Engineering Manager Forum

A long-time tenet of Squarespace's engineering culture is gathering to share knowledge and wins. These gatherings occur within formal organizational structures via All Hands meetings and team/organization demos, but also informally as independently organized meetings that bring together engineers across functional and technical disciplines. These independent meetings have grown in number over time, and now include Infrastructure Council, Backend Council, Data Council, and Frontend Forum. Although attendance is optional, the councils and forums offer a number of benefits to all who attend: public speaking opportunities, discussion about emerging technologies, and the opportunity to engage with coworkers whom you may not regularly work with. They've also spawned a number of Engineering Working Groups that have gone on to address significant cross-cutting engineering challenges.

As a long-time attendee of many of these meetings, I've experienced first hand how effective they are at creating a sense of togetherness across an ever-growing engineering organization. Coordinated by groups of dedicated volunteers, their lack of ties to formal organizational hierarchy opens the door for more engagement across a larger group of people. Presentations don't have to center on things happening at work - they can be about learnings from interesting side projects, or conference recaps, or just open questions that someone wants to bring to the floor. The outcomes are less about polish and information dispersal than discussion, learning, and fostering community.

In April 2021 I began drafting a document proposing a new forum: Engineering Manager (EM) Forum. While I will always enjoy deep dives into interesting technologies, I was several years into being firmly on the engineering management track. As a result I found myself often in a different headspace than I was as an individual contributor. Rather than thinking about the JavaScript zeitgeist, I was now reading and thinking about topics like determining priorities for quarterly planning and trying to maintain a healthy team in the midst of humanity-wide COVID burnout. And based on a series of 1:1s with peers on the management track, I knew I wasn't alone.

In the original proposal, I outlined some of my motives for EM Forum.

Management can be a lonely job

Management is a position of formal authority, and that distinction in role can feel isolating. In my personal experience, my day-to-day concerns as an individual contributor and engineering manager are completely different. Although both roles are ultimately about shipping great software, as a manager I am much more concerned with team health, culture, and strategic direction. As a result I am less likely to participate in everyday team activities like pull request review or pair programming, and the challenges I'm most deeply concerned with are outside of the scope of my teammates' concerns.

Unless I am lucky enough to work closely with managers of adjacent teams, it can feel difficult to find someone to discuss the challenges of management and leadership. And since COVID work from home began, it's become even more difficult to serendipitously strike up conversations with coworkers from other parts of the organization. An open-invite meeting to all engineering managers could be the forcing function to begin having those discussions.

Company growth can be hard to grok

Commensurate with our company growth, we’ve grown our engineering manager headcount dramatically within the last two years, both via outside hiring and internal promotion. Consequently the topology of the engineering organization continues to change over time. While reference documents exist that explain the current state of the organization, I've always valued hearing directly from engineering leaders about the mission, challenges, and wins of their teams.

The success of engineering manager roles requires cross-functional collaboration, but building organizational context and a network takes time. Meeting 1:1 with every other engineering manager on a regular cadence is impossible at our size. Presenting about your team during EM Forum could serve as the soft introduction that makes follow ups from coworkers easier.

As an additional benefit, EM Forum could be a place where new managers are introduced to the organization instead of trying to build their networks from scratch.

The collective voice of engineering managers is unique and valuable

As the layer of management closest to implementation, engineering managers are the first managers to hear about the blockers and frustrations of their teammates. Their perspectives are unique in that they encompass both people and technology problems. Not only do engineering managers hear about technical concerns with shared services like development environments or platform tooling, but they're also the first to encounter process and people problems like gaps in documentation, issues with shared third party tools (expense tracking, project management, etc.), or burnout.

More so than any other level of the management chain, front-line engineering managers are the most attuned to the day-to-day realities of shipping software. Giving them a collective voice to surface what works and what doesn’t is critical to understanding the efficacy of organizational policy and process.

In May 2021 I completed my proposal and distributed it for feedback. Within that feedback cycle we decided on a few guiding principles:

1. EM Forum is limited to those on the engineering management track.

2. EM Forum must practice good meeting hygiene. Manager calendars are already pressed for time so it’s critical that this meeting is high-signal. And as managers we must be able to run an effective and timely meeting.

3. EM Forum must be a meeting conducted in good faith. We can discuss uncomfortable topics, but we do so professionally and respectfully.

After a few rounds of comments and a full agenda (due to the willingness of a few courageous peers), the first EM forum - EM Forum #001 – was scheduled in June 2021 with 75 engineering management coworkers on the invite. Since #001 we’ve continued to iterate on the format, structure, and timing of the meeting content.

While we have yet to hold many sessions (and a meeting across all engineering managers within global time zones is extremely difficult to schedule), I’m pleased to report that EM Forum averages a consistent attendance of roughly 50% of possible attendees (~35 participants). I’ve particularly enjoyed a few outcomes:

• The opportunity to hear from managers of teams that I’m unlikely to interact with on a day-to-day basis gives me a greater appreciation of the full breadth of our company’s work.

• An extended discussion in August about how we were managing a sense of COVID burnout, both personally and on our teams, resulted in a set of crowd-sourced recommendations to teams (e.g., a “temperature check-in” before meetings, creating handoff documents for responsibilities before taking PTO).

• A one-slide, voluntary introduction for new managers is a positive, low-effort way to welcome new hires.

EM Forum #005 is now scheduled for January 2022. Overall the feedback has been enormously positive amongst participants, and it's built a sense of community among the engineering management ranks that didn't exist previously.