By Dom Tancredi // CEO // Dom & Tom

A few years ago, Tom and I were seeing dozens of projects flying out of our company. But there was a disturbance in the process: team communication was poor, tasks were being slipped, and milestones were starting to drift.

I rolled up my sleeves and tried to solve things, project by project. But every time something was “fixed,” it started to drift again when I focused on something else. I did the work! I asked everyone questions, analyzed the process and work product, and gathered feedback. It took an insightful product-owner friend to convince me about the one missing component to our company: Retrospectives (also known as “Retros”).

He and I argued about the solution. Both of us were process junkies—Were we doing enough daily stand-ups? How were our sprint reviews? Did we fail at estimating in sprint planning? He won me over with a compelling view on Retros. It’s the only sprint ceremony that allows the team to talk about the team, not the project.

So we tried them on the projects that needed the most help. I want to say it was a success, but Retros were hard to convince people to do. There were plenty of excuses: it slowed team velocity, the team didn’t feel it solved anything concrete, they already had a healthy dynamic. Sometimes when we don’t talk, everything can build up in our heads and we lose perspective.

For a long time, Retros just weren’t working for us.

So I got to work and started building a tool to help the team, especially our poor project manager/scrum master. I spent nights and weekends building a retro tool from scratch. Teams started using it and we saw results. Project velocity improved, consistency improved, but most importantly, team dynamics started to heal.

The tool process took three years to prototype, test, beta, rebuild, test again, rebuild again, and more. It’s been a journey. But I’m proud of every Retro we support.

Teams That Connect Better Are More Motivated to Listen and Improve

Digital is a tough space. Every year I hear stories of burn-out. We’re asked to learn dozens of new languages, frameworks, platforms, whizzy-wigs, acronyms, and more. No wonder folks get fried and look to pharmaceuticals to stay sharp (or mellow).

I get a lot of value out of a really well-run Retro. We get another perspective on a problem that might not be a problem, we talk about root causes no one else is aware of, we look up from the work and look at each other. If nothing else, it’s an emotional drainpipe to vent out anything on the mind. When a team opens up to each other, it’s magic.

There’ve been times when our Retro ended up being a postmortem. Other times we sit at the top of the mountain and talk about the journey. They’re all valuable and almost always conclude with one of the key takeaways being the same: do more Retros.

Facilitation Is the Key to a Successful Retrospective

From sending out a calendar invite to selecting the video-conferencing tool to setting the tone to motivating the sometimes-herd-of-cats-like product team through a meeting, there are a lot of things that can go wrong. With distributed teams, it’s even harder. I started to think, “If I could remove some of the variables, I could increase the probability of a successful outcome.”

The idea is that this tool will not only guide you through the Retrospective process, but in doing so, improve and enhance the team-relationship experience. You’ll make meaningful connections with your team members and, by extension, their work will actually create more effective teams.

Imagine one day an alien lands (in your bathroom because you left the window open) and teaches you a new behavior to clean your eyes. Doing so gives you perfect vision, but you need to do it twice a day, every day, for it to work. Whether or not you would do it, how likely is it you could commit to eyeball brushing for a reward? And how long?

Behavioral scientists found it takes nearly three months to learn a new habit or break an addiction. This dispels the old popular myth of 21 days. And why does it take so long? Because behavioral changes are tough. The human brain enjoys consistencies and habits. This is why I’ve been teaching my three-year-old to brush his teeth in the morning and night… even if he keeps wanting to use my toothbrush.

Retrospectives are the key product ceremony to bring your team together and realize change. However, as I said, it’s often a ceremony easily jettisoned when in crunch mode. And even worse, some teams never see the need to do them in the first place. So many digital-product development teams are stuck in habits they don’t even realize. They need internal reflection to “change the habit,” and that’s exactly what Retros offer when done right.

Honesty and Trust; Teams That Work Better Together, Create Better Products 

Retrospectives tend to be most valuable when people lower their guard and have honest conversations with their teams—better estimations, clearer understanding of features. People aren’t afraid to ask “stupid questions.” We find better engineering solutions when we get out of our head.

I get a lot of value out of a really well-run Retro. The team blows off any steam they’ve built up, they get another perspective on a problem—and sometimes amazing things happen. You might realize the “problem” is actually an opportunity, or finally address a hidden obstacle which had been camouflaged from everyone. When a team opens up to each other, it’s magic.

We Need Your Insight 

Here’s the link to Retro App to help you and your teams run better Retros. We’re always looking for insights from real users. There’s always a free account to help your team meaningfully connect.

👋💯 CODE for 100% off for 6 months: innovators-club-6-month-100-percent

-Dom

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