Icebreakers: An Easy Applicable Way for Engaging Sprint Retrospectives

Setting the stage for an inspiring and valuable exchange

In my first job at a start-up, I despised our retrospectives. I was not the only one, as I could feel the low energy in the room. Then one day, one of our most experienced team members, a UX designer, took a stand and said, “Today, I’m running this retrospective. I’m tired of this bad mood. I’ve got something for you guys. Just bear with me, and we will never be the same again.” I was curious, and everyone opened up to this approach.

How did we end up in this situation?

I was exhausted. I had never worked this hard in my life. I had suspected that working for startups was demanding, but this wasn’t what I expected. I doubted myself; I felt like I wasn’t ready for the job. Sprint after Sprint, we had to figure out how to change the game and find our space in the market. The truth is, we were failing and only hitting the wall. I was panicking and had no idea how to turn the ship around.

Too often, our Sprint Reviews were disastrous; we had nothing beyond features to show. We were missing the point, and as a Product Manager, I took that upon myself. I remember my mood was always down after such harsh reviews. I couldn’t contribute to an effective Sprint Retrospective. The rest of the team felt no different than me, and our retrospectives became anything but helpful. We would walk into the room with low energy and leave it feeling worse, hopeless. Each retrospective paved a tragic fate for our next Sprint. 

We were drowning and didn’t know how to save ourselves.

Reflecting on this experience, I feel embarrassed; everything seems so obvious and straightforward. We were a small company with the right ingredients to create valuable products. Top management empowered and trusted us, but something didn’t click, and we trapped ourselves. We could no longer afford our mediocrity; we had to become a self-managing team.

“Retrospectives can make your organization faster, more efficient and innovative.” - Ben Linders, Getting Value out of Agile Retrospectives — A Toolbox of Retrospective Exercises

Let me share what I learned from the power of icebreakers and how engaging retrospectives can transform an ordinary team into an outstanding one. I hope this story inspires you and you can apply my learnings to your scenario.

‍Mechanical Retrospectives Sucks

Before I continue the story of how our UX Designer transformed our team by bringing a new element to our retrospectives, I need to share how we used to run these events. Don’t be surprised; we sucked.

Nobody in our team was experienced with Scrum, though we believed we knew it all. Overconfidence got in the way of us growing as a team. We perceived Scrum as roles, events, and artifacts. We ignored the core of it—empiricism. We rarely utilized our learnings to adapt our actions. With Sprint Retrospectives, it wasn’t any different. Most sessions were mechanical.

We knew some of the common variants of Sprint Retrospectives, and we would use one of them every single session. Apart from that, hardly anyone started the session in a sociable mood. As I said, our Sprint Reviews tended to be harsh, and having the Sprint Retrospective right after them was something everybody disliked. Our sessions were predictable and boring. Let me give you an example:

1. The Scrum Master would prepare the whiteboard with the chosen dynamic. We varied between a sailboat, the four Ls (liked, learned, lacked, longed for), or drop, add, keep, improve.
2. The Scrum Master welcomed everyone and explained the format, which everyone was already tired of.
3. The team would take five minutes to write down what they wanted to share.
4. One by one, they would present, while the rest pretended to pay attention but still had the previous review on the back of their minds.
5. After everyone presented, we’d do a dot voting to decide what to discuss further and create action items.
6. We’d discuss two or three items and agree on actions.
7. The Sprint Retrospective would end, and nobody would care about the agreed actions.

We might have been physically present in the retrospectives, but our minds were not there. 

Looking back, it’s evident why we hated Sprint Retrospectives. But back then, it wasn’t clear to anyone. The Scrum Master failed to help the team members arrive at the session and be fully present. After each Sprint Review, I, as Product Manager, had the next Sprint in mind; developers wanted to avoid the harsh feedback received, and none of us believed the Sprint Retrospective would help us anyhow. The Scrum Master was the only one interested in the retrospective, but lacked the skills to get us engaged.

“Before starting a retrospective, you need to think about which exercises would be most suitable. - Ben Linders, Getting Value out of Agile Retrospectives — A Toolbox of Retrospective Exercises

Icebreakers 

Now let’s circle back to the beginning of this story. Our UX designer had an as up his sleeve. It might sound odd to you, but he said, “We’re going to have some fun in this retrospective. And that’s how we will allow ourselves to be here.” That was my introduction to icebreakers in Sprint Retrospectives. 

I must say, I felt icebreakers were pointless. I thought, “Seriously? We’ve just screwed up one more Sprint, and our solution is to have some fun in our Sprint Retrospectives?” However, I kept my mind open. I thought we had nothing to lose and perhaps there was something to gain.

Our UX Designer went to the whiteboard and wrote, “Draw a picture representing the last Sprint for you. You’ve got five minutes.” Everyone went to the whiteboard; it was fun, and Even though I don’t recall all of the pictures, some of them were:

• An airplane flying low towards high mountains
• A team building a house, bricks falling on their heads
• A scared octopus with more things to handle than tentacles

Everyone shared why they saw the Sprint that way. It took 15 minutes; after that, we understood what was on everyone’s minds. We put our frustrations into pictures, openly explained them to everyone, and carefully listened to each other. We arrived at the session and were ready to talk about becoming a better team.

That session marked a big shift for us. It might seem an exaggeration to you, but even today, I have goosebumps when I remember looking at the whiteboard and feeling the frustration each one of us shared. I didn’t want to be in that situation any longer, and everyone else felt the same. 

“We need to uncover better ways to improve and retrospectives can provide the solution.” - Ben Linders, Getting Value out of Agile Retrospectives — A Toolbox of Retrospective Exercises

After the icebreaker, the UX designer asked, “How might we have a better Sprint next time?” This question brightened up the room. Everyone took some time to write down their ideas, then we shared, challenged each other, and agreed on actions. But this time was different; we wanted to change. We didn’t only agree—we committed to each other.

Sprint after Sprint, we could improve as a team. We finally got back on track, and I believe that small icebreaker removed the stone inside our shoes that discouraged us from moving forward.

Why Are Icebreakers So Important?

Before using icebreakers, our Sprint Retrospectives were the last place we wanted to be. Our minds were not there, and we nearly died of boredom. Looking back, it’s easy to downplay the importance of icebreakers due to their simplicity, and that’s precisely what makes them powerful. They do a crucial job of enabling us to benefit from retrospectives. They help team members be mentally present in the session.

Now, let’s analyze how icebreakers support teams in achieving the goal of Sprint Retrospectives. Let’s take a quick look at the Sprint Guide to understand the purpose of retrospectives:

“The purpose of the Sprint Retrospective is to plan ways to increase quality and effectiveness.”

We must be honest with ourselves. We can only find better ways of working when we step back from our work and have an outsider’s perspective. And that’s hard. We won’t easily manage to have an outsider perspective right after the Sprint Review; no matter how the session unfolds, our mind will push us to get hands-on instead of stepping back and reflecting. Icebreakers come in handy; they create the state of mind we need to open up for the Sprint Retrospective and be mentally there instead of elsewhere.

Is it that simple? Teams start using icebreakers, and their sessions will be excellent. Can that be? Yes, but not that fast. Our brain is tricky, once we get used to something, the magic is gone, and we lose interest. That’s the challenge with icebreakers: you can’t only have a couple of variants, alternate them, and expect to get the job done. 

You must surprise the team and get their attention. Otherwise, the sessions will once again become mechanical.

You may disagree with me and think that a set of five different fun icebreaker games are enough. Logically it makes sense: five variants would ensure that nothing is repeated in at least two and half months. But you can’t ignore how smart our brain is. Once the pattern is identified, the magic is gone, and the energy of your Sprint Retrospectives slowly goes down. I assume that’s not what you want.

Building an Icebreaker Library

More than a decade ago, I had my first contact with Scrum, or at least I thought so. Since then, many things have happened. I’ve been part of dozens of Scrum teams, and they all worked differently. One thing I learned during this time is the power of retrospectives. Several times I felt like we were screwed and would never manage to overcome our challenges, only to learn that putting intelligent brains in the same room with the right mindset was the solution to our problems. Great Sprint Retrospectives can transform teams.

I admire the work of good Scrum Masters; they continuously sharpen their toolbox. They strive to uncover different ways of helping teams grow, and it’s not only about doing Scrum better—it’s about becoming a better team. One of the main keys to this is building a solid library for icebreakers. Good Scrum Masters know the importance of starting the Sprint Retrospective right; the whole session will be wasted if that fails.

“The goal of retrospectives is [to] help teams to continuously improve their way of working.” - Ben Linders, Getting Value out of Agile Retrospectives — A Toolbox of Retrospective Exercises

You might be wondering, how many variants of icebreakers should I have? I can’t give you a precise answer, but after exchanging with highly experienced Scrum Masters, I learned they have dozens, if not hundreds, of variants. However, that’s not the main point. The secret is that they continuously evaluate what the team needs and never call their toolbox ‘full’. They use Scrum principles to keep the toolbox updated and relevant. They remove outdated icebreakers, add new ones. They inspect and adapt.

I’d suggest you start building your own library. My secret is learning from market references; I recommend that you follow Chris Stone, Mark Metze, Willem-Jan, and Sjoerd Nijland. You can benefit a lot from them. Now, let me share with you some icebreakers I like to use:

• Song: Which song best represents the last Sprint and why?
• Superhero: Which superhero would the last Sprint be and why?
• Nemesis: Who is our nemesis and why?
• Three words: Which three words best describe the team and why?
• Weather report: What kind of weather would represent the last Sprint and why?
• Personal objectives: Pick something in your office and share the story behind it. 
• Two truths and a lie: Everyone shares two truths and one lie. The others need to guess what’s the lie.
• Emoji faces: Everyone picks one emoji, and the team needs to imitate that. 
• Happiness thermometer: Everyone shares their happiness level within the team’s current state and explains why they feel that way.

You will find many other variants on the internet. Be creative and try things out. Don’t limit your toolbox; learn how to surprise the team, and you can be astonished by how fast the team can grow. 

Final Thoughts

I used to hate Sprint Retrospectives; I used to perceive them as a waste of time. I didn’t understand why we had to go to a room and share what worked well, what didn’t, and the opportunities and risks we saw. For me, it sounded like a lot of blah blah blah, and nothing worthwhile came out of it. With time, I realized that I hated bad Sprint Retrospectives and had not experienced any good ones.

I won’t lie to you. It’s hard to design and facilitate retrospectives that result in actions to help the team grow. However, when one masters this skill, and it’s invaluable to any team. When done right, Sprint Retrospective can transform teams.

“Individually, we are one drop. Together we are an ocean.” — Ryūnosuke Akutagawa