Why Should You (Or Anyone) Become An Engineering Manager?

The first piece I ever wrote about engineering management, The Engineer/Manager Pendulum, was written as a love letter to a friend of mine who was unhappy at work. He was an engineering director at a large and fast-growing startup, where he had substantially built out the entire infrastructure org, but he really missed being an engineer and building things. He wasn’t getting a lot of satisfaction out of his work, and he felt like there were other people who might relish the challenge and do it better than he could.

But also, it was a lot to walk away from! He had spent years building up not only the teams, but also his influence and reputation. He was used to being in the room where decisions get made, and didn’t want to take a huge step backwards, or recede into the woodwork. He agonized over this for a longtime (and I listened over many whiskeys).

To me it seemed obvious that his power and influence would only increase if he returned to engineering and the kind of problems he was excited about. You bring your credibility and your relationships along with you, and enthusiasm is contagious. So I wrote the piece with him in mind, but it must have struck a nerve; it is still the most-read piece of writing I have ever written.

That was six, nearly seven years ago. For much of that time, anything I said or wrote about management seemed to come out with a heavy subtext of, “MANAGEMENT SUCKS!! You will be happier as an engineer!!! Go back to engineering!”. I go back and read some of those pieces now, and the pervasive anti-manager slant actually makes me a little uncomfortable, because the environment has changed quite a lot since then.

Miserable managers have miserable reports

Ten years ago, it seemed like there were a lot of unhappy, resentful people in management. Most people became managers for reasons like,

• It was seen as a promotion, and was the only form of career progression available at many places
• Managers made a lot more money
• It was the only way to get a seat at the table, or be in the loop
• They were tired of taking orders from someone else

But over the last few years, we’ve seen a lot of change. The emergence of staff+ engineering has been huge (two new books published in the last five years, and at least one conference!). The industry has broadly coalesced around engineering levels and the existence of a parallel technical leadership track.

We’ve learned more about how fragile command-and-control systems are, and that you want to engage people’s agency and critical thinking skills. You want them to feel ownership over their labor. Building software is not typically a job where you can just clock in, churn through some tasks on autopilot, and clock out. (Well.. some jobs may exist like that, but not the ones I’m talking about.) Furthermore, our systems are becoming so complex that you need people to be emotionally and mentally engaged, curious, and continuously learning and improving, both individually and as teams.

I tell people all the time that you can do most of the "fun" management things (mentoring, coaching, watching people grow, contributing to decision making) as an IC without doing all the terrible parts of management (firing, budgeting, serious HR things).

— Jill Wetzler (@JillWetzler) September 5, 2019

At the same time, our expectations for managers have gone up dramatically. Google kicked off an important conversation and awareness by publishing their research findings about the importance of psychological safety. We have all become more aware of the damage done by shoddy managers, and we expect managers to be empathetic, supportive, as well as deeply technical. Engineering management isn’t just a people problem; it’s about building, tuning, and improving sociotechnical systems using people-first tools. It’s about coordinating between teams and improving how the team operates. All this makes management more daunting.

So there was already a bit of a drift away from management as the default career path for ambitious engineers, towards staff+ engineering.

And then came the pandemic, which caused managers (poorly supported, overwhelmed, bearing the brunt of unrealistic expectations on both sides) to flee the profession in droves.

These days, management seems a lot less attractive. It’s getting harder to find engineers who are willing to give it a try, or who see any reason why they should. On the one hand, it is fucking fantastic that people aren’t being driven into management out of greed, rage, or a lust for power. It is WONDERFUL that people are finding engineering roles where they have autonomy, ownership, and career progression, and where they are recognized and rewarded for their contributions.

On the other hand, engineering managers are incredibly important and we need them. Desperately.

Good engineering managers are force multipliers

A team with a good engineering manager will build circles around a team without one. The larger or more complex the org or the product, and the faster you want to move, the more true this is. Everybody understands the emotional component, that it feels nice to have a competent manager you trust. But these aren’t just squishy feels. This shit translates directly into velocity and quality. The biggest obstacles to engineering productivity are not writing lines of code too slowly or not working long hours, they are:

• Working on the wrong thing
• Getting bogged down in arguments, or being endlessly indecisive
• Waiting on other teams to do their work, waiting on code review
• Ramping new engineers, or trying to support unfamiliar code
• When people are upset, distracted, or unmotivated
• Unfinished migrations, migrations in flight, or having to support multiple systems indefinitely
• When production systems are poorly understood and opaque, quality suffers, and firefighting skyrockets
• Terrible processes, tools, or calendars that don’t support focus time
• People who refuse to talk to each other
• Letting bad hires and chronic underperformers stick around indefinitely

Engineers are responsible for delivering products and outcomes, but managers are responsible for the systems and structural support that enables this to happen.

Managers don’t make all the decisions, but they do ensure the decisions get made. They make sure that workstreams are are staffed and resourced sufficiently, that engineers are trained and improving at their craft. They pay attention to the contracts and commitments you have made with other teams, companies or orgs. They advocate for your needs at all levels of the organization. They connect dots and nudge and suggest ideas or solutions, they connect strategy with execution.

Breaking down a complex business problem into a software project that involves the collaboration of multiple teams, and ensuring that every single contributor has work to do that is challenging and pushes their boundaries while not being overwhelming or impossible… is hard. Even the best leaders don’t get it right every time.

In systems theory, hierarchy emerges for the benefit of the subsystems. Hierarchy exists to coordinate between the subsystems and help them improve their function; it is how systems create resiliency to unknown stressors. Which means that managers are, in a very real way, the embodiment of the feedback loops and meta loops that a system depends on to align itself and all of its parts around a goal, and for the system itself to improve over time.

For some people, that is motivation enough to try being a manager. But not for all (and that’s okay!!). What are some other reasons for going into management?

Why should you (or anyone) be a manager?

I can think of a few good reasons off the top of my head, like…

• It gets you closer to how the business operates, and gives you a view into how and why decisions get made that translate eventually into the work you do as an engineer
• Which makes the work feel more meaningful and less arbitrary, I think. It connects you to the real value you are creating in the world.
• Many people get to a place in their career where they feel a gravitational pull towards mentorship. It’s almost like a biological imperative to replicate yourself and pass on what you have learned to the next generation.
• Many people also get to a point where they develop strong convictions about what not to do as a manager. They may feel compelled to use what they’ve learned to build happy teams and propagate better practices through the industry
• One way to develop a great staff engineer is to take a great senior engineer and put them through 2-3 years of management experience.

But the main reason I would encourage you to try engineering management is a reason that I’m not sure I’ve ever heard someone cite in advance, which is that…it can make you better at life and relationships, in a huge and meaningful way. Work is always about two things: what you put out into the world, and who you become while doing it.

I want to stop well short of proclaiming that “being a manager will make you a better person!” because skills are skills, and they can be used for good or ill. But it can.

It’s kind of like choosing to become a parent. You don’t decide to have kids because it sounds like a hoot (I hope); you go into it knowing it will be hard work, but meaningful work. It’s a way of processing and passing on the experiences that have shaped you and who you are. You also go into the role understanding that it will change you — it changes who you are as a person, and the relationships you have with others. You can’t spend a third of your life performing a role without it shaping you in return.

From the outside, management looks like making decisions and calling the shots. From the inside, management looks more like becoming intimately acquainted with your own limitations and motivations and those of others, combined with a lot of systems thinking.

Yes, management absolutely depends on higher-level skills that you can learn, like strategy and planning, writing reviews, mediating conflict, designing org charts, etc. But being a good manager — showing up for other people and supporting them consistently, day after day — rests on a bedrock of some much more foundational skills.

The kind of skills you learn in therapy, not in classes

Self-regulation. Can you take care of yourself consistently — sleep, eat, leave the house, socialize, balance your moods, moderate your impulses? As an engineer, you can run your tank dry on occasion, but as a manager, that’s malpractice. You always need to have fuel left in the tank, because you don’t know when it will be called upon.

Self-awareness. Recognizing your own feelings as you are having them, identifying them, unpacking where they came from, and deciding how to act on them. It’s not about clamping down on your feelings and denying you have them. It’s definitely not about making your feelings into other people’s problems, or allowing your reactions to create even bigger problems for your future self. It’s about being informed by your emotional responses without being ruled by them.

Understanding other people. You learn to read people and their reactions, starting with your direct reports. You build up a mental model for what motivates someone, what moves them, what bothers them, and what will be extremely challenging for them. You develop a complex map of how much you can trust each person’s judgment in any given situation.

Setting good boundaries. Where is the line between supporting someone, advocating for them, encouraging them, pushing them … but not propping them up at all costs, or taking responsibility for their success? How is the manager/report relationship different from the coworker relationship, or the friend relationship? How do you navigate the times when you have to hold someone accountable because their work is falling short?

Sensitivity to power dynamics. Do people treat you differently as a manager than they did as a peer? Are there things that used to be okay for you to say or do that now come across as inappropriate or coercive? How does interacting with your reports inform the way you interact with your own manager, or how you understand what they say?

Hard conversations. Telling people things that you know they don’t want to hear, or things that will make them feel afraid, angry, or upset; and then sitting with their reactions, resisting the urge to take it all back and make everything okay.

The art of being on the same side. When you’re giving someone feedback, especially constructive criticism, it’s easy to trigger a defensive response. It’s so easy for people to feel like you’re dumping on them. But the dynamic you want to foster is one where you are both side by side, shoulder to shoulder, facing the same way, working together. You are giving them feedback because you care; feedback that could help them be even better, if they agree and accept it. You are equal actors, if not peers; they always have agency.

Did you learn these skills growing up? I sure as hell didn’t.

I grew up in a family that was very nice. It was very kind and loving and peaceful, but we did not tell each other hard things. When I went off to college and started dating, I had no idea how to speak up when something bothered me. There were sentences that lingered on the tip of my tongue for years but never made it out. And if somebody raises their voice to me, to this day, I start to crumble and fall apart.

I also came painfully late to developing a so-called growth mindset. This is super common among “smart kids”, who get so used to perfect scores and praise for high achievements that any feedback or critique feels like failure, and failure feels like the end of the world.

It was only after becoming a manager that I had to practice things like giving and receiving feedback, or initiating hard conversations. I had to. And once I did, it started getting easier. Fast.

Turns out, work is actually kind of an ideal sandbox for practicing life skills, because the social contract is more explicit. These are structured relationships, with rules and conventions and expectations, and your purpose for coming together is clear: to succeed at business, to finish a project, to pull a paycheck. Even the element of depersonalization can be useful: it’s not you-you, it’s the professional version of you, performing a professional role. The stakes are lower than they would be with your mother, your partner, or your child.

You don’t have to be a manager to build these skills, of course. But it’s a great opportunity to do so! And there are tools — books and classes, mentors and review cycles. You can ask for feedback from others. It’s expected in this role.

The last thing I will say is this — technical skills do decay and become obsolete, particularly language fluency, but people skills do not. Once you have built these muscles, you will carry them with you for life. They will enhance your ability to connect with people and build trust, to listen perceptively and communicate clearly. Whatever you decide to do with your life, they will increase your optionality and make you more effective.

That is why I think you should consider being an engineering manager. Like I said, I’ve never heard someone cite this as their reason for wanting to become a manager. But if you ask managers why they do it five or ten years later, you hear a version of this over and over again.

One cautionary note

As an engineer, you can work for a company whose leadership team you don’t particularly respect, whose product you don’t especially love, or whose goals you aren’t super aligned with, and it can be “okay.” Not terrific, but not terrible.

As a manager, you can’t. Or you shouldn’t. The conflicts will eat you up inside and/or prevent you from doing excellent work.

Your job consists of representing the leadership team and their decisions, pulling people into alignment with the company’s goals, and thinking about how to better achieve the mission. As far as your team goes, you are the face of The Man. If you can’t do that, you can’t do your job. You don’t get to stand apart from the org and throw rocks, e.g. “they told me I have to tell you this, but I don’t agree with it”. That does nothing but undermine your own position and the company’s. If you’re going to be a manager, choose your company wisely.

charity

P.S. My friend (from the start of the article) went back to being an engineer, despite his trepidation, and never regretted it once. His career has been up and to the right ever since; he went on to start a company. The skills he built as a manager were a huge boost to an already stellar career.