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.

If you’re like me, it’s one of two things: either obsessively climbing the ladder or those awful mandatory ‘trainings’ that get hastily assembled. (Otherwise known as, ‘How can we have hired so many brilliant engineers, yet none of them seem to have any idea what appropriate professional behavior looks like – and how long till we get sued?!’)

No one would claim that we have things like engineering roles, levels, and career progression locked down, but it all looks quite mature and well-understood compared to the Wild Wild West that is engineering management. Engineering at least has some basic skills (data structures, algorithms etc.) that one can study and structure an interview around, whereas for managers those basic skills (communication, relationships) come from ‘being human’.

To be fair, you can (and should!) work very hard on being a better human. All of us should – our entire life! Skills like communication, empathy, discipline and self-mastery, emotional self-regulation, self-awareness, and self-acceptance are a huge part of being an effective leader.

But let’s say you know all that. You’re a manager, you were dropped into this gig with precious little guidance (most of it contradictory), and all you want (for heaven’s sake!)  is some straightforward advice on how to grow and become a better one.

Perfect. Let’s get started.

With great power comes the responsibility to understand power dynamics

‘I totally support women/LGBTQIA+/POC in tech, but come on, it’s not as bad as some of them keep going on about. It can’t be, or I would have seen it myself by now. I’ve been in tech for ten years, and we’ve always treated every woman just the same as the guys. Besides, you know, there are two sides to every story.’

Does that sound like you? If so, please don’t become anyone’s manager until you have done a lot of listening and learning.

It’s one thing to be unaware of power dynamics and structural inequities as an individual contributor, and another when you wield formal hiring and firing powers on behalf of the org. You can really mess people up that way, and it doesn’t matter if the harm came from your ignorance instead of malice.

Build a trusted peer group of other managers and talk regularly

Get yourself some peers. You need a personal circle of other managers for mutual support, swapping stories, and talking through tricky interpersonal scenarios with strict confidentiality. You need to know these people well enough, and they need to know you and the personalities in your life well enough, that when something is bothering you it won’t take an hour of preamble just to set the stage for the story you need to tell.

I enjoyed my peer circle as an engineer. I couldn’t survive without them as a manager.

It can take some time to amass the right trusted circle, and it will shift with time, as some connections drift away and new ones emerge. Building, nurturing, and curating your circle is a continuous background process.

And it’s the number one thing you can do for your managerial career.

Give as much as you have been given

If you went to university, don’t let it fool you: our profession is fundamentally a web of apprenticeships.

This is why you should be extra generous with your time; everything you learned came from someone else.

Teach, explain, and tell stories about your own successes and failures as a manager. Helping somebody else with their problem has a way of giving you fresh eyes for your own problems, and your skills become more firmly ingrained after you teach them to others.

Invest in your public speaking skills and broadcasting skills

If public speaking terrifies you, lean into that fear and crush it like a bug. Verbal fluency in front of a group is a learnable skill, just like any other. And as a manager, you will draw on this skill 20 times a day, whether it’s running efficient meetings, holding people’s attention, representing your team well, etc.

I used to be catastrophically terrified of speaking in front of people. Back in 2015, I had to give my first internal infrastructure talk in front of maybe eight people, and for weeks in advance I woke up almost every night, sick and clammy from having nightmares about it.

Personally, I have found that a combination of practice, experience, and sometimes using anti-anxiety medication has made this an easier journey for me.

Get a therapist

Get a therapist. Get a work coach too, if work will pay for it. Yes, it’s good to work on your self-awareness, your relationship patterns, etc., but it’s also super useful to learn new metaphors and descriptive phrases from people who do this for a living. The richer your descriptive arsenal, the wider your range when connecting with people.

If you’re reluctant to do this, ask yourself honestly: couldn’t you use some better coping mechanisms and tools for emotional regulation? (Couldn’t everyone?)

Such a huge part of being a manager is making sure you don’t turn your problems into other people’s problems, or make your feelings other people’s problems. And that’s hard. It’s hard, and the ground is constantly shifting beneath your feet. Just when you think you’ve got it down, things change again.

Do a tour of duty as a manager at a big company

I list this one somewhat begrudgingly, but it’s a big one. If you really want to accelerate your career as a manager and learn lots of core skills fast: consider going to work at a Google/Facebook/Amazon, or any large and relatively faster-paced (or extremely fast-growing) tech company.

I learned so, so, so much about management (and organizational politics, and bureaucracies, and formal and informal power structures) at Facebook.

None of it was what I wanted to learn, mind you, but in retrospect it turned out to be pretty darn invaluable.

These big tech companies have their flaws, but they aren’t stupid, and they have invested a lot more into sophisticated business operations than any startup. Startups get away with so, so, so much sloppy behavior from a management and human resources perspective.

Managing a team at a big company for a year is a killer crash course in the best practices and established defaults of engineering management. If you can’t or won’t go work for a big company, try Will Larson’s book An Elegant Puzzle, which outlines a lot of the same best practices and the reasons behind them.

Overcome your fear of confrontation

If you hate confrontation, I’m sorry honey, but you have to push through that barrier ASAP. It is the one thing that will hold you back, poison your relationships, result in loss of trust, and ultimately hurt your direct reports faster than anything else. Read Radical Candor, practice with your therapist, practice with your group of peers, do whatever it takes. You have got to learn to lean into that itchy feeling and open your mouth instead of shrinking away.

Experiment with your 1:1s

Learn to have better, more interesting, more fulfilling, more varied 1:1s with your reports. This is a tough one for introverts, but it’s super worth investing some time into. I will leave ‘how’ as an exercise for the reader – there are lots of interesting blog posts out there, or you could start picking the brains of other managers who you respect.

Most of us have never had a very good manager, let alone a great manager. If you dreaded your 1:1s or were bored by them, etc., it doesn’t have to be this way. 1:1s are the great bidirectional lens into each other’s roles and lives, and with a little curiosity and experimentation, they can be much more than 30 minutes of awkward conversation or the same 3 questions every week.

Run better meetings

Running great meetings – efficient, productive, interesting, with exactly the right people present – is an understated, underestimated art. We usually only notice when a meeting is being run poorly. Train yourself to notice meetings where everyone is leaning in, eyes sparkling, devices forgotten, or even just the meetings that you never dread going to: who runs those? Pay attention to those jedi masters, and copy the hell out of them.

Volunteer to do things that are new and challenging. (Nobody else knows how to do them, either)

Put your hand up and volunteer for things. Is there a new job ladder that needs to be written or revised? Does the on call schedule need refactoring? Has anyone checked to make sure salaries are fair and not biased by race or gender?

Who better than you? 😁

And finally, having saved the hardest and most open-ended for last:

Look for ways to improve and optimize your organization as a sociotechnical system

Anyone who calls themselves a technical leader, whether engineer or manager, shares responsibility for identifying, maintaining, and optimizing the inner feedback loops that help you build and ship software. They are at the heart of how your organization delivers value and becomes a place people want to work.

Figure out how high-performing your team is (start with the DORA metrics), then begin to evaluate how much time is being wasted and consumed by wheel-spinning due to inefficiencies in your core sociotechnical feedback loops.

Try to step back from fighting all the symptoms and pathologies; instead, try to address them at the source.

This may involve:

• Staying up to date on technical news
• Getting your hands dirty and tinkering from time to time
• Talking to others in the org to identify shared pain
• Learning what really motivates each person on your team
• Crafting a pitch that excites them and pushes their boundaries
• Breaking down massive technical debt into bite-sized initiatives
• Knowing when to speak and when to shut up
• Doling out strategic praise

In conclusion

Career development as a manager isn’t about racing up the org chart at a breakneck speed. What makes someone a great, fulfilled, happy engineering manager doesn’t necessarily translate into making them a great director or VP (or a happy one). Opportunities to advance to upper management are scarce and somewhat random. There’s a lot to learn about the craft of management and technical leadership, which is a much healthier thing to focus on.

Check in with yourself regularly about whether you still enjoy your work. Swinging the pendulum back to engineering every few years is a great way to ensure you remain employable and your skills remain fresh over the long run.

Building a long and rewarding career in tech is not about chasing titles or levels, it’s about learning to follow your curiosity (and learning to love the uncertain feeling of being out of your depth.)

One final warning: managers have a tendency to slip into a pattern of only doing things or growing in ways that are useful to the org, but useless to them personally (once they change jobs or leave the company). Don’t do this! Be more selfish. Insist on building skills that are transferable and inherently valuable, not just knowing where all the bodies are buried at your current employer.

Anyone who manages to be happy in management will have to seek out fresh dopamine hits to replace those they gave up in engineering. Happy hunting.

So, you need an engineering manager. Maybe what you need is to replace a departing manager – someone who is leaving the company, being promoted, or going back to hands-on individual contributor (IC) work. Maybe your team has gotten too large and unwieldy and is ready to split in two, amoeba-like, or you’re on the verge of hiring a few more people and spinning off another team. Maybe you are a baby startup and this engineering manager will be your first formal structure, or maybe something else entirely.

Whatever the genesis, the point is the same: you need to find a manager. And your very first fork in the road will be, “Should I hire one from the outside, or tap one of my engineers for the role?”

Here is a brief overview of the considerations involved in asking this question and making that decision.

First of all, I should confess to my biases. I am a big believer in the philosophy that management is not a promotion, but a change of career. There is a great deal of evidence that hierarchy produces worse outcomes in creative industries, of which software is decidedly one. I think that management is not and should not be synonymous with leadership; in fact, there are areas of technical leadership and implementation details where managers have no business exerting ownership. There should be technical leadership levels that track management levels as their equals in compensation, authority, and respect, but with different domains – ‘non-overlapping magisteria’, as the great Stephen Jay Gould might have said.

Engineering managers are ultimately responsible for the health of the team, the career progression of the engineers under their care, and for making sure that engineering teams are focused on the right priorities. They are the essential link between business and engineering; they must be able to translate between the two worlds many times a day. But once the decision is made that something is a priority, how it is done is the proper domain of engineers and technical leads.

Now, back to our choice. What should we do – hire from within, or hire from without?

Give preference to internal candidates

I am a firm believer that you always, always owe your existing team first crack at any and every opportunity that arises from within. It may not always be possible; you may need someone with more experience or a different skillset than you have on your team, but you owe it to your team to seriously explore the possibility, every time, before you give in and begin to explore outside possibilities.

That is an ethical stance which I happen to hold. But there are also pragmatic reasons for preferring internal candidates over external candidates where possible. Effective line management requires a manager to have a reasonably good understanding of the tech stack and the slate of current problems and tradeoffs; who better than one of the engineers working on it? And good management, in general, is all about relationships, relationships, relationships; someone coming in the door will always take longer to build those relationships and be effective than someone who already knows the lay of the land and the people who dwell in it. Internal candidates taking a lateral transfer to a management role are the most likely to succeed, in my experience.

So, what are some questions you might ask yourself when looking around for management candidates?

Who is the best engineer?

This is traditionally the first (and sometimes only) question leadership asks before ‘promoting’ (sic) said engineer to management. Unfortunately, this is the wrong question to ask yourself. There is no correlation that I’ve observed between someone’s engineering skills and management skills – no positive correlation, at any rate.

I do believe engineering managers need to have a strong technical background in order to be effective, but they don’t need to be the best engineer in the room. Many fervently mediocre senior engineers have developed into strong, admirable engineering managers – some of whom then swing the pendulum back to IC and leverage those hybrid skillsets to become supremely valuable senior technologists.

This is one big reason why it’s important to decouple leadership from management. Your best engineers are likely hungry for advancement, autonomy, and impact (just like everyone else), and you do not want them to conclude that management is the only vehicle for their ambitions – the only way they’ll ever get a seat in the room where it happens. You want them to solve your hardest technical problems if that is where their heart is. A better question to start with might be:

Who is senior enough to be a manager?

Don’t consider anyone for management until they have achieved a solid senior level and status – at least 5–7 years of hands-on engineering. Their technical judgment should be well-respected by their peers; they should know enough to know how much they don’t know, and where to trust their own opinion or not.

You won’t be doing them any favors by asking them to switch careers earlier in their tenure, and you might well be inflicting permanent damage on their career. At least half of those who try management end up not liking it, or go back to engineering at some point. If they make the leap to management too early, it will be extremely difficult for them to return to engineering a couple of years later. You might be sentencing them to a one-way trip whether they like it or not.

It will also be difficult for them to effectively manage junior engineers, who need mentorship and career development, or senior engineers, whose experience and judgment will far outstrip their own. Too many managers end up frustrating their teams by lurching between command-and-control leadership, and blind trust and abdication of leadership – not because they want to, but because they lack the technical subtlety to know when to speak or shut up.

Are any of your engineers interested?

Is anyone on your team interested in trying out the manager gig? Don’t guess; ask. Not just once, but regularly. And don’t wait until a position opens up to ask, either. Managers should have a chat about career plans with everyone on their team at least once or twice a year, and that includes asking whether they would like to try being a manager at some point.

Management is just a bundle of skills and practices, after all. You don’t have to have a formal manager title in order to be tasked with or practice things like running an interview loop, mentoring an intern, running team meetings, and writing up plans. If someone wants to become a manager at some point in their career, you should help them find opportunities to practice some of these skills and habits.

This is the quickest and easiest way for someone to find out if the work actually doesn’t interest them. And it’s a great low-risk way for you to watch them in action and observe their skills, without having to entrust the fate of an entire team to them yet.

When an opening does arise, you should already have a mental map of who on the team is likely to be interested, and how skilled they are.

Do I need to interview them, or what?

If you’re seriously considering an internal candidate for management, start by having a conversation with them – a different sort of conversation than you may have had up to this point. Start with some simple, open-ended questions, like:

“Why do you think there are so many more men than women in software roles?”

And let them talk for a while. You aren’t trying to trap them, or looking for ideological purity, but if you are going to put someone into a position of formal organizational power over others, it’s your responsibility to make sure they won’t inflict harm.

You have to have a higher bar for managers when it comes to awareness of structural racism and interpersonal power dynamics. Being a ‘really good person’ is not enough to do the job; ‘good people’ inflict immense harm every day without meaning to. You need managers who are humble, self-aware, and eager to learn – not ones who will have a meltdown and become the problem any time they mess up.

What if there are two or more who want it?

This is another great argument for treating management as a change of career, not a promotion, and for legitimizing and normalizing the idea that it’s okay to go back and forth between management and engineering, every few years.

If it’s not a promotion, then you don’t have any status to give up. If it’s an ordinary thing, there will be other opportunities. Not every opportunity exists at every company at every time, but the more you can do to lower the perceived scarcity and intensity, the more you will find people becoming managers or engineers for the right reasons rather than the wrong ones.

The team’s opinion matters more than yours

You should never inflict a manager on a team who doesn’t want to receive them in that role, no matter how qualified they seem on paper. If someone wants to be manager, your next move should be to quietly chat with each of the team members to see how they receive the idea, giving special weight to the opinions (and body language) of any underrepresented minorities on the team. Do they want to report to this person? If not, don’t push it – even a little.

Slight caveat: if the proposed candidate is a gender or racial minority, and if you suspect the team’s discomfort is related to their status, it’s worth digging in a little more to understand the situation and even possibly overrule some hesitation. As ever, trust your intuition but interrogate it, and use your best judgment.

Reasons to go ahead and open an external req

I said that internal candidates are my preference by default, but there remains a long, long list of reasons why you might decide to hire externally after all. A few of them include:

• Your team is mostly junior-to-intermediate, and your senior folks are lukewarm on the idea of management (never push someone into it!)
• All your existing managers are first-timers, and you really need some more experienced managers in the mix to help you formalize policies and processes as you grow
• The team is split, and there is no consensus behind any internal candidate.

Listen to your own intuition, too: if you don’t have a great feeling about any of your options, take that seriously.

If you decide to hire a manager from the outside, the first thing you need to do is sit down and take a long hard look in the mirror. Hiring isn’t about finding the ‘best person’, it’s about crafting the strongest team. Where is your team weak? Who do you worry about? What are your strategic goals for the upcoming year or two, and what kind of leadership experience will help you get there? Do you need someone who can be very hands-on with the technology, or someone skilled at systems building, or driving transformation? Will recruiting be make-or-break for you? How diverse is your team, and what are your diversity goals?

All of these archetypes call for different types of leaders. But that’s a topic for another time.