How to Run Remote Retrospectives Successfully

The recent shift to semi or permanent work-from-anywhere has changed the means and frequency of communication. We’re increasingly relying on virtual video and voice conferencing platforms such as Zoom, Google Meet or Skype to run meetings such as a remote retrospective.

A retrospective refers to reflections, capturing the lessons learnt, mistakes made and corrections applied. It is a means for both the team and the manager overseeing their work to see what measures succeeded, failed and what must not be repeated in the future.

In this post, we’ll look at what remote team retrospectives are, and how to run them successfully.

1. What is a Remote Team Retrospective?
What is a remote team retrospective?

In project management, agile retrospectives are meetings that are held at the end of a sprint. It includes teams whose members were working on meeting a specified milestone.

Remotely, such meets are known as remote team retrospectives. It’s a digital version that is conducted over virtual conferencing tools. Everyone in attendance gets updates regarding what coworkers were working on, what went off-track vs what finished on or ahead of schedule. At the end, everyone reflects on ways to improve. Retrospectives grow and shape the learning curve and enable members to learn from their mistakes.
Remote retrospectives brings the team onto the same page regarding the status of work completed during the last-run iteration.

Such meets are also a platform to recognize the team’s collective efforts and appreciate high-performers. These meetings can take time, which is why it’s important to make them engaging so that attendees are fully in the present. In a physical retrospective, you can pick up on social cues and/or body language and know if someone’s getting fidgety or is unable to understand what is going on. Online, however, it’s harder to gauge engagement and the team member’s individual attention span.

The goal of remote retrospectives, is to enable everyone to reflect on their successes, failures and be able to take with them the next course of action. Weaving team-building activities into retrospective sprints can keep things interesting; even something the team can look forward to.

2. Challenges of running retrospectives remotely
Challenges of running retrospectives remotely

Remote team retrospectives can be challenging if the intent and consistency are missing. The goal, after all, is that everyone learns something from it and walks away with a fresh (and often different) perspective. The challenges include:

2.1 Prioritizing

Everything cannot be a priority, and yet, 90% of the time, status check-ins and retrospectives are time-consuming and in a disarray. It’s difficult to cut through the clutter and take away the learning points if there’s an overload of priority and no sequence to follow.

Corrective measures

The first step to prioritizing is to break the priorities down into smaller doable goals. This makes it easier to define what success and failure per project are. The team and you can also back trace to the last achieved milestone and the goal of the task attached to it. You can document this into a template as retrospective stories to refer to at the time of the review.

2.2 Focus

Each remote sprint retrospective should have a subject to focus on so that everyone can stay on-topic. This is harder than it sounds, because come the retrospective, chaos reigns. Members may switch between topics or go on a different tangent.

Corrective measures

Decide on the number of sprints you want to run for a project in order to fix a number for the remote team retrospectives. Set a topic for each run and timebox it so that sprint participants can prepare for it and condense their notes so that it’s easier to go over the lessons to be learned from the chosen subject. This helps people bring up bottlenecks they faced, or are facing which unless resolved will carry forward to the next iteration.

2.3 Disparate tool usage

The same project may not always have the same team from start to finish. The size and members may vary from one sprint to the next. As such, some members may miss a retrospective because they’re familiar with one set of tools, which may not be what you or someone else would use.

Corrective measures

A remote team retrospective stays successful only when relevant members are at the same place and time when it’s happening. Always recheck who all are in the sprint, particularly if they are newly added or released to the task from the previous sprint. Make sure that you let them know which platform you’ll be using to run the retrospective and send out invites ahead of time so that they can make themselves available to attend it.

2.4 Lack of a standardized template

The lack of a template library is a tell-tale sign of the retrospective falling apart even before it begins.

Corrective measures

A digital whiteboarding tool  can make the experience of doing a retrospective more fun, engaging and immersive. You can create your own or choose one from a library and assign it to the team to use. They can add comments, sticky notes, draw on the board in real-time using a stylus or highlight issues on the screen while presenting. This helps everyone contribute to the retrospective. More specifically, it helps the Project Lead, or ScrumMaster determine if everyone is clear on what was discussed.

2.5 Non-uniform participation

This is a remote team retrospective challenge that arises from a lack of cohesion between cross functional teams and individual members . A team can have extraverted and introverted employees, and some who fall in-between. This can impact the uniformity and consistency with which members add to the discussion.

Corrective measures

Set aside a retrospective to emphasize on the importance of these meetings, and how it’s a forum for people to exchange ideas, pool in knowledge and come up with ways to improve. Invite questions, and encourage your team to use the opportunity to clarify, ask and answer questions.
Convey to your team the housekeeping terms, time limit, agenda and what is expected of them when an actual retrospective takes place so that they can contribute and not feel left out. Identify speakers who tend to dominate over the conversation when their speaking turn is over, or steer it in a different direction. Remain an observer in the remaining retrospectives and record your feedback so that your team knows what they’re getting right, and wrong.

3. The benefits of running remote retrospectives
The benefits of running remote retrospectives

Although 37% of meetings are estimated to not add any value to an organization, a remote team retrospective does not fall under this. In fact, it shortens timelines and saves 15-30% of project costs, given that it’s done online via video conferencing. Some benefits of running remote retrospectives are

3.1 Intentional conversations

Steve Jobs liked to call iterative learning as a means of connecting the dots. This is true, because regular updates establish context to the sprint for those members who are involved, either directly or indirectly. For example, a member whose work depends on the previous task finishing can know where their colleague is in terms of progress. It also enables the ScrumMaster facilitating such retrospectives to offer their two cents on what could have been improved, and appreciating a member who found a more efficient or faster way to solve a challenge.

3.2 Continuous quality improvement

Discussions at the end of a sprint helps to identify key issues and come up with ways of resolving or eliminating it so that it doesn’t carry forward to another iteration. The improvements also help refine the quality of the final release, because errors, deviations or issues are spotted and corrected ahead of delivery.

3.3 Nurtures a supportive and engaging work culture

Remote retrospectives involve, inform and include your team. It also motivates them to be more conscientious of communicating with their teammates rather than risk members drifting apart once the actual work begins. The more engaged the team is, the more likely they are to remain accountable. The trust factor organically weaves itself into conversations which add value to what is being shared. Whether young or old, seasoned or new, members can follow a flat hierarchy where more value is given to collaborative decision-making over unilateral trade offs.

4. What changes when you do a remote retrospective in comparison to an in person one?
What changes when you do a remote retrospective in comparison to an in person one?

A retrospective meeting typically starts with a status check on the actions from the previous retrospective. Members brainstorm over problems that continue to persist in order to resolve them before moving on to the next. These actions are recorded for reference. In a remote retrospectives, members are geographically dispersed, and the differences in doing such retrospectives virtually over in-person, are that

  • Team availability determines a common meeting time across time zones.
  • People online are more deliberate in observing social cues, so that they can speak on-turn and mute themselves when their turn ends or when someone else is speaking.
  • There’s an increased usage of whiteboard tools in order to capture workflows progress and mark them as pending, done or yet to be picked up.
  • There’s more creativity in making the retrospective interesting so that members don’t lose steam or are distracted by other messages when on the call.
  • Intentional respect and regard for what everyone is saying so that they reach a level of comfort in participating in the retrospectives.

5. Who’s involved in a remote retrospective?
Who's involved in a remote retrospective?

The ScrumMaster (sprint facilitator) chairs remote retrospectives, and ensures that meeting rules are followed, one of which is that everyone on a distributed team set up has equal opportunities to participate and contribute. Retrospective sprints are usually common in agile software development, but are now also followed by marketing teams, professional consultants and cross-skilled work. The Scrummaster is also the retrospective facilitator and is accountable for understanding the role and relevance of each member.

6. How do you do a remote retrospective?
How do you do a remote retrospective?

6.1 Identify key contributors and their tasks

The first step to running a remote team retrospective is to identify how the team has changed back from when the project kicked off. Team size can contract, expand or stay the same throughout the duration of the project. In other words, members can either be added at later stages, or leave the team once their role ends. In the latter scenario, such members will not be required in future sprints. Once you know the number, you can then identify key contributors for each retrospective and the tasks that they took up, or are delegated.

6.2 Set the agenda

The agenda should have a time-limit in order to confine the meeting to a reasonable discussion length. This prevents the agenda from going off-track and enables members to utilize their speaking time optimally. It should have a list of deliverables for each sprint, milestones reached, problems encountered along the way and the problem-solving means employed to lower the impact or mitigate risks.

6.3 Standardize times and confirm member availability

Use a time zone and calendaring app to find out and confirm individual availability. This can mean finding a time overlap that works for everyone. Next, automate reminders to be there for the retrospective closer to the finish of a sprint. Making a habit to be punctual to such meetings ensures no one else is kept waiting.

6.4 Establish context from historic reviews

The previous retrospective can be useful in the next. Factor in sufficient time to go over what was last discussed so that the current retrospective can catch everyone up. This is useful if it’s a new team, or if there are new faces. Historic reviews also give realistic projections for the timeline and efforts to be invested for current and future retrospectives.

6.5 Record inputs

Use a digital whiteboard on a collaboration platform. Remember to screen share so that you can see the edits and note down suggestions the team is making live. Members can view the board and improve upon an idea that’s in writing.

6.6 Collect retrospectives feedback

Encourage your team to come forward with their thoughts on how the retrospective went. They should be able to specify what they learned, how useful the session was, and what can be improved. This feedback can enhance the quality of future remote team retrospectives and ensure everyone gets value out of attending it.

6.7 Give virtual recognition

Always make time to recognize individuals for their work. You can try out a few virtual recognition ideas in retrospective meeting calls and add your own twist to it so that members feel appreciated and encouraged to keep up the good work!

7. Fun Ideas To Run Remote Retrospectives
How to run fun remote retrospective ideas

Treat the retrospective as a people engagement exercise. After all, the more comfortable your team is in presenting, the better sense their inputs make to the project as a whole. A few ways to make remote retrospectives fun for a distributed, remote team are as follows;

7.1 Team Theme

Most conferencing platforms like Zoom offer users the option to change backgrounds. You can have the team pick a theme and change it up every sprint to convey the unity.
Optionally, you can even encourage them to come up with a brief anthem that they can pledge as one, before the retrospective commences.

7.2 Fun Booth

Create your own photo booth online with screen grabs as the retrospective winds down. Have everyone strike a pose, which your creatives team can compile into a collage for a great memory!

7.3 Adopt a mascot

Just like sports teams and varsity clubs that have their own mascot, you could appoint a coworker’s pet as your mascot. If no one has one, you can use a plush toy or even a potted plant.
You can jokingly ask your mascot for an opinion or send out your retrospective reminder email in their name to keep things interesting! I thought of this after my own Ficus plants, who now feature in my meets ( call me crazy, but Gred and Forge are the ones who add color to my life and meetings!).

7.4 Joke-r of the day

Have everyone take turns coming up with a bad pun, wordplay or a good old humor of the day. It diffuses the tension and helps teams bond better during and after the retrospective.

7.5 Doodle-Board

Once the project ends and you’re down to your last team retrospective, you can clear the board and have everyone doodle on it. It can be a personal caricature, cartoon or pre-chosen theme. You can incentivize it by awarding a digital certificate or merch to the best artist.

8. How can I run a retro remotely?
How can I run a retro remotely?

Remote team retrospective can be a fun and engaging way for both you and your team to learn. It raises questions in the right places, such as

  1. Are you finding what you’re learning helpful and relevant?
  2. What do you need to change, and does it make sense to do it now, or later?
  3. Do your teams spend time on what matters?
  4. How can you get them to cut down their time on busywork or shallow work?
  5. Is there sufficient information to help them combat problems?
  6. Is there any member who is showing early signs of work-fatigue, stress or disengagement?
  7. What can you do to bring them back to the top?

You can use retrospectives to remind virtual teams of their accountability. It’s easier to enable everyone to recognize the milestones and goals they reach when they’re able to tie it back to their investment to the tasks.
You’ll know your remote team retrospectives are a hit when members are more communicative, intentional and collaborative by the end of it!


Aakash Gupta
Written by
Aakash Gupta

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