Questionable Advice: “My boss says we don’t need any engineering managers. Is he right?”

I recently joined a startup to run an engineering org of about 40 engineers. My title is VP Engineering. However, I have been having lots of ongoing conflict with the CEO (a former engineer) around whether or not I am allowed to have or hire any dedicated engineering managers. Right now, the engineers are clustered into small teams of 3-4, each of which has a lead engineer — someone who leads the group, but whose primary responsibility is still writing code and shipping product.

I have headcount to hire more engineers in the coming year, but no managers. My boss says we are a startup and can’t afford such luxuries. It seems obvious to me that we need engineering managers, but to him, it seems just as obvious that managers are unnecessary overhead and that all hands should be on deck writing code at our stage.

I don’t know how to make that argument. It seems so obvious to me that I actually struggle to put it into words or make the case for why we should hire EMs. Help?

— Unnecessary Overhead(?!?)

Oh boy, there’s a lot to unpack here.

It is unsurprising to me that your CEO does not understand why managers exist, given that he does not seem to understand why organizational structures exist. 🙈 Why is he micromanaging how you are structuring your org or what roles you are allowed to fill? He hired you to do a job, and he’s not letting you do it. He can’t even explain why he isn’t letting you do it. This does not bode well.

But I do think it’s an interesting question. So let’s pretend he isn’t holding your ability to do your damn job hostage until you defend yourself to his satisfaction. 😒

I can think of two ways to make the case for engineering managers: one is rather complicated, from first principles, and the other very simple, but perhaps unsatisfying.

I personally have a … vigorous … knee-jerk response to authority; I hate being told what to do. It’s only recently that I’ve found my way to an understanding of hierarchy that feels healthy and practical, and that was by looking at it through the lens of systems theory.

Why does hierarchy exist in organizations?

It makes sense that hierarchy comes with a lot of baggage. Many of us have had bad experience with managers — indeed, entire organizations — where hierarchy was used as a tool of oppression, where people rose up the leadership ranks by hoarding information and playing dominance games, and decisions got made by pulling rank.

Working at a place like that fucking sucks. Who wants to invest their creativity and life force into a place that feels like a Dilbert cartoon, knowing how little it will be valued or reciprocated, and that it will slowly but surely get crushed out of you?

But hierarchy is not intrinsically authoritarian. Hierarchy did not originate as a political structure that humans invented for controlling and dominating one another, it is in fact a property of self-organizing systems, and it emerges for the benefit of the subsystems. In fact, hierarchy is absolutely critical to the adaptability, resiliency, and scalability of complex systems.

Let’s start with few basic facts about systems, for anyone that may be unfamiliar.

Hierarchy is a property of self-organizing systems

A system is “a network of interdependent components that work together to try to accomplish a common aim” (W. Edward Deming). A pile of sand is not a system, but a car is a system; if you take out its gas tank, the car cannot achieve its aim.

A subsystem is a collection of elements with a smaller aim inside a larger system. There can be many levels of subsystems that operate interdependently. The subsystems always work to support the needs of the larger system; if the subsystem instead optimizes for its own best interests, the whole system can fail (this is where the term “suboptimize” comes from 😄).

A system is self-organizing if it has the ability to make itself more complex, by diversifying, adapting, and improving itself. As systems self-organize and their complexity increases, they tend to generate hierarchy — an arrangement of systems and subsystems. In a stable, resilient and efficient system, subsystems can largely take care of themselves, regulate themselves, and serve the needs of the larger system, while the larger system coordinates between subsystems and helps them perform better.

Hierarchy minimizes the costs of coordination and reduces the amount of information that any given part of the system has to keep track of, preventing information overload. Information transfer and relationships within a subsystem are much more dense and have fewer delays than information transfer or relationships between subsystems.

(This should all sound pretty familiar to any software engineer. Modularization, amirite?? 😍)

Applying this definition, we can say that a manager’s job is to coordinate between teams and help their team perform better.

The false binary of sociotechnical systems

You’ve probably heard this canard: “Engineers do the technical work, managers do the people work.” I hate it. ☺️ I think it misconstrues the fundamental nature of sociotechnical systems. The “socio” and “technical” of sociotechnical systems are not neatly separable, they are interwoven and interdependent. There is actually precious little that is purely technical work or purely people work; there is a metric shitload of glue work that draws upon both skill sets.

Consider a very partial list of tasks done by any functional engineering org, besides writing code:

  • Recruiting, networking, interviewing, training interviewers, synthesizing feedback, writing job descriptions and career ladders
  • Project management for each project or commitment, prioritizing backlog, managing stakeholders and resolving conflicts, estimating size and scope, running retrospectives
  • Running team meetings, having 1x1s, giving continuous growth feedback, writing reviews, representing the team’s needs
  • Architecture, code review, refactoring; capturing DORA and productivity metrics, managing alert volume to prevent burnout

A lot of this work can be done by engineers, and often is. Every company distributes the load somewhat differently. This is a good thing! You don’t WANT an org where this work is only done by managers. You want individual contributors to help co-create the org and have a stake in how it gets run. Almost all of this work would be done more effectively by someone with an engineering background.

So you can understand why someone might hesitate to spend valuable headcount on engineering managers. Why wouldn’t you want everyone in engineering to be writing and shipping code as their primary job? Isn’t that by definition the best way to maximize productivity?

Ehhh… 😉

Engineering managers are a useful abstraction

In theory, you could make a list of all the tasks that need to be done to coordinate with other teams and have each item be picked up by a different person. In practice, this is impractical because then everybody would need to know about everything. One of the primary benefits of hierarchy, remember, is to reduce information overload. Intra-team communication should be high-bandwidth and fast, inter-team communication should be more sparse.

As the company scales, you can’t expect everybody to know everyone else; we need abstractions in order to function. A manager is the point of contact and representative for their team, and they serve as routers for important information.

I sometimes imagine managers as the nervous system of the company body, carrying around messages from one limb to another to coordinate actions. Centralizing many or most of these functions into one person lets you take advantage of specialization, as a manager builds relationships and context and improves at their role, and this massively reduces context switching for everyone else.

Manager calendars vs maker calendars

Engineering labor takes concentration and focus. Context switching is expensive, and too many interrupts can be fatal. Management labor consists of context switching every hour or so, and being available for interruptions throughout the day. These are two very different modes of being, headspaces, and calendar schedules, and do not coexist well.

In general, you want people to be able to spend most of their time working on things that contribute to the success of the outcomes they are directly responsible for. Engineers can only do so much glue work before their calendar turns into Swiss cheese and they can no longer deliver on their commitments. Since managers’ calendars are already Swiss cheese, it’s typically less disruptive for them to take on a larger share of glue labor.

It isn’t up to managers to do all the glue work, but it is a manager’s job to make sure that everything that needs to get done, does gets done. It is a manager’s job to try to line up every engineer with work that is interesting and challenging, but not overwhelming, and to ensure that unpleasant labor gets equitably distributed. It’s also a manager’s job to make sure that if we are asking someone to do a job, they are equipped with the resources they need to succeed at that job. Including time to focus.

Management is a tool for accountability

When you’re an engineer, you are responsible for the software you develop, deploy, and maintain. When you’re a manager, you are responsible for your team and the organization as a whole.

Management is one way of holding people accountable for specific outcomes (building teams with the right skills, relationships, and processes to make good decisions and build value for the company), and equipping them with the resources (budget, tools, headcount) to achieve those outcomes. If you aren’t making building the organization someone’s number one job, it won’t be anyone’s number one job, which means it probably won’t get done very well. And whose responsibility will that be, Mr. CEO?

There’s a real upper limit to what you can reasonably expect tech leads, or engineers, or anyone whose actual job is shipping software to do in their “spare time”. If you’re trying to hold your tech leads responsible for building healthy engineering teams, tools, and processes, you are asking them to do two calendarily incompatible jobs with only one calendar. The likeliest scenario is that they will focus on the outcomes they feel comfortable owning (the technical ones), while you pile up organizational debt in the background.

In natural hierarchies, we look up for purpose and down for function. That, in a nutshell, is the more complicated argument for why we need engineering managers.

Choose Boring technology Culture

The simpler argument is this: most engineering orgs have engineering managers. That’s the default. Lots of people much smarter than you or me have spent lots of time thinking and tinkering with org structures over the years, and this is what we’ve got.

As Dan McKinley famously said, we should “choose boring technology“. Boring doesn’t mean bad, it means the capabilities and failure conditions are well understood. You only ever get a few innovation tokens, so you should spend those wisely on core differentiators that could make or break your business. The same goes for culture. Do you really want to spend one of your tokens on org structure? Why??

For better or for worse, the hierarchical org structure is well understood. There are plenty of people on the job market who are proficient at managing or working with managers, and you can hire them. You can get training, coaching, or read a lot of self-help books. There are various management philosophies you can coalesce around or use to rule people out. On the other hand, the manager-free experiments I’m aware of (e.g. holacracy at Medium and GitHub, or “Choose Your Own Work” at Linden Lab) have all been quietly abandoned or outgrown. Not, in my experience, because leaders went mad for power, but due to chaos, lack of focus, and poor execution.

When there is no explicit structure or hierarchy, the result is not freedom and egalitarianism, it’s “informal, unacknowledged, and unaccountable leadership”, as famously detailed in “The Tyranny of Structureless“. In reality, sadly, these teams tend to be chaotic, fragile, and frustrating. I know! I’m pissed too! 😭

This argument doesn’t necessarily prove your CEO is wrong, but I should think his bar for proof is much higher than yours. “I don’t want any of my engineers to stop writing code” is not an argument. But I’m also feeling like I haven’t quite addressed the core question of productivity, so let’s pick that up again once more.

More lines of code != more productivity

To briefly recap: we were talking about an org with ~40 engineers, broken up into 10 small clusters of 3-4 engineers, each with a tech lead. Your CEO is arguing that you can’t afford to lose any velocity, which he thinks is what would happen if anyone stops writing code full time.

Maybe. But everything I have ever experienced leads me to believe that a fewer number of larger teams, each helmed by an experienced engineering manager, should way outperform this gaggle of tiny groups. It’s not even close. And they can do so in a way that’s more efficient, sustainable, and humane than this scrappy death march.

And systems thinking shows us why! With fewer groups, but larger ones, you have less overall management overhead, and much less of the slow and costly intra-group coordination. You unlock rich, dense knowledge transfer within groups, which gives you more shared coverage of the surface area. With 7-9 engineers per group you can build a real on call rotation, which means fewer heroics and less burnout. The coordination that you do need to do can be more strategic, less tactical, and much more forward-looking.

Would five big teams ship as many lines of code as 10 small teams, even if five engineers become managers and stop writing code? Probably, but who cares? Your customers give zero fucks how many lines of code you write. They care about whether you are building the right things and solving problems that matter to them. What matters is moving the business forward, not churning out code. Don’t forget, the act of churning out code creates costs and externalities in and of itself.

What defines your velocity is that you spend your time on the right things. Learning to make good decisions about what to build is something every organization has to work out for itself, and it is always an ongoing work in progress. Engineering managers don’t do all the work or make all the decisions, but they are absolutely fucking vital, in my experience, to ensuring that work happens and is done well. As I wrote in my last piece, engineering managers are the embodiment of the feedback loops that systems use to learn and improve.

Are managers ever unnecessary overhead?

Sure, absolutely. Management is about coordinating between teams and helping teams run more optimally, so anything that decreases your need for coordination also decreases your need for management. If you are a small company, or if you have really senior folks who are used to working together, you need a lot less coordination. The next most relevant factor is probably the rate of change; if you’re growing fast or have a lot of turnover, or if there’s a lot of time pressure or frequent shifts in strategy, your need for managers goes up. But there are plenty of smaller orgs out there that are doing just fine without a lot of formal management.

Look, I’m not a fan of the word “overhead”, because a) it’s kind of rude and b) people who call managers “overhead” are typically people who disrespect or do not value the craft of management.

But management is, in fact, overhead. 😅 So is a lot of other glue work! By which I mean the work is important, but does not itself move the business forward; we should do as much of it as absolutely necessary and no more. The nature of glue work is such that it too-easily expands to consume all available time and space (and then some). Constraints are good. Feeling a bit underresourced is good, and should be the norm. It is incredibly easy for management to get a bit bloated, and managers can be very loath to acknowledge this, because it’s not like they ever feel any less stressed or stretched.[*]

Management is also very much like operations work in that when it’s being done well, it’s invisible. Evaluating managers can be very hard, especially in the near term, and making decisions about when it’s time to create or pay down organizational debt is a whole nother ball of wax, and way outside the scope of this post.

But yes, managers can absolutely be unnecessary overhead.

However, if you have 40 engineers all reporting to one VP, and nobody else whose number one job is the outcomes related to people, teams and org, I feel pretty safe in saying this is not a risk for you at this time.

<3 charity

[*] In fact, the reverse can be true; bloated management can create MORE work for managers, and they may counterintuitively feel LESS stretched or stressed with a leaner org chart. Bureaucracies do tend to pick up a momentum all their own. Especially when management gets all wrapped up in promotions and egos. Which is yet another good reason to ensure that management is not a promotion or a form of domination.

 

Questionable Advice: “My boss says we don’t need any engineering managers. Is he right?”

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. 🥰

As a former CTO coming off a sabbatical and wanting to go back to engineering, it’s 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. ☺️ 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? 😉)

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. 😭 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!

charity.

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.: 🚨unsolicited opinion alert🚨 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.💆 🥰

 

 

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

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:

“I’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.”

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.

helpfulcat

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

charity-gofmt
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