Career development for engineering managers

What comes to mind when you hear the words, ‘career development for managers’?

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.