How to Master the Retrospective Meeting While Working Remotely

Stuck in a retro rut? Even in the best of times, running a well-planned, productive, and energetic retrospective meeting isn’t easy. Sketch Agile Coach Steph Weisenbach provides her insights about keeping the team engaged and accountable in a 100% virtual environment.Pre-COVID, there was no substitute for hands-on, interactive team meetings—agile retrospective meetings included. I admit, there’s nothing quite like collecting our thoughts on a project that’s already on its feet…especially when the meeting includes good snacks, a couple of anecdotes, and a great sense of humor. Those “retros” are hard work, but they can also be freeing and fun if you handle them correctly.

I realized quickly into the pandemic that we were going to have to get creative and turn our expectations upside down. Nothing in our careers has changed our workplace as dramatically and quickly as COVID. The world we’re all working in just became a whole lot more virtual, but that doesn’t mean you have to abandon your goals and passions for relentless improvement.

When you use the right tools in the right way, your retrospectives don’t have to become frustrating and impersonal. Virtual tools and effective meeting planning keep the team engaged and focused on organizational and personal progress.

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What is the Purpose of a Retrospective Meeting?

This section may be a bit “back to basics” for some of you, but in our world, I find there are a lot of misinterpretations of what should take place in an agile retrospective meeting. (Just humor me while I put my coaching hat on for a minute.)

So, let’s review the purpose of a retro. We use retrospective meetings as dedicated time we’ve set aside as an organization or as a team to stop, focus, and discover areas and opportunities for improvement. If we don’t proactively structure this time, we will never unearth all the ways we can get better, and then the process just simply stagnates.

I’m not talking about the product – there are opportunities to inspect and adapt the product too (I’m looking at you, sprint review). I’m talking about unearthing how we work together and how satisfying the work is individually. Retros are prioritized, qualified time to examine and analyze not just quantitative data and metrics, but also qualitative data, like how we feel things are going.

Yes, feelings. Feelings matter, and so does everyone’s opportunity to articulate what we like, what we don’t like, and where we see things heading, especially if it’s not in a direction that looks healthy and satisfying for everyone in the room.

How to Keep the Retrospective Meeting Engaging and Fun

What with the disruption of life as we knew it, maybe now is the best time to examine every step of what you were doing and look at it in an entirely different way. Why not? It may not feel revolutionary or even that creative to start with something as basic as how you run a meeting, but I say: Lean into the chaos a little bit. With everything upended, you could find new and exciting ways of bringing out the best of your team by shaking things up a little.

Walk away from the generic format of: What went well, what didn’t, and what we want to change. Keep it interesting! Explore tools and exercises that disrupt everyone’s expectations a little, increase the fun and the engagement a lot, and free up intuition and creativity.

Retro Virtual Meeting Tools

Feeling just so-so about your retros? You should be forgiven if the stress of the current moment has overwhelmed you and your group. Everyone needs a spark of creativity every now and again, and for that, I put together a short list of tools to mix it up a little.

Check out these examples below and bring some energy and life back to your retros.

This site lists a bunch of free activities to facilitate a number of goals, including generating insights, gathering data, and implementing the next step in your iteration.


Who doesn’t love a game? This dynamic index of agile games provides new and flexible (and hopefully fun) structures to your meetings.


Take a tour through this list of data-gathering activities to recharge retros from the stale—and expected—format.

The Key Ingredients for Any Retrospective Meeting

No matter how you decide to structure your retro, there is still a general flow that you need to follow.

According to one of my bibles, “Agile Retrospectives: Making Good Teams Great” (Esther Derby and Diana Larsen), these are the foundational steps of a well-run retrospective meeting:

  • Set the Stage: Set it up the minute everyone sits down. Remind them why you’re all here and what specific time period or project you are reflecting on.
  • Gather Data: Download and digest the available quantitative and qualitative data.
  • Generate Insights: This is where you encourage your team to react to that data, and ask the question, “What does this data mean to us?”
  • Decide What To Do: Determine action steps and solutions to take based on the feedback you gathered during the meeting.
  • Close: Conclude the retro with actionable steps, assignments, and goals. Define what happens as soon as the meeting ends, and calendar follow ups on those determined and defined actions.


Bringing Those Ingredients into the Virtual World

Even in the best of times, running a well-planned, productive, and energetic retrospective meeting isn’t easy. A virtual retro is even harder.

How does everyone avoid distractions, like actual live children doing classwork (or even more distracting things) in the same room? How do you prevent multitasking as a virtual participant? How do you keep everyone as glued to the virtual meeting as you did when you could actually all sit in the same conference room together (and when those distractions were outside of a very real, non-virtual, door)?

Then there are the limitations inherent in virtual meetings: Slow connections, terrible lighting, and stuttering video feeds. How can you read facial or body language if the screen freezes up or when someone’s audio drops?

The best you can do is establish working agreements and protocols for all of your virtual meetings. If everyone feels heard before they dial in, the more likely they’ll feel included and focused.

These are tips I use myself with my own teams, and by making little tweaks, it helps everyone feel more connected and engaged.

Tips for virtual teams:

  • Run Video All Day: It sounds counterintuitive but open up a video conference call with your team and leave it on throughout the day. It does take some getting used to, but eventually it starts to feel like everyone is sitting in the same (virtual) room together.
  • Set Up Group Chats: That is, group chats that everyone is always in. (Think Slack, for example.) Ongoing conversation, even virtually, can be valuable.
  • Team Building: Schedule online happy hours and blocks of time where you and the team can talk about yourselves and your lives. Don’t use those as blocks of time to discuss work. Use the time to talk about how you’re all discovering the joys of baking COVID bread, or to compare beard lengths. Life is hard. Use your company time to let everyone unwind, vent, and feel human.

Best Online Tools for Virtual Collaborations

You’ve probably heard of most of these already and might in fact be using them. But if you are unsatisfied with your current collaboration tools, this list of free online tools might help you find something that works better for your team.


A free and easy-to-use online meeting tool for brainstorming ideas, voting, managing a meeting agenda, and discussing one idea at a time using a timer.


Free virtual sticky note downloads.


Free Kanban board that’s flexible for project and meeting management.

Poll Everywhere

Free polling site to give everyone an opportunity to use their voice.

Zoom or Skype

Two ubiquitous online conferencing tools that you’ve probably already heard of. But they’re easy to use, reasonably secure and private, the recording and sharing features are getting more robust all the time, and most of the team probably already has them installed.

Miro and Limnu

Two of our favorite virtual whiteboard apps.


Collaboration boards to help visual organization and workspace planning.

Stay Flexible and Open!

There’s no set way to reinvent your organization when you have to make a shift as sudden as this one. The two best verbs we all have right now are: Listen and breathe. As long as you are focusing on incremental ways to improve and remove virtual barriers to success, you’ll find new ways to adapt and remain successful.

When you open the process to experimentation, the ideas will keep coming. Eventually, you will find your way to something that works. With time, patience, humor, and even more patience, this new normal will feel a lot less new and a whole lot more normal.

Ready to learn more about how to craft more valuable retros? In our upcoming webinar, Sketch Coach James Nippert trains Scrum Masters and product leaders on how to mix up your retros and change them from meetings the team dreads into events they show up to early. Register below!

Webinar: Crafting Retros Your Team Can't Wait To Attend 

Tag(s): Agile

Steph Weisenbach

Steph has served teams in a variety of roles but the journey all started with accidentally becoming a Scrum Master. Learning the SM role was just the beginning of sparking a passion for finding a better way of working and bringing joy into the workplace.

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