Posted in Retrospectives

Practicing retrospectives – A retrospective training workshop!

How do one become a good retrospective facilitator? The same way as with anything else you want to master: Practice, Practice and Practice. But when dealing with retrospectives we run into a dilemma: You can’t really practice the execution of a retrospective unless you execute one. And it may seem hard to just throw yourself into trying it, without practicing first.  If you don’t know if you can swim (or simply keep your mouth and nose above the water) would you jump into the ocean?

Previously I have conducted workshops on the topic “facilitating retrospectives” with a combination of teaching theory and facilitating self-reflection. It was alright, but something was missing. Kind of like a swim teacher standing next to the pool telling the group of students how to swim, asking them how they think they are doing, and then telling them to jump in the pool in the deep end. Maybe the student got a few useful tips in the process, but did they learn to swim? Did they get the courage to jump in? Did the ones that jumped in survive?

If I were a swim teacher, I wouldn’t accept that uncertainty, so why should I when trying to share my knowledge on facilitating retrospectives? That’s why I wanted to put together a retrospective workshop where participants could practice preparing, planning and facilitating a retrospective in a safe zone, were total failure did not have any consequences. In the Swimming metaphor, I wanted the students to get into the pool and try swimming without risk of drowning.

In this post I will share the process and some reflections (in italic) I had, for the 4,5-hour workshop I facilitated for the ScrumMaster community in my company.

The overall agenda of the workshop, which is described in detail later in this post, was as follows:

  • Setting the stage of the workshop
  • Preparing and planning the retrospective
  • Executing the retrospective
  • Knowledge exchange from preparation and execution of the retro
  • Closing the workshop

The goals of the workshops were:

  • Everyone should facilitate at least one activity (to get hands on experience with a specific activity and try it in a safe zone)
  • Everyone should have practical experience as participants on several activities (to boost my confidence in trying them out on their own)
  • Everyone should practice the planning of an activity/a retro (To gain insight on what is needed in the planning process on both activity level and in a full retro)

To save time for practicing during the session, it was a prerequisite for participants in this workshop to know Esther Derby’s and Diana Larsen’s structure for a retrospective:

  • Set the stage
  • Gather data
  • Generate insight
  • Decide what to do
  • Close the retrospective

Setting the stage of the workshops (15 min)

A brief welcome with introduction to the goals of the workshop, as well as the agenda for the workshop was given. Then a quick 5 minutes reminder to the standard retrospective agenda, to remind participants, that this structure would serve the basis for the retros the group was going to plan and execute.

Reflection: It was very important for me that this part was very short, less than 10 minutes in order to “Get the students in the water as soon as possible”

Groups were formed, heavily inspired by the (in development) liberating structure “Folding Spectrogram”. The purpose was to distribute experienced and unexperienced facilitators evenly across groups.

Step 1) Participants were asked stand in a line of the spectrum “most facilitated retros” and “least facilitated retros”.

Step 2) The line was folded in the middle, so the least experienced was paired with the most experience.

Step 3) Groups of four was made by bringing the couple from one end (The most experienced and the least experienced) and pair them with a couple of the other end (Two medium experienced persons)

Step 4) Step 3 was repeated until 3 or less persons left

Step 5) When no 4-man group could be made, the rest was distributed to already formed groups to make them groups of 5

Reflection: This made the forming of groups “kind of” self-organizing, and participants got to stand up, walk around, talking and getting to know a little about the other participants experience. It worked like a warm-up exercise too.

Preparing and planning the retrospective (90 min)

Step 1) The group was introduced to the boundaries of the retro they were going to plan and prepare.

  • The group will plan the retro together
  • The retro will follow the standard agenda (Esther Derby and Diana Larsen)
  • Duration: 90 minutes
  • The facilitator role will take turns between group members. When not facilitator, you are participant in the retro.
  • Subject of the retro will be handed to the Facilitator of “Set the stage”.

Reflection: Acknowledging that every group work differently, I wanted to create and environment where teams could choose their own way of working together. Yet I still felt the need of guiding the process, to 1) help the groups and individual to be ready for the retro 2) Create situations were learning and insights happened. I chose to use only the first 1/3 of this planning timebox with a fixed and facilitated structure, to establish a minimum of coordination as well as highlighting some key elements to consider when planning a retro. This left 2/3 of the timebox for the group and individuals to work on what they felt as important for making the retro good.

Step 2) The group selected facilitator for the different stages, based on their own preference.

Reflection: This made participants able to choose the phase that fitted their needs. Some had challenges with a specific stage, and wanted to practice that, others just wanted to start slow.

Step 3) The facilitator of each phase selected an activity, and maybe a backup activity. For this step, all the activities from the was printed and grouped by phase. The retromat quick reference, which provides a good overview of all the activities in the retromat, was also available. The subject “Evaluating our Scrum Master development program” for the retros was revealed to the facilitators of set the stage.

Reflection: Having printed only one copy of each activity, ensured that the individuals selected different activities. The topic of the retros were loosely formed, as I wanted the facilitators of “Set the Stage” to consider how they would frame the topic.

 Step 4) The group decided on the time frame for each phase. Don’t forget shuffle time! If needed the groups switched activities to fit the time frame better.

Reflection: When planning a retrospective, skipping the time allocation part or going through it too fast, may bring you into situation where you need to end before you are done, or rush something to get to the end. Considering a good realistic timetable, is crucial for a good retrospective. In this training situation this was done together with others, and the fact that you were accountable to others, helped the dialogue on the way, as well as the commitment to the timebox later in the process.

Step 5) Each individual prepared their own activity for 10 minutes, considering the following questions:

  • What do I want to achieve with this activity?
  • Which input do I expect from previous phase? (For “Set the stage” facilitator, how do I frame the topic?)
  • Which output do I expect to hand over to the next phase? (For “Closing” facilitator, what do I want the participants to walk away with?)

Reflection: Some participants asked the question; how can I prepare my own activity without knowing what is before and/or after? The primary purpose of isolating the preparation of a single exercise was to emphasize the importance of actively considering input/output of an activity, to enable better planning of the flow of the full retro.  It also served the purpose to prepare participants for the next phase of this workshop, where alignment between phases would be dealt with.

Step 6) The group conducted 1:1’s (I called them “mini scrums” for the fun of it) to align expectations from phase to phase.

  • First the facilitators from “Set the stage” and “Gather Data” was given 2 minutes to align expectations. Every group member was listening, only active facilitators could talk. Agreements was noted on a flipchart. Known disagreements/misalignments was mentioned and noted for solving later.
  • Step above repeated with facilitator for “Gather data”/”Generate insight” and “Generate insight”/”Decide what to do” and “Decide what to”/”Close the retrospective”, in order to cover the whole flow of the retro.

Reflection: These mini scrums turned out very well. The expectations of each phase were addressed and aligned. Some groups decided to switch activities based on the dialogue to ensure a better flow of the retro. Alignment of the training retro was not the only benefit for the participants: Since the group members also listened to the mini-scrums they weren’t active in, it gave many the insight “I need to have this dialogue with my self when planning a retro”, as it displayed the value of the considerations made.

Step 7) For the rest of the timebox the individuals prepared and planned their activity as well as continuously aligned with the group and solving any mis alignment. Materials such as flipcharts posters were produced as well.

Reflection: With a minimum of coordination between the phases established, as well as key elements highlighted the groups and individuals knew what was needed to get ready for executing the retro. From here the groups and individuals took control of the process and did what was needed as group and individuals to get ready for the retro. There was a high energy in the room. Creativity took form in hand drawn posters. People were helping each other and generally the room was filled with a good vibe, and enthusiasm!

Executing the retrospective (90 min)

When groups were executing their retros. my part as the workshop facilitator was limited to “Go ahead and execute the retrospectives you have planned – see you in 90 minutes”.

Reflection: Before the workshop I was unsure what to expect from the flow of the group retros? Would it work? Would it feel natural as a participant? Would we get the feeling of a real retro, or would it feel like an awkward training situation? The short answers to this are Yes, it worked! Yes, it felt natural as a participant (I participated in a retro myself). Yes, we got the feeling of a real retro, with some suggestion to action points, that we could bring further in the process of improving our ScrumMaster community.

 So why did it work?

 A relevant topic was crucial – I believe.  We had a relevant topic to wrap the training retrospectives around – A shared experience, important for daily work of the individuals in the group. In our case evaluating our Scrum master community development program. If you don’t have an existing shared experience like this, you need to create on, which the group can evaluate on. It can be a rather simple teambuilding activity however the more this shared experience is relevant for the daily work of the whole group, the better.

 The process of the workshop ensured that the necessary coordination took place. Especially the individual considerations of “What do I want to achieve with this activity” and the mini scrums to ensure coordination between the phases stood out. These are crucial parts of planning and preparing a retrospective, however this is easy to skip or forget when you are just preparing alone. This setup emphasized the needs, and it had a positive effect on the training retros.

Knowledge exchange from preparation and execution of the retro (30-35min)

Reflection: The workshop could have ended after the retro execution, as everybody gained some experience and got some tips and tricks, they could take back to their own retrospectives. I added this reflection session in the end to anchor the knowledge in the participants minds, and thereby increasing the chance of them, doing something different in their next retro.

I decided to use the fishbowl activity to ensure the whole group could be a part of a larger discussion and knowledge exchange, as well as “forcing” non-speaking participants to listen.


The room was organized with an inner circle of chairs – one for each group – for “the fish”. Behind each fish chair, chairs for remaining group members were placed.

Round 1 – step 1
Facilitators of “Set the stage” had a 3-minute conversation about their considerations and biggest surprises when preparing the phase and planning the activity. Remaining group members where in a listening position.

Reflection: For the facilitators this gave the opportunity to discuss their experience with others who had just been in the same situation – preparing and executing the same phase. For the participants, it gave insight in the considerations and challenges in preparing and planning the phases they did not self-prepare.

Round 1 – step 2
Facilitators turned 180 degrees, to face their group. For the next 3 minutes, the facilitators were listening to the other group members experience with this face, using these questions as a guide: What did the facilitator succeed with? What opportunities could this activity open for.

Reflection: The participants reflected on what worked and what didn’t work, in that phase. This worked as direct feedback to the facilitator, but it also gave some insights and ideas to the participants on what they could try, when preparing and planning their own retrospectives.

Round 2+3 + 4 + 5
The facilitator of the next phase now took place in the inner circle for a 3 minutes discussion, followed by a 3-minute group discussion as described in step 1+2. This was repeated until all five phases were discussed in the fishbowl.

Closing the workshop (10-15min)

At this point, all participants had taken part in preparing and planning a group retro. They had prepared, planned and facilitated at least one activity, as well as being participant in a few other activities. This accomplishes the goals of the workshop. We ended the session with a classic check-out activity, where everybody stands in a circle and one by one taking a step back to check out, by answering these questions.

  • What was the greatest insight, that you will bring “home”?
  • If we were to have another retrospective workshop, what should it contain?

After this session participants were encouraged to leave their feedback on the feedback wall.

Reflection: This checkout, had more purposes. One was to guide participants to zoom in on one thing that they would try out in their next retrospective. The other was to gain some feedback on what was lacking in this workshop, which could be the potential subject of a new workshop.

Besides the fact that the group showed their fatigued about this check-out activity (since it has been used in this group a lot) it worked as intended.

 Some of the valuable feedback statements I received from the checkout as well as feedback wall was:
“It was great practicing retrospectives. I would love another workshop, with the same structure- and then I’ll just choose another phase to facilitate.”
“I have looked at this activity before, but never had the guts to try it. Now I tried it myself, as participant, so now I want to go home and try facilitating it.”
“Program was a little bit compressed in the beginning.”
“Lovely, with so much practice and feedback in a safe environment.”
“Lots of stuff to reflect on, lots of learning and inspiration.”

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s