"I wanna be in
The room where it happens
The room where it happens
The room where it happens."
-Hamilton

As a junior engineer, I don't expect to have a large role in my planning my team's work. I know that my input is welcome on all of our current projects and that my manager is interested on my thoughts on what I'd like to do in the future, but I also know that the high level future planning is general done above my level. When my manager extended an invitation to our team to participate in the team's 2021 t-shirt sizing estimation process, my original thought was that I wanted to participate, but it probably wasn't appropriate for me. After thinking about it a bit, I realized that my manager would not have extended the invitation to the whole team if it wasn't appropriate for all levels, so I decided to attend. I wasn't sure if I'd have enough context or knowledge about the projects to fully participate in the process, but I wanted to see what happens in a planning meeting - this is my chance to be in the "room" where it happens.

While this was my first time participating in t-shirt sizing, I did know a bit about the process. I know that each size (generally from S to XL) corresponds to a relative scope for stories, and that these sizes are used in planning the time and resources that should be dedicated to each story. Beyond that, I didn't know what to expect, and I was excited to learn more at our first sizing meeting, which was an introduction to the process. At this initial meeting, the person leading the process explained what the process would be, how we would vote, and how we were determining what each t-shirt size corresponds to. We were trying a new way of sizing things this year, and I was interested to see how it would work out (even though I had no experience with the old method and therefore nothing to compare it to). At this point I wasn't sure if I was going to vote on all of the stories (and the leader told us that we didn't have to vote on everything), but I knew that I wanted to at least mentally size each story (even if I didn't submit my vote) to test how well I understood the process.

Our first sizing meeting was scheduled for an hour. We started off discussing the process a bit, and then went into the first story. My initial thought on the process for this first story was that we were going very into the weeds. There was a lot of detailed back-and-forth, and while it was all relevant (although some of it wasn't really necessary context for me), it took a lot of time. Eventually we got to the voting, and while I wasn't fully confident what the right size was for this story (even with all the questions, I didn't feel like I had the full context), I decided to vote based on what I knew. There was a clear majority, but a few people had voted for other options. The leader of the session asked if anyone who had voted differently wanted to defend their choice, but nobody spoke up, so we went with the majority opinion on the size (which was the option I chose).

The second story we sized was somewhat related to a product that my team maintains. After hearing the story description, I had a question, but I wasn't really comfortable speaking up. Thankfully, someone else had the same question and asked it, which was the start of a long discussion of story and whether it involved new functionality or expanding existing functionality. Between my knowledge of the product that my team maintains and the discussion, I felt very confident in my sizing opinion when we voted. The vote was close, with two sizes having similar number of votes, so the leader of the session asked for a representative to share why they chose each size. The post-vote discussion reinforced my decision to choose the size I chose, so when we went to a second vote, I voted the same way, and after that second vote, the size I chose won out.

The third story we discussed led to a lot of questions about the exact scope of the story. There were questions about what exactly we were trying to solve and what work that entailed. All of the discussion made it hard for me to choose a size, and based on what exactly the story included, I could see the size being anywhere from S to XL. After further discussion, the group decided that the story wasn't well-defined enough for us to vote on it. This third story was the last story we had time to discuss during that first hour of planning.

After the sizing session, some participants offered thoughts and ideas (in our estimation slack channel) about the process and how to make it better. One suggestion that I thought would be very helpful was that we have an opportunity to ask questions about the projects to be sized in advance (asynchronously), so that we can focus on sizing during the session. The following morning, the leader of the session posted some "retrospective" questions on slack to see which parts of the process were working and which were not. Based on one of the questions, I offered the suggestion that we timebox discussions during the sizing session (for example, stop all discussions after 10 minutes), and if at the end of our set discussion time we still feel that we're not ready to vote, we put that story aside for later. This suggestion seemed to be received well, and I'm hoping that we can implement it and that it helps us be more productive in our next sizing session.

There is still more sizing to be done (and I'm excited to participate in another session later this week), but I did learn some things about the process from this initial work. The biggest lesson I learned is that it's okay to attempt to size something even if I don't understand every detail of the story. Having a lot of context makes a big difference in my confidence level when choosing a size, but as long as I have a fairly basic overview of the story and what work it will entail, I can make an informed decision about the size I think best applies to the story. I also found that while the extended discussion of each story added context, it also made it difficult for me to follow along and I didn't really learn much more, so I'm hoping we can find the right balance in our discussions at the next session to ensure that the discussions are productive. My goal for our next sizing session is to feel confident asking questions if I feel that will better help me understand the context of the story. T-shirt sizing is not an exact science, but the more I know about each story, the more confident I will feel that the size I vote for is the correct size for each story.