writing / Reflection is necessary

My favorite meeting genre is Reflection. It’s a meeting where everyone writes stickies with likes and wishes, then shares and clusters them into themes. That’s a normal retrospective process but what makes Reflection special is that we don’t wait for something big to happen to do it. Instead, we reflect every week.

It looks different with every team. Sometimes it’s part of the planning process, sometimes a vigorous debate, and sometimes a love fest.

The first time I did this was at Radical Candor, a seed stage startup in a shared space in an old SF office building. The team was wonderful but a bit of a hodgepodge. When my friend and I joined, the initial product hadn't been launched and the team consisted of two non-technical founders, a product lead, two remote engineers, and a team of design and engineering contractors.

The company's goal was to provide tools to help managers improve. We had an ace-in-the-hole with the Radical Candor brand and associated content. However, the exact product shape needed to be figured out. All of that is par for the course as an early stage startup, but it was a recipe for chaos and miscommunication. We had a bunch of people working together for the first time to build a vaguely defined product.

We were pursuing the main idea of the Candor Coach, a management coach in your pocket. It would guide you through exercises and content to practice managerial skills, primarily giving and receiving feedback. However, building it involved sorting out a ton of ambiguities. For example, our design contractor shared a beautiful design that everyone loved for a popup reminder to simulate your coach checking in on you. The premise of the feature was that we would engage the user at the perfect time. Unfortunately, the designer didn’t specify any conditions to show the popup, just that it would show up right when it was most useful. I was left to figure out the details and I was frustrated to say the least. I like to go for walks when I’m angry and I went for a nice long one.

We were struggling as a pre-product market fit company and I wasn’t alone in having big feelings. Fortunately, the contractors we were working with had processes to help teams in our situation, the most powerful of which was Reflection.

We met on a Friday around a big wooden table in a conference room with walls covered in sketches and mock-ups and they explained the process. We wrote down our likes and wishes, shared with the group, and discussed. We had a lot of “wishes” and a heated discussion ensued. But we also had a lot of “likes” when we appreciated each other’s work and progress we’d made as a team. It led to a group catharsis when everyone vented frustrations and was appreciated for their contributions. We resolved ambiguities and adjusted our course for the next week until we reflected again the next Friday.

I walked out of the office feeling amazing. We had productive conflict and I felt more bonded to the team. We were doing something hard, doing it together and as long as we kept reflecting on our work and collaboration, I felt like we couldn’t fail.

Teams need to iterate on what's working and what’s not. It should be safe and encouraged for people to share problems they’re facing.

Teammates need to openly appreciate each other. Everyone wants to feel valued and just hearing it from a manager every 6 months isn’t enough. It’s unfortunately common for people to see good work by a peer but say nothing, especially for distributed teams.

As a manager, it's your job to cultivate the team’s culture. If you want a team that values feedback and iterative work, you need to make those things a regular part of the team’s processes.

Once the team is comfortable sharing in Reflection, it becomes a powerful tool for a manager to debug issues. Instead of having numerous one-on-one conversations and triangulating larger themes, you can facilitate the team figuring it out together. They will hash out issues, change course nimbly, and everyone will feel part of the decision.

Conflict and confusion are part of work and it’s a manager’s responsibility to help the team resolve them.

Running a regular Reflection is an effective way to surface and address any issues quickly.

Reflection encourages praise between teammates which helps the team bond.