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FEATURE

Retention and Succession Planning in the Age of AI


By Lavezz Middleton


The insurance industry is undergoing a profound transformation, with generative artificial intelligence (AI) and other emerging technologies reshaping all areas of business and requiring medical professional liability (MPL) leaders to rethink their approach to talent. Regardless of where your organization is on its AI journey, effective succession planning and a strong commitment to employee development and retention are vital for thriving in this new era.

Amid many unknowns, one thing is certain: tech and AI transformation will continue to disrupt the industry, impacting everything from risk assessment to day-to-day operations. Gallup reports organizational adoption of AI tools increased by 6 percentage points between Q1 and Q2 2026 alone, reaching 47%. At the same time, approximately one-quarter of the insurance workforce will reach retirement age in the next 10 years.

These two trends create a compression of talent for many organizations. More seasoned professionals are choosing to retire early rather than embrace AI within their roles, while automation is impacting traditional entry-level responsibilities. It’s important for MPL organizations to recognize these new talent challenges and take a fresh approach to how they retain existing employees, develop the next generation of leaders, and approach succession planning.

Recalibrating Your Succession Plans

While succession planning has always been essential, a comprehensive approach is merited given industry challenges. The future of the industry will require a broadened set of leadership skills and the ability to move with agility, often into unknown territories. With these facts in mind, consider adopting an approach that involves identifying skill gaps, rethinking necessary roles, and aligning the C-suite and the boardroom as follows:

Identify skill gaps: Review your current succession plans through the lens of change. The individuals you’ve identified for future leadership roles may have limited experience navigating major changes or leveraging new technologies. However, as modernization becomes essential for business, leaders must possess digital literacy, a solid understanding of AI’s capabilities, and the ability to champion change. Incorporate these areas into development plans and provide opportunities for your future leaders to take on leadership roles during technology implementations, which will allow them to build confidence while revealing how they navigate uncertainty and communicate through change in a way that supports their teams.

Rethink necessary roles: Nearly 75% of insurers operate on core platforms that are at least six years old and nearly one-fifth rely on systems that are more than 11 years old. That said, US insurers are expected to invest more than $229 billion in legacy system modernization by 2029. No matter where your organization currently is within its modernization journey, updating your core platform is a large undertaking and requires the right leadership. Identify potential positions such as a chief information officer, chief technology officer, or chief transformation officer that may be required to influence and manage these projects. Investing in these areas now helps ensure your systems will be able to run new technologies and support your company’s evolving needs.

Align the C-suite and the boardroom: Many organizations face a disconnect between how executive leadership and the board view AI strategy. Ensure both groups are aligned on a vision for the organization’s future, as well as how AI fits into that picture. According to Boston Consulting Group, 35% of CEOs feel their boards overestimate what AI can replace and 60% feel boards are too impatient with the pace of transformation. Proactively address these inconsistencies to establish realistic timelines, strategically prioritize projects and define clear expectations. This undertaking includes asking difficult questions around new roles that will be required, skills that must be developed internally, and potential barriers that may slow down adoption.

Building Your Bench

The ability to lean into future opportunities and needs in an agile and timely way is largely dependent on the strength of your current employee and management bench. Consider how retirements, knowledge gaps, and automation are impacting your current talent strategy, while evaluating the skills and strengths necessary for the future of work, as follows:

Account for shifts in entry-level work: AI is affecting organizations at all levels; at the same time, impacts are disproportionate on entry-level employees. Many of the more straight-forward tasks typically handled by early-career individuals are the first to be automated, reducing the opportunity for these employees to begin building critical career skills. This dynamic results in a shrinking talent pipeline for mid-level roles, while also limiting their opportunities to gain foundational industry knowledge.



Eventually, this will lead to a talent imbalance at all professional levels. Consider these roles an investment in the organization’s future and determine how AI can be used to enhance and support—rather than replace—certain areas. This long-term approach builds the talent your organization will require amid industry shifts and lays the foundation for strong succession planning.

Capture organizational knowledge: Within the MPL space, many professionals have decades of institutional knowledge and experience, which can create potential knowledge gaps as they retire. AI provides the opportunity to capture and preserve this information in a tangible way. Consider interviewing seasoned employees on their decision-making processes, underwriting philosophy, and approach to evaluating risk. Use AI to transcribe, organize, and catalog these conversations into searchable knowledge repositories that future employees can access. This process allows long-tenured experts to mentor the entire enterprise and continue pouring into the organization long after they retire.

Organizations may also benefit from creating developmental roles for certain positions. This enables retiring individuals to train their successors, stepping back gradually until they’re ready to fully exit the workforce. Structured overlap gives future leaders the opportunity to observe decision-making, ask questions in real-time, and build necessary relationships before assuming full responsibility for the role.

Break down organizational silos: The future of work is increasingly fluid and interconnected. Building cross-functional awareness and discontinuing siloed thinking across the company encourages collaboration and a broad understanding of how departments work together to achieve larger goals. Provide transparency around organizational objectives and key results, as well as who is accountable for each piece and how success will be measured. Even individuals who are not working in a particular department will benefit from knowing what it does and how it impacts overall business performance—especially as they ascend into leadership ranks.

Emphasize soft skills: The traits that previously built strong leaders have evolved and expanded as organizations move into the new, tech-focused normal. For those who are advancing into leadership, empathy, and communication are vital for effectively managing future periods of transition. Provide opportunities for individuals to strengthen these skills while ensuring executives are also modeling them. Soft and interpersonal skills are increasingly valuable and remain uniquely human. Recognize and reward individuals who demonstrate thoughtful decision-making, strong judgement, and the ability to think creatively when working with new tools. Questioning data, thinking critically, and being able to catch errors and inconsistencies are important skills at all levels.

Retaining Top Employees

Employee expectations continue to shift and top talent remains in high demand. It’s essential for organizations to focus on retaining their high performers and creating environments that foster loyalty and productivity through steps such as building concrete and actionable development plans, effectively leading through change and engaging middle managers in the following ways:

Build concrete and actionable development plans: Employees are more likely to remain with organizations where they can clearly envision their future. Career development conversations should begin early in the individual’s tenure and evolve alongside their growth, strengths—and interests. As high performers demonstrate their capabilities, employers should provide opportunities for increased visibility, broader responsibilities—and stretch assignments. Work to identify any blockers that may prohibit the growth or ability of employees to advance to the next level, while determining if the right people are in the right seats. Often, top talent excels in a variety of positions—be creative in aligning your long-term needs with their skills and passions.

Effectively lead through change: To successfully adopt AI, organization communication is critical. Be open about why changes are occurring and how employees’ roles will be impacted. Ensure your leadership team has a consistent understanding of what they are aiming to accomplish, how success will be defined, and how resources will be reallocated as bandwidth and capacity are gained. Transparency and honesty are key during times of change and are crucial for helping build employer-employee trust.

Set your teams up for success with comprehensive training and accessible resources, along with open office hours, dedicated times for questions, and opportunities for shadowing and mentoring. Regularly seek feedback—both formally and informally—to improve processes, while helping individuals feel connected and heard.

Engage middle managers: Managers are not only experiencing change themselves, they are also serving as employees’ primary connection to the organization—particularly in remote and hybrid environments. Gallup found employees whose managers support AI are 7.4 times more likely to agree AI gives them more opportunities to do what they do best. Additionally, 21% of employees who left their roles said having more positive interactions with their manager could have retained them. Managers’ ability to effectively relay information and frame change heavily influences their employees’ overall experience and attitudes. Managers who provide information and resources to employees to enable them to best support their teams. Change that isn’t well communicated at every level often results in resistance, lower productivity, and increased turnover.

A Final Word

The question is no longer simply who will fill tomorrow’s leadership roles. MPL organizations must also determine what those roles will require, how emerging leaders will gain the necessary experience and how institutional knowledge will survive the transition. Organizations that begin answering those questions now will enter the next era with a stronger, more adaptable leadership bench.


 


Lavezz Middleton is a Managing Director for the executive search practice of The Jacobson Group.
Employees are more likely to remain with organizations where they can clearly envision their future. Career development conversations should begin early in the individual’s tenure and evolve alongside their growth, strengths and interests.