Making retros in project management fun: how to keep your team engaged - part 1

1. Why retrospectives matter

Retrospectives are more than just a box to tick on an Agile project management checklist. They are powerful tools for fostering continuous improvement and strengthening team bonds. By dedicating time to reflect on past sprints or projects, teams can identify what’s working, what’s not, and what can be improved. Effective retrospectives enable teams to learn from their experiences, celebrate successes, and address challenges proactively.

With this in mind, and always looking for ways to optimize the work of project teams, I decided to introduce retrospectives into our project flow—but with a twist. Instead of sticking strictly to the traditional Scrum format, we not only review our work after each sprint, but also hold a larger retrospective meeting at the very end of the project, once it’s been released. This final retro is particularly valuable to me, as it offers a comprehensive view of the project’s lifecycle and allows us to dive deeper into the challenges and successes we encountered along the way.

I’ve found that this additional meeting encourages everyone to think more holistically, beyond the details of a single sprint, and provides a safe space to share both positive reflections and constructive feedback. It helps us uncover recurring patterns, gain insights into the root causes of issues, and brainstorm improvements together. Ultimately, this approach not only enriches our understanding of the project but also fosters a culture of growth and collaboration that continues to benefit our team on future projects.

2. Challenges

Implementing retrospective (retro) meetings, both in-person and online, can present several challenges. Retrospectives are essential for fostering continuous improvement, team bonding, and identifying areas of growth, but without careful planning, they can become ineffective or disengaging.

Challenges in Implementing Retro Meetings

a. Challenges for In-Person Teams

- Engagement and Participation: A 2021 Atlassian survey found that 40% of team members stay passive during retrospectives, especially in longer or larger meetings. In-person, keeping engagement high is challenging, particularly in diverse teams. Groupthink or dominant voices often overshadow quieter members, diminishing the retrospective’s value.

- Time Constraints: In-person meetings often face time limits, with 53% of teams struggling to find enough time for effective retrospectives (State of Agile, 2021). This can lead to rushed, shallow discussions, especially in long or complex projects.

- Team Dynamics: In-person retrospectives at the end of a tough sprint often suffer from low energy and focus due to team exhaustion, which reduces their effectiveness.

b. Challenges for Remote Teams

- Technical Issues: For remote teams, technical problems are common. McKinsey reports 30% of remote workers face connectivity or tool issues, disrupting retrospectives and reducing their effectiveness.

- Lack of Non-Verbal Cues: MIT research shows non-verbal cues are essential in communication. Remote teams often miss these cues, making it harder to gauge emotions and engagement, which limits understanding and issue resolution.

- Disconnection and Engagement: The State of Agile report shows 40% of remote teams struggle with disengagement, as virtual settings reduce accountability and collaboration, often making retrospectives feel like mere formalities.

Practical Solutions to Overcome These Challenges

a. Shorter, More Frequent Retrospectives To combat engagement drop-off after long sprints, one effective solution is to hold shorter, more frequent retrospectives rather than a single long meeting at the end of the project. Regular, smaller meetings give teams the chance to address problems in real-time, reducing the mental load of a large, end-of-project retro and ensuring continuous improvement.

Frequent retrospectives allow teams to discuss emerging issues while they’re still fresh in their minds. This approach helps avoid the buildup of frustration and burnout that can result from long stretches without reflection. Research from the Agile Coaching Institute suggests that shorter, targeted retrospectives allow for more focused discussions and greater accountability for action items.

b. Engaging Formats and Themes Introducing more interactive, creative retro formats can significantly boost team engagement. For example, many Project Managers find success using tools like Miro, Mural, or digital boards to facilitate virtual retrospectives in a fun, visually appealing way.

In my experience, I also found that setting the retro in a game-inspired universe (like the world of GTA Vice City) can capture the team's attention and provide a fun, non-traditional twist. By incorporating elements that resonate with the team (such as pop culture references or playful themes), you can lighten the mood and make retrospectives feel less like a chore. This creative approach led to much higher engagement from the team in my own experience.

c. Bringing Remote Teams Together In-Person For remote teams, one of the best solutions for improving engagement and collaboration is bringing the team together in person when possible. The lack of physical presence in virtual meetings can lead to disconnection, so a single-day meet-up or a day in the office for a final retrospective can be highly effective in building stronger team bonds and improving the retro’s quality.

I personally encountered this challenge when working with a remote team spread across three offices. Organizing a meeting where everyone worked remotely was difficult because remote team members lacked the same level of discipline and connection as in-person teams. As a solution, I worked with HR to bring everyone together in one location, which allowed us to have a more focused, productive, and engaging retrospective. The in-person setting removed many of the distractions and technical issues that remote teams often face and helped us align on action points more effectively.