How We Run Retrospectives (and Why They Actually Work)
Retrospectives are one of the few rituals that, done well, actually make a difference. They give teams a structured moment to step back, say what worked, surface what didn't, and agree on what to change. At HipSquare, we run them at two levels: every other sprint within projects, and once a year for the whole company.
The Format
We use EasyRetro to run our sessions, which is organized around three columns: "Went Well," "To Improve," and "Action Items." Before the retro starts, everyone can already add cards to the first two columns. That preparation time matters, because people arrive with their thoughts already organized rather than trying to recall the past two weeks on the spot.
The session itself runs 60 minutes. The first 10 are reserved for anyone who still wants to add cards. Then we go through "Went Well" first, with each person briefly explaining what they wrote. Same for "To Improve." Clarifying questions are welcome at this stage, but actual discussions are saved for later. That keeps things moving and ensures every card gets heard before anyone goes deep on any single topic. Action items that come out of the discussions land in the third column, giving everyone a clear, shared record of what was agreed.
Voting and Prioritization
Once every "To Improve" card has been presented, the team votes. Everyone gets 10 votes and can distribute them however they like, including putting multiple votes on a single card. The results speak for themselves: cards are sorted by vote count, and that order becomes the agenda for the discussion phase.
This matters because it takes the prioritization out of any one person's hands. The team collectively decides what deserves attention, and the discussion time goes where it's most needed.
Discussion and Action Items
Working through the "To Improve" cards in order of votes, the team discusses each one and agrees on concrete action items together. Those get added to the third column in EasyRetro and saved to the wiki afterward, so they're accessible to everyone, not just the people in the room.
At the start of the next retro, we briefly review what came out of the previous one. Not a lengthy debrief, just a quick check on whether the action items were followed through.
Why This Works
A retro is only useful if people actually engage with it. The format we use makes that easier in a few ways.
Preparing cards in advance lowers the barrier to participation. People don't have to think on their feet in front of the group, and quieter team members have the same opportunity to surface issues as the more vocal ones. The voting mechanism has a similar effect: it distributes influence across the whole team rather than letting the loudest voice in the room set the agenda.
The separation between presenting cards and discussing them is deliberate. It prevents early comments from anchoring the conversation before everyone has been heard. And keeping discussions tied to concrete action items means the retro produces something tangible, not just a list of frustrations.
Saving results to the wiki and reviewing them at the next retro closes the loop. It signals that the input was taken seriously, which is what keeps people engaged over time.
If you're evaluating whether HipSquare is the right partner for your project, this is one small indicator of how we work. We believe that good processes, consistently followed, lead to better outcomes, and that includes the less glamorous parts like structured retrospectives. Teams that reflect regularly tend to improve steadily, and that improvement shows up in the work.