I saw an interesting heuristic regarding habits recently but I couldn’t find the source anymore. Bear with me while I paraphrase a bit.

If you want to build a habit, never skip it twice. Skipping your workout once is okay, we’re all human, we all have changing priorities or just shitty days. Skipping it twice is potentially problematic, as it might be the start of a new habit you’re building.

In essence, breaking your planned habit could be considered “a mistake.” So one could rephrase the original idea as “Never make the same mistake twice, lest it becomes a habit“. To me, that looks like a great filter for retrospection. Let me explain.

You made a mistake?

That’s fine. Everybody does. It probably impacted other people in the team so check for potential fallout damage. Learn from it; don’t repeat it again. If it’s something worth sharing, share it with the whole team so they can learn from it in their own time. 

You made the same mistake again?

Hmm, time to take a step back. What learning did you miss the first time that could have prevented you from making it again? Is there a bigger systemic issue that needs to be tackled? Now is a good time to bring it up with the team and talk about it. Others might see something you missed the first time.

The retrospective meeting

Discussing a problem with the entire team right when it occurs might be difficult when a team is working async or when certain team members are only available part-time. In this instance, it makes sense to reserve dedicated time to talk about the bigger issues, the things that happened more than once.

Notice how I deliberately left out the mistakes that were made only once? These are often flukes, small individual slips. They don’t require the entire team talking about it. If you want to build a team with high psychological safety, you need to leave room for error and personal learning without the entire team jumping on the problem and talking about it. Sharing what you learned and helping others afterwards is fine, but there’s no need to repeat it in a dedicated meeting.

Many prescribed retrospective formats seem to be tailor-made to identify these individual one-off mistakes. If everyone individually writes the good and the bad on some post-its, people are going to magnify their personal mistakes. Even worse, we’re going to talk about it with the entire group. We should instead encourage teams to focus on learning from mistakes every minute of every day and spend our dedicated retrospective time on things that keep happening, things that might look like they are outside of our control. Then, we collectively figure out how we can bring things under control and prevent recurring issues from popping up.

Represent the last week as a type of dinosaur

This is something I tried recently and it was completely awesome. There was someone who was feeling great and energetic and identified a T-Rex. There was a Pterodactyl for the person who had a hectic week, flying all over the place. You get the idea.

My 8-year-old and my 6-year-old really loved it and we might do it again in the near future. We didn’t solve any specific problems, but they learned to talk about their feelings using a cool and creative structure.

Luckily, at work, we’re all adults. We know when something’s not going well and we can probably pinpoint the underlying reason when it is work related. There’s no need for coloring contests or Dinosaur Driven Development. When you hold a retrospective with adults, have an adult conversation that focuses on the recurring, bigger issues and results in tangible outcomes such as experiments to try and solve these issues.

Read more about guiding teams towards a better way of working or take a look at some of the startups and scale-ups we’ve helped recently