November is when two important threads meet in the workplace: the practical work of Open Enrollment (for most) and the cultural lift that comes from gratitude. Handled well, you help employees make confident benefit choices while nudging the whole team toward a calmer, more connected close to the year.
Why pair gratitude with Open Enrollment
- Better decisions under lower stress. Benefits choices feel less overwhelming when employees feel supported and seen.
- Higher participation and fewer corrections. Clear, human communication reduces last-minute questions and form errors.
- Positive culture signal. Recognizing people’s efforts builds trust, which makes policy and plan updates easier to roll out.
A simple plan for the month
Week 1: Kickoff and clarity
- Send a short Open Enrollment overview that answers what’s changing, what’s not, key dates, where to enroll, and who to contact.
- Publish a thank-you note from leadership that acknowledges the team’s work this year and invites questions.
Week 2: Decision support
- Offer two paths: a Quick Guide for most employees and a Deeper Dive for those comparing plan details.
- Host a 20-minute Q&A session with your advisor. Record it and share the link for on-demand viewing.
Week 3: Nudge and recognize
- Send targeted reminders to employees who have not started or have not submitted.
- Share two or three real examples of how specific benefits were used this year, and thank the teams that helped make those outcomes possible.
Week 4: Final pass and gratitude
- Issue a final, plain-language reminder with exact deadlines and what happens if no action is taken.
- Close the month with a short note that celebrates wins and calls out behind-the-scenes work from HR, Finance, and People Ops.
Communications you can copy
Email 1: OE kickoff
Subject: Open Enrollment begins today
Body:
Hi Team,
Open Enrollment runs from [start date] to [end date]. This year, [list one to three meaningful updates in a sentence each].
Enroll at: [portal link]. Need help? Contact [HR contact] at [email] or join our Q&A on [date, time].
Thank you for everything you do. We appreciate the work that keeps this place running.
[Leader name and title]
Email 2: One-week reminder
Subject: One week left to choose your 2026 benefits
Body:
Quick reminder that Open Enrollment closes on [date] at [time]. If you have already submitted, thank you. If not, here are your next steps:
- Log in to [portal link]
- Review the Quick Guide
- Submit your selections Questions are welcome at [email]. Thank you for taking a few minutes to set yourself up for next year.
Slack or Intranet post: Gratitude note
Thank you to every manager who reminded teams about enrollment windows, to HR for answering the hard questions, and to Finance for keeping the numbers straight. Your work makes it easier for everyone to take care of themselves and their families.
Tools that reduce confusion
- One-page Quick Guide. Plain language, screenshots, and definitions of key terms.
- Comparison table. Medical plans side by side, plus a reminder of HSA and FSA basics.
- Office hours. Two short windows each week where employees can drop in to ask a question.
- Recorded demo. Five minutes that show where to click and how to submit.
Gratitude habits that actually stick
- Start meetings with one specific acknowledgment tied to recent work.
- Encourage peer-to-peer notes. A short thank-you in Slack or email has outsized impact.
- Spotlight a team each week in your intranet with a one-paragraph story of the problem they solved.
- Give managers a prompt list: recognize effort, collaboration, and follow-through, not only outcomes.
Manager talking points for 1:1s
- “Do you have what you need to make your benefits choices?”
- “Anything in the plan changes that feels unclear?”
- “Who helped you recently that we should recognize?” Capture open questions and route them to HR the same day.
Metrics to watch
- Enrollment started, enrollment submitted, and submission rate by team
- Questions answered within 24 hours
- Number of corrections after the window closes
- Participation in Q&A sessions and video views
Common pitfalls and how to avoid them
- Too much detail in the first email. Lead with dates, what changed, and the link to enroll. Put the rest in guides and Q&A.
- Vague deadlines. Always include the exact date and time, plus what happens if no action is taken.
- Missing a contact path. Every message should include who to email and when office hours are held.
- Forgetting dependents. Remind employees to verify dependents and beneficiaries before submitting.
How 1706 Advisors can help
If you want a turnkey package, we can deliver a ready-to-use Open Enrollment communications kit that matches your brand: kickoff and reminder emails, a one-page Quick Guide, a recorded five-minute walkthrough, and a simple Q&A deck. We can also staff two virtual office hours and provide a post-OE checklist for HR to reduce corrections and ticket volume.