Reluctant Leadership
My haphazard journey from maker to manager
About two years before accepting a role as an Engineering Manager, I was sitting in my boss’s office in a 1:1, just chatting. Our working relationship was a uniquely easy one, as far as bosses go, with him serving as both mentor and listening ear. But when he asked me if I’d be interested in management one day, I gave a nervous laugh. Surely, he was joking.
He wasn’t.
At the time I was a developer. And not even a very good one, either. I was just sort of…okay. It always felt like it took me twice as long to understand something. I slowed my team members down, asked them to repeat words or sentences, asked them to draw out their ideas on a whiteboard so that I could understand the things that seemed obvious to everyone else. It was a gift, being surrounded by brilliant people who challenged me to grow. But it was also a constant reminder of how much I had to learn.
It was a gift, being surrounded by brilliant people who challenged me to grow. But it was also a constant reminder of how much I had to learn.
My peers happily supported the decision to make me the Team Lead, but I figured that this had more to do with the fact that I could talk PMs off of ledges and calm a chaotic meeting (most of the time) than with my technical ability as a developer. I “spoke manager” and could bridge the distance between a frustrated executive and a bemused engineer. I could be an impartial moderator and occasional referee in a spirited debate.
I did the dirty work, the kind of communication and coordination that many of my peers found tedious and distracting. Intentionally wedging myself between engineers and external stakeholders, I negotiated with each side, a job that seemed necessary but not especially difficult. When my team had technical questions, they usually passed by my desk without comment, heading straight to our most senior engineer — the actual technical expert on the team.
I wasn’t the one to perform the kind of heroics that I saw from the rest of my team. Things like spotting the needle-in-a-haystack production bug, navigating JavaScript idiosyncrasies, or reviving an environment from the grave. Instead, I fielded Jira comments from PMs, wrote documentation, attended client calls, enforced processes and boundaries, and coordinated meetings. Easy, boring stuff.
Not only could I not imagine myself being good at management, I couldn’t imagine enjoying it, either. Though I didn’t mind my role, some days I lived for the breaks between emails and meetings. I walked the line of maker/manager and experienced all of the pain that comes with not choosing a side. But the benefit was that I didn’t have to relinquish my keyboard just yet.
Near the end of my time as a Team Lead, it wasn’t uncommon for me to finish fewer than 5 points per sprint. But I lived for those 5 points. Some weekends, I went home and combed through our backlog, trimming low-hanging fruit and submitting my PRs on Monday morning. There, I would think as I pushed another one-line change. At least I’m not totally useless.
In private, my manager reminded me to take a seat at the table — metaphorically and literally. The thought of doing so made my stomach hurt.
It probably didn’t help that I felt so completely out of place among the other leads. I spent a lot of time being the only woman in the room, but I was accustomed to that. It was my age and experience level that I couldn’t stop worrying about. At 24, I was the youngest lead at the company. I wasn’t formally educated, nor did I have the kind of domain expertise that seemed effortless and natural in other leads. I’d been at the company for six months when I’d been selected as a lead, and had been in full-time development for a little over a year. It was no surprise that I regularly looked around the room in meetings and wondered, why I am here..?
My gender, on the other hand, just felt like a burden. It carried with it an unspoken pressure, the source of which I’m still trying to locate. Thoughts would run through my mind during the day. You’re the only female engineering leader at this company. When you screw up, you’re confirming the stereotypes. You’re making us look bad. You’re letting us all down. Try harder. Work faster. Do more. It was bad. Selfishly, I was relieved when another female leader joined our company. The pressure was off. At least, kind of.
Every day, I was painfully aware of the fact that I was an unconventional choice for leadership — and that not everyone agreed with that choice. I was uncomfortable with the leadership that I’d taken on so far, and it showed in the way that I presented myself. I was embarrassed. Occasionally my manager or my team would applaud my work in a meeting and my face would burn red. I wanted to sink into the floor. I’d shrug off compliments and change the subject, talking about the external team who helped us, the UX designers, or the developers themselves. Anything to stop talking about me.
In the beginning of my first Lead role, whenever I entered rooms, I hovered around the edge. In private, my manager reminded me to take a seat at the table — metaphorically and literally. The thought of doing so made my stomach hurt. But I faked it, fighting to keep my voice steady and strong when speaking, clasping shaking hands in my lap underneath conference tables, forcing myself to ask or say at least one or two things per meeting — not so that I sounded smart or important, but so that I didn’t allow myself to fade completely into the background.
When you operate from a place of insecurity and fear, every little negative thing is amplified.
In those days I voiced my opinions as though I was flinching, waiting for something to strike me. Waiting for someone to call me out for the pretender that I was.
And I was called out, in a way. Not to my face. But things got back to me. I was under-qualified. Management was playing favorites. And the one that bugged me most, I was a diversity initiative and a token.
These voices were small and for every negative one that I heard, there were ten cheerleaders in my corner, expressing their appreciation for my work. Still, I couldn’t get it out of my mind. When you operate from a place of insecurity and fear, every little negative thing is amplified.
But I took comfort in the fact that, at the end of the day, I wasn’t in charge. Internal to the company, I was a Team Lead, which had been explained to me as a designation and not a title, a list of responsibilities but not final authority. There was something liberating in knowing that. That if things were on fire, my manager was the last stop, not me. There was still a safety net. I told myself I wasn’t acting as a leader. I was more like a go-between. Just a chaos coordinator who went to some extra weekly meetings.
So when my boss first asked me if I was interested in management, I think I shrugged and gave a noncommittal answer. Maybe. Not now. Someday. I don’t know. But internally, the answer was a resounding no.
Over the next year and a half, that answer became less certain, until eventually I was admitting — reluctantly so — that I’d like to be considered for management opportunities. Admitting that I wanted this opened me up to a new set of standards and feedback. It meant raising the bar. And it meant wondering, if I was promoted, what theories some people might have to explain how I’d gotten the promotion to begin with. And far worse, what theories of my own I might invent to discredit myself.
My eventual exit was a surprise to everyone, including myself. Though I’m still unraveling what happened, one thing that I’ve ascertained is this: You cannot succeed in a role that you don’t embrace. It’s a self-fulfilling prophecy. First, you buy into the negativity. Then, those negative thoughts manifest through the way that you show up in the world. And if that was too Self-Help Guru for you, then here’s the condensed version: People can tell when you’re full of shit.
I was warned that I’d eventually have to make a choice between maker and manager, but I never expected that this fork in the road would present itself to me in a form as literal and immediately demanding as two offer letters in the same week. One was for a front end development role, the other for engineering management. Not maker/manager. Not manager with a small dose of code on the side. Just: management.
I wanted to believe that I had closed the door on that idea, but there was a voice in the back of my mind that kept telling me that I was backing away because I was scared. At the time, I felt like the last two years of my career had been a fluke — a combination of a few lucky breaks and highly visible wins, a manager who relentlessly advocated for me, and a team of engineers who were so intelligent and autonomous that the job of “leading” them felt somewhat effortless most of the time.
Take the manager job, that antagonistic voice in the back of my mind dared me. To see if it had all been luck, or if I could recreate or build on the success I’d seen so far as a leader. To see if maybe, just maybe, my manager had been onto something when he said I had leadership potential. Until that point, I’d convinced a lot of people to buy into the idea of me as a leader. Everyone except myself. I had learned to put on a brave face and to project confidence even when I didn’t feel it. Inside, I felt like the same small-voiced woman who had entered the technology industry three years prior.
I was lucky to be pulled forward into leadership by my peers, my manager, even recruiters and hiring managers. With so many people in my corner, I could afford to be incompletely invested in my own success. Whatever. We’ll see where this goes. If it doesn’t work out, that’s fine. I don’t care. But you can only do that for so long. Eventually, you have to allow yourself to want things. You have to make a choice. And it’s not the maker/manager choice that I mentioned above. It’s a different sort of choice, and one that everyone has to make in order to be successful, but one that is especially important for a prospective manager:
You have to choose to go all in on yourself. To place bets on yourself and to believe — really believe — that you have what it takes to succeed. Fear of commitment is a defense mechanism. It’s a method of stalling risk and with it, failure.
One Final Note
The subtitle of this post is “My haphazard journey from maker to manager.” As much as I would love to wrap this up neatly and tell you that I feel like I’ve finally arrived as a leader, the journey has just begun.
The thing that I didn’t have before, the thing that keeps me going during the difficult times, is the certainty that this work is important. It’s an importance I failed to recognize when the initial question of management was posed to me, years ago. I had this idea of management in my mind, and it looked something like this:
I could extoll all of the important things that managers can do for culture, for hiring, for the development of their employees. It’s all been written about before, by people with far more experience than myself. Rachel Nabors’ article on the subject arrived on my Twitter timeline just as I was in the midst of burnout and served as a swift reminder that, as personal as this journey has felt for me, there’s something bigger that I was failing to look at: other people.
Caree Youngman is a self-taught Front End Engineer turned Engineering Manager. She works at Creative Market and is a Regional Director of Women Who Code. Find her just about everywhere @CareeCodes.
