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Optimism Amidst Uncertainty: Insights from Large Business Leaders

In a recent survey conducted by Sentry Insurance and Wakefield Research, executives from large organizations showcased remarkable confidence for the upcoming year of 2026. Despite facing an increasingly complicated risk landscape, almost three-quarters (74%) of the surveyed leaders expressed belief in their companies' ability to maintain stability or achieve growth this year.

Rising Stress Levels

However, this optimism is tempered by escalating stress levels within the industry. A staggering 93% of executives reported experiencing the same or heightened stress compared to the previous year. This uptick in tension reflects the myriad risks associated with litigation, workforce management, and insurance coverage adequacy. The complexities of the current business environment are a significant concern, yet many leaders are committed to navigating these challenges successfully.

Gaps in Risk Management

The survey results highlight concerning gaps in how organizations are preparing for potential risks. A mere 18% of leaders expressed complete confidence that their current insurance policies are sufficient to shield them from emerging threats. In response to the shifting risk landscape, 98% of executives plan to reconsider their insurance coverage strategies within 2026. As Jeff Cole, Assistant Vice President of National Accounts at Sentry, noted, organizations are increasingly focused on reevaluating their risk management practices to better align with operational needs amid uncertainties.

Concerns About Litigation

Moreover, the research unveiled the growing anxiety surrounding litigation and its financial ramifications. Approximately 76% of large business executives identified the rising trend of litigation and multimillion-dollar verdicts as a significant concern within their industries. Alarmingly, 63% concurred that even a single substantial verdict could jeopardize their company’s viability. In comparison, 77% of businesses expressed apprehension about third-party litigation funding, which is especially noteworthy as it represents a shift in how litigation is financing itself, impacting countless organizations across the board.

Tony Trenzeluk, Managing Director of Government Affairs at Sentry, emphasized that the landscape of litigation is becoming more intricate, especially as the prevalence of third-party funding increases. Developing a clear understanding of these dynamics is crucial for businesses as they assess their vulnerabilities and work toward long-term sustainability.

Investments in Workforce Safety

In light of ongoing challenges, large business leaders are prioritizing investments in workforce safety and operational resilience. The study revealed that a majority, around 85%, of executives plan to boost their investments in worker safety initiatives for 2026. This dedication stems from the desire to enhance operational output and reduce lost work hours while curbing workplace incidents that may lead to costly workers’ compensation claims. Greg Larson, Assistant Vice President of Workers' Compensation Claims at Sentry, pointed out a shift toward proactive safety strategies, emphasizing the connection between understanding recovery factors and managing related costs in the long term.

Reevaluating Insurance Coverage

As part of their risk management approach, executives are also reevaluating how their insurance programs align with business objectives. Notably, 49% indicated plans to add coverage to minimize risk exposure, while 42% acknowledged that changes in their business operations have rendered certain coverages unnecessary. In addition, cost considerations remain a significant factor influencing policy reevaluation among nearly 39% of leaders. The findings suggest a continuous focus on balancing insurance coverage decisions with operational priorities and financial goals.

The survey also unveils a cumulative impact of risks encountered in recent years. Many large organizations reported an uptick in legal and insurance expenses, deteriorating operational efficiency linked to litigation, and other external pressures. Nevertheless, business leaders are responding decisively by taking an active role in molding their risk strategies, leading to safety investments, policy reassessments, and necessary operational modifications.

Conclusion

In conclusion, the Sentry survey reflects a nuanced landscape where optimism coexists with significant challenges. Leaders in the business sector remain hopeful, yet they recognize the necessity for improved risk management strategies, especially in the face of rising litigation concerns and employee safety investments. As 2026 approaches, it will be pivotal for these organizations to navigate through their anxieties and place the right strategies in place for sustainability and success.

About Sentry® Insurance

Sentry Insurance is part of a major mutual insurance group in the United States, rated A+ (superior) by AM Best. They offer an extensive range of insurance products, including property, casualty, life insurance, and retirement solutions. So for more information, visit sentry.com.

About the Survey

The survey was conducted by Wakefield Research, involving 1,250 U.S. executives leading organizations with at least ten employees from December 4 to December 16, 2025. The results underscore the state of mind of large business leaders as they prepare for the upcoming year.