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.

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!)

• Managing a team of ICs
• Managing ICs and managers
• Managing just managers
• And so on

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:

• I’d hired folks at a previous job, but working with recruiters and more process for onsite interviews was new to me.
• How to write a performance improvement plan. And how to help a direct report improve when they don’t immediately see what the problem is.
• How to terminate an employee, and through this process, also learned how to roleplay these kinds of difficult conversations (which is a skill I’ve used a LOT to help other managers through this).
• How to have less stilted one-on-ones.
• How to tweak my management style to better-fit a direct report’s personality or management needs.
• How to navigate politics between different organizations, and how to effect some change without having a lot of authority.

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:

• Managing managers. It’s entirely different than managing ICs, to me. Especially managing people who are new to management.
• Iterating on team meetings. I learned a lot about how to routinely check in on and improve standing meetings to keep them interesting, make sure they’re still valuable, or just proactively kill them.
• Taking better control of my calendar. I noticed that my brain was being way too drained when I switched back and forth between talking with ICs about their work, and talking with managers. So I started to group stuff together better, or at least gave myself more space to breathe between context switching.
• “Giving away my Legos.” Gosh, I loved managing the Performance team. I loved building the device lab. I loved running the new manager roundtable. I learned how to step away from the things I had grown and adored, to create more leadership opportunities for others. To help them have space to make it their own, and make it even better.
• Being vulnerable with people who don’t report to you, like in skip-level 1:1s. Figuring out what it means to be transparent and honest and human while also trying to be a leader.
• Trying out new leadership styles that aren’t the one I was born with. I started to watch and try on styles of other people I work with - and then I started to figure out the situations in which those alternate styles are more effective.

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:

• Strategy and vision-setting. I still remember how much of a challenge and shift this was from me. I had felt so strong about my management skill sets, executing other people’s visions. It was super hard to try and develop my own thoughts on strategy.
• Coaching managers through their own iterating on team meetings and other processes.
• Being okay with not being the go-to Performance person anymore. Being okay with turning down speaking opportunities and other thought leadering (heh) because my day job wasn’t even close to the work that I was known for anymore.
• Eventually, strategy and vision-setting that saw past 6 months. Coaching teams within my organization to do their own strategy and vision-setting. I started to be able to see the forest for the trees.
• Reorgs. The lessons in this probably warrant their own post.
• Developing talking points for my reports to share. I started to rely more than ever on managers to communicate to everybody, and it’s really hard to get folks to say effectively the same things in a way that effectively everyone hears them similarly.
• Getting comfortable talking in terms of my own failure. Previously, I used language about failure that put a more positive spin on it - I couldn’t help but see only “opportunities for improvement” or other silver linings. But sometimes, failure is just failure. I got more comfortable with this idea.

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.