15 mins

Exploring seven common leadership scenarios.

If you’re looking for a very traditional breakdown of engineering manager archetypes – tech lead manager, team manager, director, and so forth – you can’t do better than Will Larson’s post, and I won’t try. I enthusiastically endorse everything he says, especially about Tech Lead Management roles being mostly a trap.

This post aims to capture a different set of archetypes: the common inflection points in a senior engineering manager’s career trajectory, what contributes to these, and some recommended next steps.

I’m of the opinion that career ‘planning’ is mostly overrated. There are just so many variables that go into what makes you feel happy, challenged, and content over the course of your life, and trying to predict how you’ll feel more than two or three years down the line is a fool’s game. You might get married, have kids, deal with immigration status or work visas, or family or health issues that suddenly throw a wrench in things. The company you work at might get acquired, go public, make some bad hires, get pummeled by changing market conditions or an economic downturn, or reorg you under somebody you absolutely loathe. The plum role you want might go to someone else. You might hitch your career to a technology that takes off like a rocket, or sputters out quietly, or suffers a series of community scandals.

Everything fails sooner or later, and most fail sooner rather than later.

And then there’s the fact that people who do plan their careers tend to plan in terms of hierarchy. They are eager to ‘make management’. Then they’re hungry to manage managers. They read ‘30 under 30’ lists and obsessively track which of their peers has climbed the ladder to director or vice president first, and their heart swells in tune with their headcount growth.

Few of us are completely immune to the siren song of such external signifiers of success. (Everybody’s mom congratulates them when they move into management – this shit runs deep in our culture.) But for most of us, nothing breaks the spell like spending time in those upper-hierarchical roles.

When you’re an engineer, it seems like managers hold all the power. Two or three years into a managerial role, you should be thoroughly cured of that illusion – aware of the constraints managers operate under and the multiple stakeholders they serve, but also newly appreciative of the powers and freedoms held by engineers, and attuned to how wielding influence and marshaling results may have little if anything to do with formal decision-making powers.

So, if you’re an ambitious person who wants a long, happy, rewarding career in technology, what’s the alternative?

Self-knowledge. Never stop working on self-awareness, being honest with yourself and others. Try to understand what truly matters to you – is it status and public acclaim? Is it spending half your life in the wilderness? Do you have a singular passion for compilers? Whatever it is, expect it to shift over the years.

  1. Do set goals for yourself – know what you want to achieve over the next few years, and have a hazy idea of where your nose is pointing five years from now.
  2. Whenever you don’t feel strongly compelled to make a particular move, act to preserve or expand optionality.

Don’t get comfortable. Once you’ve been doing any job for two or three years, it’s time for a change.

Let’s examine some archetypes and what to do if one of these applies to you. Keep in mind that these are just rules of thumb, and rules are meant to be broken. If your heart is pulling you in one direction, by all means, follow it.

The junior engineer who became an early manager

If you have worked as an engineer for less than seven-ish years before becoming a manager, you’re in risky territory. You’ll lose your fluency very quickly, and find it much harder to go back to engineering than if you had waited until you were more solidly senior. This can feel like a big compliment – and it is! – but this is your long-term career we’re talking about, not theirs, and too often those who progress early in their career aren’t warned about the downsides and the loss of optionality.

You’ll probably be fine as long as you stay at that same company, given that you know the systems well and management is all about relationships, but you may struggle when you try to find your next job, and you may also struggle finding someone willing to hire you as an engineer when you’re rusty. Technical skills buy credibility.

It’s worth noting that this seems to disproportionately happen to women, who are tapped for management because they are perceived as having better social skills, and then suffer a double penalty when they are rusty and judged ‘not technical’. If you’re a young woman, be extra cautious – make sure you ardently guard and grow your technical credibility.

The novice manager who wants to go back to engineering, six months in

When you’re deciding whether to be a manager or not, think of it as a tour of duty that will last for two to three years. Can you commit to that? If not, this probably isn’t the right time for you to try it out. If you aren’t sure, or you don’t feel like you have any idea what the job entails, don’t accept. Find ways to level up at managerial skills without taking on full responsibility for a team.

This might include taking ownership over a hiring loop – defining the role, writing a posting, designing the interview loop, training the interviewers, screening the candidates, adopting an intern or two (or even running the intern program), updating or open-sourcing your engineering job ladder, subbing for a manager while they’re out on paternity leave for a few months – any number of things. It’s okay to say no, and far better than saying yes, then backing out.

Why? First and foremost, it’s really disruptive to the team, and not fair to them. Secondly, you need to be prepared to shelve your own opinion of your work for the next two years and just keep doggedly plugging away, doing your best to learn and taking loads of feedback, without worrying too much about whether you personally think you’re doing a good job or not. You can’t base your self-esteem on how well you think you’re doing, because frankly, you’re not to be trusted. You have to gain a lot of experience and rewire a lot of neural pathways before you can once again trust your own inner voice on the topic of your job performance.

Management isn’t a promotion, it’s a change of career. And if you aren’t up for resetting the dial to ‘NOOB’ for a couple years, with all of the ups and downs, anxieties and discombobulations, then you aren’t up for management.

The manager who wants to go back to engineering, but only temporarily

One thing I hear surprisingly often from people is that they’re anxious that they’ll never get another shot at management if they step away from it – to take a new job at a new company, for instance, or to solidify their senior engineering skills. But they like management! – and are afraid of getting ‘stuck’ back in engineering.

It’s true: there are no guarantees in life. But in my experience, this fear is particularly overblown. There is a chronic shortage of good engineering managers, especially ones who genuinely enjoy the work. It’s pretty obvious when someone has the engineering manager’s skill set in their tool box; it permeates how you do your job, how you interact with your coworkers, and how you get things done. This means that it’s only a matter of time before you get tapped again. (And again.)

Engineers who have been managers tend to bat the question away over and over again – job after job, year after year. It takes more effort not to be a manager once you’re capable of it.

The manager who was forced into it and wants out...has wanted out for years

This is a tricky one, because it comes in two different guises. Sometimes it’s the person who got pushed into management unwillingly, or had a really rough time of it for a while, or maybe they have never worked in an environment where management was spoken of respectfully. For whatever reason, they still openly grump and groan about it despite the fact that they have actually come around and quite like the job now, and don’t actually want to go back to engineering after all.

Other times, the person got pushed into management unwillingly and genuinely dislikes it. Perhaps they were better as an engineer than they are as a manager, or maybe they simply never grew to love the management role enough to compensate for what they miss about engineering. If they’ve been complaining about it for years, and haven’t done anything about it, there are a few possible reasons: 1) they are genuinely getting pressured by their own boss and the organization to stay in their current role 2) they can’t bring themselves to give up the salary, the control, or the perceived status 3) there’s some other fear holding them back – for example, maybe they’re afraid it’s been too long and they’re too rusty.

In the first case, you should stay a manager, by all means, but own up to the fact that you enjoy it and find it rewarding. Even if you didn’t initially choose the gig, you’re choosing it now, so shut the hell up about being forced into it. Nobody wants to report to a manager who doesn’t want to be there, or is doing the job begrudgingly. Your complaining is toxic, and makes it impossible for you to coach others to have a healthy relationship with their roles.

In the latter case, if you genuinely don’t enjoy your job, then get the hell out. If it’s been years, then you have all the data you need. Your boss has no place forcing you into doing something you hate. You’re never going to do as well at a job you don’t enjoy as one that you do, so ultimately it’s a career-limiting move to stay where you are. Think long and hard about the distorting role that hierarchy has played in your life, and find a place where you are respected and valued for doing what you love.

Personally, I think the worst reason of all for not wanting to give up management is because it means giving up control. How do you think everyone else on your team feels? The good news is that you are ideally positioned to go back to engineering and model what a healthy power balance should look like between management and engineering – to demand transparency and model autonomy and ownership as a senior engineer.

The manager who has been managing for several years … now what?

If you’re a line manager who has been doing the job for around five years, and you feel pretty confident in your craft … what’s next?

That’s a great question. As you know, your technical credibility is grounded to some extent in your ability to do the same work as your team. So one question to ask yourself is, how wobbly are you on that front? Some managers manage to keep a hand in (but out of the critical path) the whole time; most managers do not. There is no right or wrong answer here, only an honest assessment of where you’re at. If you’re rusty, and you want to keep doing line management, it’s probably time to go back to the well for at least six months work as an engineer.

(This could be a GREAT opportunity to swap places with someone who’s questioning whether or not to be a manager full time.)

That’s definitely the choice that preserves the most optionality for you career-wise. It ensures you will still be hireable as an engineer or an engineering manager anywhere, regardless of how much technical knowledge the interview requires (and it does run the gamut, up to and including places that make you work as an engineer for six months before assuming your managerial role).

But most managers are at least slightly curious about what it would be like to move up the chain, or expand their managerial repertoire. This might be: managing teams where you are not the technical domain expert, taking on more of a hybrid product manager role, managing multiple teams, spinning off one or more subteams and managing those managers in addition to your primary team, or managing managers as a director.

Here your choices will likely be constrained by opportunities, which means that the company you work for matters A LOT. At a company with hundreds of engineers and high growth, there’s usually a nonstop trickle of reorgs, reteaming, and other opportunities opening up. If you work at a smaller company (or a place with less growth) and your bosses show no interest in leaving soon, you may need to switch companies to seek out those opportunities.

If this is important to you, you may want to consider switching earlier rather than later. You should pay extra attention to managing ‘out’ and ‘up’; building close relationships with your peers and those above you, in other words. Don’t be afraid to open your mouth and state your goals, and ask for your manager’s advice in getting there. People don’t get randomly tapped for these opportunities so much as they share their goals and are then grown into those positions over time.

The engineer who wants to be a manager, but hasn’t had the opportunity

The most demystifying thing about management is actually being a manager. To those who haven’t had the chance yet – or worse, who have seen colleague after colleague tapped for opportunities while being repeatedly overlooked– that can be cold comfort, or even infuriating to hear. If you want a shot at management, and haven’t had one yet: why not? What should you do or try differently?

Every circumstance is different, but I can offer some suggestions.

First of all, my personal belief is that in an ideal world, any senior engineer who wants to give management a try (and who demonstrates sufficient self-awareness, emotional intelligence, and respect for their colleagues), should get a shot at it. I also believe managers and engineers should both have parallel career ladders, should make equal salaries across their bands, and that technical leadership should be the purview of technical contributors. Leadership is not synonymous with management, and the more we can drain the relationships of hierarchy, the better people will be equipped to find the work that they love and find most fulfilling.

I live in the real world, so I know that most places don’t operate this way (although I believe the number is growing).

I also think that engineers tend to systematically underestimate and undervalue their own power, and they fail to inhabit and flex the power they should have. This leaves a vacuum, so managers step in to fill by default.

All that said. First, look at your company. How many opportunities are there for new managers, really? Is it too small, or not growing fast enough, or do you work in a specialty niche? Most companies aren’t bristling with new opportunities; if this is important to you, you should go work for a company that is growing fast, and you should state your ambition from the outset – yes, to the recruiter or hiring manager in the interview process.

Second, make friends with your manager and the other managers, and eagerly absorb as many managerial tasks or responsibilities as you can. Be more concerned with learning the skills and gaining the experience than with the title itself.

Third, work on your communication skills, written and spoken. Consider doing some public speaking. Run a workshop for your coworkers in something you know well. Take good meeting notes, write great technical project docs.

Fourth, ask your manager (and any other trusted senior people you work with) what you’re missing. Make it clear that you want to hear honest feedback, even if it hurts. If there’s something holding you back that you don’t know about, and someone is willing to tell you, that’s an incredible gift.

Fifth, educate yourself about diversity and inclusion issues. Stand up for others on your team who are getting talked over or having their ideas stolen. Be a leader among your peers, be someone who is willing to do what is right despite the temporary social costs.

The senior manager, director or vice president who daydreams about being an engineer again

Very often, people who were in the right place at the right time and climbed the ladder rapidly, get to the top and realize they feel restless and empty inside – they miss the intrinsic stimulation of writing code, solving problems, delighting users. Very few of them have the courage to go back.

It’s a true fact: the higher you climb the ladder, the further removed you are from the work that brings most people intrinsic joy, that feels real. Some manage to find dopamine hits in their work as a director or a vice president, but the dose is usually fainter and always on a delay.

It’s also a true fact that you’d have to go from being atop the monkey pyramid to being just another individual contributor, slinging code in the mines with the rest of them. That’s a lot for an ego to take. And it’s rough to pick up the skills again if you’ve been ten years or more away from writing code on a daily basis. Lots of people who are in their 30s, 40s or 50s feel like they have lost the mental agility to do so and therefore it might not even be an option anymore.

I don’t have an enormous sample size, but what I do have suggests the above is bullshit.

Consider my friend Molly Stamos, who was a software engineer from 1997-2001, then rapidly climbed the corporate ladder working in product, as a director, then as a vice president. She actually joined Honeycomb as our vice president of customer success, but she was burnt, and admitted to herself shortly after that she deeply missed software engineering and that was where her heart still lay. She worked in support for a while and picked up tasks from the backlog, and formally joined the engineering team in 2020, almost 20 years after she stopped coding full time. She’s freaking great at it and says she’s never been happier.

Be like Molly. Life’s too short to be miserable at work.

And P.S. most of the prestige is in your head. If you go from being an exec to being a senior engineer, I guarantee you that lots of people, especially other engineers, will actually respect you tons more.