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#496 Hints While Grouping in a Retrospective

Friday Ship #496 | June 19th, 2026

Our latest feature in retrospectives: Grouping hints

As the number of reflections in a retrospective grow longer, the grouping phase gets harder. And not just a little bit—exponentially harder! For the math nerds out there, the number of unique comparisons follows the formula $n(n−1)​/2$. For the rest of us, that means if your retro has 10 reflections, you have to make 45 comparisons. If it has 100 reflections, you have to make 4950!

Our job at Parabol is to reduce this complexity so your meeting runs smoother. The most effective way to do that is by making sure that the next reflection you read is similar to the one you just read. That way, you read it, pair it with the last one, and move on to the next. The next will either join the previous group, or start a new group. For the nerds, we’re talking about reducing the complexity from O(n²) to O(n log₂n) via ordered lists.

Now, if we already know which cards go together, why not just automatically group them from the beginning? The answer is human nature. If we pre-grouped the reflections, we’re using AI to greatly influence human perception. ”Oh, AI thinks these belong together, let’s just leave them.” Nope, not here. Even worse, some reflections may not even be read if they were pre-grouped, which removes someone’s voice entirely. The challenge is striking the right balance between efficiency and empathy, AI and human.

That’s why we built Grouping Hints. As a user hovers over a reflection, similar reflections receive a light purple outline. This may encourage you to read that outlined card next, but doesn’t force it. If it’s a match, then you can group those cards earlier than before, which means less time re-reading the same reflection, performing extra comparisons, and hunting down that one card that mentioned that one similar thing. It also doesn’t allow the human to take their hand off the steering wheel— humans still perform the grouping themselves, which encourages the team to read every reflection. Let us know what you think!

Metrics

The seasonal summer usage dip is here, with most metrics flat to down. It’s nice to see total signups staying resilient while facing those headwinds.

This week we…

shipped retrospective grouping hints

upgraded our realtime Parabol Pages server to v4

Next week we’ll

continue our work on new features as part of Shape Up Cycle 14 while welcoming back our CEO, Jordan, from a well deserved vacation

Matthew Krick

Matthew Krick

Matt is a full-stack web developer, data scientist, and global project manager. He has previously worked for Peace Corps, Ecova, and Boeing, and is the creator and lead developer of several open-source projects including Meatier and Cashay. Matt lives and works in San Diego, CA.

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