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: ✨directors run the business✨.

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. 😁

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 ✨can not✨ 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. 🙃 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!.☺️

charity

Footnotes:

[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

5 thoughts on “Advice for Engineering Managers Who Want to Climb the Ladder

  1. Great post!

    There’s something about delegation becomeing a crucial skill at this level. As an EM you might get away depending on context by not delegating, even if it’s not a great idea. At DoE or above it’s a big weakness.

  2. Ben Floyd says:

    The picture of the mug really doesn’t do much to give me confidence in your management style, unless you have no white men with imposter syndrome on your team [and don’t want any]. Take a shot at my confidence as a mediocre white man if you want, but if I’m on your team and I see that mug I know you’re not someone I can take my concerns to. Racism is racism and sheeeesh is that a tasteless example of it. I both suck at my job and excel at my job – as do most people in tech – and I need a manager who doesn’t carry around a racist mug to help build my actual confidence and career. If you’re giving career advice in an article, maybe leave the racism out next time.

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