At the beginning of 2020, I was commuting after a long day of work. There is nothing better for some thinking time than a ride on a train. I was wondering, how can I make sure I’m blogging more regularly? The idea popped in my mind to do the Retrospective challenge for 2020. The experiment I wanted to try was the following:

If I write a blog post in the form of every retrospective I host, I will prepare them better

Jelle Smeets – January 21, 2020

For this retrospective challenge I set myself 3 ambitious goals:

  • Prepare my retrospectives better
  • Bring my retrospective game to the next level
  • Blog more regularly

In this blog post, we will dive into 2020 with the retrospective challenge. We will take a look at how it went, and what are the lessons I learned.

Lessons learned in the retrospective challenge

At the time no one expected the curveball 2020 threw at us. At the moment of writing this blog post, I am working from home for longer than a year. My employer was one of the first companies to close the office. At that time it was suspected to be nothing more than a 2 to 4 week period. Little did we know.

Lessons learned in the retrospective challenge.
Lessons learned

Personal life

Besides Covid and working from home my personal life had some life-changing events as well. Before Covid happened we started to sell our apartment. For a few months moved in with my in-laws and moved into our new home. Just a week after sharing the original challenge, my father-in-law passed away. My grandfather followed due to Covid a month later. Even if I don’t consider Covid, just in terms of all the personal things that happened 2020 was an intense year. All these events led up to me not getting the full 20+ blogposts I expected at the beginning of the challenge.


The experiment was to see if writing about retrospectives helped me to level up my “retrospective game”. And I can verify that this has helped me tremendously. As a result, the quality of my retrospectives is higher, I experiment more with retrospective forms. In Retrospective ideas, I described my entire process of preparing a retrospective.

I learned that one of my favorite moments is preparing larger department retrospectives. Collaborating with other Scrum Masters. And taking a moment to really prepare a retrospective and customize it to the group/process is awesome. As a result, these retrospectives were usually the place where the best new ideas came from.

A sad thing is that with everyone working from home, is the number of retrospectives I host has dropped dramatically. As a result, retrospectives were hosted online. Where I discovered Retrium, where I host most of my retrospectives. I also wrote a review on Retrium.

In the original challenge, I describe hosting several kinds of retrospectives through the organization. The lockdown has led to me only hosting retrospectives for my own teams, with a very occasional retrospective for someone else.


This challenge was not just to improve my retrospective game. By blogging more I hoped to also develop my skills as a blogger. In my blogging journey of 2020 I learned the following things:

  • I got to use the lessons I learned from stakeholders regarding SEO and Marketing
  • I discovered new tools that can help me with writing better headlines, content and do research.
  • Experimented with several things to make my blog more succesful.

Favorite retrospectives

While I am reading through the list of all retrospectives I posted in the retrospective category, I noticed that my favorite retrospectives have a pattern. My favorite type is the retrospectives that are out of the box, creative, and a little bit of fun. My favorite retrospectives are:


The retrospective challenge of 2020 resulted in me improving the retrospectives I host. By preparing them better and writing blog posts about it. I learned what I like about preparing and hosting retrospectives. As a result, I now can customize my retrospectives better to the team and situation.

In the process, I learned a lot of things about blogging, but I expect to write a blog post about that in the future.

All in all, I would recommend doing the retrospective challenge. It is always good to challenge yourself and learn new things in the process. Is there any way you can challenge yourself?

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