Last night I was out with a dear friend who has been an engineering manager for a year now, and by two drinks in I was rattling off a long list things I always say to newer engineering managers.

Then I remembered: I should write a post! It’s one of my goals this year to write more long form instead of just twittering off into the abyss.

There’s a piece I wrote two years ago, The Engineer/Manager Pendulum, which is probably my all time favorite. It was a love letter to a friend who I desperately wanted to see go back to engineering, for his own happiness and mental health. Well, this piece is a sequel to that one.

It’s primarily aimed at new managers, who aren’t sure what their career options look like or how to evaluate the opportunities that come their way, or how it may expand or shrink their future opportunities.

The first fork in the manager’s path

Every manager reaches a point where they need to choose: do they want to manage engineers (a “line manager”), or do they want to try to climb the org chart? — manage managers, managers of other managers, even other divisions; while

being “promoted” from manager to senior manager, director to senior director, all the way up to VP and so forth. Almost everyone’s instinct is to say “climb the org chart”, but we’ll talk about why you should be critical of this instinct.

They also face a closely related question: how technical do they wish to stay, and how badly do they care?

Are you an “engineering MANAGER” or an “ENGINEERING manager”?

These are not unlike the decisions every engineer ends up making about whether to go deep or go broad, whether to specialize or be a generalist. The problem is that both engineers and managers often make these career choices with very little information — or even awareness that they are doing it.

And managers in particular then have a tendency to look up ten years later and realize that those choices, witting or unwitting, have made them a) less employable and b) deeply unhappy.

Lots of people have the mindset that once they become an engineering manager, they should just go from gig to gig as an engineering manager who manages other engineers: that’s who they are now. But this is actually a very fragile place to sit long-term, as we’ll discuss further on in this piece.

But let’s start at to the beginning, so I can speak to those of you who are considering management for the very first time.

“So you want to try engineering management.”

COOL! I think lots of senior engineers should try management, maybe even most senior engineers. It’s so good for you, it makes you better at your job. (If you aren’t a senior engineer, and by that I mean at least 7+ years of engineering experience, be very wary; know this isn’t usually in your best interest.)

Hopefully you have already gathered that management is a career change, not a promotion, and you’re aware that nobody is very good at it when they first start.

That’s okay! It takes a solid year or two to find new rhythms and reward mechanisms before you can even begin to find your own voice or trust your judgment. Management problems look easy, deceptively so. Reasons this is hard include:

Most tech companies are absolutely abysmal at providing any sort of training or structure to help you learn the ropes and find your feet. Even if they do, you still have to own your own career development. If learning to be a good engineer was sort of like getting your bachelor’s, learning to be a good manager is like getting your PhD — much more custom to who you are. It will exhaust you mentally and emotionally in the weirdest ways for much longer than you think it should. You’ll be tired a lot, and you’ll miss feeling like you’re good at something (anything).

This is because you need to change your habits and practices, which in turn will actually change who you are. This takes time. Which is why …

The minimum tour of duty as a new manager is two years .

If you really want to try being a manager, and the opportunity presents itself, do it! But only if you are prepared to fully commit to a two year long experiment.

Commit to it like a proper career change. Seek out new peers, find new heroes. Bring fresh eyes and a beginner’s mindset. Ask lots of questions. Re-examine every one of your patterns and habits and priorities: do they still serve you? your team?

Don’t even bother thinking about in terms of whether you “enjoy managing” for a while, or trying to figure out if you are are any good at it. Of course you aren’t any good at it yet. And even if you are, you don’t know how to recognize when you’ve succeeded at something, and you haven’t yet connected your brain’s reward systems to your successes. A long stretch of time without satisfying brain drugs is just the price of admission if you want to earn these experiences, sadly.

It takes more than one year to learn management skills and wire up your brain to like it. If you are waffling over the two year commitment, maybe now is not the time. Switching managers too frequently is disruptive to the team, and it’s not fair to make them report to someone who would rather be doing something else or isn’t trying their ass off.

It takes about 3-5 years for your skills to deteriorate.

So you’ve been managing a team for a couple years, and it’s starting to feel … comfortable? Hey, you’re pretty good at this! Yay!

With a couple of years under your belt as a line manager, you now have TWO powerful skill sets. You can build things, AND you can organize people into teams to build even bigger things. Right now, both sets are sharp. You could return to engineering pretty easily, or keep on as a manager — your choice.

But this state of grace doesn’t last very long. Your technical skills stop advancing when you become a manager, and instead begin eroding. Two years in, you aren’t the effective tech lead you once were; your information is out of date and full of gaps, the hard parts are led by other people these days.

More critically, your patterns of mind and habits shift over time, and become those of a manager, not an engineer. Consider how excited an engineer becomes at the prospect of a justifiable greenfield project; now compare to her manager’s glum reaction as she instinctively winces at having to plan for something so reprehensibly unpredictable and difficult to estimate. It takes time to rewire yourself back.

If you like engineering management, your tendency is to go “cool, now I’m a manager”, and move from job to job as an engineering manager, managing team after team of engineers. But this is a trap. It is not a sound long term plan. It leads too many people off to a place they never wanted to end up: technically sidelined.

Why can’t I just make a career out of being a combo tech lead+line manager?

One of the most common paths to management is this: you’re a tech lead, you’re directing ever larger chunks of technical work, doing 1x1s and picking up some of the people stuff, when your boss asks if you’d like to manage the team. “Sure!”, you say, and voila — you are an engineering manager with deep domain expertise.

But if you are doing your job, you begin the process of divesting yourself of technical leadership responsibilities starting immediately. Your own technical development should screech to a halt once you become a manager, because you have a whole new career to focus on learning.

Your job is to leverage that technical expertise to grow your engineers into great senior engineers and tech leads themselves. Your job is not to hog the glory and squat on the hard problems yourself, it’s to empower and challenge and guide your team. Don’t suck up all the oxygen: you’ll stunt the growth of your team.

But your technical knowledge gets dated, and your skills atrophy.. The longer it’s been since you worked as an engineer, the harder it will be to switch back. It gets real hard around three years, and five years seems like a tipping point.[1]

And because so much of your credibility and effectiveness as an engineering leader comes from your expertise in the technology that your team uses every day, ultimately you will be no longer capable of technical leadership, only people management.

On being an “engineering manager” who only does people management

I mean, there’s a reason we don’t lure good people managers away from Starbucks to run engineering teams. It’s the intersection and juxtaposition of skill sets that gives engineering managers such outsize impact.

The great ones can make a large team thrum with energy. The great ones can break down a massive project into projects that challenge (but do not overwhelm) a dozen or more engineers, from new grads to grizzled veterans, pushing everyone to grow. The great ones can look ahead and guess which rocks you are going to die on if you don’t work to avoid them right now.

The great ones are a treasure: and they are rare. And in order to stay great, they regularly need to go back to the well to refresh their own hands-on technical abilities.

There is an enormous demand for technical engineering leaders — far more demand than supply. The most common hackaround is to pair a people manager (who can speak the language and knows the concepts, but stopped engineering ages ago) with a tech lead, and make them collaborate to co-lead the team. This unwieldy setup often works pretty well.

But most of those people managers didn’t want or expect to end up sidelined in this way when they were told to stop engineering.

If you want to be a pure people manager and not do engineering work, and don’t want to climb the ladder or can’t find a ladder to climb, more power to you. I don’t know that I’ve met many of these people in my life. I have met a lot of people in this situation by accident, and they are always kinda angsty and unhappy about it. Don’t let yourself become this person by accident. Please.

Which brings me to my next point.

You will be advised to stop writing code or engineering.

✨

Fuck

That.

✨

Everybody’s favorite hobby is hassling new managers about whether or not they’ve stopped writing code yet, and not letting up until they say that they have. This is a terrible, horrible, no-good VERY bad idea that seems like it must originally have been a botched repeating of the correct advice, which is:

Stop writing code and engineering in the critical path

Can you spot the difference? It’s very subtle. Let’s run a quick test:

Authoring a feature? ⛔️

Covering on-call when someone needs a break? ✅

Diving on the biggest project after a post mortem? ⛔️

Code reviews? ✅

Picking up a p2 bug that’s annoying but never seems to become top priority? ✅

Insisting that all commits be gated on their approval? ⛔️

Cleaning up the monitoring checks and writing a library to generate coverage? ✅

The more you can keep your hands warm, the more effective you will be as a coach and a leader. You’ll have a richer instinct for what people need and want from you and each other, which will help you keep a light touch. You will write better reviews and resolve technical disputes with more authority. You will also slow the erosion and geriatric creep of your own technical chops.

I firmly believe every line manager should either be in the on call rotation or pinch hit liberally and regularly, but that’s a different post.

Technical Leadership track

If you love technology and want to remain a subject-matter expert in designing, building and shipping cutting-edge technical products and systems, you cannot afford to let yourself drift too far or too long away from hands-on engineering work. You need to consciously cultivate your path , probably by practicing some form of the engineer/manager pendulum.

If you love managing engineers — if being a technical leader is a part of your identity that you take great pride in, then you must keep up your technical skills and periodically

invest in your practice and renew your education. Again: this is simply the price of admission. You need to renew your technical abilities, your habits of mind, and your visceral senses around creating and maintaining systems. There is no way to do this besides doing it.. Right?

One warning: Your company may be great, but it doesn’t exist for your benefit. You and only you can decide what your needs are and advocate for them. Remember that next time your boss tries to guilt you into staying on as manager because you’re so badly needed, when you can feel your skills getting rusty and your effectiveness dwindling. You owe it to yourself to figure out what makes you happy and build a portfolio of experiences that liberate you to do what you love. Don’t sacrifice your happiness at the altar of any company. There are always other companies.

Honestly, I would try not to think of yourself as a manager at all: you are an “engineering leader” performing a tour of duty in management. You’re pursuing a long term strategy towards being a well-respected technologist, someone who can sling code, give informed technical guidance and explain in detail customized for to anyone at any level of sophistication.

Organizational Leadership Track

Most managers assume they want to climb the ladder. Leveling up feels like an achievement, and that can feel impossible to resist.

Resist it. Or at least, resist doing it unthinkingly. Don’t do it because the ladder is there and must be climbed. Know as much as you can about what you’re in for before you decide it’s what you want.

Here are a few reasons to think critically about climbing the ladder to director and executive roles.

Your choices shrink. There are fewer jobs, with more competition, mostly at bigger companies. (Do you even like big companies?) You basically need to do real time at a big company where they teach effective management skills, or you’ll start from a disadvantage. Bureaucracies are highly idiosyncratic, skills and relationships may or may not transfer with you between companies. As an engineer you could skip every year or two for greener pastures if you landed a crap gig. An engineer has … about 2-3x more leeway in this regard than an exec does. A string of short director/exec gigs is a career ender or a coach seat straight to consultant life. You are going to become less employable overall. The ever-higher continuous climb almost never happens, usually for reasons you have no control over. This can be a very bitter pill. Your employability becomes more about your “likability” and other problematic things. Your company’s success determines the shape of your career much more than your own performance. (Actually, this probably begins the day you start managing people.) Your time is not your own. Your flaws are no longer cute. You will see your worst failings ripple outward and be magnified and reflected. (Ditto, applies to all leaders but intensifies as you rise.) You may never feel the dopamine hit of “i learned something, i fixed something, i did something” that comes so freely as an I.C. Some people learn to feel satisfaction from managery things, others never do. Most describe it as a very subdued version of the thrill you get from building things. You will go home tired every night, unable to articulate what you did that day. You cannot compartmentalize or push it aside. If the project failed for reasons outside your control, you will be identified with the failure anyway. Nobody really thinks of you as a person anymore, you turn into a totem for them to project shit on. (Things will only get worse if you hit back.) Can you handle that? Are you sure? It’s pretty much a one-way trip.

Sure, there are compensating rewards. Money, power, impact. But I’m pointing out the negatives because most people don’t stop to consider them when they start saying they want to try managing managers. Every manager says that.

The mere existence of a ladder compels us all to climb.

I know people who have climbed, gotten stuck, and wished they hadn’t. I know people who never realized how hard it would be for them to go back to something they loved doing after 5+ years climbing the ladder farther and farther away from tech. I know some who are struggling their way back, others who have no idea how or where to start. For those who try, it is hard.

You can’t go back and forth from engineering to executive, or even director to manager, in the way you can traverse freely between management and engineering as a technologist.

I just want more of you entering management with eyes wide open. That’s all I’m saying.

If you don’t know what you want, act to maximize your options.

Engineering is a creative act. Managing engineers will require your full attentive and authentic self. You will be more successful if you figure out what that self is, and honor its needs. Try to resist the default narratives about promotions and titles and roles, they have nothing to do with what satisfies your soul. If you have influence, use it to lean hard against things like paying managers more than ICs of the same level.[2]

It’s totally normal not to know who you want to be, or have some passionate end goal. It’s great to live your life and work your work and keep an eye out for interesting opportunities, and see what resonates. It’s awesome when you get asked to step up and opportunistically build on your successes.

If you want a sustainable career in tech, you are going to need to keep learning your whole life. The world is changing much faster than humans evolved to naturally adapt, so you need to stay a little bit restless and unnaturally hungry to succeed in this industry.

The best way to do that is to make sure you a) know yourself and what makes you happy, b) spend your time mostly in alignment with that. Doing things that make you happy give you energy. Doing things that drain you are antithetical to your success. Find out what those things are, and don’t do them.

Don’t be a martyr, don’t let your spending habits shackle you, and don’t build things that trouble your conscience.

And have fun.

Yours in inverting $(allthehierarchies),

charity.

[1] Important point: I am not saying you can’t pick up the skills and patience to practice engineering again. You probably can! But employers are extremely reluctant to pay you a salary as an engineer if you haven’t been paid to ship code recently. The tipping point for hireability comes long before the tipping point for learning ability, in my experience.

[2] It is in no one’s best interest for money to factor into the decision of whether to be a manager or not. Slack pays their managers LESS than engineers of the same level, and I think this is incredibly smart: sends a strong signal of servant leadership.

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