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đź’š Schedule a Yearly Retro With Your Team
#39. We’ve done a lot of the work for you!

Hello and Happy Thursday!
It’s November and we are creeping closer and closer to the holiday season, so you know the rest of the year is going to fly by! This is the perfect time to sit down, look back, and do some end-of-year reflections. I know what you’re thinking - “I don’t have time for that, Jill!” - and believe me, I KNOW.
The end of the year can be so hectic with the holiday fun (and stress) and lots of people on PTO while you’re desperately trying to finish up your 2024 projects. But a yearly retrospective is an exercise you’ll definitely want to squeeze in, and your future self will thank you.
Why is this process so important? When you think back on your projects from this past year, you can probably name your favorites, and those that caused you the most frustration. But if you and the members of your team were to each make a list of the top three wins and top three lessons learned for the year, would they match? Can you even remember the details of your first projects of 2024? I know it’s a struggle for me!
True to the mission of this newsletter, we have done a lot of the legwork for you and created a step-by-step guide to hosting an End-of-Year People Team Retrospective Workshop. It’s chock full of templates and instructions and all of the parts of this process that would otherwise take up precious headspace. I hope you’ll take a look, see how easy we’ve made it for you, and schedule your workshop in the coming weeks.
Yours in looking back to look forward,
Jill
P.S. This process can be used by ANY team interested in doing a retrospective - we’re just extra passionate about supporting people ops teams.
Reflect on this...
âž™ What projects did you and your team enjoy working on this year?
âž™ What would you like to be including in your end-of-year report this time next year?
âž™ If you could change one thing about your workplace or team, what would it be?
Look Back to Look Forward
Need a little more convincing on the value of a team retro? Here are three reasons for doing a comprehensive People Team Yearly Retro for your HR/People Ops team:
Our work matters too. The foundational purpose of People Ops is to help others. Between supporting business objectives, functional and leadership teams, and individual employees, it’s easy to get caught up in helping others solve their problems and reach their goals. But the goals and priorities of People Ops are just as important. After all - our work has a very tangible impact on every single employee.
You won’t remember how you did it. Maybe you did something really cool or got great results from a new project or strategy, and you plan to build upon it next year. Well, now’s the time to document it before the logistics you ironed out and speed bumps you encountered become fuzzy memories.
No one’s perfect. Every year is an opportunity to learn something and build upon the great things you’re already doing. Innovation is important and not every idea will be groundbreaking. Documenting what you tried that didn’t go as expected is just as important as celebrating the wins.
Now that you’re convinced and ready to start - let's begin!
Forward Planning Your Workshop
We have created the EOY People Team Retrospective Workshop | A Step-By-Step Guide, and we’re giving it to you for free! It’s a comprehensive resource to help you execute a 2-hour workshop with your team, including:
Workshop requirements, purpose and goals
Pre- and post-workshop email templates
Instructions and questions to add to 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
It’s basically a fill-in-the-blank template to wash away your dread and make this vital project something you can look forward to. You’ll come out of the workshop with a valuable list of 3 wins, 3 lessons learned, and 3 opportunities for the coming year. Take a look!
Post-Retro Action Planning
We’ve added one additional component to the End-of-Year Retro process this year - action planning. In the guide you’ll see it marked as optional, but if you can find the extra 30 minutes I think you’ll find it time well spent.
You’ll find an action-planning worksheet that will help you turn your three opportunities into a set of specific, attainable, measurable goals so you can start working toward them. This would be a great exercise for a smaller group to tackle about a week after your workshop and should only take about 30 minutes.
Your Turn
If this is all sounding like a lot, and you aren’t sure you can pull it off, here’s an overview of how much time it will actually take:
30 minutes: Schedule the meeting, send out a short description and some pre-meeting details to get attendees' wheels turning. In our guide we’ve provided an email template and some questions for a survey to prepare in advance of the meeting.
2 hours: Conduct the workshop. Our guide has done a lot of the legwork for you, so put it to use and jump right in! You’ll find a timed agenda to ensure you optimize the time, a facilitation guidance for each section, activity instructions, and lots of notes to help you make this a meaningful, productive, positive experience for everyone.
30 minutes: Distill and send out notes, ideally the day after the workshop, including the year’s wins, misses, opportunities, and hopes and dreams for the coming year. And - you guessed it - we have some templates for this too.
30 minutes (optional): Invite a small group to set some actionable goals for the opportunities you identify, using our worksheet template.
Hopefully this breakdown helps you feel less overwhelmed and more excited to get started.
P.S. - this activity works for non-HR teams as well! Feel free to share the workshop guide with other managers across your company!
P.P.S. - Let us know if you use the guide! Tell us how it went, what you learned as a team, and any improvements you’d suggest.
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