Although I’m well into my adult years, nothing makes me feel like I’m “adulting” quite like trying to make sense of employee benefits. Not my mortgage, not the bills — it’s this. Each year when open enrollment rolls around, I get a sinking feeling that I’m about to make an expensive mistake. After all, my entire family’s health coverage rests on understanding what I’m reading in the PDFs and slide deck given to me by the HR department.
To be fair, HR is always willing to help, but sometimes I’m not even sure which questions to ask. So, like a lot of people, I just guess my way through open enrollment.
But this year, I tried something different. Having used ChatGPT to plan everything from meals to travel, I asked the chatbot to walk me through my employee benefits step by step — from health plans to HSA questions to disability insurance and life insurance coverage I never fully understood. It actually helped me make clearer, more confident choices.
Here’s exactly how I used ChatGPT, the prompts that worked best, and the features that made open enrollment less overwhelming.
1. ChatGPT explained my health plan options in plain English
My company offers multiple medical plans, and I’ve always struggled to understand the trade-offs — particularly between high-deductible plans and PPOs. (What even is a PPO?!)
I uploaded the plan comparison chart (if yours is PDF, just upload it into the chat box) into ChatGPT and used the following prompt:
Prompt:
I used ChatGPT to make sense of my employee benefits – here’s how it saved my open enrollment
