Open Enrollment: it’s the annual ritual of benefits choices, HR overload, and endless questions. This year, Cascade AI jumped in to simplify the multitude of tasks and activity. By providing employees with personalized, confidential AI assistants, we enabled them to ask questions on their own terms and receive immediate answers. The insights we’ve gathered from the questions our customers’ employees asked during this period reveal not only what employees value but also how organizations can better support their teams with greater transparency, accessibility, and immediacy.

Privacy is a Game-Changer 

When employees have tools to ask questions confidentially at their convenience and get instant answers, they engage more freely. Sensitive topics like mental health, pregnancy benefits, financial hardships, and family deaths came up regularly. AI offered a private space to ask personal questions that live agents simply can’t replicate. 

Simple Questions from Employees, Big Insights for HR 

Turns out, a lot of employees are still unsure about basics like, “What is a deductible?” or “What’s a qualifying life event?” By handling these simple questions, AI reduced HR’s workload while empowering employees to make informed decisions. 

In fact, one company saw a 9x surge in HR-related questions during Open Enrollment, many of which came as “teach me” inquiries—like “What happens when I meet my deductible?”—proving that easy, anonymous access to information drives employee curiosity and confidence. 

Complex Queries? No Problem 

Then there were the complicated ones: 

• “Which health plan works best for someone on a GLP-1?” 

• “Can I be reimbursed for diabetes sensors bought online, and will it count toward my deductible?” 

With AI, these detailed, time-consuming questions were answered in seconds, saving time and frustration for employees and HR alike. 

Open Enrollment = Teachable Moment 

We discovered Open Enrollment isn’t just about picking benefits—it’s also a time when employees are planning their year ahead. Questions about family leave, medical electives, and vacation policies showed employees want to make smarter decisions, and Open Enrollment is the perfect time to educate them. 

Adapting in Real-Time 

One interesting surprise? Braces! A flood of orthodontia-related questions led a company to quickly update their AI assistant with new dental plan details. That agility—powered by AI—meant employees got the information and answers they needed, fast. 

What Companies Can Learn 

The questions employees ask reveal gaps, opportunities, and teachable moments. With tools like Cascade AI, companies can: 

• Foster transparency and accessibility. 

• Reduce HR workloads while boosting employee satisfaction. 

• Quickly adapt to emerging trends and communication gaps. 

Open Enrollment is complex, but it’s also a goldmine of insights. When companies are able to listen and respond, they unlock the full potential of their benefits programs—and their people.