Emerging Business Risks to Watch in 2026: A Q&A with David Gilbert

Running a business has never been simple, and as we look ahead to 2026, the risk landscape continues to evolve. New technologies, shifting regulations, climate impacts, and workforce challenges are changing how businesses operate and how they protect themselves.

To help business owners make sense of what’s coming, we sat down with David Gilbert, Vice President of Gilbert Insurance, to discuss the risks he’s seeing and how businesses can start planning for success in the upcoming year.

Q: When you look ahead to 2026, what’s changing most when it comes to business risk?

David: What stands out to me is that many of the risks businesses already know about are becoming more complex. Cyberthreats, weather events, and supply chain disruptions are not new topics, but the way they impact businesses is changing rapidly. Technology is evolving, costs are higher than they were just a few years ago, and regulations are adapting in response to these new challenges. This combination means business owners need to take a fresh look at how exposed they really are.

Q: Cyber risk has been a major concern for years. What’s different now?

David: Cyberthreats are getting more sophisticated, especially as businesses adopt tools that use artificial intelligence and automation. We’re seeing more advanced phishing attempts, misuse of AI, and situations where employees are using applications that haven’t been approved by their IT departments, often called “shadow IT.” These issues can create serious security vulnerabilities, even for smaller businesses.

From an insurance standpoint, it’s important to review cyber liability coverage to make sure it reflects today’s risks, including data breach expenses, system restoration, and potential business interruption tied to a cyber event.

Q: We’re seeing more severe weather here in New England. How does that factor into risk planning?

David: The weather in New England has never been what anyone would call predictable, but weather patterns are becoming more extreme and we’re seeing increasingly frequent flooding, stronger storms, heavier rain, and higher winds. For businesses, that can mean property damage, downtime, or temporary closures.

This is a good time for business owners to review their commercial property coverage and, where appropriate, flood insurance. It’s also important to understand storm deductibles and to think through continuity plans so the business can be more resilient and recover quickly after an event.

Q: Regulations seem to be changing constantly. What should businesses watch for?

David: We’re seeing expanded regulations around data privacy, technology use, and artificial intelligence at both the state and federal levels. For businesses, this can create compliance challenges and potential exposure to fines or legal action in instances such as the mishandling of personally identifiable information.

Insurance can also play a role here. Certain cyber policies include coverage for regulatory defense costs or privacy-related claims, but it’s important to understand what’s included and what isn’t.

Q: Workforce issues continue to make headlines. How do they impact insurance considerations?

David: Hiring and retaining employees is still difficult for many businesses, and high turnover can introduce new risks. Lack of training, less experienced workers, and tighter staffing can all increase the likelihood of accidents or employment-related claims.

Carrying high limits on your workers’ compensation and employment practices liability insurance coverage is key. Beyond insurance, businesses that invest in safety programs and employee support often see fewer claims and experience better long-term outcomes.

Q: Inflation has affected nearly every industry. How does that translate to insurance?

David: The cost to repair, rebuild, or replace property has increased significantly. Construction materials, labor, and equipment all cost more than they did just a few years ago. As a result, some businesses may be carrying limits that no longer reflect today’s replacement costs. These higher costs also contribute to rising insurance premiums, as insurers are paying more when claims occur.

It is important to conduct regular coverage reviews to ensure that policy limits keep pace with inflation and reduce the risk of being underinsured after a loss.

Q: If you had one piece of advice for business owners heading into 2026, what would it be?

David: Don’t assume your coverage still fits just because it worked in the past. Businesses change, risks evolve, and insurance should keep up. Having regular conversations with a Gilbert Insurance professional about coverage, operations, and future plans can help uncover gaps before they turn into problems.

At Gilbert Insurance, we focus on understanding how each unique business operates so coverage decisions are practical and aligned with real-world risks.

Questions about your business insurance coverage? Contact our own David Gilbert, Certified Insurance Counselor, at 781-909-7143. David takes the time to understand how your business operates, so coverage conversations are tailored to fit the specific needs of you and your business.