Updated: Work at different management levels

Originally posted Jul 23, 2019

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“As a leader, your job should change every six months even if you stay put.” —Cate Huston

In 2016, I published a blog post titled “Work at different management levels”, which was about how my work drastically changed over time as a manager, whether it was because of my team’s growth, my own growth, or the company’s growth.

What I did day-to-day changed, what was hard about it changed, and how I measured my own success changed. Though these experiences built upon one another, it was an enormous shift in brainpower each time these changes happened. So, given how intangible (and often hidden) management work can be, I wrote that blog post to shine a light on how this work evolves.

It’s been making the rounds recently, so I’ve dedicated this newsletter to iterate on it—complete with PLENTY of additional resources and things to try if you’re finding yourself bumping into the same hurdles and changes.

—Lara

P.S. An 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 individual contributors

My first three management roles were managing a single team of developers, ranging between three and seven engineers on the team. Most of the teams were already formed when I became their manager.

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. (Pro tip: if you’re a hiring manager, follow these tips for setting expectations with your team, and working with a recruiter!)
• 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. (Camille Fournier wrote about these in The Manager’s Path)
• 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). (Pro tip: practice roleplaying these conversations in manager meetings!)
• How to have less stilted one-on-ones. (Pro tip: use my First 1:1 Questions!)
• How to tweak my management style to better-fit a direct report’s personality or management needs. (Pro tip: use those same 1:1 questions to know HOW you should tweak your approach!)
• How to navigate politics between different organizations, and how to effect some change without having a lot of authority. (Read Switch by Chip and Dan Heath if you’re currently wrestling with this!)

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. (Here’s a blog post I wrote about making this transition, and why I found it so different than managing ICs. If you’re not sure how to do this well, learn about how to be a good sponsor.)
• 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. (Pro tip: do some work before, during, and after your meetings to make them WAY better!)
• 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. (Pro tip: defrag your calendar!)
• “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. (Pro tip: experiment with these other approaches and styles, and see what works for you!)

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. (Again, if you haven’t tried this already, defrag your calendar!)

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.

For each of the skills listed next, I realized I was referencing back to a ton of stuff I wrote in Resilient Management. Specifically:

• The “Grow Your Teammates” chapter to help you hone your coaching skills (you can also read this part of the chapter as a free excerpt here!)
• The “Communicate Effectively” chapter for more on how to announce reorgs and other kinds of big scary changes, and how to develop talking points
• The “Build Resiliency” chapter as well as the Conclusion for more on how to survive with these kinds of stretchy growth seasons So definitely grab the book if you’re currently wrestling with any of the following skills!

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.

“Senior skills”

When I coach senior managers and directors, there a couple of skills that come up as more clearly senior manager skills, rather than new manager or mid-level manager skills:

• Comfort working within ambiguity, and creating clarity for your team when none is given to you from above
• Comfort setting direction, without waiting for a strategy or vision to be handed down to you
• Making impossible calls, where there’s no obvious right answer, and folks’ livelihoods might be at stake
• ‘Being more strategic’, which could mean so many different things, in different organizations, and to different people. Usually, this means you have a hand in setting the future vision for your organization. (This could be about the organizational design, product roadmap, business goals and objectives, how everyone works together, etc.)

If you’re tasked with doing some of these things, and are finding it challenging or frustrating, GREAT. That’s a signal that you’re in a growth stage!

If you haven’t started practicing these skills, but are looking to continue to grow as a manager and as a leader, find some opportunities to practice and develop these muscles. This exercise will pay off in the future.