A Blind Retrospective

No sprints, releases, recent significant events, or even a common thread of problems with a group I’ve never met is the backdrop for a recent retrospective that I facilitated. I refer to a scenario like this as facilitating a blind retrospective. Did I mention this was their first retrospective?

One of the significant questions that were in my mind was around framing the retrospective. All retrospectives have a frame or a theme that give people a direction as they diverge and converge around improvement. In a case like this, there were no timeframes, events, or even a problem focus to provide that frame. Software teams, and scrum teams, in particular, benefit from sprint boundaries and releases to give a theme for retrospectives. Kanban teams can similarly frame around releases and individual or categories of work items to have a retrospective. This team lacked any such traits to hang a retrospective around.

I mentioned earlier that this was their first retrospective. This fact means history is an uneven frame as well. Some members of the teams have been involved for over a decade and others just a few months. Framing with time would be challenging due to this wide variation of shared history.

My Approach

Before planning the retrospective, I sought permission to interview everyone. I consider this to be critical when working with a new group and when facilitating a meeting where people may have concerns. I found myself without enough time to talk with everyone individually, so I wrote an email with a set of questions.

Some of the questions that I asked were:

  • If we left our retrospective with a clear way to improve, what area would you wish to see that improvement in the most?
  • What are some other areas that are weighing on you?
  • In your previous experiences, what made retrospectives really powerful for you?
  • Similarly, what have you seen in previous retrospectives that you want to avoid?

Each of these questions existed for me to get a sense of areas that I could fame a retrospective around and get a preview of people’s disposition and needs within a retrospective.

I used the responses I received to plan my agenda for the retrospective then.

In my responses, I found there were no common problems or recent events that would act as useful frames. This information led me down a path to plan a retrospective that would be a, “Turn up the good,” retrospective. Did I mention I had a remote participant?

The Agenda

The challenge now was to plan a retrospective that focused on amplifying what seems to work well for everyone while also making it easy to include a single remote participant.

For my remote person, I was going to employ a buddy system where someone that was there in-person would take the laptop around and help act as their eyes and ears. The buddy system has worked well in the past, and I hoped the group would participate. Beyond that, I needed to keep in mind what activities the group would do so that the remote person could participate.

For this, I had an important choice, which was to employ fully remote tools or leverage retrospective activities that allowed for individual notes and conversation. I opted for the ladder.

At this point I knew I needed to plan a retrospective that would ask them to amplify the things that worked well for them, I would use activities that were mostly conversational and relied on individual notes, and I’d have people buddy up with the remote person. Now it was time to create an agenda.

The agenda below was for 2.5 hours.

Set the Stage

After welcoming people to the retrospective and presenting the theme and agenda, I would ask permission to proceed.

Considering this was the group’s first retrospective and it was going to be one that existed to amplify the group I opted for a check-in that went something like this, “What is one word that describes the best part about working together?”

Gather Data

Sometimes there is serendipity in the world. In the group that I’m in for Esther Derby’s Powerful Retrospectives, there was a recent video chat about hard retrospectives. One of the activities that discussed was Appreciative Interviews. This activity seemed like a natural fit for my criteria.

This activity would involve the group splitting and interviewing one another around the question, “Think of a time where you were successful together, and you were proud or pleased about it.” The interviewer would ask clarifying questions and dig into what the elements were that led to that success.

From there, the groups would combine, distill their information, and share their information back to the group.

Generate Insights

The moment where we try to turn a lot of information into insights is the moment where I see a retrospective succeed and fail. It is the moment my hands shake.

Here I was going to walk through a set of debriefing questions that I would ask the entire group. I would count slowly in my head to allow silence to do its job and watch the room for reactions to what people said. I’d hold that this was a time for people to share, not to be right.

Decide What to Do

By now, the group will hopefully have discovered something that stands out that is true for them, and they can brainstorm ideas that could lead to improvement.

I was not entirely sure how I was going to split the group at this point, as I didn’t know how they’d work best. I reserved the choice to split the group. What I was sure of was that I wanted this to be a moment of divergence, so I’d rely on setting up a brainstorming scenario.

When I prepare a group to brainstorm, there are a few key things that I say. Generally, I timebox brainstorming to 5-7 minutes. I tell them to brainstorm an idea that might lead to any amount of improvement. I tell them that if they find themselves filtering out or judging an idea, they write it down. That all ideas are valid at this point. I have noticed that many groups tend to stall out around 2 to 2.5 minutes. I plan to interrupt at that moment and say, “Many people run out of ideas around now. Those ideas that you’ve put down are the easy ones. Stay with this. Keep searching for ideas. Everything beyond this moment is new. Surprise yourself.” This interjection tends to keep a few more engaged while others fall off.

I also wasn’t sure what kind of ideas they’d generate. Would they be experiments, working agreements, or something else? Where they’d go would indicate how I’d advise them to refine their ideas. Similarly, would they need to group them because there is similarity, and how would we choose?

I left these as open questions I’d decide at the moment. These were the consequences of a blind retrospective.


Closings are sometimes really challenging in a retrospective due to the timing of everything that comes before it. I was going to hold the time boxes so that we had time to close this retrospective.

I would thank everyone for the opportunity to facilitate the retrospective, and I’d ask them to do a return on time invested. I wouldn’t ask for feedback for me, as I was a guest and I’d be asking at other times anyway.

I wanted them to have this last exercise as a way to quickly show if this retrospective or retrospectives, in general, are going to be a part of who they were going forward. After all, this was their very first one.

The Best Laid Plans

The retrospective moved smoothly through setting the stage and gathering data. After that, things went wobbly.

As we closed our appreciative interviews, we had identified numerous factors that led to success, but the group was unsure what to do with them as they viewed them as factors unique to specific scenarios. They also saw that many of them were the same factors.

Also, about half the group wanted to work at this from the perspective of moments when those factors weren’t there, so they could understand how to create those factors.

After a brief discussion, I proposed that the room split into cohorts. Some want to look at times when these factors weren’t here, and others may want to think about these factors as is. The group liked that idea and split. I held a 10-minute timebox to look at what they’ve learned and find actions.

When the group returned, nobody had an action.

At this point, the lack of actions concerned me, and I worried we were not going to find any actions. I expressed my concern and openly asked, “What do we need before we can come up with any ideas that can lead to any improvement.” After a 5 minute discussion, the group decided they were ready.

From here, I had them brainstorm individually for 5 minutes. We then decided to group our ideas as there were many common threads. We voted on improvements, and there was a clear winner. Ultimately it led to an experiment with their working agreements that they implemented immediately.

When we came back from appreciative interviews, my hands were shaking. Turning what the group had discovered into insights is a crucial moment for me, and selfishly, this was a retrospective I wanted to succeed. I focused on my breathing. I watched the time box. I reminded myself of the basics and who I knew I needed to be. I permitted myself to be nervous.

When we closed, and I asked the group about the return on the time they invested, they voted fours and fives. We finished five minutes over the 2.5 hours planned time, and I was exhausted.