Retrospective Meetings Masterclass

Retrospective Meetings Masterclass
ℹ️ Skip to key parts of the session by clicking on the chapter dots along the timeline.

Charles, Author of Workshop Tactics, explains a bit about the background and value of Retrospective meetings before running a live demo (with Pip Decks community members) of the three retrospective Workshop Tactics cards:

  1. Start, Stop, Continue
  2. Three Little Piggies
  3. Mad, Sad, Glad

You’ll notice that the Chapters of the video line up with the headings of the text below, so you can choose which bits you’d like to watch - or watch the whole thing!

You’ll also get a preview of the Miro (virtual collaboration platform) boards for each tactic, which you can download on each tactic’s webpage, as well as an insight into how you could use Butter (video conferencing/workshopping platform) to help you manage things like timed activities, votes and more.

What is a retrospective meeting?

They originate from the agile development playbook. The purpose comes from the root philosophy of continuous improvement. It helps improve the team and the product/process. They’re pretty informal. You can run them fortnightly to reflect on what went well, what didn’t and what can be improved next time. That’s the core format - the retro cards are just three examples of the thousand options out there. You can even create your own.

Why are retrospective meetings important?

They should be part of your business-as-usual process. If you’re not looking back and critically assessing what has happened, there’s not much chance of improving your team except by chance. This is proactive, intentional improvement. That’s the selling point for having another regular meeting in the diary!

Like running a faster mile or lifting heavier weights, you need to repeat actions and assess the impact of different things you’ve tried. Other benefits include: culture of honesty and transparency, psychological safety (it’s okay to talk about the problems), the team members know they have somewhere to raise this stuff. It’s also a bonding experience.

How to organise your retrospective meeting

Charles top tips for organising successful retrospectives:

  • Timing: weekly is too much and monthly is too little.
  • Priority: give it utmost importance in your diary.
  • Facilitation: get someone experienced with retrospectives and facilitation to run the first few sessions. 

After that, get team members to take it in turns to run these sessions - you’ll get to see the Ikea effect in action! That’s where we value things more if we play a role in their construction. People feel more ownership, involvement and pride in something if they are more than just a passive presence.

It also helps you make the most of the diversity in your team: different ways of thinking, different perspectives and different approaches could all bring something new and valuable.

These sessions can and should be used with any product team or group of people earnestly working together towards a common goal.

Watch this section for a little aside into how individuals, freelancers, couples and parents might also apply this approach...

The three Pip Decks retrospective meeting tactics

Start, Stop, Continue retrospective

Start, Stop, Continue is the bread-and-butter retrospective - the foundational format.

You get everyone together and throw up three columns on a physical or digital board. They use their post-its (also real or digital) to spend five mins each on writing down each of the following:

For the past fortnight:

  1. Everything that you think you should be doing but are not yet doing.
  2. What you have been doing that you should stop doing in future.
  3. All the things you have been doing that you think it’s valuable to continue doing.

The next step is to group similar post-its together (Theme Sort) to see if any themes start to emerge. These categories can take post-its from any of the columns. Then you give everyone three votes each to apply to the topic they think is the most important to discuss. This is best done as a Blind Vote so that more dominant or senior people don’t influence the decisions of others.

Then you have a time-boxed chat about the most popular topic. At the end, you work out if you solved it, or if you need another five minutes. If you’ve solved it, use Who, What, When to create a list of actions and people to carry them out. Then, you can move onto the next item until you’ve got through as many as you can in the time (Charles suggests an hour to an hour and a half). Et voila! You have a list of actions to inform your work for the next fortnight and a checklist to start the next retrospective session with.

This Theme Sort, Blind Vote and discussion approach is outlined in the Democratic Discussion tactic.

Three Little Pigs

Once again, you frame the session as focussing on the past fortnight. Tell a bit of a fairytale! Get people to think about what those Three Little Pigs built:

  • House of straw: what’s failing and won’t support the success of the project?
  • House of sticks: what are you doing that’s a bit ropey and needs to be strengthened?
  • House of brick: what have you done that’s rock solid and creates a good foundation for success?

You can get people to do one post-it per common if you have a lot of people or not much time. Then you do the Theme Sort and Blind Vote and discussion as described above.

This frames the conversation as being more risk-focussed, which leads to slightly different answers to the previous tactic. That’s why it’s great to mix up the different retrospectives instead of running the same one every fortnight.

Mad, Sad, Glad

This is Charles’ favourite of the three tactics! Mad, Sad, Glad is more emotive as it gets to the heart of how your work has made you feel. It can create some quite difficult conversations, too, but that is valuable - those frank and honest conversations help build stronger teams.

Similar to above, everyone writes down one of each of the following:

  • What are you mad about?
  • What are you sad about?
  • What are you glad about?

Ending on ‘Glad’ is a pro tip - it’s always good to end on a high note! Once again, you do the Theme Sort and Blind Vote and discuss the most popular topics.

Watching each of these sessions being demonstrated shows how different answers to each of the sessions can be, even in this fairly artificial situation (where the participants didn’t have a shared project to write about, and they only had 1.5 minutes to answer).

Retro Retro

In this part of the session, Charles asked the Pip Decks community members in attendance to reflect on which ones they preferred and what resonated most.

Sea thinks they are all useful for different purposes: Mad, Sad, Glad is great for exploring how people really feel, especially if they are withholding answers to questions about how the project is going. You can’t escape when someone asks you what makes you Mad!

Michelle thinks that for projects where things aren’t going well, the same tactic includes a positive column that will lead to the good things being discussed when they may otherwise have been overlooked.

John thinks it would be good for team building, while Three Little Pigs feels quite managerial… but then he realised that trying to box each tactic into a context could be counterintuitive. Using them for everyone means people get to think a little bit differently and talk about things in a way they aren’t used to - which is great!

Watch this section for an idea of how to come up with new approaches (goldilocks, rollercoasters and donkeys are included).

And that's a wrap! Thanks for joining Charles and the Pip Decks community for a whistlestop tour of retrospective meetings. Now it's time to put what you've learned to work!


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