The Ultimate Guide to Employee Benefits Questions (And How to Stop Answering Them)

Every HR professional has a mental catalog of benefits questions burned into their brain. You've answered them so many times you could do it in your sleep. (You probably have done it in your sleep. Benefits questions follow you into your dreams.)

This guide covers the most common benefits questions employees ask, why they're asking, and—most importantly—how to stop being the human interface to your benefits portal.

The Benefits Question Hall of Fame

After surveying HR teams at 50+ SaaS companies, these are the most frequently asked benefits questions:

Health Insurance Questions (The Heavy Hitters)

1. "Does our insurance cover [specific thing]?" — Orthodontics, therapy, fertility treatments, that weird specialist
2. "How do I add my spouse/partner/newborn to my plan?"
3. "What's the difference between the PPO and HDHP?"
4. "Where do I find my insurance card?"
5. "Is [specific doctor/hospital] in-network?"
6. "When can I change my plan?"
7. "What's my deductible again?"

Dental & Vision (The Supporting Cast)

1. "Does dental cover Invisalign?" — The #1 dental question of all time
2. "How much does vision cover for glasses/contacts?"
3. "Can I use my FSA for [random item]?"

Retirement & Financial Benefits

1. "When do I become eligible for 401k matching?"
2. "How much does the company match?"
3. "How do I change my 401k contributions?"
4. "What happens to my 401k if I leave?"

Life Events & Changes

1. "I'm getting married. What do I need to do?"
2. "I'm having a baby. What's covered/what do I do?"
3. "I'm getting divorced. How do I remove my spouse?"
4. "I moved to a new state. Does my insurance still work?"

Why Benefits Questions Are Especially Painful

Benefits questions hit different than other HR questions. Here's why:

1. The Stakes Feel High

When someone asks about health insurance coverage, there's usually a real situation behind it. They're not asking hypothetically—they're trying to make a decision about their health or their family's health. This adds emotional weight to every question.

2. The Answers Are Buried in PDFs

Benefits information lives in Summary Plan Descriptions that are 47 pages long, written by lawyers, and stored in a folder nobody remembers creating. Finding the answer often takes longer than just knowing it by heart.

3. You're Terrified of Getting It Wrong

Unlike "where's the coffee machine," getting a benefits answer wrong has consequences. What if you tell someone something is covered and it isn't? What if they make a decision based on your answer? The liability anxiety is real.

4. Every Situation Is "Unique"

Or at least, employees think it is. "But my situation is different because..." No, usually it's not. But you can't say that.

The Benefits Question Lifecycle

Every benefits question follows the same tragic arc:

1. The Slack Ping: "Hey, quick question about benefits..."
2. The Clarification: "Can you be more specific about what you're asking?"
3. The Research: You dig through the SPD, the carrier portal, and your own notes
4. The Careful Response: You craft an answer that's accurate but includes appropriate disclaimers
5. The Follow-Up: "Oh, one more thing..."
6. Repeat: Someone else asks the same question 2 hours later

The Real Cost of Manual Benefits Support

Metric	Average
Time per benefits question	8-15 minutes
Benefits questions per week (100 employees)	10-20
Hours per week on benefits Q&A	2-5 hours
Hours per year	100-260 hours

That's up to 6.5 weeks per year spent answering benefits questions. For a solo HR person, that's significant chunk of your capacity.

What Doesn't Work

The "Read the SPD" Approach

Telling employees to read the Summary Plan Description is technically correct and practically useless. Nobody reads those. Nobody will ever read those. Accepting this is the first step toward recovery.

The Benefits Portal

Your benefits carrier probably has a portal. Your employees have definitely forgotten the login. Even if they remember, the information architecture is designed by people who hate users.

The FAQ Document

You spent 8 hours creating it. Nobody has opened it. It's already outdated because insurance changed carriers last year.

The All-Hands Presentation

You covered everything during open enrollment. Employees retained approximately 0% of it. They were checking Slack the whole time.

What Actually Works

The only thing that scales is meeting employees where they are (Slack/Teams) with instant, accurate answers that don't require your involvement.

This means:

• An AI that knows your specific benefits — not generic benefits information
• That lives in Slack/Teams — where questions happen anyway
• That can cite sources — so employees trust the answers
• That escalates appropriately — complex situations still come to you

How to Set Yourself Up for Success

Whether you use Deb or another solution, here's how to actually reduce benefits questions:

1. Create a Benefits Source of Truth

Gather all your current benefits information in one place: SPDs, carrier one-pagers, plan comparison charts, enrollment guides. This becomes your knowledge base.

2. Document the Gotchas

What questions do you answer over and over? What exceptions exist? What do employees always get wrong? Write these down. They're the foundation of actually helpful benefits support.

3. Separate "Lookup" from "Judgment Call"

90% of benefits questions are lookup questions with factual answers. 10% require human judgment. Route accordingly.

4. Make Self-Service the Path of Least Resistance

The only way employees will stop asking you is if asking the alternative is genuinely easier. If self-service has more friction than Slacking you, they'll Slack you.

The Future of Benefits Support

Benefits administration is ripe for automation. The information is structured (it just lives in annoying formats). The questions are repetitive. The answers are mostly factual.

In 2026, there's no reason you should be manually answering "does dental cover Invisalign" for the 500th time. The technology exists. The only question is whether you're using it.

Ready to stop being a human benefits encyclopedia? Check out Deb — she's read your SPD cover to cover and actually remembers it.