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Writer's pictureJill Felska

Your step-by-step guide to hosting a 2023 team retro

Think about the work your People or HR team (even if that’s just you!) took on in 2023 💛


➜ How do you feel about the work you did (and didn’t) accomplish?


➜ Where did you really deliver on your stated goals? Fall short?


➜ When did you and your team get to best play to your strengths?




The case for looking back


Have you ever met a colleague in people ops or HR who didn’t have enough on their plate? Someone who was part of a team that had all the time, resources, headcount, and support they needed?

Pshhhh, yeah. Me neither. People teams operate in an interesting space, working in service to both business goals and the employees and teams directly impacting those outcomes. It’s a function that stands at the ready to mitigate disaster and put out fires, one wherein focus on the People team’s own goals, strategy, and priorities can easily get lost. Well I’m here to make the case that our teams need (and deserve) the same planning, clarity, and focus as any business unit. That the time to get proactive and strategic is just as – if not more – important on a People team than on any other team. It’s hard to find that time and space, and I totally respect that. No one person is responsible for the fact that People and HR teams often work at the mercy of whatever fire needs to be put out that day, month, or quarter.


There is something so powerful in making time and space to move towards a culture of proactivity and following through with the strategy, operations, and processes to match! Now, that shift doesn’t happen overnight. But there’s no time like the present, as we wind down one year and prepare for a new one, to get a little proactive in a big way.

We can’t move forward without looking back

I know time is tight, and it’s not like those everyday HR fires are going out anytime before December 31st. I so get it. I implore you to challenge yourself and your team to meaningfully reflect on your 2023, no matter how busy you are or how eager you are to lay groundwork for 2024. There’s no better opportunity to learn from your mistakes, better understand what contributed to hold ups and slow downs, reflect on what drove your successes, and align on a full team perspective - one that incorporates reflection and input from every member of your team. Mine all that gold, add it up, and what do you get? The exact understanding, insight, and alignment that’s going to better – and more quickly, effectively, and accurately – inform the decisions you make and the work you undertake as a team in 2024. Struggling with where to start? Fret not, the resource is going to walk you through each and every step!

Two hands can be seen holding two sparklers together to light them. Make sure you celebrate your successes with your team during your end of year retrospectives.

Let’s give you (and your team) the time and space to process the struggles and successes you experienced in 2023

We’ve designed a workshop you can hold with your team where – together – you’ll align on key takeaways from the year. Pressed for time? I get it! This workshop is designed to run for a synchronous 2 hours, with limited pre- and post- work for you and your teammates.


End of year retrospective

  1. Schedule, communicate and prep for your workshop (30 min): Schedule a 2-hour block of time for your team. Along with the invite, send out some context on what you’ll be discussing, as well as what questions you’ll ask teammates to consider ahead of time. Our Workshop Guide includes a pre-workshop email template you can edit to put your own spin on, and guidance on prepping a short survey to use in the session.

  2. Conduct your workshop (120 min): In 2 hours, you and your team will discuss the good, bad, and befuddling of 2023, aligning on key insights and core truths of your team’s work this year. Don’t worry - we haven’t left you in the dark here. Our Workshop Guide includes a full start-to-finish facilitation guide and agenda to help you navigate some meaty discussion!

  3. Distill and send out notes (15-30 min): Soon after finishing your workshop (ideally by end of the following day), ensure that you send out a summary of the discussion for the team, taking care to clearly communicate your team’s aligned wins, misses, and most impactful unmet needs.

Join the newsletter to find out how to take all the insights you glean from the data and put them into action in 2024.

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