An Elegant Puzzle: Systems of Engineering Management

by Will Larson

Importantly, while generalized career paths won’t necessarily align cleanly with your goals, they are also unlikely to take full advantage of your strengths. An important part of setting your goals is developing areas you’re less experienced in to maximize your global success, but it’s equally important to succeed locally within your current environment by prioritizing doing what you do well.

With all of this in mind, take an hour and write up as many goals as you can for what you’d like to accomplish in the next one to five years. Then prioritize the list, pick a few that you’d like to focus on for the next three to six months, and share it with your manager at your next one-on-one.

This refined list of goals, aligned to your company’s priorities, then becomes a central artifact for how you and your manager collaborate on your career evolution. Every quarter or so, take some time to refresh the document and review it together.

That said, if you don’t, then there is probably no one guiding your career. Chasing the next promotion is at best a marker on a mass-produced treasure map, with every shovel and metal detector re-covering the same patch. Don’t go there. Go somewhere that’s disproportionately valuable to you because of who you are and what you want.

The three rules for speaking with the media: Answer the question you want to be asked. If someone asks a very difficult or challenging question, reframe it into one that you’re comfortable answering. Don’t accept a question’s implicit framing, but instead take the opportunity to frame it yourself. Don’t Think of An Elephant by George Lakoff 32 is a phenomenal, compact guide to framing issues. Stay positive. Negative stories can be very compelling. They are quite risky, too! As an interviewee, find a positive framing and stick to it. This is especially true when it comes to competitors and controversy. Speak in threes. Narrow your message down to three concise points, make them your refrain, and continue to refer back to your three speaking points. That was it! Concise, compact, and I’m still using and learning from that advice a decade later.

You’ll spend the majority of your time refining approaches that work effectively for your team, a bit of your time documenting how you did it, and almost no time trying to convince folks to change their approach. Strangely, in my experience, this has often led to more adoption than top-down mandates have.

Make a clear ask. If you don’t go into a meeting with leadership with a clear goal, your meeting will either go nowhere or go poorly. Start the meeting by explicitly framing your goal!

My general approach to presenting to senior leaders is: Tie topic to business value. One or two sentences to answer the question “Why should anyone care?” Establish historical narrative. Two to four sentences to help folks understand how things are going, how we got here, and what the next planned step is. Explicit ask. What are you looking for from the audience? One or two sentences. Data-driven diagnosis. Along the lines of a strategy’s diagnosis phase,39 explain the current constraints and context, primarily through data. Try to provide enough raw data to allow people to follow your analysis. If you only provide analysis, then you’re asking folks to take you on trust, which can come across as evasive. This should be a few paragraphs, up to a page. Decision-making principles. Explain the principles that you’re applying against the diagnosis, articulating the mental model you are using to make decisions. What’s next and when it’ll be done. Apply your principles to the diagnosis to generate the next steps.

Return to explicit ask. The final step is to return to your explicit ask and ensure that you get the information or guidance you need.

When you sit down for coffee with a manager, you can probably guess the biggest challenge on their mind: time management. Sure, time management isn’t always everyone’s biggest challenge, but once the crises of the day recede, it comes to the fore.

I’m still pretty busy on a day-to-day basis, but I’ve gotten much, much better at getting things done, not by getting faster but by getting more logical about solving problems.

Prioritize long-term success over short-term quality. As your scope increases, the important work that you’re responsible for may simply not be possible to finish.

Finish small, leveraged things. If you’re doing leveraged work,40 then each thing that you finish41 should create more bandwidth to do more future work. It’s also very rewarding to finish things. Together, these factors allow large volumes of quick things to build into crescendoing momentum.

Identify some critical work that you won’t do, recategorize that newly unstaffed work as organizational risk,42 and then alert your team and management chain that you won’t be doing it. This last bit is essential: it’s fine to drop things, but it’s quite bad to silently drop them.

Trust the system you build. Once you’ve built the system, at some point you have to learn to trust it. The most important case of this is handing off the responsibility to handle exceptions.

Calendar blocking. Creating blocks of time on your calendar is the perennial trick of time management: add three or four two-hour blocks scattered across your week to support more focused work. It’s not especially effective, but it does work to some extent and is quick to set up, which has made me a devoted user.

You unravel most puzzles knowing they’re solvable. You play most games guided by a rule book. For engineering managers, challenges emerge unexpected from a hundred small decisions, with few rules and no promises. Many of these challenges are difficult in the worst sense. There are few options for next steps and pursuing any one of them feels problematic.

Management is an ethical profession, and our decisions matter, especially the hard ones.

At an early job, I worked with a coworker whose philosophy was “If you don’t ask for it, you’ll never get it.” Which culminated in continuous escalations to management for exceptional treatment. This approach was pretty far from my intuition of how a well-run organization should work, and it grated on my belief that consistency is a precondition of fairness.

Conversely, organizations survive by adapting to the dynamic circumstances they live in. An organization stubbornly insisting on its established routines is a company pacing a path whose grooves lead to failure. How do you reconcile consistency and change? As with most seemingly opposing goals, the more time I spent considering them, the less they were mutually exclusive. Eventually, a unified approach emerged, which I call “Work the policy, not the exceptions.”

Policy success is directly dependent on how we handle requests for exception. Granting exceptions undermines people’s sense of fairness, and sets a precedent that undermines future policy.

Organizations spending significant time on exceptions are experiencing exception debt. The escape is to stop working the exceptions, and instead work the policy.

The next time you’re about to dive into fixing a complicated one-off situation, consider taking a step back and documenting the problem but not trying to solve it. Commit to refreshing the policy in a month, and batch all exceptions requests until then. Merge the escalations and your current policy into a new revision. This will save your time, build teams’ trust in the system, and move you from working the exceptions to working the policy.

This no is explaining your team’s constraints to folks outside the team, and it’s one of the most important activities you undertake as an engineering leader.

Folks who communicate a no effectively are not the firmest speakers, nor do they make frequent use of the word itself. They are able to convincingly explain their team’s constraints and articulate why the proposed path is either unattainable or undesirable.

I believe that management, at its core, is an ethical profession. To see ourselves, we don’t look at the mirror, but rather at how we treat a member of the team who is not succeeding. Not at the mirror, but at our compensation philosophy. Not at the mirror, but at how we pitch the roles to candidates. Whom we promote. How we assign raises. Provide growth opportunities. PTO requests. Working hours.

We have such a huge impact on the people we work with—and especially on the people who work “for” us—and taking responsibility for that impact is fundamental to good management.

It’s remembering that you leave a broad wake, and that your actions have a profound impact on those around you.

I believe that almost every internal problem can be traced back to a missing or poor relationship, and that with great relationships it is possible to come together and solve almost anything.

A few years back, one of the leaders I worked with told me, “With the right people, any process works, and with the wrong people, no process works.”

Do the hard thing now In this profession, we’re often asked to deal with difficult situations. No set of rules can guide you safely through every scenario, but I have found that postponement is never the best solution.

Instead of avoiding the hardest parts, double down on them.

Lately, I’ve come to have something of a mantra for guiding decisionmaking: do the right thing for the company, the right thing for the team, and the right thing for yourself, in that order. This is pretty obvious on some levels, but I’ve found it to be a useful thinking aid.

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.

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.

The message I’d end with is a simple one: be thoughtful about carrying your values with you from one context into another.

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.

There is a lot less competition for hard work.

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 tha...

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.

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.

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.

In this context, there are two kinds of projects: critical projects and everything else. Critical projects are scarce. There are more people who want them than can get access to them. Other projects are abundant. You might not be able to get one immediately, but if you wait a month or two the odds are good. There’s no need to be structured about abundant projects!

The best learning doesn’t always come directly from your manager, and one of the most important things a first team does is provide a community of learning. Your peers can only provide excellent feedback if they’re aware of your work and are thinking about your work similarly to how you are.

Long term, I believe that your career will be largely defined by getting lucky and the rate at which you learn. I have no advice about luck, but to speed up learning I have two suggestions: join a rapidly expanding company, and make your peers your first team.

Jason Wong’s “Building a First Team Mindset”6 is an excellent read on this theme if you’re looking for more!

Running this process, and enduring the awkwardness in doing so, is the most rewarding thing I’ve done as a manager. I recommend it.

I believe that the balancing of positive and negative freedoms is a fundamental task of managers and management.