An Elegant Puzzle- Systems of Engineering Management

by Will Larson

  Last in the list is yourself, but while I do believe that you should generally put yourself last, it’s also a reminder to “pay yourself.” Burnout is endemic in our industry, and a burned-out manager often leaks onto their team. Give as much as you can sustainably give, and draw the line there.

  4.3.6 Think for yourself

  So much of what we take for granted is cargo-culted instead of done with intention. Early in your management career, you’ll have to figure out how to approach common challenges: interviewing, performance management, promotions, raises. It’s totally all right to start out by following what you see around you—learning from your peers is critical to success. However, it’s also important to be honest about which of your practices are truly best practices and which you’re following on autopilot.

  The recent focus on programming interviews7 is a great example. Most hiring managers, myself certainly included, are aware that they’re conducting mediocre interviews, but over time it’s easy to lose that perspective. You can’t fix everything at once, so you’ll often be doing something mediocre at any given point in time, but remember to come back and improve it when you can (e.g., pay down your management debt).

  As a final thought, the best management philosophy never stands still, but—in the model of the Hegelian dialectic8—continues to evolve as it comes in contact with reality. The worst theory of management is to not have one at all, but the second worst is one that doesn’t change.

  4.4 Managing in the growth plates

  My last year at Digg, we were heads-down executing, trying to carve a path out of falling user numbers and an evaporating cash reserve. When we were acquired by SocialCode, I jumped right into execution mode, and instant conflict. What I’d learned over the past two years about leadership—execute, execute, execute—was disruptive, and I couldn’t figure out why. I’ve seen the opposite happen just as often, when experienced, successful managers from well-established companies dive into a startup and exit soon thereafter with a legacy of ineffective initiatives.

  The most confusing places to start are midsize, rapidly growing companies. That’s because parts of the company are growing quickly, with an emphasis on execution, and other parts have largely stabilized, with ideas becoming the more valued currency. Long bones have growth plates at their ends, which is where the growth happens, and the middle doesn’t grow. This is a pretty apt metaphor for rapidly growing companies, and a useful mental model when trying to understand why your behaviors might not be resonating in a new role.

  4.4.1 In the growth plates

  At a small startup or in a rapidly growing company’s growth plates, you’re mostly dealing with new problems. These new problems aren’t necessarily novel (most problems are people problems), but they are problems that your company has never prioritized long enough to get a usable solution out the door. This means that you can’t expect to succeed by iterating on the status quo.

  You’d expect that novel ideas would be heavily valued in these circumstances, but, interestingly, it’s the opposite: execution is the primary currency in the growth plates. That’s because you typically have a surplus of fairly obvious ideas to try, and there is constrained bandwidth for evaluating those ideas.

  It’s common for well-meaning individuals from outside the growth plates to jump in to help by supplying more ideas, but that’s counterproductive. What folks in the growth plates need is help reducing and executing the existing backlog of ideas, not adding more ideas that must be evaluated. Teams in these scenarios are missing the concrete resources necessary to execute, and supplying those resources is the only way to help. Giving more ideas feels helpful, but isn’t.

  Finally, I think it’s important to recognize to recognize that, in the growth plates, you are focused on surviving to the next round, which might be a different growth challenge, or might be the team stabilizing. It is extremely hard to consistently do the basics well in these circumstances, because you simply won’t have enough time to do them well. You’ll have to get comfortable doing as well as time constraints allow, and sometimes that will lead to being mediocre at things you’re passionate about. I personally find that I shift into working on the system,9 and—embarrassingly and unfortunately—tend to cut down on many facets of people management.

  4.4.2 Outside the growth plates

  Away from the growth plates, you are mostly working on problems with known solutions. Known solutions are amenable to iterative improvement, so it would make sense for execution to be highly valued, but I find that, in practice, ideas—especially ideas that are new within your company—are most highly prized.

  All slow-growth environments used to be high-growth environments, which means they were once run by someone who was a sufficiently effective executor to evolve them into a slow-growth environment. Consequently there tends to be less iterative improvement available than you’d expect. So often, we make solid executors responsible for slower-growth areas—we need the innovators in the highest-growth ones—but the opposite tends to work better.

  As a manager, this is the environment for you to do the basics very, very well. Spend time building rich relationships, gelling your team, working with them on career development. Build up so that when innovation or external change pushes you off your local maxima, you and the team are ready and rested.

  4.4.3 Aligning with values

  The message I’d end with is a simple one: be thoughtful about carrying your values with you from one context into another. Leadership is matching appropriate action to your current context, and it’s pretty uncommon that any two situations will flourish from the same behaviors. If you’re working in the growth plates—or outside of them—for the first time, treat it like a brand-new role. It is!

  4.5 Ways engineering managers get stuck

  As a new manager, I found it useful to start each performance review season by rereading! Which also means it’s an excellent time to reread Camille Fournier’s “How Do Individual Contributors Get Stuck?”10 Over time, I found myself wanting a manager-centric version, and eventually that desire solidified into the following list.

  Following in Fournier’s tradition, I was thinking about the parallels for engineering managers. Managers work more indirectly, so when we get stuck it isn’t always quite as obvious, but we absolutely do get stuck, both on individual projects and in our careers.

  Here are a few ways that happens.

  Newer managers, often in their first couple of years:

  Only manage down. This often manifests in building something your team wants to build, but which the company and your customers aren’t interested in.

  Only manage up. In Pearl S. Buck’s The Good Earth,11 she writes, “All power comes from the Earth.” In management, power comes from a healthy team. Some managers focus so much on following their management’s wishes that their team evaporates beneath them.

  Never manage up. Your team’s success and recognition depend significantly on your relationship with your management chain. It’s common for excellent work to go unnoticed because it was never shared upward.

  Optimize locally. Picking technologies that the company can’t support, or building a product that puts you in competition with another team.

  Assume that hiring never solves any problems. When you’re behind, it can be tempting to spend all of your time firefighting and neglect hiring, but if your business is growing quickly, then eventually you hire or burn out.

  Don’t spend time building relationships. Your team’s impact depends largely on doing something that other teams or customers want, and getting it shipped out the door. This is extraordinarily hard without a supportive social network within the company.

  Define their role too narrowly. Effective managers tend to become the glue in their team, filling any gaps. Sometimes that means doing things you don’t really want to do, in order to set a good example.

  Forget that their manager is a human being. It’s easy to get frustrated with your manager when they put you i
n bad situations, forget to tell you something important, or commit your team to something without consulting you, but they almost certainly did it with the best of intentions. To have a good relationship with your manager, you have to give them room to make mistakes.

  More experienced managers:

  Do what worked at their previous company. When you start a new job or new role, it’s important to pause to listen and foster awareness before you start “fixing” everything. Otherwise, you’re fixing problems that may not exist, and doing so with tools that may not be appropriate.

  Spend too much time building relationships. This is particularly common in managers coming from larger companies into smaller ones, and it creates the perception that the manager isn’t contributing anything of value. This tends to be because smaller companies expect more execution focus than relationship management focus from their managers.

  Assume that more hiring can solve every problem. Adding a few wonderful people to the team can solve many problems, but adding too many people can dilute your culture, and lead to people with unclear roles and responsibilities.

  Abscond rather than delegate. Delegation is important, but it’s easy to go too far and ignore the critical responsibilities that you’ve asked others to take on, only to discover an easily averted disaster later on.

  Become disconnected from ground truth. Particularly at larger companies, it can become frequent to make decisions that appear to be fundamentally disconnected from reality.

  Managers of any and all levels of experience:

  Mistake team size for impact. Managing a larger team is not a better job, it’s a different job. It also won’t make you important or make you happier. It’s hard to unlearn a fixation on team size, but if you can, it’ll change your career for the better.

  Mistake title for impact. Titles are arbitrary social constructs that only make sense in the context they’re given. Titles don’t translate across companies meaningfully, and they’re a deeply flawed way to judge yourself or others. Don’t let them become your goal.

  Confuse authority with truth. Authority lets you get away with weak arguments and poor justifications, but it’s a pretty expensive way to work with people, because they’ll eventually turn off their minds and simply follow orders—if they’re in a complicated compensation or life situation, that is. Otherwise, they’ll just leave.

  Don’t trust the team enough to delegate. You can’t scale your impact or engage your team if you don’t give them enough room to do things differently than you would. Many organizations become bottlenecked on approvals, which is a sure proxy for lack of trust.

  Let other people manage their time. Most managers have significantly more work they could be doing than they’re able to do. This will probably be your status quo for the rest of your career, and it’s important to prioritize your time on important things, and not simply on whatever happens to end up on your calendar.

  Only see the problems. It can be easy to only see what’s going wrong, and forget to celebrate the good stuff. Down this path lie frustration and madness.

  I’m certain there are hundreds more ways that managers get stuck, but those are the ones that came to mind first!

  4.6 Partnering with your manager

  At my first software job, I chatted one-on-one with my manager twice in two years, including my first year, when I was remote and three time zones away. In that situation, you either become self-managing or you get let go for inactivity, and somehow I found things to do. (I’d like to add useful to things, but as best I can tell, my team’s software was unilaterally thrown away, so that’s hard to justify.)

  Something that experience didn’t equip me to do well is partner with my manager. I came away without a mental model for what management does, let alone how you would work with them. It’s been a rocky path for me to figure out a healthier approach, and if you’ve faced a similar struggle, hopefully these ideas will help.

  To partner successfully with your manager:

  You need them to know a few things about you.

  You need to know a few things about them.

  You should occasionally update the things you know about each other.

  Things your manager should know about you:

  What problems you’re trying solve. How you’re trying to solve each of them.

  That you’re making progress. (Specifically, that you’re not stuck.)

  What you prefer to work on. (So that they can staff you properly.)

  How busy you are. (So that they know if you can take on an opportunity that comes up.)

  What your professional goals and growth areas are. Where you are between bored and challenged.

  How you believe you’re being measured. (A rubric, company values, some KPIs, etc.)

  Some managers are easier to keep informed than others, and success hinges on finding the communication mechanism that works for them. The approach that I’ve found works well is:

  Maintain a document with this information, which you keep updated and share with your manager. For some managers, this will be enough! Mission accomplished.

  Sprinkle this information into your one-on-ones, focusing on information gaps (you’re not seeing support around a growth area, you’re too busy, or not busy enough, and so on). Success is filling in information gaps, not reciting a mantra.

  At some regular point, maybe quarterly, write up a self-reflection that covers each of those aspects. (I’ve been experimenting with a “career narrative” format that is essentially a stack of quarterly self-reflections.) Share that with your manager, and maybe with your peers too!

  A few managers seemingly just don’t care, and I’ve always found that those managers do care, and are too stressed to participate in successful communication. This leads to the other key aspect of managing up: knowing some things about your manager and their needs.

  Here are some good things to know:

  What are their current priorities? Particularly, what are their problems and key initiatives. When I get asked this question, I often can’t answer it directly, because what I’m focused on is people-related, but it’s a warning sign if your manager never answers it (either because because they don’t know, or they are always working on people issues).

  How stressed are they? How busy are they? Do they feel like they have time to grow in their role or are they grinding?

  Is there anything you can do to help? This is particularly valuable for managers who don’t have strong delegation instincts.

  What is their management’s priority for them?

  What are they trying to improve on themselves, and what are their goals? This is particularly valuable to know if they appear stuck,12 because you may be able to help unstick them. (You could be especially helpful by redefining impact in terms of work that your team can accomplish versus growing team size, which is a frequent source of stickiness!)

  It’s relatively uncommon for managers to be unwilling to answer these kinds of questions. (Either they’re open and glad to share or are willing to speak about themselves.) However, it is fairly common for them to not know the answers. In those cases, each of these questions can be a pretty expansive topic for a one-on-one.

  4.7 Finding managerial scope

  I was chatting with an engineering manager last week, and he mentioned that the jobs he really wants are VP of Engineering roles, but he feels that no one is willing to take a gamble on him. Instead, he’s looking at line management opportunities in fast-growing companies where he can go in with a small team and rapidly grow managerial scope as the company grows around him.

  Rather than casting a stone, I promptly threw all my stones away: I’ve been guilty of pursuing exactly that strategy in a previous job hunt.

  If you luck into a good situation, career progression can be so automatic early in your career that it can take a while to realize later in your career that your progression’s slope has flattened out like a penny thrown off the Empire State Building and then run over by a coal
train.

  Broadly, there are three types of engineering management jobs:

  Manager: you manage a team directly,

  Director: you manage a team of managers,

  VP: you manage an organization.

  Especially early in your management career, it’s easy to conflate reaching the next “rung” with reaching a certain number of people you’ve managed. Following this line of reasoning, for a 100-person company to hire you, you might need five direct reports to be a manager, 20 to be a director, and 40 to be a VP.

  It’s easier to focus on team size than title because the low cost of minting titles drives a fiercely inflationary economy. At Digg, I became a Director of Engineering because the company and my team kept shrinking. Far from a recognition of my success, this was a party favor for participating in one of history’s great showcases of snatching defeat from the jaws of victory.

  As managers looking to grow ourselves, we should really be pursuing scope: not enumerating people but taking responsibility for the success of increasingly important and complex facets of the organization and company. This is where advancing your career can veer away from a zero-sum competition to have the largest team and evolve into a virtuous cycle of empowering the organization and taking on more responsibility.