While open enrollment is still months away at most employers, now is the time for HR leaders to apply learnings from last year that can make the 2026 benefit selection period more successful.
HR leaders and benefits teams may not know what’s keeping employees from focusing on their benefits decisions, but they do know this is an expensive undertaking. The Kaiser Family Foundation 2025 Employer Health Benefits Survey documents that average family premiums reached $26,993 in 2025, a 6% increase that outpaced wage growth of 4%.
The report also found that workers are contributing an average of $6,850 toward family coverage. The average deductible for single coverage has climbed 43% over the last decade, now sitting at $1,886. These numbers show that benefits decisions require time, focus and the ability to ask follow-up questions.
However, here are some of the pitfalls that reared their head during open enrollment last year, each a signal to HR leaders about what might need to change for this year.
Benefit questions happen around the clock
More than 20% of benefits questions arrived outside standard business hours, with nearly 10% more coming in on weekends, according to a new report from HR service platform Cascade AI, which analyzed thousands of anonymized employee questions asked during open enrollment this fall. The research found that employees were tending to enrollment decisions at night, on mobile devices and in the margins of their day.
More than an FAQ is needed
When Cascade’s AI gave employees an anonymous, always-on channel to ask whatever they needed, the nature of the questions changed. Cascade found that 59% of sessions involved four or more exchanges with employees building on previous answers, testing scenarios, and circling back.
One employee asked 59 questions in a single sitting, working through HSA mechanics, critical illness scenarios and family coverage options in sequence.
Read more: Employers have helped rein in healthcare costs, but the fight isn’t over
Cost concerns cause anxiety
KFF asked employers how concerned they believed their employees were about the affordability of benefits. Only 20% of large firms believed employees had a high level of concern about the affordability of cost sharing.
However, Cascade’s behavioral data tells a different story about cost fears. “Employees ran worst-case math over and over, stress-testing what happens when things go wrong, according to the report. “They’re anxious about making the wrong call.” Employees expressed concerns about managing multiple specialist visits, a high-cost prescription or a carrier change that disrupts existing care relationships.
Network transitions aren’t easy
KFF research provides context for why the transition anxiety Cascade documented is rational rather than uninformed. Eight percent of firms offer narrow network plans, and nearly one in three employers acknowledges gaps in timely access to mental health services.
When an employee is wondering late at night about whether their therapist is still covered under the new plan, they are not being unreasonable, because network changes and access gaps can make coverage continuity uncertain.
The nature of questions is changing
Cascade also tracked a year-over-year change in the character of employee questions. In 2024, employees asked foundational questions such as what benefits were and how they worked. In 2025, they arrived ready to decide, asking which plan made sense for their specific family, their specific childcare costs and their specific tax situation. Health plan comparison questions grew from 38% to 55% of all activity in a single year, according to the report.
KFF’s data helps explain what employees may be thinking. The spread between average PPO and HDHP family premiums is nearly $3,000 annually. Choosing correctly requires mapping individual healthcare usage onto each plan’s deductible, out-of-pocket maximum and cost-sharing structure.
Cascade found that when employees had access to a tool that could reason through their circumstances, they used it, and they stopped defaulting to last year’s plan. While this study was produced by a vendor with a commercial interest in the outcome, this is still insight that HR leaders can use even if they don’t use a new tool during next year’s open enrollment.
“The next frontier for AI in open enrollment isn’t answering more questions,” according to Cascade’s report. “It’s closing the distance between understanding and action.”
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