Shadow Systems

There’s the system, and then the system behind the system.

I’ve written in the past about how the job of increasingly senior management is really about frameworks and mental models, that a big part of the job is about creating, applying, and maintaining systems1 to people and teams. The art in it all is about drawing from past experiences in that application, while appreciating that context and circumstances still make for very different outcomes. The complexity of people and all that jazz.

A few months back, there were a couple of articles highlighting misbehaviors of Away’s former—but now somehow co-—CEO. Of course, the journalism focused on her abusive Slack messages and bad treatment of their understaffed customer support, and predictably there were folks on both sides of the “whatever it takes for a startup to succeed, even if the people at the top act like jerks” argument. That the CEO was a woman founder added another wrinkle to the discussions, one that proved hard to disentangle.

I was struck by another part of the story: where the founders insisted on using public Slack channels as the primary means of communication throughout the company, over more traditional email and more private systems. The policy was intended to promote complete transparency, but ended up legislating out formally approved means of employee privacy, which had the unintended—though entirely predictable—side effect of creating shadow systems to meet that demand. In this case, the mildest form of that outlet was simply private employee Slack channels where people went to vent about their bosses and work lives.

The thing with absolutist systems is that they seek to tamper the symptoms but rarely get to root causes. In the best case scenarios, constricting the visible problems creates a dampening effect, the system working as intended. But without addressing the underlying why, issues just manifest in unpredictable ways, unofficial channels and shadow systems that sometimes end up harboring worse problems. For what Away tried the do, the wide and public Slack channels could only address broad strokes and lowest common denominators, so any resentments would only be left to be commiserated privately, and may very well be amplified in isolation.

Away’s management problems may sound tone deaf and unusually acute, but I find this pattern repeated over and over again. Once in a while, flat org structures and alternatives like holacracy would get some attention, as folks get frustrated with the bureaucracies of traditional corporate hierarchies without necessarily appreciating its explicit definition and its associated clarity. Google has kept, for decades now, a misc mailing list internally for employees to chat about any and all topics, and has served as a honeypot of sorts2.

Of course, all of this relies on the thesis that it’s better to not have shadow systems, that explicitness is better than keeping things hidden. Transparency, though, is wholly separate from simplicity; attempts to “start from scratch” seem to go astray when they try to paint with an overly broad brush, trying to keep things simple but not acknowledging that application is indeed complex and messy. In that way, it reminds me of a classic article on the foibles of software rewrites: there may be fundamental issues with the current way of doing things that necessitate a replacement, but by the time you’re done with it, it might look a hell of a lot like what you had—for good reason.

  1. Or in business vernacular, processes.

  2. Admittedly, Google is perhaps not the best example of stellar employee management given their recent policy changes.

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