A Brief History of (My Time In) Middle Management

It’s half a year into worldwide lockdown and by now, most of us are back to our new normal. Sure, we wear masks everywhere (ready for “Top 10 Masks for Fall 2020”?) but it’s a very different state from where we were in March: stuck at home and teetering on the edge of an apocalyptic haze. Some good things came out of it. I spent the time first settling into COVID life, then when I was done with that (there’s only so much closet organization and Netflix I can handle), I built my very first Ruby on Rails app. It’s here and it’s mostly dead (I’m not sure yet), another project brought to life to exist briefly in a moment of time. This is what I imagine it must feel like for an amateur gardener to sow seeds for a one-time bloom. They will not say never again. Maybe during another perfect season of discontented boredom meets manic surreality, drawn out and pulled together by lockdown.

I have 5 half-drafts in limbo—one of them about the pandemic—none of them written with enough momentum to make it to the finish line.

So here we are at Middle Management.

Are you already bored?

I’m here because I’ve started reading about management again. You may already know my favorite internet hangout for management advice: Ask a Manager. More recently, I’ve been reading Making of a Manager, written by former Facebook VP of Design Julie Zhuo. In the first paragraphs, Julie writes about how she had accepted her first management role on the basis of her being able to “get along with everyone”. Not one to turn down a promotion and a raise, she said yes. Her recollection of that very first 1:1 with the surly ex-peer— there weren’t many details but I could feel it because I’ve been there too.

My journey in and out of management went like this: my husband had just moved out and I was, for the first time since high school, independent. That’s my preferred term for “single”; let’s call it my Gwynethesized version. I wasn’t quite settled yet in my new life, still trying to pick up the pieces to find something to rearrange and build from. With no time yet to consider where I would go and what I would do now that I was free, I had just dyed my hair peach and most of my leisure time was spent trying to perfect the shade between K-pop star and next gen mermaid. I was closer to popsicle but I worked it and called it neon peach.

My path to management felt like luck’s draw, especially after realizing how much of an aspiration it is for many people to manage and how difficult it is to get there. I know; I was eventually on the hiring teams, where, in the end, it didn’t come down so much to capability but fit. We knew better than to look for culture fit; that’s sometimes code for “same as us”. At the type of company I worked at, same was not good enough. Diversity was a competitive advantage, not a tokenism. But non-culture fit, that was more nuanced. It was always a risk, not because of who we ended up hiring but because of who we had to turn down.

My manager presented an idea to me, a curious thought. Would you be interested in becoming a manager? I was shocked. After a couple of chats on topics including the difference between management and leading, the mandatory talk on imposter syndrome, and access to my manager’s HBR account, I was given the promotion during a surprise meeting, along with a team of 4 to manage, all of whom were, just the day before, my peers. I thought she was proposing that I work towards being a manager in maybe a year. I didn’t realize my life was about to change, and who I thought I was along with it.

I had no idea what I was doing—thankfully, and even more luckily, I had her support and mentorship. She was just about my polar opposite: warm and vulnerable by default, had a frantic energy, and was the kind of person who could go by last name alone, which she did.

By the time I left, I had graduated from ugly ducking to swan, from Bambi walking for the first time to a stag, mentoring new managers while leading a team of 7 and acting as project manager for 17+. I may be off by 5 or so; in the three weeks before I left, I was on duty to hire 7 more. I went from no experience in tech to leading operations, knowledge management and social content, for a team and discipline that really had no precedent, somewhere in between support, community and PR firefighting. The wonderful things people who knew me as a manager said about me were in direct opposition to who I thought I was; was I growing or was I adapting? Maybe it didn’t matter. Maybe they’re the same thing.

And I was still hungry for more.

In the beginning, it wasn’t something I wanted. But I, like Julie, just wasn’t one to say no. I was nervous—I knew that if I screwed up, I wasn’t just impacting myself. I was also impacting the work and livelihoods of others.

Before this, I had vehemently opposed the idea of needing a manager—it was quite possibly the reason, before this job, that I had never worked at a company any larger than me and my boss, sometimes me and my boss being the same person. I had always been an independent worker, not to mention a thinker and an introvert, and in my mind, the opposite of a people person. No, that was my bubbly, outgoing, beloved sister. It almost felt like a betrayal of my values and what I perceived to be my strengths, but I was vulnerable and open to change. It amused me to realize that somehow, I was doing well enough that someone else trusted me to try. So I did. That trust alone meant a lot to me, and it became a part of how I managed others: by giving everyone a chance to rise to a level that they may not realize they’re capable of. That’s the principle behind 10x growth, the driving philosophy of our employee manual. There is failure, lots of it. But we move quickly and we adapt.

Of the many things I learned: Self-awareness is the precursor to the awareness it takes to lead others.

Middle management as an institution began in the 20th century, the first time in the history of the world where companies were large enough and industrialized enough that they needed someone in the middle, managing output and performance. Efficiency was the name of the game and input/output easily measured, easily quantified, easily managed.

Then everyone started hating managers. It’s a cultural norm to dislike your manager. To like your manager is, apparently, rare. Half of them, a la Meryl Streep’s Miranda Priestley, are portrayed as cutthroat, mean and demanding. (The character is based on Vogue Editor-in-Chief Anna Wintour, who is rumoured to be the same, and fascinatingly, has a course called “How to be a Boss”.) The other half are portrayed as idiots, the archetypal “bad boss”. Every time I flip through Netflix and inevitably stop over The Office, I hear Steve Carrell’s Michael Scott declare: “People say I’m the best boss.” Untrue. But in another Michael Scott-ism—“And I knew exactly what to do. But in a much more real sense, I had no idea what to do.”—True! Or at least accurate.

More recently, some analysts and modern philosophers believe that middle management will soon be made obsolete due to advances in technology. I think middle management will become even more important for the same reasons. After all, what is technology and what does it do? It’s a tool or machine to make things easier or solves a problem. What’ll happen when all our problems are solved and everything is as easy as it can be? Transcendence? It’s the same question and answer I have for AI’s impact on the world: we solve the problems that can be solved with machines, and open up space, time, and energy to solve more human problems in ways only humans can solve. (It’s the transition period we’re all so scared of.)

A good middle manager will have less to do to tell someone what to do and how to do it, and the bad ones will be made obsolete. They will no longer act as middlemen when information is automated and Gen Z values transparency and demands dialogue and inclusion by default; good managers will need to act as strategists and coaches, a super-amplifier of creativity and growth. A co-creator, not a boss.

Research shows that the vast majority of middle managers are unhappy. The Harvard Business Review studied 320,000 employees and found that middle managers were the unhappiest of them all. They’re sandwiched in between the top-down pressures of executives and the bottom-up pressures of their reports. They may be a “boss” but they’re constantly juggling the requirement to get results and be liked enough to keep their teams happy.

Last year, after I emerged from the ashes of my twenties just as my peach hair was fading back to black, I decided that it was time for me to make an active choice in my career, rather than have my path handed to me. And I wanted something quieter, less like the grainy white noise in the background and un-metaphorically and plainly, something that I could forget when I shut my laptop off at the end of the day.

I had given it 2.5 years for things to settle but people management never became an effortless activity for me.

But, it was one of my favorite things I’ve ever done in my career and life, if not my favorite. I was very proud of myself and of my team for everything we accomplished, for all the ways I grew and for all the ways they did too.

Here’s something I realized: most people hope to work in jobs to make money and to do interesting/impactful things but when they leave, it’s hard to remember what the real impact of their work was, especially in a world where so much is changing, where the average lifespan of a business can be measured in human teenage years, where we move on and we forget.

It’s hard to forget your impact as a manager.

That whole “listen to authority just because!!!” thing was never my schtick. I tried to make management fun and interesting for me, and I was really interested in breaking boundaries and self-perception because I was living through that too.

Because I was no longer measured on my own performance and on something much more arbitrary (a strange and wonderful mix between my team’s performance, their happiness and their engagement), I wanted to find something to work towards. So I put more than necessary/minimum effort into listening to my team and figuring out what their career goals were and who they were. For those who weren’t sure (this was mostly everyone), I worked hard to help. We did career exercises, had frequent 1:1s, and talked about all kinds of goals. But I never micro-managed. I did the opposite; most days, I didn’t even work the same hours as my team did. I shared values and priorities, and people did amazing things with that when I spent just as much time on who they were as I did on the work. I took the time to build opportunities around what they might be interested in and what they were good at; many of these things grew far beyond the job expectations and many of them were promoted. I couldn’t solve every problem and promote everyone. Some people didn’t last. But together, our once small team built our first QA program, designed graphics for Canada’s most valuable company, supported our expansion into international markets and built a community, both in a concrete way when we re-platformed our entire forums community and in other ways when we became the day-to-day public voice of the company.

I had one north star: that at whatever point I leave, that I leave this person and this company better than when I started. Things were moving too fast for us to ever expect perfection but I think we did better than that. We grew.

I can’t credit myself for this, of course. Who else was it? My own lead, also a middle manager.

I worked in the perfect environment for all of this to happen: a growing, startup team within a larger company. We needed the team to grow. When we weren’t looking ahead far enough, we were scrambling to catch up, trying to forecast the demand for a job and department that hadn’t even existed a year earlier. We indexed for the capacity to grow in our hiring process, looking for signs like curiosity, adaptability, and yes, self-awareness.

Maybe you weren’t expecting an essay on middle management. How can I propose that this dry topic is a source of inspiration, to the point that, if you’re reading this, it means I’ve finally gotten over my pandemic writer’s block and that Middle Management was the thing that did it?

My experience as a manager is an allegory for what it takes to scale impact and how who we are is sometimes not what we think. What so many of us want is not as limiting as a specific role or task, and we trick ourselves into thinking this is the case. I’ve seen people start out as creatives who become operators and mentors, people who were operators become creative, entrepreneurs become happy intrapreneurs, and many become entrepreneurs—all real people I’ve managed, by the way.

If we want to do better and get better, we need to consider that the two cornerstones of managing, people and process, are the ways to get there. Not everyone has to be a manager, and in fact, if everyone were a manager, that wouldn’t really work.

But middle management was proof to me that impact isn’t linear, but exponential and compounding.

An ill-managed company will die a slow death with even the most talented people on board. A team is a machine; it needs an engine. If I knew anything about machinery, I might have a better metaphor. But I think it gets the point across. Good parts aren’t enough.

Good management combines the mind of a strategist, the people skills of a connector, and the technical skills of a generalist into one, built to be the often (and ideally) invisible puppeteer to connect the dots between the vision, the people and the work. It is the work of the juicy, sweet spot middle, the impact multiplier and at the end of the day, the single most important factor in employee happiness and retention (—ever heard that people don’t quit their jobs, they quit their managers?)

(Very importantly: managers aren’t the best at doing the work, and that’s why so many of them turn out to be bad ones.)

If you’re a founder or exec, invest in the hiring, training and support of your middle managers. Start with why: make sure they’ve bought into the company and its vision and they believe in it as much as you do. Make sure they’re smart, adaptable and can think critically; this is more important than someone with experience. Then, make sure they understand growth, what it takes from a business perspective and from a people perspective. People who feel they’re outpacing the support of their managers get bored and they leave, or try to. If you’re the middle manager, diversify your learning and build your self-awareness. Learn to apologize quickly and earnestly when you’re wrong, and rethink your perception of what wrong is (hint: it’s not the opposite of true). And if you have a manager (this is almost everyone), tell them you want feedback if you’re prepared to learn and grow. And try their feedback on, even if you don’t agree with it. I worked extra hard to build opportunities for the people who really wanted it, and I made sure to let them know too that if now wasn’t the right time, that was okay too. Your manager sees things you can’t. They’re looking ahead just as they’re looking out. If you have a bad manager, I’m not sure if I can help other than have some empathy (because you, like the rest of us, might have a bias of disliking your manager) and consider if you should let them know (because it’s in their best interest to fix something that needs to be fixed, if you’re someone they want to keep and they’re a good manager or at least trying to be)—oh, and check out the wise words of Alison Green.

A few weeks ago, I received a reference request for someone I used to manage, Lily. She had decided to leave tech to grow cannabis, in the fields and all. She wrote me a really nice email and thanked me after she got the job. Later that week, I bumped into Andres, someone else I had managed, while out and about in Subway of all places, while ordering my first cold cut sandwich in 10 years. He’s now working at a blockchain startup. I remember our 1:1s about what it must be like to build the future.

We work hard to give our jobs our best but when we focus on people first, we create a ripple effect of forever growth, one person, one brief moment in time. I accidentally found out the truth of the/my universe during my stint as a middle manager: when people are happy and engaged, they work better, are more creative and are less likely to make things worse for other people too. They go on to do more. They may become managers one day too. Or not. But they become better people. I know this not because I asked if anyone I’ve managed, but because my manager made me better.

All jobs are ephemeral. People too, but the network effect of one positive relationship and interaction, especially one during which you really and truly have grown, that expands everything.

It’s been one year now after I’ve left that job and management, and it’s possible I may or may not be diving back in one day. I joined a growing startup and well, growing startups need managers at some point.

Sometimes the remnants of my stint as a manager come through, even when I try to keep my head down. One of my fears is managing the politics of ambition and insecurity, whether real or not; being a manager puts you in the line of fire. But, the chant of “IC, IC, IC” as a reminder of what I came to try has become “I see, I see, I see”—I can’t un-see and unlearn what I know about what it takes to build a successful team.

A new coworker recently told me that he thought I was a natural leader. I went wide-eyed and chuckled. Really, me? Management changed a lot about me, but it didn’t change me. I’m still reserved, prefer to be behind the scenes more than ever, and I still hate telling people what to do. I probably use “maybe”, “try..”, “perhaps” and “what if?” too much. I’ve tried to stay in my lane because I worry about offending others and of accidentally taking on too much again, and of not giving myself a shot a proper to become amazing at one thing. I thought I was doing a good job of not acting “like a manager”, mostly because I know how people feel about managers in general: pretty icky. But also, I was here to try something different.

And so, I was again, surprised.

If only he knew the work it took to get there—it may have been inevitable (or luck) but it wasn’t by nature. I don’t think it’s meant to be effortless. But, it’s where the magic comes alive or gets lost, in the often invisible and underrated in-between.