Planning effective retros

Felipe Carvalho
8 min readDec 26, 2021
Photo by Tim Marshall on Unsplash

Retrospectives can be a great tool for evolving teams. If used for having conversations that matter, in an engaging and time effective way, teams usually come out of it feeling happier, energised and more cohesive.

Quite often I face teams that disagree about the effectiveness of retros. When asked why, the reasons are usually similar: they consider it to be a ceremony where they get into a room to talk about things they already know, seldom get to actionable conclusions and time just drags. Many of those teams either do it for the sake of saying they “do Scrum” or remove it from their process altogether.

Back in 2013 I attended a workshop hosted by Paulo Caroli, where I learned his way of doing retrospectives in a fun and engaging way. Surprisingly enough, he calls his method Fun Retrospectives. Ever since that workshop, I’ve been having fun and facilitating retros using his 7 steps, and in this small series of 2 posts I’ll try to pass on to you how to make people go out of a room saying “this is the best retro I’ve ever had!”.

Short summary: preparation is key!

Fun retrospectives crash course: the 7 steps

For the sake of your time, I don’t intend to get too deep on the reasoning behind each step. Paulo does it much better than me and you can check out his book about fun retrospectives. Instead, I’ll give a quick tour on my own thoughts about the method.

Getting to the point, Caroli proposes to break a retrospective into 7 parts:

1. Setting the context: the first step to make any meeting effective and worth its time is clearly setting its context.

Have you ever received an invite to a meeting that simply says “Team Meeting”, a day, a time and nothing else? No description, no notes, no nothing? I have. And usually what happens to me is that I spend the first few minutes trying to understand what that meeting is really about. I see people talking about different things and my mind is going nuts, trying to understand how those things connect and how can I contribute to that discussion. When I finally understand what that session is about, at least 10 minutes have already passed and I barely had time to prepare any thoughts or notes in advance, I have to improvise on the fly.

On the other hand, if I know what a given meeting is about, first I can decide if I can actually contribute to that or not, and if I want to attend or not. Second, when the session starts, my mind is already adjusted and focused on the topic at hand, my brain doesn’t get overloaded trying to understand anything on the fly. Time is more effectively used.

And that’s why it’s important to set a context for a retro, so that people can kick it off already reducing the cognitive load on their brains and focusing on information that really matters for that session.

2. Prime directive: simply put, the prime directive is a prepared statement that we read in the beginning of a retro to remind people that we're humans and to put everyone in a collaborative mood. Sounds not so important, right?

Quite the opposite. Even though it’s a very simple step, it’s super important and I strongly recommend always doing it. And then if conversations derail for whatever reason, you can always come back to it and say “hey, let’s not be judgemental, we’re all trying to do our best”.

3. Energizer: it’s an optional activity, but I’d suggest aiming at always doing it. Why?

First, it helps shifting people’s focus from their previous activities to the retro. Especially in remote times, where people can easily hit Alt + Tab and switch to their IDE and finish that quick last piece of code, having something fun that makes them want to stay focused on the meeting at hand usually results in more meaningful discussions.

Also, it generates engagement among the team. People usually enjoy having fun and getting to know their team mates better. If we can make people’s lives more fun in 5 minutes, why not doing it? :)

4. Check-in: this activity is another step in the direction of fine tuning focus. I like to use it in connection to the context of the meeting.

For instance, if we want to talk about the last 2 weeks, I usually ask people how they felt about the last 2 weeks, or about the best and worst things that happened over the last 2 weeks. This way they start bringing back to the top of their minds the main events of the last 14 days, instead of retaining only the events of the last 1–2 days.

5. Main course: this is what most people would usually consider the retrospective per se. It’s the brainstorming part, where usually the teams’ brainstormed thoughts are plotted on a quadrant, a hot air balloon, a F-1 race car or something similar. This is a space for teams to diverge and go wild.

6. Filtering: an optional activity, where we converge on the topics that really matter and we want to spend the rest of meeting talking about.

7. Check-out: a closure activity, to cool everyone down and either collect feedback from the team about how it went or end a tense meeting in a positive tone.

Planning a retro

Ok, you know the basics. You know the 7 steps. Now how do we use them and combine them to foster conversations that matter in an engaging and time effective way?

The What

Can a retrospective be as simple as walking into a room with a white board split into 3 columns called Start, Stop & Continue where someone tells you to write whatever you want on stickies? Yes, for sure. Will it the best possible use of everyone’s time? Hm… Not too sure about that.

When I sign up for facilitating a retrospective, the first thing I ask myself is the What. What do we want to talk about? What matters the most now? What is the team struggling with? What was the most important thing that happened recently? What do we want to have as output of this meeting?

Maybe the people are going through a phase of too much conflict and are struggling to become an actual team. Maybe there was an outage recently that caused loss of revenue. Maybe 3 new people joined the team. Maybe all of this happened at the same time and those are examples of topics that should be tackled on a retro.

A retro doesn’t necessarily need to be about the last 2 weeks. It can be focused on a particular topic. It can be used to shake up a team that has been working together for quite some time. It can be about making people feel recognised. It can (and should) be used to make a team great! That’s the true value of retrospectives.

The activities

Once I know what I want to tackle in a retro, then I pick activities for each step that fit that particular goal.

For instance, if half of the team has recently joined, having an energizer where they can share fun facts about each other can be a great way of generating team spirit. Or if you happen to have everyone in the office on that particular day, asking the team to find their pairs can be a great way of generating some laughs.

Once the team is energised and has disconnected from their previous tasks, it’s time to help them surface their initial thoughts.

Let’s say you have the feeling the team is not 100% satisfied with their setup and you want to help them understand where to focus their improvement efforts. A check-in activity like Happiness Radar can be really useful to check on which particular area(s) they want to focus. Or maybe you have the feeling that the level of trust among the team is low and you want to make it bright clear to the whole team that not everyone is feeling safe to share their thoughts. In that case, a Safety Check can be quite handy.

Once everyone’s thoughts are ready to be shared, it’s time for the main course. Now what activity to pick? There are just so many, right? Well, once again, go back to your main goal as a facilitator, go back to the What. Are you at the end of a cycle and you want to extract lessons from that cycle? Maybe a FLAT quadrant can be handy. Maybe you don’t want to talk about the past, but instead you want to prepare for the future, in which case a RAID quadrant can be super helpful. Or maybe you don’t want to have hundreds of post-it’s on the board, you just want to make sure everyone has the space to talk about what matters to each of them. In this case, you don’t need a quadrant, just ask everyone to put up one post-it each and go thru every single one of them with the team. It all depends on what you, as a facilitator, want to help the team uncover.

Next, you need to ask yourself: do you want to filter? If you have a quadrant with hundreds of post-it’s, maybe filtering is necessary, so that you can cover the most important things on the time you have available. On the other hand, if you only have one post-it per person and your idea is giving everyone space to share their thoughts, maybe filtering is not the way to go, as you’d be silencing one or more people along the way.

It all depends on the What.

The time

Now comes the tricky part, one that is not usually mentioned: time management.

Ok, so you’ve picked the funniest energiser ever, a killer check-in, a main course that will make people go wild and unleash their deepest thoughts, and… how much time is left for discussions?

Let’s go back to basics: what’s a retrospective about? First and foremost, it’s about evolving teams, making them stronger. How do we do that? Through conversations.

You might have prepared the best activities ever, but if the team only has 5 minutes for discussions, I’m afraid this is not going to be the best retro ever. For sure it’s going to be fun and engaging, but it’s probably not going to be very effective.

When I prepare retros, I try and maximise the amount of time for discussions. If I have one hour to run a retro, I usually try to spend the following amounts of time in between the explanation of the step, clarification of questions and the actual execution of the step:
- setting the context + prime directive: 2–3 minutes (I try to do both activities in one go, as they're not too complex)
- energiser: 5 minutes
- check-in: 5–10 minutes
- main course: 3–5 minutes
- filtering: 1 minute
- check-out: 5 minutes

If we sum up the time spent on the best scenario, we’d have spent roughly 20 minutes in everything else, leaving 40 minutes for discussions. It’s a great time split, and unfortunately mostly unachievable most of the time, depending on the size of the team, how opinionated they are, where they come from, their cultures, and many other factors.

Many times I’ve seen myself in situations where I picked an energiser that took too long, or a check-in that took 1 minute per person (in a 16 people team), or ran out of time for a check-out, or had people leaving the retro because we were running over time and they had other meetings. I learned the hard way that to make effective retros, as a facilitator I need to keep a close eye on the clock and balance the time we spent on a topic vs how fruitful a discussion is. I can tell you it’s a hard balance, and that’s why I insist that preparation is key for effective retros.

Facilitating an effective retro

Is the topic of the next post :) In a few days I’ll share what I’ve learned about the role of the facilitator and its responsibilities towards effective retros.

See you in a bit!

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