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Raising a Teenager: retrospectives

This article is part of a series about how we tried to help our teenage son through his secondary school career, using techniques and practices from the workplace. For an overview of all articles, a good place to start is the introduction (introduction to this article series), where I set the scene and at links to all subsequent articles.

This specific episode is about retrospectives.

How the story unfolded

A school year typically evolves in a fixed cadence, consisting of a holiday, a couple of weeks in school that ends up in an assessment during a series of exams, to roll up into the next holiday. This year, we decided to try and make some agreements on a few key elements we thought we could expect. And then, aligned with the closing of each cycle, we sat down and took some focussed time together with our son to review how things had gone and where we could improve. We approached this with the format of a true retrospective.

To facilitate the event, I had taken the time to document the agreements we had made and put them on sticky notes, as you can see here:


In a first round, we invited our son to categorise each agreement (the blue cards) across 3 categories: went really well | room for improvement | sheer disaster. That only took one or two minutes. After that, we created room for discussion, guided by the simple question: why did you put that card in that category. We made sure to let him do the talking. No judgement, just listening to his take on the situation.

In the next round, we asked him to rearrange the cards to the category he thought they should be in by the end of the next cycle. He spontaneously decided that most of the cards in room for improvement and sheer disaster should move towards went really well. Interestingly enough, he also thought that one of the cards didn’t make any sense. Which was a great piece of feedback as well.

After that second round, we took the time to discuss what he thought was necessary to make the improvement happen. From that input, we defined a couple of focus areas / activities and documented them. Those are the yellow cards in the picture.

Some lessons we learnt

Having a structured format to run a retrospective really created focus for the discussion. Ranking the cards was a very easy exercise for our son to do and it really gave him the feeling that he could own his input, without being manipulated in any direction.

Similarly, letting him decide where he genuinely wanted to be by the end of the next cycle also contributed to a positive vibe in the conversation. I believe it is incredibly important that we very consciously did not interfere in any way with his judgment at that stage. We just observed what he was doing and encouraged him to place the cards as he believed they should eventually land. Creating that safe space is what actually helped him to share his honest thoughts and feelings.

In the discussion stage at the end, we also noticed that it became easy to discuss everything that was on the board (or actually the cupboard in this case). Each card was a placeholder for a short and targeted conversation, which went really smooth.

Taking notes and jotting down the action items we agreed upon also proved a very valuable asset in the process. At the end of our retrospective, we had succeeded in evaluating the past cycle, defined the desired state by the end of the next cycle and documented action points to take with us along the way. And we didn’t even have to right meeting notes; just moving the cards up against the wall in our son’s room was all we needed to do to create a lasting reminder.

Nothing but good news! However, a retrospective is a key ceremony in becoming a (continuously) learning team. But it does not stand on its own: while it’s great to define improvement steps, you also need to make sure they are implemented. I’ll gladly dive into that topic in a later episode.

How this relates to the workplace

Retrospectives are (or should be) more and more a commonly adopted practice in the workplace. Taking the time to reflect on what your team has been up to, how it is doing things and what could improved is a cornerstone of continuous improvement. Scrum teams usually have a sprint retro at the end of each sprint. IT Service Teams may have a post incident review process in place to learn from something that went wrong. And team leads may have regular check-ins with their team members on performance, growth and wellbeing every now and then.

Obviously, running a retrospective with a team is more complex and takes more time than doing so as two parents with their son. Having more people at the table requires more time and moderation. From that perspective, Atlassian’s Retrospective Play from the Team Playbook may be a very helpful guide to get you started.

From personal experience, taking a step-by-step approach to a retrospective works best: gather input first, give people time to write down their input, collect and clarify the information and discuss actions at the end. Appreciate every piece of feedback and keep an open, positive attitude. If you want to participate fully in the discussion with your team or may be touching more delicate conversations, don’t be afraid to bring in an external facilitator.

If you run retrospectives regularly, changing the format every now and then may spark creativity. A simple online search on retrospective formats will quickly showcase tons of different approaches. We have experimented in the past with formats like these:

  • Mad | Sad | Glad: very much a variation on the format we used with our son. It is very clear for team members to understand and relate to their gut feeling about the way things are going. At the same time, it has a minor risk of thriving primarily on those emotions;

  • Start | Stop | Continue: less emotionally charged and putting a bit more focus on tasks, processes and practices. Depending on the audience, it sometimes makes people forget there may also be things that can be improved;

  • Sailboat retro: if you have some drawing skills, this one is nice to impress your audience. The canvas you draw exists of a sailboat (with sails and anchor(s)), an island, some rocks and clouds. The island represents the team goals and vision. The clouds and wind are everything that is helping the team move forward, whereas the anchors are everything that slows them down. The rocks represents risks they need to overcome to reach the island goals.

Just a small tip: whatever format you choose, be sure to always include the positive things as well. What went well and what you are proud of is just as much a lesson learned as something that went wrong!

Just like in the exercise we did with our son, doing retrospectives is a very valuable team practice. But many organisations do struggle with doing this effectively. In its essence, it is a meeting that you have (regularly) with your team, so it takes time out of your day. Moderating it effectively can be challenging, as well as getting everyone involved equally. Defining actions supported by the whole team is not easy. And one we see very often: actually implementing what you came up with during a retro is a potential adventure in itself.

Wrapping up, in an attempt to turn this article into a bit of interaction: if you are willing to, a very friendly invite to share some of your major successes and failures in the following areas:

  • How regular do you have a retrospective with your team(s)? What form does that usually take?

  • What other practice(s) do you use to assess and improve the way you work together on a regular basis?

  • How do you effectively manage to implement improvement actions (from retrospectives) with your team?

  • Have you tried running a retrospective at home at some point? How did that turn out?


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Those new to the Atlassian Community have posted less than three times. Give them a warm welcome!
June 12, 2023

A Story read in newspaper long back goes like this.

A family of 4 lived in a modern town. The family consisted of Mother, Father and 2 Childrens. Every month they will sit together and decide on monthly expenditures. This schedule was running from years and years. Once the children got new project and field excursions. The father refused children to go on field trips and explained that this month they are short on money and children were supportive for a day and then they couldn't hold they emotions and complained to father that they know he had money, and they want it. Father told come tomorrow and get it. Mother was aware of this situation and asked her husband from where he will arrange the money. Father smiled and told  please join me for a below experiment.


Father next day gave the accounts book and money to children and told them to figure out the money and use it if anything is left. The Mother also joined children to help in account. she brought the bills which were important to pay and they started making all list of task and job where money was spent for this month. the activity ran for 3 days and they had detailed plan where money will be spent and then father approached on 4th day to take charge of account and children had learned their lesson that before you spend money you need to keep account of it.


after reading child and father story i remembered the above story and if they had Team poster or work board i would have been easier for them to teach the lesson.

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Collista Lewingdon
Community Leader
Community Leader
Community Leaders are connectors, ambassadors, and mentors. On the online community, they serve as thought leaders, product experts, and moderators.
August 2, 2023

I like to see other people teaching their teenagers to look at their lives from another viewpoint other than as a child. I think far too many parents don't teach them to think of their lives as adults and all that does is hinder their abilities as adults. 

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