An Elegant Puzzle- Systems of Engineering Management

by Will Larson

  There is a lot less competition for hard work.

  Companies will always need someone to run their cost-accounting initiatives, to set up their approach to on-call, to iterate on their engineer-recruiting process. Strong execution in these crosscutting projects will give you the same personal and career growth as managing a larger team. Project-managing an initiative working with 50 engineering managers is a far better learning opportunity than managing an organization of 50, and it builds the same skills.

  This realization was very important and empowering for me: you can always find an opportunity to increase your scope and learning, even in a company that doesn’t have room for more directors or vice presidents.

  It also changed how I hire engineering managers, allowing me to switch from the pitch of managing a larger team as the company grows—an oversubscribed dream if there ever was one—to a more meaningful and more reliably attainable dream of growing scope through broad, complex projects.

  If you’ve been focused on growing the size of your team as the gateway to career growth, call bullshit on all that,13 and look for a gap in your organization or company that you can try to fill.

  You’ll be a lot happier.

  4.8 Setting organizational direction

  It took me two years as a manager to reach the “leadership is lonely” phase. Folks had warned me that it would happen, and it did. The team was struggling to acclimatize after acquisition, and I felt like I was carrying the stress alone. I saw the problems, but didn’t know how to make progress on them. Two years later, I’d learned more about management, was increasingly able to rely on experience over invention, and was no longer lonely.

  When I began managing managers, things shifted. I felt certain that I knew how to solve all the problems, but I didn’t know how to rely on others to solve them, and often learned of problems long after they’d deteriorated. Delegation, metrics, meetings, and process—practices that I’d considered obvious or unimportant—crept into my tool kit, and I started to regain my footing.

  Over the past year, as I’ve transitioned into largely working with managers of managers, things have shifted again. Let’s explore that a bit.

  4.8.1 Scarce feedback, vague direction

  For much of your early career, you’ll have folks who are routinely giving feedback on your work. As your span of responsibility grows, particularly if it’s somewhat specialized, increasingly no one will feel responsible for or able to provide that feedback. In a new function, at a small company, your team might be two people, and already you’re inhabiting this realm of muted feedback.

  Where you used to get direct, actionable advice, now you’re listening for ghosts: grumbles on your team about too much technical debt, the rumor that two peers are engaged in some light feuding, agitation where there was previously calm.

  As a functional leader, you’ll be expected to set your own direction with little direction from others. When things in your area are going poorly, you’ll be swamped with more direction and input than you can readily absorb, but when things are going well, you’ll often be responsible for supplying your own direction and that of your team.

  If you don’t supply it yourself, you’ll start to feel the pull of irrelevance: Maybe no one really cares what we do? What would happen if I stopped showing up? Maybe I should be doing something different?

  That initial instinct to leave after hitting a pocket of seeming irrelevance is a comforting one, but it’s the wrong way to go. You can certainly avoid the current swells of ambivalence by switching jobs, but if you’re successful at another company then you’ll end up in the same situation.

  This is a symptom of success. You have to learn the lesson it’s trying to teach you: How to set your organization’s direction and your own.

  4.8.2 Mining for direction

  The first step to setting direction is to cast the widest possible net for ideas. Talk to folks at your company who have worked at different kinds of companies, and ask what those companies did really well. Talk to your team and see if there are ideas to draw out that they’ve been noodling on but haven’t yet volunteered. Read some new technical papers.14 Meet with peer companies and ask them what they’re focused on. Do the same with the Googles/Facebooks and the smallest, most interesting companies.

  This first phase is discovery without judgement. You should take ideas from everywhere and generate a pile of ideas that folks are pursuing, even if you think they’re terrible.

  Once your pile of ideas has gotten large enough, craft it into a strategy,15 and then start testing that strategy. Keep refining and exploring your strategy until you can figure out what the key decisions are, a kind of ad hoc sensitivity analysis.16 Once you identify the key pivots in your strategy, you’re finally prepared to define a direction!

  Make a clear decision on each of those pivots, write up a document explaining those decisions, and then see if you can get anyone to read it. They’ll disagree with a lot of what you’ve written, or else they’ll be confused by it. Keep testing, and refine the confusion down to the smallest group of controversial problems possible.

  Once you have those problems, return to your rounds of engaging with experienced leaders at other companies, and ask them how they’ve made those trade-offs before. Ask them for their stories. Ask them for the context that made one path perfect early on, and why they changed their minds as their company grew larger.

  Incorporate everything you’ve learned into your strategy document, and you’re done.

  Well, almost. The one remaining problem is that almost no one will have the time to soak up the full detail of your overly precise document, so the final step is to distill it into something comprehensible without hours of close reading. I’m still working on the best way to do this, but I suspect that it’s cutting all unnecessary, and even most essential, complexity in order to capture as much of the meaning as possible in three to four bullet points.

  4.9 Close out, solve, or delegate

  In a recent chat with an engineering manager, they mentioned a low-grade, ambient anxiety around their impact, which they’d felt since moving into a role focused on supporting managers rather than on leading a team directly. I think that this resonates with everyone’s transition to managing managers: it’s an unsettling period when you lose access to what used to make you happy—partnering directly with a team—and haven’t found new sources of self-worth in your work.

  This isn’t the only reason this transition is hard, it’s also hard because a lot of your skills and habits stop working well. The skill that scales the worst is outworking your problems.

  This is particularly frustrating, because your ability to put your head down and solve gritty, important problems was probably a big part of how you were promoted. Now it’s the wrong answer to most of your problems. This isn’t because it’s bad behavior, just because it’s too inefficient to accomplish the breadth and quantity of things you need to get done.

  If you’re sitting at the post-transition moment, detached from the work you loved, and with your instincts driving you into a pile of work you can’t make a dent in, I have a tool that’s been useful for me and might be useful for you!

  For every problem that comes your way—an email asking for a decision, a production problem, a dispute around on-call, a request to transfer from one team to another—you must pick one of three options:

  Close out. Close it out in a way such that this specific ask is entirely resolved. This means making a decision and communicating it to all involved participants. This strategy is a success if this particular task never comes back to you; and your goal is to finish this particular task as quickly and as permanently as possible.

  Solve. Design a solution such that you won’t need to spend time on this particular kind of ask again in the next six months. This is often designing norms or process, but depending on the kind of issue, this might be coaching an individual. With this option, your goal is to finish off an entire category of tasks.

/>   Delegate. Ideally, this is to redirect the ask to someone who is responsible for that kind of work, but sometimes it is a one-off. If you can’t close out a task or solve it, your only other option is to delegate it to someone who either has the specialized skills to close/solve it, or who can work in the system.

  No matter what problem comes your way, you’re not allowed to solve issues any other way! Give this method a try for a week, and see if it helps you navigate your role more effectively.

  5

  Chapter 5

  Culture

  Figure 5.1

  Membership in multiple teams: peers, managers, and the supported team.

  Culture

  When I’m working on a presentation to a large organization, I spend a great deal of time on framing it properly. There are so many perspectives that I want my message to resonate with, and I want folks to walk away humming the right notes. However, in the long run our measure is not in what we say or how skillfully we say it, but in what we do, and the abacus tallying our actions is organizational culture.

  Sometimes that tally doesn’t show a result that we’re proud of, but the good news is that culture evolves. Nonetheless, this evolution only yields positive change to persistent effort. In this chapter, we explore some of the persistent efforts I’ve used to shift culture in organizations that I’ve supported.

  5.1 Opportunity and membership

  For a long time, I’ve found the idea of fostering an inclusive organization to be somewhat intimidating. For most tasks, I’ve been able to plan out a roadmap, identify some reasonable metrics, and get to work, but for inclusion I was apt to stare at the blank page, filled with uncertainty.

  Since then, I’ve found a framework for thinking about inclusion efforts that is simple but that has allowed me to think about the problem broadly, identify useful programs, and move from anxiety to implementation. The basis: an inclusive organization is one in which individuals have access to opportunity and membership. Opportunity is having access to professional success and development. Membership is participating as a version of themselves that they feel comfortable with.

  I’ve found this framework powerful for reflecting on what is going well and where we can improve, and I hope you’ll find it useful as well. For both themes, I’ve written notes on investment and measurement.

  5.1.1 Opportunity

  There are workplaces where everyone around you is delightful, the customers are friendly, and you feel respected, but you still return home each night dissatisfied. Occasionally an interesting project will come up, but those typically go to more tenured folks. When I think about having access to opportunity, I think about ensuring that folks can go home most days feeling fulfilled by challenge and growth.

  The most effective way to provide opportunity to the members of your organization is through the structured application of good process. Good process is as lightweight as possible, while being rigorous enough to consistently work. Structure application allows folks to learn how the processes work, and lets them build trust by watching the consistent, repeated application of those processes.

  As the saying goes, this is simple to do but far from easy. The key question is whether you’ll continue to respect your processes when it’s inconvenient to do so. If one of your best team members wants a specific opportunity, are you willing to run an open application process? What if they plan to leave your company otherwise? Would you be willing to bypass your processes to keep them?

  There are infinite ways to create and distribute opportunity! Some of the programs that I have found more helpful are:

  Rubrics everywhere. Every important people decision should have a rubric around how folks are evaluated. This is true for promotions, performance designations, hiring, transitions into management, and pretty much everything else!

  Selecting project leaders.1 Having a structured approach to selecting project leads allows you to learn from previous selections, and to ensure that you’re not concentrating opportunity on a small set of individuals.

  Explicit budgets. Many companies take a “spend it like your own money” approach to budgets, which often leads to large inconsistencies across individuals. Instead of saying that you’ll pay for teams to attend a reasonable number of conferences per year, specify a fixed number. Instead of maintaining a general ongoing education budget, make it explicit.

  Nudge involvement. Many people are uncomfortable applying to opportunities, using education budgets, asking for mentorship, etc. It’s very effective to reach out to those folks directly and recommend they apply. Even more powerful is showing them where they fall on a distribution: it’s one thing to know that you’ve never used your education budget, and something else entirely to know that you’re the only person who isn’t using it.

  Education programs. Create ongoing training and learning programs that are available for everyone, or, for example, for all managers.

  I’m pretty confident that these measures will significantly improve the distribution of and access to opportunity, but we can do better. We can measure. I’ve found measurability of opportunity to be surprisingly high, which is one of the reasons I think it’s an effective pillar in thinking about inclusion.

  The metrics that have been useful for me:

  Retention is the most important measure of availability of opportunity, although it’s also a very lagging indicator. This should be the first thing you’re paying attention to, but you must recognize that it’s slow to show change.

  Usage rate is how often folks get picked in project selection.2 The number of distinct team members picked to lead critical projects is a particularly interesting measure.

  Level distribution is useful, in particular comparing cohorts of folks with different backgrounds. People want role models for themselves in senior roles at the company where they work, which is why looking at the representation of underrepresented minorities and women is only a start. You also want to look in each role and level of seniority.

  Time at level is how long team members wait between promotions. How does this compare across cohorts? Something to watch for is that this number is also greatly influenced by initial level at hiring. For example, time at level might look equivalent because some cohorts are being under-leveled at time of hire.

  Getting access to some of this data will require partnering with your human resources team, but I’ve found that friendly persistence, along with sharing your thinking behind the asks, works well to get coworkers working with you.

  5.1.2 Membership

  Membership is a bit harder to measure, but equally important. I can remember once having coffee with a coworker who described their daily calculus of trying to find someone to eat lunch with. Their work was generally going well, but each day, as noon approached, what they thought about most was feeling lonely.

  If you’re spending so much energy wondering whom you’ll eat lunch with, that’s energy you can’t spend being creative. If the idea of going to work gives you anxiety, at some point you’re going to decide to stop coming. Membership is the precondition to belonging.

  The programs I’ve found most impactful here:

  Recurring weekly events allow coworkers to interact socially. These are held during working hours, are open to folks from many different teams to attend, and are optional. One of my personal favorites is hosting a paper-reading group.3

  Employee Resource Groups (ERGs) create opportunities for folks with similar backgrounds to build community.

  Team offsites once a quarter or so are a good chance to pause, reflect, and work together differently. Spending a day together learning and discussing is surprisingly effective at making individuals feel like a team. This is particularly true for groups of managers, whose daily cadence is typically more in tune with their teams than with their peers.

  Coffee chats, perhaps randomly assigned by Donut,4 get folks from different teams interacting when they don’t need something from each other.

  Team lunches give fo
lks time to relax a bit and interact socially. Held once a week or so, they can become a pleasant ritual. These can be a bit risky, at least for folks (like early hires) who feel uncomfortable in their team. Navigating the social mores of an entire team can be much more difficult than in a one-on-one.

  These programs are all simple, and their simplicity can hide the degree of thoughtful care necessary to do them well. Depending on where a team or organization is, you’ll have to adjust your approach to make them effective. Always take the extra day to test your implementation proposal with a variety of coworkers.

  As you roll these out, measuring remains extremely important, although I’ve found membership rather harder to measure than opportunity. Here are some of the potential measures:

  Retention is once again the golden measure, and once again a long-trailing indicator.

  Referral rate by cohort provides insight into which individuals feel comfortable asking their friends and previous coworkers to join the company.

  Attendance rates for recurring events and team lunches provide some insight into whether folks feel comfortable with those groups.

  The quantity and completion rate of coffee chats are automatically measured with Donut.

  Just as when you collect the data to measure opportunity, this will require some partnership with human resources, but it’s well worth the effort.