An Elegant Puzzle- Systems of Engineering Management

by Will Larson

  A second similarity between the two is that balancing opportunities for membership across a large population is pretty tricky. Many activities and events don’t work well for everyone—meals can be difficult for individuals with complex dietary restrictions, physical activities make some uncomfortable, activities after working hours can exclude parents—and success here requires both a broad portfolio of options and a willingness to balance concerns across events and time.

  5.1.3 Keep going

  Combine efforts on opportunity and membership, and you will find yourself solidly on the path to an inclusive organization. This strategy doesn’t have much flash, but results are louder than proclamations. The most important thing is continuing your investment over the long term. Pick a few things that you are able to sustainably continue, get started, and layer in more as you build steam.

  5.2 Select project leads

  Have you ever worked at a company where the same two people always got the most important projects? Me too. It’s frustrating to watch these opportunities to learn from the sidelines, and reliance on a small group can easily limit a company’s throughput as it grows. This is so important that I’ve come to believe that having a wide cohort of coworkers who lead critical projects is one of the most important signifiers of good organizational health.

  It’s a particularly powerful metric because it simultaneously measures the company’s capability to execute projects and the extent that its members have access to growth. The former measurement helps determine the company’s potential throughput, and the latter correlates heavily with inclusivity.

  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!

  To increase the number of folks leading this kind of project, I’ve iterated into a structured process that has worked quite well:

  Define the project’s scope and goals in a short document. Particularly important are identifying:

  Time commitment. People need to decide if they must ask permission from their managers.

  Requirements to apply. If there are no requirements, say so explicitly; otherwise, a lot of folks will assume that there are, and will opt out.

  Selection criteria. If multiple individuals apply, how will you select the project leader between them?

  Announce the project to a public email list, at an all-hands, over Slack, or however your company does persistent communication; I tend to use email for these. What’s most important is that you:

  Allow folks to apply in private. Some individuals will be uncomfortable applying in public.

  Make sure that applicants don’t see who else has applied. Some people will see someone they view as senior apply, and will immediately disengage because they feel that they are less qualified.

  Give at least three working days for people to apply. Do this whenever possible, as some folks will need to talk with their manager or peers to muster up the confidence to apply.

  Nudge folks to apply who you think would be good candidates but who might not self-select. This is particularly important for getting new people into the process.

  Select a project leader based on the selection criteria you specified. Take the time to consider every single applicant against the criteria, and, if possible write up a paragraph or two about each of them. Once you’ve selected the leader, privately reach out to them to confirm that they’re able to commit.

  Sponsor the project leader by finding someone who has successfully completed a similar project to be their advisor. This sponsor will be accountable for coaching the leader to successful completion. This is a great learning opportunity for sponsors, as they are typically folks who are great at doing things themselves, but not as used to teaching others how to lead large and ambiguous projects.

  Notify other individuals who applied that they were not selected. It’s extremely helpful if you provide them feedback on why you didn’t select them. Sometimes it’s because they’ve already done something great and you want to create room for another person to learn, and that’s a totally reasonable thing to tell them!

  Kick off the project, notifying the same folks who received the application announcement who the project leader is, who the sponsor is, and what their plan for running the project is.

  Record the project, who was selected, and who the sponsor is into a public spreadsheet. Also link out to a project brief!

  If you do this, over time you’ll get a clear sense of who gets leaned on for the most important projects. If you do this well, you’ll see that cohort continue to grow!

  The first few times you do this, it will feel very constraining and inefficient. Previously, you would have just sent a ping to a favored individual and they’d have been off and running, but now you have to run a slower and more deliberate process. Increasingly, though, I believe this is the most important change in my approach to leadership over the past few years. Done well, it can be the cornerstone in your efforts to grow an inclusive organization.

  5.3 Make your peers your first team

  While companies are literally composed of teams,5 I’ve found it surprisingly common to meet folks who feel as if they are not a member of any team. Managers working directly with engineers tend to feel some membership in that team, but even the rarest occasions of authority create a certain distance. Managing managers lets you pierce the veil a bit more, but the curtain falls when it comes to performance management or assigning resources.

  Looking toward your peers can be uncomfortable in a different way. As your span of responsibility grows, you may not know much of your peers’ work, or you may find yourself frequently contesting against them for constrained resources. Even when surrounded by the fastest of growth, you may be awkwardly aware that you’re aspiring to move into the same, rare, roles.

  These dynamics can lead to teams whose camaraderie is at best a qualified non-aggression pact, and in which collaboration is infrequent. It’s a strange tragedy that we hold ourselves accountable for building healthy, functional teams, and yet are so rarely on them ourselves.

  But it can be better. It’s okay to expect more.

  I’ve worked on a few teams in which folks consistently looked out for each other, and believed they’d all come out better together. These were teams that had individuals willing to disappoint the teams they managed in order to help their peers succeed. It wasn’t that these folks were ready to callously disappoint people. Rather, they balanced outcomes from a broad perspective that included their peers.

  The members of such a team have shifted their first team from the folks they support to their peers. While these teams are rare, I’ve come to believe that supporting their creation is simple—albeit hard—work, and when the conditions are fostered, they lead to an exceptionally rewarding work environment.

  The ingredients necessary for such a team are:

  Awareness of each other’s work. Even with the best intentions, a member cannot optimize for their team if they’re not familiar with other members’ work. The first step to moving someone’s identity to their peers is to ensure that they know about their peers’ work. This will require a significant investment of time, likely in the form of sharing weekly progress, and the occasional opportunity for folks to dive deep into each other’s work.

  Evolution from character to person. When we don’t know someone well, we tend to project intentions onto them, casting them as a character in a play they themselves are unaware exists. It’s quite challenging to optimize on behalf of characters in your mental play, but it’s much easier to be understanding of people you know personally. Spending time together learning about each other, often at a team offsite, will slowly transform strangers into people.

  Refereeing defection. In game theory, there is an inte
resting concept of a dominant strategy. A dominant strategy is one that is expected to return the maximum value regardless of the actions of other players. Team collaboration is not a dominant strategy. Rather, it depends on everyone participating together in good faith. If you see someone acting against the interests of the team, you, too, will likely defect to pursue your own self-interest. Some teams are tightly knit enough that no one ever attempts defection, but most teams experience frequent changes in membership and external conditions. I believe that on such teams coordination is only possible when the manager or a highly respected member operates as a referee, holding team members accountable for good behavior.

  Avoiding zero-sum culture. Some companies foster zero-sum cultures, in which perceived success depends on capturing scarce, metered resources, like head count. It’s hard to convince folks to coordinate under such conditions. Positive cultures center on recognizing impact, support, and development, which are all avenues that support widespread success.

  Making it explicit. If you have the first four ingredients, you still have to explicitly discuss the idea of shifting folks’ identities away from the team they support and toward the team of their peers. It’s hard to move membership from the team you spend the most time with, and I haven’t seen it happen organically.

  Given how much energy it takes to shift the identities of a team of managers away from the folks they support and toward their peers, I think it’s quite reasonable to question whether it’s genuinely worth doing it. You’ll be unsurprised to know that I think it is.

  As you move into larger roles, you’ll need to start considering challenges from the perspectives of more teams and people. In this sense, treating your peers as your first team allows you to begin practicing your manager’s job, without having to get promoted into the role first. The more fully you embrace optimizing for your collective peers, the closer your priorities will mirror your manager’s. Beyond practicing working from this broader lens, it will also position you for particularly useful feedback from your manager, as you’ll both be considering similar problems with shared goals.

  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. Likewise, as you’re thinking about your peers’ work, you’ll be able to learn from how they approach it differently than you anticipate. Soon, your team’s rate of learning will be the sum of everyone’s challenges, no longer restricted to just your own experiences.

  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!

  5.4 Consider the team you have for senior positions

  Over the past six months, I’ve been hiring engineering manager-ofmanagers roles. These roles are scarcer than line management roles, and they vary more across companies. This process has taught me a bunch of new things.

  Manager-of-managers searches are interesting in at least four ways:

  There are many folks who can’t find upward mobility within their current company. They have not managed managers before, and are looking for the opportunity.

  Most people with experience managing managers are happy in their current roles.

  The individuals interested in these roles outpace supply. This makes it more important to put in place processes like the Rooney Rule.7

  You need a fair way to consider candidates within your company. It must be respectful to them yet allow you to uphold your responsibilities to the company.

  The last aspect what has taught me the most, and what I want to focus on. Ensuring that internal candidates take part is essential to an inclusive culture. Fair consideration doesn’t mean that we prefer internal candidates. Rather, it means that there is a structured way for them to apply, and for us to consider them.

  Letting individuals apply is the easy part. You must announce each position and ask for internal candidates. You should persuade eligible candidates to apply, especially if they are uncertain. You should give them a week or two to consider whether they want to apply.

  Then comes the trickier part: evaluation. We’ve focused on testing these categories:

  Partnership. Have they been effective partners to their peers, and to the team that they’ve managed?

  Execution. Can they support the team in operational excellence?

  Vision. Can they present a compelling, energizing vision of the future state of their team and its scope?

  Strategy. Can they identify the necessary steps to transform the present into their vision?

  Spoken and written communication. Can they convey complicated topics in both written and verbal communication? Can they do all this while being engaging and tuning the level of detail to their audience?

  Stakeholder management. Can they make others, especially executives, feel heard? Can they make these stakeholders feel confident that they’ll address any concerns?

  This evaluation doesn’t cover every aspect of being an effective senior leader. But it does cover the raw skills that form the foundation of one’s success. You already know if an internal candidate has hired managers. You know if they’ve done organization design. There’s no need to ask all that.

  To test these categories, we’re using these tools:

  Peer and team feedback. Collect written feedback from four or five coworkers. Include peers on other teams. Include people the applicants have managed. Include people they would not have managed. My biggest advice? Lean into controversial feedback, not away from it. Listen to would-be dissenters, and hear their concerns.

  A 90-day plan. The applicant writes a 90-day plan of how they’d transition into the role, and what they would focus on. They emphasize specific tactics, time management, and where they’d put their attention. This is also a great opportunity to understand their diagnosis of the current situation. Provide written feedback to them on their plan. Have them incorporate that feedback into their plan. This is an opportunity to try out working together in the new role.

  Vision/strategy document. The applicant writes a combined vision/strategy document. It outlines where the new team will be in two to three years, and how they’ll steer the team to get there. Provide written feedback on the document. Have them incorporate that feedback.

  Vision/strategy presentation. Have the applicant present their vision/strategy document to a group of three to four peers. Have the peers ask questions, and see how the applicant responds to this feedback.

  Executive presentation. Have the applicant present their strategy document, one-on-one, with an executive. In particular, test for their ability to adapt communication to different stakeholders.

  Running the process takes a lot of time, but it’s rewarding time. In fact, this has generated more useful feedback than anything else I’ve done over the past year. It brings an element of intentional practice that’s uncommon in engineering management. Folks get to take risks in their plans. You get to give direct feedback without risk of micromanagement. It’s been useful enough that I’m now figuring out whether we can use a similar format for training managers.

  Know that internal processes are awkward. You’ll have many internal candidates. They will talk to each other. They will interview external candidates for a role they are applying for themselves. One candidate may end up managing the others. Don’t decide to avoid this morass of awkwardness. You can’t. You’re deferring it until later. It’ll still be awkward, but now awkwardly in the realm of gossip.

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

>   5.5 Company culture and managing freedoms

  In 1969, Roger Miller (and later, much more famously, Janis Joplin) sang:

  “Freedom’s just another word for nothing left to lose.” 8

  This gives us yet another peculiar entrant toward defining freedom. Perhaps it’s nothing more than an apologetic9 ode to despair: law requires consequences, and there are no consequences when you’ve already been reduced to nothing.

  Lousy hooks and confusing segues aside, the topic for discussion is the relationship between a company’s culture and its freedoms. Rather than starting down the path of examining the kinship of freedom and consequence—which is a rather dismal place to begin anything—we instead look toward kinds of freedom, which immediately brings us to the distinction between positive and negative freedoms.10

  Positive freedom is your freedom to do: to vote, to wear the clothing you want, to own arms, to blow smoke into your neighbor’s porch when they’re trying to read a book outside on a sunny day. Negative freedom is your freedom from things: from being forced to take an impossible literacy exam before being allowed to vote, from to wear clothing you dislike or find oppressive, from having your cellular traffic recorded, from having your neighbors blow smoke onto your porch when you’re trying to read a book outside on a sunny day.

  Wielding this distinction, “freedom” is neither inherently good nor inherently just, and descends into the murky gray that already embroils everything else in our lives. Each positive freedom we enforce strips away a negative freedom, and each negative freedom we guarantee eliminates a corresponding positive freedom. This sad state of affairs is often referred to as the Paradox of Positive Liberty.11