From Chaos to Clarity: A Modern Open Enrollment Communication Timeline

Published on 5/6/24 · Updated 7/9/25

Open enrollment comms are stuck in a time loop—and it shows.

A few emails. A giant PDF. A meeting no one remembers. A mad dash at the deadline.

But 2025 is different.

Healthcare costs are spiking. Employees are more skeptical. HR teams are stretched thinner than ever. And the old playbook isn’t cutting it.

This year, it’s not about pushing out information. It’s about building understanding—and trust—through the right channels, at the right time, with tools that can scale when you can’t.

Here’s how to build an open enrollment communication timeline that actually works.

🚫 The Old Timeline: What HR Used to Do

• Write the same benefits guide (again)
• Send three company-wide emails
• Host one all-hands and call it a day
• Hope employees understand (or at least don’t ask too many questions)

✅ The Modern Timeline: What Works Now

• Lead with clarity, not content
• Use AI to scale personalization
• Let managers reinforce the message
• Put tools like ALEX and Ask ALEX on the frontlines
• Track what’s working—and adjust midstream

Let’s break it down.

Phase 1: Set the Strategy (8–12 Weeks Before OE)

Old Way: “Here’s what we’re offering this year.”
New Way: “Here’s what employees need to hear—and how we’ll get them to listen.”

Diagnose what’s changed

Start with your benefits usage data and employee needs—not your vendor spreadsheet. What are employees not using? What are they confused by? That’s where you dig in.

Tip: HR is prioritizing financial wellness, mental health, and voluntary benefits. Your open enrollment message should too.

Audit last year’s approach

What got clicks? What didn’t? What blew up your inbox? Review your open enrollment communication strategy, and cut anything that underperformed.

Set goals based on outcomes—not outputs

Get clear on what success actually looks like. Not “check the box” tasks like sending out a benefits guide. Think impact: Do you want 80% of employees to use ALEX before enrolling? Cut HR tickets by 30% with Ask ALEX? When your goals are outcome-driven, your strategy has something real to aim for—and measure against.

Phase 2: Build the Infrastructure (6–8 Weeks Before)

Old Way: Print materials, update the intranet, prep the all-hands.
New Way: Build a communication system that runs without you.

Update your benefits guide—for real

Your employee benefits guide should be skimmable, digital-first, and loaded with action cues. Lead with what’s changed, cut the wall of text, and think bullets over paragraphs. And don’t forget the MVP: put ALEX front and center—because nothing drives confident decisions like an empathetic guide.

Deploy your decision support early

Don’t wait for questions to pile up. Launch benefits decision support tools like ALEX early and often. Use teaser emails, QR codes, and intranet embeds to drive awareness so employees can explore before they enroll.

Pick your channels with intention

Email is table stakes. But don’t underestimate the power of Slack posts, mobile push, or manager mentions to spread the message. Build a layered open enrollment communications plan across digital, verbal, and physical channels.

Phase 3: Announce + Activate (3–4 Weeks Before)

Old Way: Send an email. Host a meeting. Move on.
New Way: Drive awareness in waves, from every angle.

Proactively address big changes

Don’t bury the lead. If you’re shifting plan types or cutting costs, be clear, empathetic, and specific. Give employees time to digest and respond.

Send the kick-off message

Your open enrollment announcement should include:

• Enrollment dates
• Quick bullets on what’s new
• Link to ALEX
• Reminder: this is your only chance to make changes this year

Need to boost engagement? Here are six ways to improve your OE emails.

Arm your managers

They’re the most trusted source of information for many employees. Equip them with toolkits, key dates, and answers to FAQs—and ask for a quick plug in their next team meeting or email.

Phase 4: Engage + Nudge (During OE)

Old Way: Send a reminder email halfway through.
New Way: Treat open enrollment like a campaign.

Send personalized nudges

Use employee segments and behavior (who hasn’t clicked? who hasn’t started?) to trigger timely, relevant reminders. Make it feel personal—even if it’s automated.

Host office hours—but do it smart

Don’t sit in an empty Zoom room. Offer targeted office hours for key segments—new hires, HDHP users, employees with families—and promote them via Slack or email.

Let Ask ALEX take the load

Your team can’t be everywhere. But Ask ALEX can. Our AI-powered chatbot answers plan-specific questions 24/7, so you don’t have to. And yes—it’s actually trained on your documents, not just generic internet advice.

Phase 5: Follow Through + Future-Proof

Old Way: Collapse into a chair.
New Way: Capture insights while they’re fresh—and keep the momentum going.

Debrief while it’s still real

What questions came up most often? Which messages hit? What did ALEX data show? Don’t wait six months to remember what worked.

Try this post open enrollment survey to capture feedback now.

Keep benefits alive year-round

Benefits don’t stop in November. Your benefits communication strategy shouldn’t either. Re-engage employees with timely nudges, wellness campaigns, and year-round guidance through ALEX.

TL;DR

If your open enrollment plan starts with a timeline and ends with a slide deck, you’re missing the point.

What employees need is understanding. What HR needs is scale. That’s why forward-thinking teams are replacing outdated checklists with modern tools, AI-powered support, and a smarter communication strategy—powered by ALEX.