Complexity isn't Allowed in Enterprise Tech Leadership

In order to consider complexity in decision-making, senior leaders need to be willing to admit there are things they can't know.

So, I was recently pleased to attend an online event hosted by the Complexity Lounge. Alicia Juarrero, a Doctor of Philosophy and visiting research scholar at the University of Miami, would speak about constraintomes, a concept in complexity regarding mutually interdependent contextual constraints. (buy her latest book here or read it for free here)

Many of my favorite people from the complexity community were there, and it was nice to reacquaint myself with them after not seeing them for many years. I was honored to speak at a conference where Alicia presented in NYC in 2014, and I met her in person. She’s a lovely person who can explain complex subjects in an approachable and engaging way.

The talk was great; Alicia is a fantastic speaker who dives deeply into complexity science. The things she discusses are not entry-level, and I enjoyed getting extra nerdy.

Ultimately, as I enjoyed this deep dive into interdependent constraints, I was saddened because these are the things high-level decision-makers in organizations should think about and learn. Instead, senior vice presidents worry about which text editor a given programmer prefers or whether they like tabs or spaces more.

The fact of the matter is complexity is a huge factor in managing organizations filled with people. Too many leaders get where they are by being the confident sociopath in the room. If you are presented with a difficult challenge and you start to ask questions like “What do we think is driving this behavior?” or “In what ways are the systems designed to produce this outcome?” you are immediately shouted down by some psycho who yells “This is clearly because so-and-so is a lazy asshole and needs to be fired!” or “Are we considering how Cloudwatch factors into this?!”

In a coherent world, that buffoon would be laughed out of the room, but too often, that buffoon is the “HiPPO” or a representative of the “Highest Paid Person’s Opinion,” and even if anyone in the room is knowledgable enough to challenge them, it’d be a career-limiting move to do so.

When I was hired as Chief of Staff at the supply chain technology division of a fashion retail hereditary oligarchy, one of the first things I did with the leadership team, I was ostensibly a member of was to lead a half-day leadership workshop.

The final exercise was a complexity-informed problem-solving categorization approach. We applied the Cynefin model to understand some of our supply chain’s hairiest problems and develop appropriate response categories.

We identified a specific, actionable problem and agreed to pursue context-appropriate countermeasures and measure what the expected vs. actual results of those interventions would be later.

In this organization, you’re not allowed to refer to your boss as your boss or say that you “report to” your boss; you have to pretend there’s an inverted pyramid organizational hierarchy wherein this person “supports you” even though, in practice, they usually “support” you by denigrating you, uncritically relaying vague unactionable feedback and reprimanding you without seeking to understand your experience.

The senior director, who “supported” me in all the manners listed above, came into my office after the session to give me feedback.

”It’s clear to me you’re very good at that. You clearly know what you’re talking about and are quite expert at running that workshop. But, as an engineer, I find it really hard to sit through that kind of stuff.”

I refrained, despite how much I’d been informed about the incredibly high psychological safety of the inverted pyramid in which I was currently being “supported,” from saying what I wanted to say.

”What a pity; I’d hoped you were a Sr. Director because we have 160 engineers and only one Senior Director.”

We never actually followed through on the problem we agreed to solve, and this poor, suffering engineer with a senior director title led no subsequent action.

In fact, the most common response I got from some very capable and sharp engineering managers on the leadership team was that they’d love to solve those problems. They understand what we need to do, but they also know senior leadership always shuts down such efforts and that I am essentially in a Quixotic role.

I once admitted to a close friend and director who advocated for hiring me there that I felt ashamed over how things ultimately turned out, and they said….

“Don’t feel bad; I said when we decided to hire you that you were the best possible person for the job and you would never be permitted to do anything.”

That’s where we seem to be in enterprise technology leadership: a bunch of “engineers” with nary a leader to be found.