Questionable Advice: Is there a path back from CTO to engineer?

I received this question in the comments section of my piece on The Twin Anxieties of the Engineer/Manager Pendulum, and figured I might as well answer it. It definitely isn’t a question I’ve spent a lot of time thinking about or anything. ūü•į

As a former CTO coming off a sabbatical and wanting to go back to engineering, it‚Äôs good to hear that this can be done. Having had coding, architecting, and scaling skills before getting pushed to more lead role and looking to get back to working after the sabbatical, what would the roadmap look like to achieve this? Is it still possible having been away for a few years? What would be a good role to target for re-entry: principal/staff engineer? architect? — Mark

Personally? If I were you, I would return to engineering as a regular old software engineer, writing and shipping code every day in the trenches with (this cannot be emphasized enough) a really, really good team.

Your rustiest skill sets are always going to be the most tactical ones — writing software, reviewing code, reproducing bugs, understanding a new production system.

As a former CTO, you have many other skill sets to pull from — management, strategy, architecture, coaching, staffing, fundraising, etc. These skills are valuable. But they don’t degrade the way hands-on development does. You’ll still remember how to write a performance review two (or twenty) years from now, but writing code is like speaking a language: you use it or lose it. And just like with a language, the best way to freshen up is full immersion.

It’s not just about refreshing your technical chops, it’s also about re-acclimating yourself to the rhythms of hours, days, and weeks spent in focus mode, building and creating.

Think back to the time you first moved from engineering into a management role. Do you remember how exhausting and intrusive it was at first, having meeting after meeting after meeting on your calendar? You had to context switch twenty times a day — you were context switching constantly. You had to walk into room after room after room full of people and their words and emotions. By the end of the day you would be drained dry (and the days felt so long).

As an engineer, you spent your days in stretches of deep focus and concentration, punctuated by the occasional meal, meeting or interruption. But as a manager, your life is nothing but interruptions (and time boxes, and time-boxed interruptions). It took time to for you adjust to manager life and learn where to seek out new dopamine hits. And it’s going to take time for you to adjust back.

How much time? About six months, at least for me. I don’t think it’s being overly dramatic to say that you have to allow enough time to become a different version of yourself. You can’t just change personas and entire ways of being like you change your clothing. The process is more like…a snake shedding its skin, or a caterpillar turning into a butterfly. Don’t rush the process.

And don’t just pick up where you left off as an engineer. This is a beautiful opportunity for you to enjoy the terrible frustration of beginner eyes. ‚ėļÔłŹ Learn a new language, learn a new framework, learn a new way of packaging and deploying your code. Freshen up your toolchain. Try a new editor. Catch up on some new testing or validation ideas that have developed or gone mainstream since you were last in the coal mines. (Take modern observability for a test drive?¬†ūüėČ)

Shit moves fast. A lot will have changed.

If you try to pick up where you left off as an expert, it’s really going to suck as you stumble through the motions that used to feel effortless and automatic. But if you start with something new, the friction of learning will feel ordinary and predictable instead. And pretty soon you’ll feel the engine start to kick in: the accelerated learning curve you’ll remember from learning a new technical skill for the 50,000th time.

Because it’s not just about refreshing your technical skills and your daily cadence, either… it’s also about reconnecting with your curiosity, and your attachment to (and love for) technology.

And you better fucking love it, if you plan to inflict the world of agonies that is software development on yourself day after day. ūüė≠ So you have to reconnect with that dopamine drip you get from learning things, fixing shit, and solving problems. And you have to reconnect with the emotional intensity of shipping code that will impact people’s lives — for better or for worse — and of being personally responsible for that code in production. Of knowing viscerally what it’s like to ship a diff that brings production down, or wakes up your coworker in the middle of the night, or corrupts user data.

So yes. It is absolutely possible to return to engineering after a few years away. And yeah, you could come back as a principal or staff engineer. Someone will definitely hire you. However, I suggest otherwise. I suggest you come back as a senior engineer, writing software every day, for a good 6-9 months.

Your grounding in the technical challenges and solution space will be much deeper and richer if you come back hands on than if you came in at a higher level, detached from the rhythms of daily development. Working closer to production and closer to users will give you the chance to rebuild the intense empathy and connectedness to your work and team that tends to seep away the higher you go up the food chain. You’ll be more confident in yourself as a technologist if you honor your need to relearn and rebuild. And you will earn much more respect from your fellow engineers this way. Engineers respect people who respect what they do.

It’s better than jumping straight into the role of a staff+ engineer and trying to refresh your tactical/technical skills on the side. And you’ll be an infinitely more effective staff+ engineer once you’ve done the refreshing.

But if it feels like a demotion, or it’s too hard to swallow, or if the politics of promotions at this company make you leery: compromise by getting yourself hired as a staff or principal engineer, while being clear with your hiring manager that you plan to spend the first 6+ months slinging diffs. They should be fine with it (delighted, really) since a) ANY staff+ hire is an investment for the long run, b) this is a great way to onboard any staff+ engineer, and c) I don’t believe anybody can actually have staff+ level impact during their first 6-12 months at a company, since so much of the job has to do with people, process, technical context, systems history, etc which accrues over time.

Have fun, and do report back! Tell us how it goes!


P.S.: You don’t say how long it’s been, but I’m operating under the assumption that it’s been 5-10 years since you last worked as an engineer.

P.P.S.: ūüö®unsolicited opinion alertūüö® I would personally avoid any role that includes “Architect” in its title (except solutions architects). To me, “software architect” rings of “someone who can no longer write code or perform as a software engineer, who has probably been at the same company for so long that their skills and knowledge now consist entirely of minutiae about that particular company’s technology. likely to be useless and/or helpless at any other company.” I say this with all due apologies to my architect friends, every one of whom is technically dazzling, operationally up-to-date, and has beautiful hair.ūüíܬ†ūü•į



Questionable Advice: Is there a path back from CTO to engineer?

Advice for Engineering Managers Who Want to Climb the Ladder

We have been interviewing and hiring a pile of engineering directors at Honeycomb lately. In so doing, I’ve had some fascinating conversations with engineering managers who have been trying unsuccessfully to make the leap to director.

Here is a roundup of some of the ideas and advice I shared with them, and the original twitter thread that spawned this post.

What is an engineering director?

Given all the title inflation and general inconsistency out there, it seems worth describing what I have in mind when I say or hear “Engineering Director.”

In a traditional org chart, an engineering manager usually manages about 5-8 engineers, an engineering director manages 2-5 engineering managers, and a VP of engineering manages the directors. (At big companies, you may see managers and directors reporting to other managers and directors, and/or you may find a bunch of ‘title padding’ roles like Senior Manager, Senior Director etc.)

In smaller companies, it’s common to have a “Head of Engineering” (this is an appropriately weaselly title that commands just the right amount of respect while leaving plenty of space to hire additional people below or above them). Or all of engineering might roll up to a director or VP or CTO. It varies a lot.

When it comes to the work a director is expected to do, though, there’s a fair bit of consistency: we expect managers to manage ICs, and directors to manage managers.¬† Directors sit between the line managers and the strategic leadership roles. (More on this later.)

So if you’re an engineering manager, and you want to try being a director, the first thing you’ll want to understand is this: it is generally better to get there by being promoted than by getting offered a director title at a different company.

How to level up

Lots of engineers get tapped by their management to become managers, but not many become directors without a conversation and some intentional growth first. This means that for many of you, trying to become a director may be the first time you have ever consciously solicited a role outside the interview process. This can bring up feelings of awkwardness, even shamefulness or inappropriateness. You’ll just have to push through those.

If you ever want a job in upper leadership, you are going to have to learn how to shamelessly state your career goals. We want people in senior leadership who want to be there and are honing their skills in anticipation of an opportunity. Not “oops, I accidentally a VP.”

It is better to get promoted than hired up a level

There are a few reasons for this. It’s usually¬†easier to get promoted than to get hired straight into a job you’ve never held before (at a org with high standards), and it also tends to be more sustainable/more likely to succeed if you get promoted in as well. Being a director is NOT just being a super-duper manager, it’s a different role and function entirely.

A lot of your ability to be successful as a director (or any kind of manager) comes from knowing the landscape, the product and the people, and having good relationships internally. When you are internally promoted, you already know the company and the people, so you get a leg up towards being successful. Whereas if you’ve just joined the company and are trying to learn the tech, the people, the relationships, and how the company works all at once, on top of trying to perform a new role for the first time.. well, that is a lot to take on at once.

There are exceptions, sure! Oodles of them[1]. But I would frankly look sideways at a place that wanted to hire me as a director if I haven’t been one, or hadn’t at least managed managers before. It’s at least a yellow flag. It tells me they are probably either a) very desperate or b) very sloppy with handing out titles.

If you want a promotion…

The obvious first step involves asking your manager, “what is the skill gap for me between the job I am doing right now and a director role?” Unlike in the movies, promotions don’t usually get surprise-dropped on people’s heads; people are usually cultivated for them. Registering your interest makes it more likely they will consider you, or help you develop skills in that direction as time moves on.

If you have a good manager who believes in you, and the opportunities exist at your company, that might even be all you have to do.(!)

And if so, lucky you. But as for the remaining ~80-90% of us (ha!) … well, we’ll need a bit more hustle.

Take inventory of your opportunities

Lots of companies aren’t large enough to need directors, or growing fast enough to create new opportunities. This can actually be the most challenging part of the equation, because there are generally a lot more managers who want to be directors than there are available openings.

If you do need to find a new job to reach your career goals, I would target fast-growing companies with at least 100 engineers. If you’re evaluating prospective employers based on your chance of advancement, consider the following::

  • Ask about their policies on internal vs external hires. Do they give preference to existing employees? How do they decide when to recruit vs grow from within?
  • Ask about the last time that someone was promoted into a similar role.
  • Tell the recruiter and hiring manager about your career goals. Don’t be shy. “My next career goal is to gain some experience managing managers” is fine. (That shouldn’t be the only reason you’re interested, of course.)
  • Size up the playing field. Is there oxygen at that level? Or are there a dozen other managers senior to you lined up for the same shot?

There are no sure bets. But you can do a lot to put yourself in the right place at the right time, signal your interest, and be prepared for the opportunity when it strikes.

a director is not a ‘super-senior manager’

A director is not just a manager on steroids: it is an entirely different job. It helps to have been a good manager before becoming a director, because many management skills will translate, but others will be entirely new to you. Expect this.

How being a good director is different from being a good manager

Let’s look at some of the ways that being a good engineering manager is different than being a good director.

  1. You can be a great EM, beloved by your team, without giving much thought to managing out or up. Directors cannot. If anything, it’s the opposite. You may get away with not coddling your EMs, but you must pull your weight for your peers and upper management.
  2. You can have a bit of a reputation for being stubborn or difficult as an EM, and that can be just fine. But having such a rep will probably sabotage your attempt at being promoted to director.
  3. You can be a powerful technical EM who sometimes jumps in to train engineers, be on call, or course correct technical and architectural decisions. This can even burnish your value and reputation as an EM. But this would all be a solid knock against you as a director.

Managers can get away with being opinionated and attached to technology, to some extent, while directors absolutely must balance lots of different stakeholders to achieve healthy business outcomes.

This difference of perspective is why managers will sometimes sniff about directors having sold out, or being “all about politics.”

(Blaming something on “politics” is usually a way of accidentally confessing that you don’t actually understand the constraints someone is operating under, IMO.)

A director’s job is running the business

Here’s the key fact: ‚ú®directors run the business‚ú®.

Managers should be focused on high-performing engineering teams. VPs should be focused on strategy and the longer term. Directors are the execution machines that knit technology with business objectives. (I like this piece, although the lede is a little buried. Key graf:)

managers, directors, VPs

Directors run the business. They are accountable for results. You can’t be bopping in and writing or reviewing code, or tossing off technical opinions. That’s not your job anymore.

Managing managers is a whole new skill set

The distance between managing engineers and managing managers is nearly as vast as the gulf between being an engineer and being a manager.

But it’s sneakier, because you don’t feel out of your depth as much as you did when you became a manager. ūüėĀ

As a manager, each of us instinctively draws on our own unique blend of strength¬†and¬†charisma — whatever it is that makes people look up to you and willing to accept your influence. Most of us can’t explain how we do it, because we run on instinct.

But as a director, you have to figure it out. Because you need to be able to debug it when the magic breaks down. You need to help your managers influence and lead using *their* unique strengths. What works for you won’t work for them. You have to learn how to unpack different leadership styles and support them in the way they need.

If you’re working towards a director role:

There are lots of areas where you can improve your director skills and increase your chances of being viewed as director material without any help whatsoever from your manager.

You ‚ú®can not‚ú® be a blocker

Directors run the business … so you CANNOT be seen as a blocker. People must come to you of their own accord to get shit done and break through the blockers.

If they are going to other people for advice on how to break through YOU, you are not a good candidate for director. Figure out how to fix this before you do anything else.

Demonstrate impact beyond your team(s)

Another way to make yourself an attractive prospect for director is to work on systemic problems, driving impact at the org or company level. You could:

  • work to substantially increase the diversity of your teams or your candidate pipeline, and offer to work with recruiting and other managers to help them do the same (becoming BFFs with recruiting is often a canny move)
  • drive some cross-platform initiative to consolidate dozens of snowflake deploy processes and significantly reduce CI/CD build/deploy times, set an internal SLO for artifact build times, or successfully champion auto-deployment
  • champion an internal tools team with a mandate to increase developer productivity, and quantify the hell out of it
  • lead a revamp of the new hire onboarding process. Or add training and structure to the interview process and set an SLO of responding to every candidate within one week

I dunno — it all depends on what’s broken at your company. ūüôÉ Identify something causing widespread pain and frustration at the organizational level and fix it.¬†

Managing ‘up’ is not a ‘nice-to-have’…

If there’s a problem, make sure you are the one to bring it to your manager (and swiftly), along with “Here is the context, here’s where I went wrong, and this is what I’m planning to do about it.” No surprises.

At this point in your career, you should have mastered the art of not being a giant pain in the ass to your manager. Nobody wants a high-maintenance director. Do you reliably make problems go away, or do they boomerang back five times worse after you “fix” them?

…Neither is managing ‘out’

Managing “out” is important too. (Not “managing out”, which means terminating people from the company, but managing “out” as in horizontally, meaning your relationship with your peers.)

What do your peers think of you? Do you invest in those relationships? Do they see you as an ally and a source of wise counsel, or a source of chaos, gossip and instability, or a competitor with turf to protect? If you’re the manager that other managers seek out for a peer check, you might be a good candidate for director.

psst.. People are watching you

One of the most uncomfortable things to internalize if you climb the ladder is how much people will make snap judgments about you based on the tiniest fragments of information about you, and how those judgments may forever color the way they think of you or interact with you.

First impressions might be made by ten minutes together on the same zoom call…a few overheard fragments of people talking about you…even the expressions on your face as they pass you in the hallway. People will extrapolate a lot from a very little, and changing their impression of you later is hard work.

(Yes it’s frustrating, but you can’t really get upset about it, because you and I do it too. It’s part of being human. )

Because of that, you really do have to guard against being too cranky, too tired, or out of spoons. People WILL take it personally. It WILL come back to hurt you.

Remember, you don’t hear most feedback. If you visibly disagree with someone, assume 10x as many silently agree with them. If one person gives you a piece of hard feedback, assume 10x as many will never tell you. Be grateful. The more power you are perceived to have, the less feedback you will ever hear.

Pro tip

You can infer a surprising amount about how good a director candidate may be at their job, simply by listening closely to how they talk about their colleagues. Do they complain about being misunderstood or mistreated, do they minimize the difficulty or quality of others’ work, do they humblebrag, or do they take full responsibility for outcomes? And does their empathy fully extend to their peers in other departments, like sales and marketing?

Does it sound like they enjoy their work, and look forward to beginning it every day? Does it sound like they are all in the same little tugboat, all pulling in the same direction, or is there a baseline disconnect and lack of trust?

In conclusion…

Be approachable, be a drama dampener, project warmth. Control your calendar and carve out regular focus time. Guard your energy — never run your engine under 30%, and always leave something in the tank.

There are a lot more great responses and advice in the replies to my thread, btw. Go check them out if you’re interested.. and if you have something to say, contribute!.‚ėļÔłŹ



[1] Occasionally, it may work out to your benefit to jump into a new, higher title at a new company. This can happen when someone is already well qualified for the higher role, but is finding it difficult to get promoted (possibly due to insufficient opportunity or systemic biases). Just be aware that the job you were hired into is likely to be one where the titles are meaningless and/or the roles are chaotic. You may want to stay just long enough to get the title, then bounce to a healthier org.

Advice for Engineering Managers Who Want to Climb the Ladder

Twin Anxieties of the Engineer/Manager Pendulum

I have written a lot about the pendulum swing between engineering and management, so I often hear from people who are angsting about the transition.

A quick recap of the relevant posts:

There are two anxieties I hear people express above all the rest.

The first one is something I hear over and over again, particularly from first-time managers as they contemplate the possibility of leaving management and returning to IC (individual contributor) work as an engineer:

“What if I never get another shot at people management?”
“Maybe this is the only chance I’ll ever get … and I’m about to give it up??”
“Am I going to regret this?”

“Will I ever get another shot at management?”

People decide to go back to engineering for lots of reasons. Maybe they’re burned out, or they work someplace with a poisonous management culture, or they’re having a kid and want to return to a role that feels more comfortable for a while. Or maybe they’ve been managing teams for a few years now, and have decided it’s time to go back to the well and refresh their technical skills in the interest of their long-term employability.

Regardless, these are not typically people who disliked being a manager. Rather they tend to be engineers who really enjoyed people management, and find it bittersweet to give up. Maybe they will miss the strategic elements and roadmap work, but they’re excited to clear their calendar and spend time in flow again, or they will miss having 1x1s but can’t wait to have time to mentor people. Whatever. They want to manage teams again someday, and worry they won’t get another chance.

Their anxiety is understandable! Lots of people feel like they waited a long time to be tapped for management, or like they were passed over again and again. Our cultural scripts about management definitely contribute to this sense of scarcity and diminution of agency (i.e. that management is a promotion, it is bestowed on you by your “superiors” as a reward for your performance, and it is pushy or improper to openly seek the role for yourself).

This anxiety is also, in my experience, ridiculously misplaced. ‚ėļÔłŹ

Once a manager, marked for life as a manager

You may have struggled to get your first opportunity to manage a team. But it’s a whole different story once you’ve done the job. Now you have the skills and the experience, and people can smell it on you.

I’m not joking. If you’re a good manager it’s actually nearly impossible to hide that you have the skills, because of the way it infuses your work and everything that you do as an IC. You get better at prioritization, more attuned to the needs of the business, and restless about work that doesn’t materially move the business forward. You get better at asking questions about why things need to be done and at communicating with stakeholders. You get better at motivating the people you work with, understanding their motivations and your own, and mediating conflicts or putting a damper on drama between peers. People come to you for advice and may seem to just do what you say, or go where you point.

Senior engineers with management experience are worth their weight in gold. They are valuable contributors and influential teammates. It’s a palpable shift! And every experienced manager in their vicinity will sense it.

So yes, you will be tapped for management again. And again and again and again. You are more likely to spend the rest of your career fending off management “opportunities” with a baseball bat than you are to wither away, pining for another shot.

There is a chronic shortage of good engineering managers, just like there is a chronic shortage of good, empathetic managers in every line of work. The challenge you will face from now on will not be about getting the chance to manage a team, but about being intentional and firm in carving out the time you need to recover and recharge your skills as an engineer.

“Am I too rusty to go back to engineering?”

The second anxiety is in some ways a mirror of the first:

“Can I still perform as an engineer?”
“Will anyone hire me for an engineering role?”
“Has it been too long, am I too rusty, will I be able to pull my weight?”

This is a more materially valid concern than the first one, in my opinion. Your engineering skills¬†do wither and erode as time goes on. It will take longer and longer to refresh your skills the longer you go without using them. Management skills don’t decay in the same way that technical ones do, nor do they go out of date every few years as languages, frameworks and technologies tend to do.

If you aren’t interested in climbing the ladder and becoming a director or VP — or rather, if you aren’t actively, successfully climbing the ladder — you should have a strategy for keeping your hands-on skills sharp, because your ability to be a strong line manager is grounded in your own engineering skills.

Never, ever accept a managerial role until you are already¬†solidly senior as an engineer. To me this means at least seven years or more writing and shipping code; definitely, absolutely no less than five. It may feel like a compliment when someone offers you the job of manager — hell, take the compliment ūüôÉ — but they are not doing you any favors when it comes to your career or your ability to be effective.

When you accept your first manager job, I think you should make a commitment to yourself to stick it out for two years. That’s how long it takes to rewire your instincts and synapses, to learn enough that you can tell whether you’re doing a good job or not.

After two or three years of management, it’s still pretty easy to go back to engineering. After five years, it gets progressively harder. But it can be done. And it should be worth it to your employer to invest in keeping you while you refresh your skills over the six months or whatever it may take. Insist on it, if you must. It’s better to refresh your skills while employed, on a system and codebase you’re familiar with, than to find yourself struggling to brush up enough to pass a coding interview.

Engineering fluency == job security

There is one more reason to refresh your engineering skills from time to time, one I don’t often see mentioned, and that is job security and optionality.

The higher you go up the ladder, the more money you will get paid…but the fewer jobs there be, and the fewer still that match your profile.

As a senior software engineer, there are fifteen bajillion job openings for you. Everyone wants to hire you. You can get a new job in a matter of days, no matter how picky you want to be about location, flexibility, technologies, product types, whatever. You’ve reached Peak Hire.

If you are looking for management roles, there will be an order of magnitude fewer opportunities (and more idiosyncratic hiring criteria), but still plenty for the most part. But for every step up the ladder you go, the opportunities drop by another order of magnitude, and the scrutiny becomes much more intense and particular. If you’re looking for VP roles, it may take months to find a place you want to work at, and then they might not choose you. ¬Į\_(„ÉĄ)_/¬Į

Maintaining your technical chops is a stellar way to hedge against uncertainties and maintain your optionality.


Twin Anxieties of the Engineer/Manager Pendulum

Engineering Management: The Pendulum Or The Ladder

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.Buffy Jaguar 3.5x5

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 Does Not Kill Us Puppy UPDATEDbeing “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:

  1. Most tech companies are absolutely abysmal at providing any sort of training or structure to help you learn the ropes and find your feet.
  2. 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.
  3. 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.

Root Causes DolphinCommit 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.

Sunglasses Tiger Debugger 3.3x5

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.

Pointless Ice Cream 3x2.5There 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.





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?¬† ‚õĒÔłŹ
  • Covering on-call when someone needs a break?¬† ‚úÖ
  • Diving on the biggest project after a post mortem?¬† ‚õĒÔłŹ
  • Code reviews?¬†¬†‚úÖ
  • Picking up a p2 bug that’s annoying but never seems to become top priority?¬†¬†‚úÖ
  • Insisting that all commits be gated on their approval?¬† ‚õĒÔłŹ
  • Cleaning up the monitoring checks and writing a library to generate coverage?¬†¬†‚úÖ

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 DIstrust Kittens 2.5x3invest 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.¬† If management isn’t a promotion, then returning to hands-on work isn’t a demotion,¬†either.¬† 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 ‚Äúengineering 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.

  1. Your choices shrink. There are fewer jobs, with more competition, mostly at bigger companies.  (Do you even like big companies?)
  2. You basically need to do real time at a big company where they teach effective management skills, or you’ll start from a disadvantage.
  3. 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.
  4. 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.
  5. Your employability becomes more about your ‚Äúlikability‚ÄĚ 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.)
  6. 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.)
  7. You may never feel the dopamine hit of ‚Äúi learned something, i fixed something, i did something‚ÄĚ 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.
  8. 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.
  9. 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?
  10. 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),



[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.


Engineering Management: The Pendulum Or The Ladder

The Engineer/Manager Pendulum

Lately I’ve been doing some¬†career counseling for people¬†off Twitter (long story). The central drama for many people goes something like this:

‚ÄúI’m a senior engineer, but I’m thinking about being a manager. I really like engineering, but I feel like I’m just solving the same problems over and over and it seems like the real problems are people problems. I have to be a manager to get promoted. I hope it isn’t terrible, once I make the switch. I hear it’s terrible.‚ÄĚ

I’ve been meaning to write this post for a while. There’s a lot but let’s start with: Fuck the whole idea that only managers get career progression. And fuckkkk the idea you have to choose a “lane” and grow old¬†there. ¬†I completely reject this kind of slotting.

“Your advice is bad and you should feel bad”:

The best frontline eng managers in the world are the ones that are never more than 2-3 years removed from hands-on work, full time down in the trenches. The best individual contributors are the ones who have done time in management.

unicorns-are-jerksAnd the best technical leaders in the world are often the ones who do both. Back and forth.  Like a pendulum.

I’ve done this a few times¬†myself now; start out as an early or first infra engineering hire, build the stack, then build the team, then manage the team, then … leave and start it all over again. I get antsy, I get restless. I start to feel like I know what I’m doing (… a telltale sign something’s wrong).

It’s a good¬†cycle for people who like early stage companies, or have ADD. But¬†I don’t see people talking about it as a career path. So I’m here to advocate for it, as an intentional and awesome way of life.

(h/t to @sarahmei who was tweetstorming this up at the EXACT SAME TIME as i was writing this.  Yes Virginia, internet feminists ARE linked by a mystical hive brain.)

On being a manager (of technical projects)

Promoting managers from within means you get those razor sharp skills from the people who just built the thing. That gives them credibility, while they struggle with their newly achieved incompetence in a different role.


That’s one of the only ways you can achieve the temporary glory of a hybrid¬†manager+tech lead. This is an unstable combination, because your engineering skills and context-sharpness are decaying the longer you do it.

You can only really¬†improve at one of these¬†things at a time: engineering or management. ¬†And if you’re a manager, your job is to get better at management. ¬†Don’t try to cling to your former glory.

Management is highly interruptive, and great engineering — where you’re learning things — requires blocking out interruptions. You can’t do these two opposite things at once. ¬†As a manager,¬†it is your job to be available for your team, to be interrupted. It is your job to choose to hand off¬†the challenging assignments, so that your engineers can get better at engineering.

On being a tech lead (of people):

Conversely: the best tech leads in the world are always the ones who done time in management. This is not because they’re always the best programmers or debuggers; it’s because they know how to get shit done, which means they know how to communicate and manage other people.

A tech lead is a manager¬†…¬†but their first priority is achieving the task at hand, not grooming and minding the humans who work on it.

They still need the full manager toolset. ¬†They’ll need¬†to know how to rally people and teams and motivate them, or how to triage¬†and restart a stalled project that everybody dreads. They still need to¬†connect the dots between business objectives and technical objectives, and break down big objectives¬†rainbow-swooshinto components. They need to be able to¬†size up a junior engineer’s ability and craft a meaningful assignment, one that pushes their boundaries without crushing them … then do the same for another twenty contributors.¬†This is management work, from the slightly shifted perspective of “Get Thing X¬†Done” not “care for these people”.

So these tech leads usually spend more time in meetings than building things, and they will bitch about it but do it anyway, because writing code is not the best use of their time.  Tech is the easy part, herding humans is the harder part.

Senior engineers who have both these toolsets are the kind of tech leads you can build an org around, or a company around. They get shit done. And they are rare.

Almost all of them have spent considerable time in management.

The Pendulum

We don’t talk about this nearly enough: the immense breadth and strength that accrues to engineers who make a practice of going back and forth.

Being an IC is like reverse-engineering how a company works with very little Rainbow_dash_12_by_xpesifeindx-d5giyirinformation. A lot of things seem ridiculous, or pointless or inefficient from the perspective of a leaf node. .

Being a manager teaches you how the business works. ¬†It also teaches you how people work. You will learn to have uncomfortable conversations. You will learn how to still get good work out of people who are irritated, or resentful, or who hate your guts. ¬†You will learn how to resolve conflicts, dear god¬†will you ever learn to resolve conflicts. ¬†(Actually you’ll learn to YEARN for conflicts because straightforward¬†conflict is usually better than all the other¬†options.) You’ll go home exhausted every day and unable to articulate anything¬†you actually did. ¬†But you did stuff.rainbow-clouds

You’ll miss the dopamine hit of fixing something or solving something. ¬†You’ll miss it desperately.

One last¬†thing about management. There’s a myth that makes it really hard for people¬†to stop¬†managing, even when it makes them and everyone around them miserable. ¬†And that’s the idea that management is a promotion.

Management is NOT a promotion.

Seriously, fuck that so hard. It is SUCH an insidious myth, and it leads to so many people managing even though they hate managing and have no business managing, and also starves the senior eng pool of the great mentors and elder wizards we need.

Management is not a promotion, management is a change of profession.¬†And you will be bad at it for a long time after you start doing it. ¬†If you don’t think you’re bad at it, you aren’t¬†doing your job.

Managing because it feeds your ego is a terrific way to be sure that your engineers get to report to someone miserable and resentful, someone who should really be writing code

my feelings on having to only manager OR engineer for the rest of my life

or finding something else that brings them joy.


There’s nothing worse than reporting to someone forced into managing. ¬†Please don’t be one of the reasons people burn out hard on tech.

It isn’t a promotion, so you don’t have any status to give up. Do it as long as it makes you happy, and the people around you happy. Then stop. Go back to building things. Wait til you get that itch again.

Then do it all over again. <3

The Engineer/Manager Pendulum