The Growth Team's Retrospective Culture

Becoming a better team today than we were yesterday

In my previous post, The Growth Team's Metric Meeting (1) — Monitoring Alarmy's Subscription Metrics Based on Growth Hacking Methodologies, I briefly outlined our growth hacking process as shown below.

It's a series of product growth processes where multiple hypotheses for product growth are built based on product data (or user feedback), prioritized together, and once design and engineering are completed and shipped, the success or failure of the hypotheses is analyzed to draw follow-up hypotheses and lessons. As each backlog item moves through this pipeline, we hold timely (and minimal) collaboration meetings, which are sprint planning meetings, sprint reviews & retrospectives, and metric meetings. If the previous post covered the uniquely special metric meetings of DelightRoom's Subscription Squad, this post will delve into another uniquely special aspect: the Subscription Squad's retrospective culture.

The Purpose of Retrospectives

Retrospectives are usually held alongside reviews. During the sprint review, we sync up on what was accomplished in the current sprint. We share experiment analysis details, design assets, and engineering demos. Then, we update the status of each backlog item in the pipeline to match the progress made. The purpose of the retrospective that follows is to figure out how our team can do better in the next sprint, so we can sync up on even higher-quality deliverables during future 'reviews.' We look at everything from all angles and share opinions on what went well or what needs improvement while executing our respective to-dos that we synced up on during the review. 'Taking a full day off because I felt a cold coming on was effective,' 'It was a sprint with a long cycle, so a team lunch in the middle would have been nice,' or 'It was a task that touched critical code, so the code review took longer; I need to allocate more estimated time during the next planning session.' We can share absolutely anything, as long as the goal of the conversation is to boost our team's collaboration efficiency.

Why the Subscription Squad's Retrospectives Are Special

Although the retrospective process seems easier and simpler than you'd think, it actually rarely works properly in most organizations. They often just superficially skim over what happened, and in many cases, entirely skip over some major events. A 'retrospective' that is carried out in such a loose, perfunctory manner ends up failing to yield any sharp action items that can actually drive team improvement. And you fall into a vicious cycle of experiencing the exact same inefficiencies over and over, learning zero lessons from the trial and error you've already been through. DelightRoom's Subscription Squad is the exact opposite. Every sprint retrospective overflows with highly nutritious discussion points, and everyone feels the team's efficiency gradually improving thanks to those action items.

I'd like to sum up the secret to why our organization's retrospectives actually work unlike other orgs, as follows.

1. Honesty

'How honestly can you share about the things that happened during this sprint?' This is a highly difficult condition because you have to know how to expose your weaknesses without hiding them. If you try to cover up your mistakes out of pointless pride or treat them as no big deal, there can be no team growth. In the Subscription Squad, members know how to honestly share their individual failures and mistakes, and the teammates on the receiving end don't reprimand or blame them; instead, they console the heartbreak and brainstorm action items together to prevent recurrence. Thanks to this culture—which we jokingly call 'My Failure for You'—we pinpoint easily overlooked team problems in every nook and cranny and identify areas for improvement. This honesty doesn't just shine when discussing things to improve; it also maximizes the things that went well. Have you ever delivered a heavy, deeply sincere message of gratitude that's usually too embarrassing to say out loud? The Subscription Squad unreservedly expresses the gratitude they felt toward each other during every retrospective, and this leads to powerful, invisible team bonding that profoundly impacts the increase in our collaboration efficiency. I believe this kind of 'honesty' is the absolute number one prerequisite for a healthy retrospective culture.

2. Sharpness

Alongside honesty, the contents of the Subscription Squad's retrospectives are sharp. We know how to dig deep into the causes of events to uncover that single, sharp root cause. If the contents of the retrospective are dull, the action items drawn will also be vague, making it easy for improvements to fall flat. For example, if you stop defining the problem at 'I worked late a lot, so fatigue built up and efficiency dropped,' your action item simply becomes 'I should work late less.' You have to think a couple of layers deeper about exactly why you worked late so much. Was it because we over-planned compared to our available resources, or because there were many unexpected surprises that forced us to stay late, or did analyzing the experiment take more time than we thought? Depending on each reason, the actionable responses vary, as do their efficacies and effects. Ultimately, this depends on how seriously you approach the retrospective (the realm of willpower) and how sharply you can define the problem (the realm of competency), and it seems our Subscription Squad is made up of teammates completely brimming with both willpower and competency. Lol.

When retrospective time rolls around, we line up the events that occurred over the past two weeks and mark the ones that gave us significant jolts. It's essentially a time to gather retrospective materials. Based on this, we each spend about 20 minutes carefully writing down what was Good and what needs To Improve. We calmly look back on the past two weeks and write down the phenomena honestly and sharply. At this point, the more a person has felt the efficacy of retrospectives, the more they naturally crave to be more honest and more sharp. Some members are so dead serious about retrospectives that they spend even longer meticulously writing them out the night before. It's almost like they're competing to see who can do the retrospective better...!

Armed with honesty and sharpness, the Subscription Squad is that serious about retrospectives.