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The Best Money I Spent in 2018

My wife and I sometimes joke that 2019 is the year of Ryan. My career seems to be accelerating very rapidly, and I’m exploring new ideas and activities with success. I think one of the reasons that are happening is because of a few key things that I started in 2018.

In 2018 I started speaking at conferences. Conference speaking was something that I had wanted to do for something time, and I finally started to get accepted at conferences. I also started to seek out classes so I could learn more intentionally. I started with violin lessons and expanded to a class on Wardley Mapping, the Responsibility Process, and most importantly Powerful Retrospectives.

In all of that, the Powerful Retrospectives class stands out as the best money I spent in 2018. Esther Derby created this online class, and I believe I was in the first cohort that signed up. So what about it would cause me to claim that it was the best money that I spent?

It was a combination of a few things that were unlikely to be part of the standard billing that the class offers. I’ve spent years of my life focused on doing retrospectives as well as I possibly can. I devour and absorb any material related to retrospectives. My first taste began with the Agile Retrospectives book by Diana Larson and Esther Derby. Esther’s class provides nuance, depth, and extends the material it contains.

While I was taking this class, I was working as a scrum master for a company. I facilitated their retrospectives with the content of the course fresh in my mind as it unfolded each week. The class prompted me to reflect deeply on myself, my understanding, and abilities. Reflection led to me facilitating retrospectives where every single time the team had an improvement that they could remember. I consider this the most important measure of success for retrospectives.

When the team knows and remembers that they’re improving, retrospectives are working.

My circumstances changed, and I was about to take a new job. The team asked me to facilitate one last retrospective for them. They didn’t want to make their sprints better or anything like that. They desired to make their retrospectives better forever.

I led a retrospectives on retrospectives.

The team saw that they had improved every single time I led a retrospective for them. When I started, the team described their retrospectives as, “An hour-long bitching session.” They named every single improvement they had made over five months. They didn’t want to lose what they had to a new scrum master who wasn’t as capable as me.

We went through our retrospective. The team uncovered the ingredients that they needed to have for a retrospective to succeed. They made commitments to one another to hold those ingredients firmly in their future. They asked if they could call me. I let them know I gave them my number because I wanted them to have it.

This was a powerful retrospective. The techniques I applied during that retrospective I learned from that class.

Other great things happened too. Joining the class gets access to a few extra perks. First, some webinars came up where Esther brought in someone or led a discussion about a particular topic. One such example was on remote facilitation. An issue that is so important today, and we were able to pick the brains of people who are the best at it.

One of my favorite pieces of the class though was the online community. Joining Esther’s class gets access to a Slack group full of people who are sincere and kind about wanting to grow their ability to lead great retrospectives. We would pose questions to one another and work through our answers. We’d wait with bated breath until Esther would drop some bomb of wisdom on us all.

I found myself with a community of people that would help me plan and navigate the challenges of running retrospectives better than I ever had.

Eventually, I brought that community a new challenge. I wanted to run a retrospective with four teams at the same time about a release that had gone wrong and would span data for four months. There was a significant facilitation problem to solve and the community, along with Esther, jumped in and helped me come up with a plan. That retrospective garnered feedback that they wanted to do this again, it was incredibly valuable, and that they came away with clear action items.

Also, since joining that class, and more specifically that community I grew a lot professionally. I did a podcast as a direct result of being in that group. I made contacts with people that I respect and highly value that I can now call on. I found more conferences to apply since there were people in the group that we’re inclined to do that.

That community that was born out of understanding how to do retrospectives together has grown my career in 2019. We’re quiet now, mostly checking in now and then with ideas and challenges. We are waiting for the next group of people to find out about this class and join in on our fun.