collaboration, leadership, and the ability to learn continuously.

Deloitte’s findings reveal the gap insurance leaders still have to close. If 90% recognize the urgency of redesigning work around human-machine collaboration but only 25% have taken tangible action to elevate human skills, recognizing the future of work is not the same as preparing people for it.

Progress requires execution.

Build the Roster Before You Need It

Walter’s Make Progress framework asks leaders to think deliberately about the Roster: Who will execute the Playbook required to reach the Target?

For insurers, that question cannot be answered only by looking at today’s organizational chart. Leaders have to consider which capabilities the business will need several years from now, which knowledge is at risk of leaving, which people have the potential to grow, and what development needs to begin today.

That turns workforce planning from a recruiting exercise into a leadership discipline.

The strongest organizations will create deliberate connections between experienced professionals and developing talent. They will identify critical knowledge before it walks out the door. They will reskill people rather than assuming every new capability has to be hired externally. And they will create a culture in which developing the next generation is part of how experienced leaders measure their own success.

The goal isn’t simply succession.

It’s continuity and evolution.

You Can’t Replace Experience Overnight

Insurance will continue recruiting new people, and it should. The industry needs fresh perspectives, new capabilities, and professionals prepared for a changing business environment.

But the next generation shouldn’t have to rebuild decades of organizational knowledge from scratch.

There is an opportunity right now to connect what experienced insurance professionals have learned with what emerging professionals will need to know next. Doing that well requires leaders to treat development, coaching, succession, and knowledge transfer as part of the organization’s Playbook—not as HR initiatives that sit alongside the business.

A position can be filled.

Experience has to be transferred. Judgment has to be developed. And the next Roster has to be built before the current one walks out the door.