Release lead reflection

I wanted to do a quick reflection after getting some time and space after being release lead for WordPress 7.1 in hopes of helping future release leads with the role. As part of this, I updated the WordPress Release Team and Focus Leads with the following for the Release Lead role:

• Set and share the overall focuses for the release balanced against available contributors. This takes the form of a combination of creating necessary trac issues and GitHub issues, culminating in a release roadmap on Make Core that is either written by the release lead or pulled together by someone working with the release lead.
• Review work in progress with the aim to remove blockers, manage scope, and keep work on track. This involves making little decisions, bringing in necessary contributors for feedback, and determining when something needs to be shared on Make Core for a broader audience.
• Make any big final decisions on feature readiness for the release, including whether to merge any feature plugins. Every decision needs to be clearly made in public and with reasons that future release squads can learn from.
• Align with project leadership as needed, especially around priorities and far reaching decisions.
• Support the release squad members in whatever they might need to do their respective roles to the best of their ability.
• Give final review to and publish the news blog post announcing the release. Previous ones can be found on this page for inspiration and context.

The tricky piece of this is that Matt has recently mainly been the release lead and he wears a million hats so the approach he takes is inherently different than for someone like me in the role with more time/capacity to give to it. I wrote the above assuming it’s for someone like me rather than for him. May a future release lead find it helpful.

How did I end up with this approach? I dug into both the history of the role as best as I could and my own lived experience of being on a release squad and seeing certain gaps. I found Release leads for WordPress 4.3 and 4.4 from Andrew Nacin from 2015 as the best lead (get it) for what the role likely entailed:

A release lead determines all important parameters for a release, like schedule, deadlines, which feature plugins are merged; and more generally, scope, goals, vision, and process. They take point when it comes to holding meetings, shepherding contributions, and writing announcement posts and updates. A release lead is a connector and facilitator, identifying bottlenecks and friction wherever they may be. They’re in frequent communication with the developers and plugin teams that are aiming to have something in a given release. The release lead follows what’s being committed, and sets the tone for prioritizing and gardening tickets. Given the constraint of time in hitting deadlines, help with prioritization and ensuring good communication lines are two of the most valuable things a lead can contribute.

In thinking of the gaps I try to fill with releases, that list covers the biggest items that I think can reasonably be done by one person. I went back and forth about whether to include a more detailed list (like reviewing every release related post) but I decided to stick with high level buckets for now. I also tried to leave breadcrumbs along the way on this site of how I approached some of these items and to make the specific items easier:

• Defining expectations for Iteration issues. This was done before I realized I would be release lead but the entire point is to make it easier to pull together roadmaps, follow major areas of work, know who is working on what, and understand when blockers are coming up for these pieces.
• Behind the scenes of a punted feature of 7.1. I shared this to give a sense of how I’d expect someone to be hands on out in the open for specific features when blockers arise and help both bring the right people in for feedback/help and offer solutions themselves.
• WordPress 7.1 Release Lead Decision Log. I recapped different kinds of decisions made during the cycle with links to where those same decisions were shared. I don’t think a release lead needs to recap high level decisions but I am hoping this serves as a good spread around the kinds of decisions that came up.

I want to pause to talk about this line: “Support the release squad members in whatever they might need to do their respective roles to the best of their ability.” I wasn’t quite sure how best to add this part in and I may go back to edit it later because this is one of the gaps I have felt most on releases. Building a culture and camaraderie is incredibly important. Every release and every release squad is different. Finding that different as early as possible is something I think a release lead should do. Do you have a giant, complex technical feature that’s slated for your release or do you have a massive spread of smaller areas of work that you need to tie in together? Do you have a release squad that’s roughly in a similar enough set of timezones or spread across the world? Do you have a very tenured release squad or mostly new folks? Have folks worked together before? All of these factors greatly impact how a release goes and how a squad can and needs to work together. This is no one’s job and everyone’s job but I think it should start with the release lead.

Speaking more personally, when we had to delay WordPress 5.9, it mattered immensely that there was shared psychological safety to speak up and make a sound decision. I was very nervous to do so at the time as it was my very first release squad and it was a massive decision but I also knew the items we were debating inside and out. After that experience and in thinking about the many sports teams I’ve been on, I realized it’s something to be intentional about. I ran two different calls to cover timezones for the release squad and did my best to check in with folks throughout both via DMs and in the channel itself. I still think I could have done more here and had a moment of wishing I wasn’t such an introvert so I could do calls with each person. As I said when announcing the calls themselves, I just know it helps a lot to hear someone’s voice and get a better sense of them long before any big decisions need to be made.

Let me know what else might be helpful to reflect on or share while my memory is still fresh (and 7.2 hasn’t taken over my life just yet).