Work at different management levels

I remember working as a developer at a company and complaining that I had no idea what the bosses did all day. It felt like while we engineers were working hard and shipping stuff, managers just talked to a lot of people all the time, or sat in their offices behind closed doors, and I had no idea what their work looked like.1

I find that when someone switches from individual contributor (IC) work to management, it’s a huge shock to the system. Managering is so weirdly different: a different skill set to grow, a less tangible way of measuring success, and a kind of work that’s often so intangible that it doesn’t feel like “real” work.

I’ve had the privilege of experiencing a few different management levels (responsibilities? jobs?) at Etsy since I’ve joined. At each stage, I felt like the job of being a manager totally changed. What I did day-to-day changed, what was hard about it changed, how I measured my own success changed, and though I feel like the experiences built on one another, it continues to be an enormous shift in brainpower each time the gig changes a bit.

Given how intangible (and often hidden) management work can be, I’ve outlined some highlights of what my work has been like as a manager over the last four years. (Obvious, major caveat: this is just my experience, and there’s lots in here that is unique to this particular work environment, hierarchy, requirements, and challenges!)

1 One thing I've found helpful to combat this as a manager is to be super transparent about what my days and weeks look like to my teammates. During a show-and-tell meeting, I'll talk about what's on my mind that week, or show a Google doc I'm writing, or even just a calendar invite I made. It helps to demystify what the role is, and if I'm lucky, it does something to help folks value the different kind of work managers do.

Managing a team of individual contributors

My first two roles at Etsy were managing a single team of developers, ranging between three and seven engineers on the team. The first team was started from scratch before I got there, and the second team (which I started managing after the first one disbanded, for strategic reasons) I inherited from another manager who was moving into his next role - growing a new team.

IC work: During this time, I still shipped a little production code here and there.

1:1s: I had hour-long 1:1s with my direct reports weekly.

New skills acquired:

What I was accountable for: my reports’ growth, and the visible output of the team.

My favorite responsibility: During this time, I started coaching new managers, and implemented someone else’s idea (that they didn’t have time to do, and were cool with me running with it) to create a roundtable for new managers at Etsy to talk to each other.

Hardest part of the job: Learning how to emotionally survive incredibly challenging stretches of time with a particular report.

Managing a team of ICs, and also some managers

Eventually, in addition to managing a team of engineers, I started to manage a manager or two of related teams. The sizes of these teams were all generally still relatively small (fewer than 5 engineers per team).

IC work: I wrote some code that made it to internal dashboards once in a while.

1:1s: Weekly, hour-long 1:1s with everyone who reported to me. Skip-level 1:1s for an hour every two weeks with people reporting to the managers who reported to me.

New skills acquired:

What I was accountable for: my direct reports’ growth, my direct team’s visible output, and checks/balances so that the managers who reported to me were keeping their teams healthy and delivering.

My favorite responsibility: Running show-and-tell for more than just the people who report directly to me. I started to realize the huge value of having face time with everyone in one room. Bootcampers, people from other teams, and sometimes senior leaders would join occasionally. Also, people laughed a lot during this meeting; it felt like we were really building something amazing together.

Hardest part of the job: That context switching between managing ICs and managing managers. For one, your brain is focused on team context; you’re talking about code debugging or how to better surface the work that the team is doing to the large org. For the other, your brain is focused not on team mission or delivering on that, but much much more about the human stuff that you only tangentially have an impact on – you need to coach this manager through it, and help them do it on their own. I found switching between the two brains really hard.

Managing just managers, and eventually, an identifiable group of teams

“Identifiable group of teams” happened for me when I had a handful of teams who reported in to me that felt closely aligned in their missions (Performance, Front End Infrastructure, and the App Training team). We originally called this “lhogan-org” for convenience, and then as it grew it got a much better name, “UX Infrastructure”.

IC work: hahaha

1:1s: Hour-long weekly 1:1s with my direct reports, all managers. Hour-long skip level 1:1s with their reports, at first every two weeks, then every three, then every four as the teams grew. At some point I think I also shortened them to a half-hour for skip levels. By the time we hit 30+ people in the organization due to inheriting some teams from folks who left, I switched skip-levels to be every eight weeks.

New skills acquired:

What I was accountable for: all the above, plus: strategy and vision for the group of teams, pitching in with other related orgs’ strategy and vision needs.

My favorite responsibility: There was something magical about the moment when I realized there was a cohesive idea surrounding this group of teams - the moment it really felt like an organization. It felt like I was helping to support this group of people in doing their strong work, all together. I started to feel much more like I had moved into a facilitation role, where my work was to create a space so that folks in the org could kick ass, have an impact, get recognition. (It’s tricky to talk about this shift; I’d previously been known for doing A Thing whether it was perf or the new manager roundtable or whatever. But at this stage, my work became so much less visible, and I think that’s right.)

Hardest part of the job: At this point, I found myself in new kinds of meetings, meetings with people more senior to me who were going through challenges I hadn’t seen before. It was really hard to figure out how to contribute or help without looking like a total n00b. This more than anything in recent memory pushed me well out of my comfort zone and forced me to grow up a lot as a leader.

Further growth

More recently, I’ve started managing a group of teams that contains groups of teams. (“Product Infrastructure” is made up of eight teams, between “Pipeline Engineering” and “UX Infrastructure”.) These days, I rely heavily on communication with all my managers at once (whether via email or in a meeting). I also rely heavily on the folks running those orgs within the larger org - talking with them way more often.

I think at each stage, I’ve “sat at the table” differently in large meetings with senior managers+. I remember very clearly moments of raising my voice differently than in previous roles - more loudly, or more confidently, or more confidently saying that I don’t at all understand what’s happening. I’m more comfortable vocally disagreeing in real time (rather than doing a lot of side chats or iterating on my words before gaining the confidence to speak them).

I’ve also found myself more often saying “no” to second-shift diversity work when I don’t have the energy for it.

A really cool thing about these stages is that getting out of the way, giving away your legos, means that you get to see some really fucking amazing people nail it. You see the whole thing - from the time when they sucked at a part of the job through the time when they are the go-to person for it. You have the privilege of talking to them behind closed doors about how they’re feeling and what a challenge it is they’re dealing with. No one else gets to see how far they’ve come, really, because they can’t see all those moments of defeat and struggle and sometimes anger and tears and all. I can’t describe what an honor this is. To be trusted with someone’s super honest moments and then to see them totally succeed, all on their own. Most of my job these days is just listening to people and asking them open questions to help them figure out what they already know to do, deep inside. It’s unreal.

The hardest bit of all? People say that growth is beautiful. We all want to grow! We use such positive language about it! But in the last year or so, my leadership coach and I started to talk a lot about how growth is awful and painful and hard. Caterpillars are gross and goopy in that cocoon before they emerge as butterflies. I’ve been in and out of that gross painful goopy stage a lot this year. I’m looking forward to a lot more of this.

Lara Callender Hogan

I'm an Engineering Director at Etsy and the author of Designing for Performance, Building a device lab, and Demystifying Public Speaking. Follow me on Twitter, read my blog.

I champion performance as a part of the overall user experience, help people get comfortable giving presentations, and believe it's important to celebrate career achievements with donuts.