Reflecting on My First Year in Management | by Christine Chapman | Oct, 2022

Tips and tricks for new engineering managers

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I never wanted to be a manager, but everyone always brought it up. In my first performance review, my manager suggested it as a possible career path, and when I changed teams, new managers would often ask if that was on my horizon. I remember being offended that it kept coming up because I thought it meant they saw me as more of a leader than a technical leader. I thought they were saying I wasn’t a good software engineer. I grew more and more adamant that I would never become a manager.

Looking back, I realize I made a few assumptions in these conversations. Back then, I believed:

  1. Managers are not as technical/respected as software engineers
  2. Once you become a manager, you can never go back to being a software engineer
  3. Being great at one thing means you’re inevitably worse at other things

In my experience, these statements are false or at least not always true, but I pushed back against becoming a manager because I believed them.

But over the next four years, I found myself increasingly drawn to manager-like activities:

  • Becoming the go-to person for interns who wanted to talk about team issues even when I wasn’t on their team
  • Mentoring several interns and software engineers and coaching peers to their first promotion
  • Creating team and office-wide process improvements
  • Caring a ton about retention and supporting team members to find a place at the company where they would succeed
Photo by Sincerely Media on Unsplash

Management still wasn’t on my radar until, one day, it was. I attended a panel at an internal conference about career paths in tech. One of the panelists had an identical path to mine. She had been an intern at the company and an engineer for about four years. Then, she transitioned to management, and after several years as a manager, she transitioned back to senior engineer. One of the moderators asked her the question that was on my mind:

“How did you transition from manager back to engineer, and senior engineer at that? Were you worried you may have lost the engineering skills?”

The panelist’s answer changed my whole career path:

“Why would you think I couldn’t go back to being an engineer? I had been an engineer for four years.”

A lightbulb went off in my head, and I realized I was holding myself back from considering management because of this fear that I could never go back once I left engineering. Why was I doing that? Of course, I would have what it takes to become an engineer again, I already was an engineer. If I could do my role today, I could definitely do my role again in a few years when I had more experience. Without this fear holding me back, I realized there was a lot to like about engineering management, and it seemed the next best step for me.

I returned from the conference and shared my plan with my manager. She was extremely supportive and shared that our team needed a new manager. After years of not considering it, my readiness and the opportunity aligned perfectly. It was October 2018, and by January 2019, I was managing a team of five.

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My first team had five engineers:

  • One SDE who has been on the team for more than a year
  • One SDE who had transferred from another team
  • Two new hires
  • One intern

Because the team was so junior, I served as the tech lead for the team’s first year. I reviewed most of the code reviews, advised the team on specific technical solutions, answered questions about the codebase, and helped the team debug issues. I knew this wasn’t sustainable in the long term and that I needed to build up those skills in the team, but for the short term, this allowed me to start managing while still helping the team grow. It helped that this new team owned features I had built as a software engineer, so I didn’t need to ramp up the codebase and learn to be a manager simultaneously. I recommend this approach whenever possible.

During this time, I said yes to every opportunity someone was willing to give me. I overly prepared for every 1×1 wanting to make the best impression on my new team. Urgent tasks came up for my team, and I struggled to know what was urgent and what was a lower priority.

My team ramped up to some new and ambiguous projects, I felt like I didn’t know the answer to anything, and I was suddenly responsible for people’s careers. It was intimidating. I felt a paralyzing need to be perfect, something I still struggle with today, and I was overwhelmed by the number of meetings. There was so much I needed to do and so little time. Looking back at my bullet journal from that time, I was doing way too much all the time. No wonder I was stressed. But I’m glad I invested the time in learning and embracing new experiences because it paid off later in the year.

What to expect in the first three months

  1. Feeling like a new hire again — You will go from an independent and dependable IC to someone who needs to always ask for help. You have so much to learn, and when your team asks you for help, you don’t know the answer off the top of your head. That’s ok.
  2. Impostor Syndrome — When you realize your peers are now other managers, many of whom have decades of management experience, it can be pretty intimidating. While some companies have a junior manager role, you are often at the same level initially as much more senior managers. Even though everyone was supportive and understood I was new, I remember feeling so stressed before my first few engineering manager meetings or when representing my team in big meetings. I wanted to do the job well, and I felt like I was already behind.
  3. Balancing technical lead work with management is tricky. It can feel like you never have time for code reviews, and you can be tempted to work long hours to keep up. As you grow, you will get better at prioritizing and delegation, and it won’t always feel this stressful.

Learning

During these first three months, I immersed myself in learning as much as possible. Here are my top recommendations:

Books

  • “The Making of a Manager” by Julie Zhuo— This was probably my favorite that I read during the transition.
  • “The Manager’s Path” by Camille Fournier — One line really resonated during the transition: “if your team needs a manager more than they need an engineer, you have to accept that being a manager means that, by definition, you can’t be an engineer.” This reminded me that while I was exploring management, I should commit fully to being a manager. Many will disagree, I’m sure, but this embodies the type of engineering management that I am drawn to, where you don’t let the technical work overshadow the people management work. It is important to give yourself time to manage and not just become an engineer with a manager title.
  • “Three Signs of a Miserable Job” by Patrick Lencioni (sometimes called “The Truth About Employee Engagement”) This is a super practical and interesting manager book because it’s told via a fable. This gave me a framework to apply in my early 1x1s. I took the three concepts of engagement and asked 1×1 questions that related to them, rotating to the next topic every week. It was nice to have a framework when I sometimes felt lost leading 1x1s.

LinkedIn Learning Courses

Advice for the transition

  • Leverage your strengths —At a time dedicated to being new and learning, remember that you still have so much to offer. Whether that’s knowledge of the company codebase, a deep network at the company, experience on another team, or even specific skills like empathy, attention to detail, organization, etc. Bring in those strengths even while learning. You will feel better, and others will benefit from your expertise.
  • Embrace the transition — You only get to be a new manager once. Embrace it, don’t resent it. This is your time to be new, to learn, and to ask for help unapologetically.
  • Get to know your team — If you don’t love your team and see the value in everyone you work with, what has this all been about? Get to know everyone on your team, ask lots of questions, learn what motivates them, what excites them, what frustrates them, and what they want to get better at. Find quick wins and long-term wins you can fight for that will improve their company experience. People commonly say once you become a manager, your team becomes your peer managers, but I disagree. Your team is your team, the people you manage. Don’t lose sight of that.
  • Stay true to yourself — It is tempting to become the version of manager most valued at your company. It is easy to mirror your favorite manager and replicate their approach. Don’t reinvent the wheel to be different, but remember that your company trusted you to become a manager because you have important skills to offer. They want you to be the best version of yourself as a manager. Even on your first day.
A few rocks in the ocean. I’m doing this. Right? What have I gotten myself into? Am I cut out for this? I have a lot more to learn.

Three months in, and everything was going great. I was an engineering manager. I had a good grasp of my team and the projects we were taking on. I led career conversations, estimated projects, and represented my team in meetings. Every day didn’t feel so challenging anymore. I was doing this. Then, with one giant, team-altering project, it all went downhill.

In retrospect, the problems were obvious from the start. I got too wrapped up in the exciting vision of this project, and I knew it would be a good learning opportunity for someone on my team who wanted a bigger challenge. I had to make this work. On the airplane home from an offsite meeting, I chatted back and forth with the lead for the project, estimating it together. Eight weeks for 1–2 engineers. Sure! I didn’t ask a lot of questions, I didn’t challenge assumptions, or dig deep into the estimates. I didn’t wonder if there were better or less risky ways to do this. The sizing worked well with our team’s capacity, and I left it at that.

When it was all said and done, it took 24 weeks and the entire team. We even had a few engineers from other teams join to get it over the line. Everyone was incredibly stressed. I was stressed, and rather than taking charge like a leader and pushing back on the deadlines, helping the team to break down the work, I kept asking for updates, and I ended up stressing the whole team out. Many people shared that I wasn’t giving enough positive feedback and that it felt like I only cared about the deadline. I was horrified; I had let everyone down. What a failure.

I almost quit management, thinking I was doing more harm than good and knowing I had messed up in a major way, not just because of the project delivery schedule but because I had failed to support the team in a difficult moment. If I wasn’t supporting my team, what had this all been about?

A friend talked me down from quitting by reminding me that I could improve. I took the time to reflect on how my actions had hurt the team and sincerely tried to improve and grow from the experience. Looking back three and half years later, this moment changed my whole approach to management, and I feel lucky that my team supported me despite the mistake.

I am glad this happened so early on, but at the time, it was so hard. Whether it’s at three months, six months, or one year, most new managers have a big moment of failure. My best advice is to approach the situation and feedback with humility, really consider what you did wrong, even if you think your intentions were positive, and learn and grow from the experience. After all, you’re still a new manager.

  • Give more positive feedback than you think and give feedback in the way the team members like to receive it
  • Triple-check estimates and account for things going wrong
  • Watch out for your strengths becoming a weakness. I was always very deadline-focused as an engineer, and one of my strengths is productivity/getting things done when I say I will. When I overvalue my strengths as a manager and only value when the team hits deadlines and not the other work that it takes to get to that point, I can create a stressful and, at times, toxic culture on the team. This can happen with almost any strength, and sometimes, the greatest challenge for us as managers is to manage people who are completely different from us.

What to expect in months 4–6

  • Delivery of key projects
  • Performance management
  • Writing your first promotion doc
  • Immigration/visa support for team members
  • Onboarding new team members
  • Hiring

Resources

People running a race. I’ve trained for this. There is a community here with me. One mile at a time. I am proud of what I’ve accomplished.
image from unsplash

Around six months, I had my first team member decide to leave the team. I helped her research teams throughout the transfer process and tried to be as supportive as possible, but I was sad that she was leaving. It was hard not to take it as a personal failure.

My team made progress on our roadmap. The project that had spiraled out of control eventually launched. We spent a few months fixing the tech debt we had accumulated, then ramped up for an international launch in eight countries. Before the end of the year, we had expanded the tool to cover new use cases for v2. It was satisfying; things were improving. Our work had paid off.

I started working more actively on promotion documents. By this time, I had a larger team, and a few were ready for SDE II. I was onboarding new team members, regularly giving positive feedback, and coaching team members to grow.

I was so busy, but a good level of busy. More manageable than it had been my first three months. Projects were often chaotic. I often left 1x1s knowing I should have done better, and I still relied on my manager for a lot, but I was an engineering manager. I had learned and grown so much in my first year.

What to expect

  • Larger challenges (people and project)
  • Increased scope
  • More independence
  • Defining and refining your management style
  • Retention becomes more important
  • Harder days and more rewarding days

Resources

  • Create or join a network of other engineering managers within your company and beyond. It’s important to have manager friends that you can be candid with and people who you can ask for advice. Being a manager can be lonely at times. Lean on your community.
  • Retaining Diverse Talent (my LinkedIn learning course) that covers manager fundamentals from the perspective of retaining women in tech.
  • Subscribe to changingthestory.org to be updated with my latest resources for managers.

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