A team asked me to facilitate their retrospective, and I panicked. I’d been in plenty of retrospectives before, but I’d never actually run one. What if I picked the wrong activities? What if people didn’t participate? What if it turned into a blame session? What if I couldn’t keep the conversation moving?
The team’s previous retrospectives had been terrible. They’d devolved into status meetings where people just reported what they’d done rather than reflecting on how they could improve. Same issues kept coming up without resolution. People were checked out. The whole thing felt like a waste of time.
I spent a week preparing. I read books about facilitation, studied different retrospective formats, practiced activities in my head. I observed the team’s dynamics to understand who spoke up, who stayed quiet, what their communication patterns were like. I wanted to understand what had gone wrong before so I could avoid those pitfalls.
The day of the retrospective, I got there early to set up the room. I arranged the chairs in a circle, put up flip charts, laid out sticky notes and markers. I wrote the Prime Directive on the wall - the idea that everyone did the best job they could given the circumstances. I wanted to create a safe space where people could be honest without fear of judgment.
When people started arriving, I could see they were skeptical. They’d been through bad retrospectives before. I started by asking everyone to share one word about how they were feeling. Some people said “tired,” others said “hopeful,” one person said “skeptical.” I appreciated the honesty.
Then I introduced the Four L’s activity. Each person would reflect individually on what they liked, what they learned, what was lacking, and what they longed for. I gave them time to write their thoughts on sticky notes, then had them share in small groups before bringing it back to the whole team.
The energy in the room started to shift. People were actually talking about process and improvement, not just reporting status. They were listening to each other, building on each other’s ideas. The small group discussions had given quieter people a chance to speak up, and the structure had kept the more vocal people from dominating.
We spent time consolidating the themes that emerged. I split them into groups to work on different areas, then had each group present their findings. People were engaged, asking questions, offering suggestions. They were starting to see patterns in their work that they hadn’t noticed before.
The hardest part was converting insights into action. I used dot voting to help them prioritize the most important issues, then we worked on making the action items specific and measurable. Who would do what by when? How would we know if it was working? I wanted to avoid the vague commitments that had doomed their previous retrospectives.
By the end of the session, people were energized. They had concrete plans for improvement, clear ownership of action items, and a sense that they could actually make things better. One person said it was the most productive meeting they’d had in months.
What I learned is that running a retrospective isn’t about being the smartest person in the room or having all the answers. It’s about creating the right conditions for honest reflection and meaningful conversation. It’s about choosing activities that fit the team’s personality and needs. It’s about keeping the focus on improvement rather than blame.
The preparation mattered, but not in the way I expected. Having a variety of activities ready was important, but the real work was reading the room and adjusting in the moment. I had to be comfortable with silence, with difficult conversations, with not knowing exactly how things would go.
The team’s follow-through on their action items was impressive. They actually implemented the changes they’d committed to, and the next retrospective was even better. They’d built momentum and confidence in their ability to improve.
What I ended up doing was treating the retrospective like a conversation rather than a presentation. I focused on creating psychological safety, choosing activities that encouraged participation, and helping the team convert insights into concrete action. The structure provided a framework, but the real magic happened in the honest dialogue that emerged.
The key insight is that retrospectives fail not because teams don’t want to improve, but because they don’t feel safe enough to be honest or don’t have the right structure to turn insights into action. Good facilitation creates both the safety and the structure that teams need to have meaningful conversations about improvement.
I tried to capture my learnings in a guide for myself and others who want to run effective retrospectives.