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Fun Retrospectives

One of the most powerful tools I’ve found for building strong teams has been running safe, regular, fun, challenging, personal and focussed retrospectives. Retrospectives are about the way the team is interacting and the way the work is being done, rather than the work itself. They are private, internal, and for the benefit of the team. I’ve already talked about making retrospectives safe and explained why regularity is key.

In this 3rd post about retrospectives, we’re going deep on having fun.

Humans are social animals, even in work. When we allow the focus to be solely about the work we miss the fact that the work is being done by people with lives, feelings, relationships, challenges, characters and perspectives of their own. Deliberately creating space for a team to enjoy each other’s company deepens connections and reminds us that in any system of work with people, processes and tools, it's people that come first.

There are lots of ways of inject fun into a retrospectives. Here are a few that have worked for me and the teams I’ve been part of.

Start with a game

If your retrospective is 90 mins long use the first 30 mins to play a game. It will make the final 60 mins so much more productive and enjoyable. When a member of my team first suggested “playing games” in work time, I had to overcome the lurch towards “What would the rest of the organisation say if they saw us playing games?”. Fortunately I was able to put that to one side and give permission to try it. It was, quite literally, a game changer. The project we were working on was hard and we were facing both internal and external challenges.  In that first 30 minutes the entire mood of the team was lifted, we laughed, we competed, we saw the quirky side, any team tension thoroughly unwrapped leaving just people smiling at each other. It’s a brilliant place to start the hard work of improving a team together. From then on, all our retrospectives started with a game, several other teams tried it and found it had a similar positive impact.

As our retrospectives were lockdown remote we used a number of online games. Here are some of our favourites.

Mix things up by using different retrospective templates

Keeping things fresh maintains the element of surprise. Though there are constants with retrospectives, such as safety and regularity, what you actually do during the time together can vary a great deal. The traditional style Start, Stop, Continue is a great place to start but can get stale quickly 

Bright future retrospective

In the future retrospective the team think about a future point in time, say 4 weeks from now, when they are celebrating a massive improvement in performance, and everything has gone great. From that future perspective the team can then reflect on the things they did to get to the positive outcome. It’s a relatively simple but very effective way of reframing a conversation about the changes the team need to make to improve but from an alternative perspective.

Sailboat retrospective

Time to get the pencils and paper out for this one. Each person draws their own sail boat to represent the team, they then label 4 elements of the picture.

  • The island or shore – The goal that we are heading towards
  • The wind in the sails – The things that are helping the team move forwards
  • The anchor(s) – The thing(s) that is holding the back or slowing them down
  • The rocks – The risks or potential pitfalls of the project

Once the boats have been drawn we look at them one at a time and consider the things that have been raised. It also exposes the real artists and the creative process helps everyone to express issues in new ways.

Other ideas

There are hundreds of really good ideas for running retrospectives all over the web. Check out

About the author

Tom Styles

From over 20 years of crafting digital solutions in both the public and private sectors, Tom has a wealth of experience at delivery and leadership level. Tom’s passion for human-centred innovative use of technology and his ability to communicate with both a technical and business audience help maximise value from technology investments.

Tom blogs about agile, technology, and occasionally DJing or Ultimate Frisbee.