Work Tech Support: How to run a retro

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Along with our independent reviews of the tools defining the future of work, we're offering something new: a four-week guide on integrating retrospective meetings into your team practices. Sign up here, and over one month, you’ll learn how to use a remote retro tool based on our independent reviews, facilitate a productive reflection meeting, and work with your team to make improvements to your process or product.

As hybrid and remote work gained popularity, in-person retrospectives—traditionally involving team members writing ideas on sticky notes, adding them to a wall or whiteboard, and voting on them with dot stickers—have largely moved online, giving rise to a new set of tools developed to make facilitation easy.

Before we dive into the specifics of setting up tools and choosing formats, we’re going to focus this first installment on the why: why retros are so effective at helping teams share equitable feedback, and why they’re such a powerful tool for cross-functional collaboration and psychological safety. To understand that, we have to get into the retro’s origin story.

Background

If you’ve read our review, you’ll know that retros have roots in agile engineering, which focuses on quickly launching, iterating, testing, and gathering feedback on products, and Scrum, a project-management framework that aims to increase productivity and team communication.

Created in 2001 by a group of programmers, engineers, and tech executives, the Agile Manifesto for Software Development was more than a set of rules for engineering teams to follow. It was “a set of values based on trust and respect for each other and promoting organizational models based on people, collaboration, and building the types of organizational communities in which we would want to work,” according to co-author Jim Highsmith.

The authors envisioned working environments in which peoples’ talents were harnessed to their full extent and the sharing of ideas thrived—something that all of us want to create when collaborating with others, whether in person or remotely.

The manifesto includes values of honoring “individuals and interactions over processes and tools,” meaning sometimes hopping on a video call to have a conversation is better than trying to formally document expectations. Similarly, considering peoples’ working habits, feedback preferences, disabilities, and abilities is more important than barreling people over to adhere to a process or ensure they’ve followed the rules. One of the manifesto’s principles notes that teams should “build projects around motivated individuals,” giving them “the environment and support they need, and trust them to get the job done.”

Another major part of the agile way is “responding to change over following a plan.” We all know that changes are going to happen in the middle of a project: We learn about a new strategic tactic, our experiments are not working out, a team member has to shift priorities, or we forgot about an important element to the original plan. Instead of assuming we can know all the answers and plan out a final project’s every detail from the start, agile practices encourage teams to assess success iteratively to see what kind of changes need to be made based on new information and unseen challenges. One key principle notes that teams should “build projects around motivated individuals,” giving them “the environment and support they need, and trust them to get the job done.”

According to agile and Scrum materials, a retrospective can be a critical part of creating this environment. The meeting is designed to:

• Allow room for reflection
• Increase effectiveness
• Increase quality
• Help the team identify next steps and adjust their behavior accordingly

Recommended reading:

• Agile Manifesto
• Scrum: The Art of Doing Twice the Work in Half the Time by Jeff Sutherland

Research

Bringing together your cross-functional team to discuss shared projects and goals isn’t just important to the work itself. Retros can also be a way to facilitate learning and development for individual team members, giving them a place to share knowledge with one another and forge relationships across your organization.

That’s especially true in remote workplaces. In a study conducted over the first half of 2020 and published last year, researchers from Microsoft and the University of California, Berkeley, Haas School of Business examined the emails, messages, calls, calendars, and work schedules of 61,182 Microsoft employees. They found that the shift to remote work made collaboration networks more siloed, with less communication between different departments within a company.

Employees doubled down on their strong ties, “which are better suited to information transfer,” the researchers explained, “and a smaller share of their time with weak ties, which are more likely to provide access to new information.”

Working cross-functionally can help break down these silos, but it’s just a first step. Retros are a dedicated space for cross-functional teams to go further, examining how they communicate and how they work together to drive results. Having this space can also increase empathy, helping others understand the stresses or concerns of other departments that they don’t normally see.

More recommended research on retrospectives:

• A study on tactics to help generate new ideas and perspectives during retros
• Two research papers outlining specific exercises that can help improve retrospectives through game-like experiences

Next steps

This week, take a manageable step toward bringing retrospectives to your team:

• Decide a specific project you’d like to conduct a remote retro on and schedule it with your team within the next few weeks. This could be based on a project that was recently finished or one still underway. The key is to choose something cross-functional—for example, perhaps you’re working on delivering a major new marketing campaign and reached a major milestone where all of the art and copy is ready for launch. Or maybe you presented a big proposal to a client and the whole team had to pull together the ideas, deck, and meeting presentation.

Some tips:

• Schedule the retro for a full hour, or 55 minutes to leave some breathing room between meetings.
• If you are uncomfortable with facilitating the retro, recruit someone from your team who has facilitation, communication, and collaboration skills to lead. Sign them up for this Work Tech Support guide.
• Send an agenda to the team so they know what the meeting is about and what the purpose and outcome will be. Here’s an example you can adapt:

Read the full review of our picks for the best retro tools.