Structural Lessons in Engineering Management

Software engineers are attracted to formulas, algorithms, and structures. As people whose job it is to take ideas and turn them into predictable executable code, it is unsurprising that we’re drawn to ways of thinking that categorize and systematize things. This attraction continues as engineers become engineering managers and leaders. I should know, I wrote a pretty popular book that is full of best practices, tips, tricks, and process suggestions to apply to the various challenges of leadership.

However, I think it’s worth talking about the downside of going too far with structural thinking as it pertains to teams and organizations. Let’s take a common area where this structural approach happens, namely that of organizational structures and interactions.

There are certain rules that I believe in, one of which is that engineering managers do not scale well beyond about 7–8 direct reports. It’s hard to keep the context of what each of these people is doing and thinking about in your head well enough that you can effectively guide them. You end up spending an outsized amount of time on management tasks when your direct team size grows much beyond this number; or, even worse, you just start doing a bad job at those management tasks because you don’t have the time to do them well.

On the flip side, many organizations do not want managers who only manage a couple of people directly. Someone who manages only two people is often in a limbo state: are they an individual contributor? Are they a manager? The HR system is binary: if they have direct reports, they must be a manager. But the reality is that if you only manage a couple of people, most of your time is spent doing things other than management. If this person is a new manager, they may not be learning the things they need to learn to grow into a confident managerial role. On the other hand, if this person is and wants to remain an individual contributor, their management is likely to be a bit lacking for these two individuals.

The temptation is to move from these two beliefs into the notion that you must create a clean tree structure for your organization. Each manager manages three to eight people; when a team grows too large you rebalance the tree. All is clean, and easy; our organizational structure works.

Experienced managers know how quickly this falls apart. People quit, and suddenly the manager of 5 people only has 2 direct reports. Managers don’t just drift between teams depending on the immediate size of the organization, they have skills and interests that make them sticky to their group. Individual contributors get rightly frustrated when their manager changes too often, and they prefer managers who have some understanding of their work. The teams need to have some coherence of vision and purpose; hiring is never a steady drip but comes and goes in bursts. Your ideals quickly fall apart when faced with the reality of a living organization and the needs of the people in it, so your trees sometimes have skinny branches, and sometimes very fat ones. The best you can do is try to nudge it back into shape over time, or very occasionally, reorganize into something more appropriate.

Photo by Gilly Stewart on Unsplash

Another failure mode happens when leaders get enamored of applying engineering analogies to define team interactions. APIs are a fine concept but the idea that team interactions can be strictly defined by an API is as laughable as the idea that programmers won’t figure out a way to exploit every undocumented feature you provide in one. In this case, Hyrum’s Law applies as much to engineering organizations as it does to software. Humans will and must talk to each other, trade favors, and negotiate based on changing circumstances. When you are in the thick of trying to get things done, you will use what you can find, whether it’s an undocumented API or an engineer on another team who is willing to lend a hand.

Ironically, a lot of software engineers turned managers believe that they are taking humans into account with these rigid structures. When you see the world in systems, interactions, and efficiencies, you can trick yourself into believing that the humans inside of these systems will be happier if the system is well-organized. While I agree that there is value to organizing your teams effectively, the marginal value that the teams might experience is likely to be offset by the unintentional friction that happens for the people who don’t fit perfectly into your structure. If you don’t work to stay ahead of what the people in your team want and need, if you don’t create growth opportunities or appropriate technical challenges even though it’s not the most optimal thing for the system as it currently exists, you will find yourself losing good engineers and managers. The people in the system are much trickier than you are imagining, and the structure that accounts for their skills and happiness will have organic features as much as centrally-planned ones.

Managing a startup team at a new and growing company can lead inexperienced managers to believe that they can define the structures and processes to be perfectly tuned to what their company needs at the moment. I went through this phase myself, and I know the temptation to allow the ever-changing demands of startup life to justify changing and tweaking of teams and processes and projects in pursuit of the ideal execution machine. While managing a large organization at a more stable company, I’ve come to appreciate the cost and overhead of such a systems-focused approach. When you are thinking in terms of years and not months, it becomes important to accept that you may hang out in imperfect structures for many months or even longer, because you are trying to hang onto people for years.

So, new leaders, read those books and expose yourself to those ideas, but don’t stop there. Listen to your people, and don’t be afraid to break your perfect structures to accommodate their needs. They are your best source of learning, and your most valuable asset.

Enjoy this post? You might like my book, The Manager’s Path, available on Amazon and Safari Online!

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