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- 💛 The EOY Retro Guide Managers Will Thank You For
💛 The EOY Retro Guide Managers Will Thank You For
#62. A free, step-by-step guide to help teams reflect, celebrate wins, and set a strong tone for 2026.
Jill Felska
October 02, 2025 • Estimated Reading Time: 7 minutes
Hello and Happy Thursday!
I hate to say it, but the end of the year is coming fast. 🙈
This is always the time when I start making long mental lists of things I want to finish before December 31. High on that list every year is hosting a team retro. But if I’m honest, it’s also one of the things that gets pushed back until suddenly it’s February… and then the moment is gone.
The truth is, team retrospectives are one of the most powerful tools we have. They give us the chance to pause, take stock of what worked and what didn’t, and set ourselves up to do better moving forward. Every retro I’ve been part of has sparked clarity, brought my team closer, and made our planning stronger. That’s the kind of momentum I want heading into the new year!
So this time around, we’re making it easier than ever. Introducing our newest free resource: The Modern Manager’s Guide to Hosting an EOY Team Retro Session! We’ve built step-by-step instructions to guide any manager through hosting their own retro, no matter the team or department.
If you’ve been here a while, you may recognize parts of this guide. We’ve shared it before, but this version is fresh, more flexible, and designed to be shared across your organization. It’s built to support managers everywhere in ending the year with celebration, reflection, and focus.
Yours in embracing the end-of-year frenzy,
Jill
Reflect on this…
What surprised you about the past year? Where did you encounter unexpected wins or challenges?
What new processes or practices from 2025 do you want to carry into 2026?
How can you implement moments of reflection throughout the year?
Everything You Need to Plan Your Retrospective Workshop
Ready to dive into the year-end retro? Let’s go. We’ve updated the Modern Manager’s Guide to Hosting an EOY Team Retro Session, a comprehensive resource to help any manager execute a 2-hour workshop with their team.
Teams will come out of this time with a valuable list of 3 wins, 3 lessons learned, and 3 opportunities for the coming year. Inside the guide you’ll find:
Workshop requirements, purpose, and goals
Pre- and post-workshop email templates
Instructions and questions for a survey to be used in the workshop
A full facilitation guide that you can use to guide your group through the workshop step-by-step
Pretty much everything you need to host an ultra-productive two-hour workshop with your team
We’ve done a lot of the heavy lifting for you. All you have to do is follow the instructions, fill in the blanks, and show up. Take a look — it’s free!
This resource is built to spread!
Forwarding it on to managers is one of the most valuable steps you can take. The more managers who host retros, the more alignment, celebration, and forward momentum your company will carry into the new year.
To make it easy, we’ve drafted a short message you can copy, personalize, and send. A quick note like this helps managers understand what the workshop is, why it matters, and gives them everything they need to get started.
Here’s your copy/paste email template!
💌 EMAIL TEMPLATE 💌
Subject: A Simple Guide for Hosting Your Team’s End of Year Retro
Hi [Manager’s Name],
As we head into the final stretch of the year, I wanted to share a simple and meaningful activity for you and your team. I recently came across this End of Year Retro Workshop Guide from Want to Work There, and it’s a wonderful way to close things out together.
The guide walks you through a structured conversation where your team can reflect on the year, celebrate accomplishments, and talk about what they’d like to see more of in the year ahead.
You’ll come away with 3 wins, 3 lessons learned, and 3 opportunities for the coming year. And your team will leave the session feeling more connected, seen, and aligned.
Here’s the link to the article if you’d like to read more: https://wtwt.beehiiv.com/p/issue-62
And here’s the free resource you can download and use right away: https://wanttoworkthere.notion.site/eoy-retro-guide
If you’re looking for a thoughtful way to wrap up the year and set a positive tone for what’s next, this is an easy win.
Best,
[Your Name]
Your Turn
Why are we talking about end-of-year retrospectives at the end of October? The New Year might feel far away, but 2026 will be here faster than you think. Between navigating holiday vacations and last minute projects, you might not have time to set up a retrospective when December comes.
Use this timeline to get ahead of the holiday rush and make sure your retrospective happens without a hitch:
This Week: Spend 30 minutes reviewing the facilitation guide and share the template with your managers.
In November: Set aside 45 minutes to schedule your own team’s retro and send out reflection questions.
One Week Prior: Send a reminder to your teammates! Schedule a 15-minute calendar block for your team to review and reflect on the workshop questions, if they haven’t already.
Day Of: You got this! Bring snacks, keep your team on task (see “Make the most of your retrospective”), and encourage everyone to submit their forms at the end of the meeting. Their answers might develop during group discussion.
Day After: Reserve 30 minutes to send the recap email (we have a template for this!) and schedule an action planning session, either with yourself or relevant teammates. (30 mins)
Things We’re Loving Right Now
True self-care. The world is a tough place to be right now - especially for those of us who live in the US. This list of 12 ways to cope during chaos (each from a different therapist) was exactly what I (Jill) needed earlier this week. Maybe you do too?
Showcasing what CAN be. “The future of work must include disability & chronic illness” is a statement we are fully behind. The Rethink Ability Summit (October 28-30th) will showcase the exact steps we need to take to make it a reality. Grab your free ticket here and we’ll see you at the virtual Summit!
Did someone say new music? As I type this we are less than 12 (yes, twelve!) hours away from Taylor’s latest album drop. Don’t know about you, but our team will be listening on repeat all day tomorrow. Bring on the dopamine!
