How to conduct a retrospective

Semyon Kolosov
6 min readOct 11, 2023

A retrospective is one of the regular meetings for teams that work on Scrum. We can say that retrospective is called retrospective reflection in Scrum. Since the purpose of the retrospective is to analyze and discuss the work done in order to improve the results in the future. Before working at red_mad_robot, I never consciously conducted a retrospective. On my first project, not everything went smoothly.

Photo by Parabol | The Agile Meeting Toolbox on Unsplash

After its completion, we gathered with the team for a retrospective. I knew there was such a ritual, but I didn’t take it seriously. All such experience of such meetings for me has always been associated with negativity. At previous jobs at the end of the project, we usually looked for the guilty ones or sighed how bad everything was.

In red_mad_robot, everything was different. The team and I marked what went well, what problems there were and their causes, what we learned during the project, and what we will do differently in the next project to avoid problems and improve the process. No blame, no negativity and finger-pointing. Then I found out what a team is that wants to grow. Instead of stating the facts, we analyzed the situation and drew conclusions. This is a correct and conscious process of learning from mistakes and squeezing out experience.

If you don’t do a retrospective, then you get little value from the experience. The longer you ignore retrospect, the longer you burn through resources on experience without benefit.

“You can learn from both successes and failures, and make the good even better. This is comparable to evolution: what did not work, dies out, but everything that contributes to the conservation of species remains and develops. In the end, each of these adaptations is nothing more than an experiment, because the result is never exactly known. In the optimal case, experiments lead to an improvement in the situation. But sometimes they only aggravate it, and it needs to be analyzed in the next retrospective”

Mark Knopfler

Therefore, it is very important to organize the process of retrospection in life in order to complicate the life of the autopilot of the brain. Sometimes we don’t know why we do certain actions or experience certain feelings. Conclusions are the product of logical and critical thinking. A retrospective is a tool to start the right thinking. People who know how to draw conclusions from mistakes and successes will always improve themselves regularly.

When people talk about mistakes, everything seems simple. Most will say that they draw conclusions from mistakes, but then we see how they find themselves in the same situation again. Falling into a trap is not scary and even sometimes useful, but it is impossible to fall into the same trap over and over again. Every time you do a retrospective, you build a new route past the old traps and can go further.

How to conduct a retrospective

Flexible project management methodologies are rushing to the rescue. In Scrum, after the end of the iteration of work on the project, a retrospective is held in order to develop solutions to improve teamwork and processes. Such a meeting is held every 2–4 weeks, depending on the length of the iteration. In the IT field, a more or less standard template is used for a retrospective. The team takes a board, a flipchart or an online service. Then they consistently attach the stickers into columns:

● “What was good?”

● “What went wrong (problems)?”

● “What are the ideas to improve and avoid problems in the future?”

● “What set of cases is being taken into work?”

This is a familiar, open and positive process that allows for systematic reflection in the team to find out the mood and working condition of each team member, as well as to identify weaknesses in the workflow and communication. It is assumed that everyone is familiar with the rules of retrospective, and they are respected. The meeting takes place in a safe environment.

No one beats each other for criticism, makes no excuses and does not point fingers. In life and at work, it’s the same process for me. I use a working approach from Scrum for any purpose, but if you are just starting to practice retrospective for yourself, then I suggest using a more creative and empathic approach. It was invented by the already well-known thought optimizer Edward de Bono. The approach is called the “Six-hat Method”. It is designed for brainstorming, to consider ideas or problems from different angles.

A person should try on six hats in a row and look at the situation through the prism of each hat. A certain color of the hat means a separate mode of thinking, which allows you to form a holistic opinion about the situation. This organization of thinking greatly helps a retrospective. The approach can be used when conducting a retrospective for personal or team purposes. There is no need to buy six multi-colored hats. It is enough to draw 6 columns, where each corresponds to each hat. Each hat is responsible for its own prism of thinking. You only need to write down your thoughts under each of the hats.

● The blue hat is responsible for management and organization. In this column, you need to write down the goals of the retrospective and summarize the results at the end. If the retrospective is done by a team, then in this role you need to explain the rules and goals to everyone.

● The white hat is responsible for data and facts. In this column, you need to write down all the positive and negative facts about the situation without emotions. You can also write down what information is missing, and you need to look for it additionally.;

● The red hat is responsible for intuition and feelings. In this column we write down positive and negative feelings about the situation. Here you need to give free rein to your feelings and write everything down as it is. It is very important to understand your own or team’s emotional background. This way you will be able to decompose what caused you to experience specific feelings;

● The black hat is responsible for critical judgments. In this column we write constructive criticism and the whole truth. We do not lie to ourselves, we do not defend, we write as is, the reasons why everything is exactly the way it is, and not otherwise;

● The yellow hat is responsible for optimism. In this column we write down all the good and positive things that happened. A yellow hat is like a painkiller after a black one. The goal is not to justify criticism, but to notice the positive sides and results of the situation;

● The green hat is responsible for creativity. By this point, we already have the facts, emotions, pros and cons of the situation. In this column, you need to write down ideas and solutions on how to avoid all the disadvantages and negative emotions in the future. Here you need to be creative to write down all the ideas, even the super-creative ones. You will select them later in the list of changes and tasks.

Based on the results of the retrospective, you will have an improvement plan for the next iteration of actions. Then you go back to the business planning stage again. Take ideas and transfer them into a set of tasks. Thus, you will already do the next iteration a little differently. And hence, get different results.

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Semyon Kolosov

I'm a book author, сonsultant and mentor for entrepreneurs and managers. I write about management for life and work.