Team Retrospectives: The Good, The Bad, The Feels

This isn’t the first time we’ve shared a look into our own processes and how we cultivate open and trusting relationships within our team culture. One of the ways our commitment to transparency and continuous improvement comes to life is through our monthly retrospectives as a team.

There are many business-y names for the practice of reflecting on the past—debrief, post-mortem, retrospective (retro for short)—and there’s a good chance you’ve been a participant in this type of meeting at some point. There’s an even better chance that it wasn’t your favorite meeting. We believe strongly in the benefits of routine reflection and in meetings that don’t suck. Here’s an overview of how we do it.

Plan Ahead + Prioritize

Save the dates for our end of month retros are sent out at least 30 days in advance so that we can all hold the time as other commitments are added to our calendars. If it’s planned ahead of time and understood to be a high-priority meeting, you’re less likely to cancel it or have absent team members.

Retro Gear

If you’re taking on the role of facilitator, you’ll want to be prepared. Here’s a handy checklist I use to run a seamless meeting when facilitating our retros.

  • Reserve a room with plenty of wall space or a large whiteboard
  • Make sure each person has a chair and table space or a surface to write on
  • 3×5” sticky notes in five different colors. Everyone should have a stack of each color
  • Sharpies for each person + a handful of whiteboard markers
  • Chill tunes and a speaker—you can use our massive TDG Reflection playlist
  • Food + drink to keep the humans running top notch for the duration of the session

Retro Categories

Looking back without a framework to guide the conversation can feel more like a dump of “oh shit, what just happened” moments instead of a supportive and positive share-out.


We use the following five categories to capture our thoughts into a shared format for discussion and to identify themes and insights. These categories are not only used to sort through our own projects, but also to call out awesome work that our teammates have been cranking on.

  • Good: Things that went well.
  • Bad: Things that did not go well, but are generally one-off events—things that we don’t expect to repeat.
  • Do Better: Things that we can do better next time. These can include a suggestion on how to do it better.
  • Best: Things that went really well. Celebrate! How can we do more of this?
  • Feels + Open Questions: Emotions, mindsets, areas of confusion, and opportunities to consider.

It’s helpful, from a visual perspective, to use a different color Post-it note for each category.


Here’s how our wall looked, in our most recent retro, after everyone on the team shared out their thoughts for each category. All the Best! So much Do Better!


Retro Agenda

As is the case for any meeting you’re planning, an agenda is essential. We’ve tested out a few different agenda formats and this one works best for us.

Feel free to try it out, but as always, make adjustments based on your own team culture. The time blocks for each section will be different depending on how many people you have on your team and how long you can all be together. We have a five person team and we usually block 90 minutes total.

1. Check-in: Before getting into the nitty gritty, we take 30 seconds to each write down and share one word, a short phrase, or emoji sketch that comes to mind to describe the past month. It helps us get a quick read on everyone’s state of mind about the state of our union.

2. Solo Reflection: We put 15 minutes on the timer, turn on the chill tunes, and review our calendars and notebooks silently while capturing thoughts on each of the categories on sticky notes.

3. Share Out: Each person gets 5-10 minutes to share out their thoughts and add their sticky notes to the board. We try to stay silent and reserve questions and “me toos” for the next phase in order to give each person our full attention while they share.


4. Themes, Insights, and Red Flags: We step back, consider everything that was shared, and call out any recurring themes, insights, and red flags that we want to avoid. We capture these on the whiteboard and document them digitally. This way we can keep them in mind throughout the following month and then refer back to them at the next retro to see how we’ve improved (or not—no judgements).

We’ve had “less but better” on our theme list almost every month since January, and instead of beating ourselves up because we still take on more than we probably should, we acknowledge it, and discuss what it means for each of us and how we can continue to make progress towards refining our work (and load).

5. Commitments: Before closing, we take a few minutes to write, “I will __________” statements for what we each personally want to focus on improving or changing, as well as any shared goals or actions. This doesn’t have to be huge or feel like yet another addition to our to-do lists, but rather it’s something that’s aspirational and has a sense of shared accountability.

For example, in January we all said we wanted to commit to working out consistently and we allowed ourselves the permission to go midday or leave a little early to make it happen. We are all happier, healthier and more productive because of it.

6. Check-out: Similar to the one word check-in activity, we take 30 seconds to write down one word that reflects our state of mind in this very moment having just spent the last 60-90 minutes in reflection mode.

Retro on Retros

(So meta!) In reflecting on our process while writing this blog post, we were able to chat about why we do retros, their importance to each of us, and how they benefit the team as a whole. There have been times when we miss a month (or two) and we double up and have a longer retro, but we fully acknowledge that not having time each month to share our thoughts and feelings adds unnecessary strain to the team. We’re a team that embraces getting a little existential every once in awhile, so our reflection time is a shared value. Retros have saved us from burnout, reduced anxiety, and helped us build empathy and create shared enthusiasm for all of our projects and programs.


If you try out this framework with your team or you use a different format let us know! We’d love to hear your stories and tips for facilitating these types of conversations.



Erin Lamberty
[email protected]

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