Shades of grey

It was definitely one of those weeks. I was in a sour mood from the get-go, a consequence of setting up an apartment for the first time in nearly 20 years, worrying about my kids, and failing to compartmentalize the feelings all of that generated. And when I received an email first thing on Monday that sent my absurd-o-meter into overdrive, I should have taken some deep breaths or an ice plunge or something that would have lowered my core temperature. Instead, I jumped onto a client call, tried to make light of the absurdity, and chaos ensued.

That I should have been more professional is a given: a big part of the role of leading is to be empathetic and smooth the path for your team, not start mud wrestling with them. I failed pretty dismally. But the whole episode—capped later in the day by a conversation reaching such peak absurdity it’ll surely never be topped—did make me think long and hard. That I should do and be better is obvious. But the real question was: what’s changed that suddenly makes work seem like such a minefield?

It’s too easy to conclude everyone’s on edge—and erring 100 miles on the side of caution—in the evolving cultural environment. That may well be true—at least within big organizations, it’s today terrifyingly risky to buck the status quo or decide the path of greater resistance is worthwhile. But noodling on this week’s events for a few days got me thinking there are a few other factors at play.

Bill Maher’s pre-Halloween episode had a riff on how the things that scare teenagers have changed. Among the most terrifying? “A boss who tells you to do something and doesn’t ask for your feedback.” It’s funny because it’s true: everyone seems to feel not only entitled but obliged to provide feedback on everything and anything at any time, irrespective of whether they have the experience or context (this goes hand-in-hand with the growing belief everyone should be looped into everything).

Now, feedback and constructive criticism are incredibly valuable, as is a culture of “if you see something, say something.” This is especially true when it comes to content creation—we all know how easy it is to stare at something for so long that you become blind to mistakes or flaws. I also happen to love a robust discussion to land on a better outcome. Vanishingly few decisions are black-and-white: when there are so many options, everything is a shade of grey. A leader’s job is to sift through everything, weighing the risks and rewards to come to the best decision in often complex circumstances.

Yet shades of grey are in short supply these days. A lot of feedback is presented not as an opportunity for discussion, but an order in disguise. The attitude seems to be, “I have a problem with this—it needs to change.” It’s as though the feedback culture has morphed into one where all opinions are held to be equally valid—in which case I look forward to the disappearance of all managerial roles from CEO down (and hereby trademark the term “Flat Org Society”).

I had an example of this a couple of weeks ago when an objection was raised to one element of a piece of content, and it was immediately clear the expectation was I’d just change it. Yet it wasn’t that simple. A lot of thought had gone into the design as a whole, of which this was just one part. We were up against a deadline, and implementing the change may have required commissioning new work at the expense of time and money. And, at the end of the day, this was a sample size of two people and there was the question of risk versus reward: would users really complain, and would it be material if they did?

These are the thoughts that raced through my head within a nanosecond of the “feedback.” I wasn’t rejecting its validity, but feeling slightly incredulous at the suggestion it must be changed before thinking through those dreaded shades of grey. As it happened, I could see how the element could be problematic and we changed it (even if we had valid reasons for including it in the first place). If I appeared to do so grudgingly, it was because this was definitely one of those instances where a nuanced discussion was needed, not a flat assertion that one course was right and one wrong.

This leads to my third factor: how did we end up in a situation where everything is so polarized? Are organizations just reflecting society more broadly, or vice versa? I was pondering this when a short section in a column by Scott Galloway provided some insight: he noted Sam Harris told him people become where they spend their time (which presumably means I truly am eating pasta in Italy while driving a Porsche). Then Galloway spoke about his former Twitter addiction.

“I had noticed I’d become more curt, venal, and reactionary,” he wrote. “Also, I was having thoughts in 140 characters (no joke). [Harris] pointed out that humans are more influenced by our environments than we’d like to think. If I spend 5% of my waking hours getting angry on Twitter, I become a 5% angrier individual. Same is true if I spend more time with my kids expressing and receiving love. We become where we spend our time.”

In the corporate world, email is where we spend our time. And for those of us old enough to remember the early days of electronic mail, I find this really interesting. I cling somewhat grimly and pathetically to wanting to truly converse over email: I like to ask how someone is doing, write in full sentences with correct punctuation and grammar, and try to inject humor and personality (which seems more and more risky in a world where humor is an endangered commodity).

That isn’t where the email world is today. Email is increasingly curt and transactional, devoid of nuance or real discussion, and most of the time borderline rude. One example: a former colleague’s modus operandi was to just flatly state a bunch of things—adopting a “this must happen” tone of informing rather than asking, even though they weren’t in a position of authority—and just sign “thanks all.” Every email felt like a presidential order, only it was the equivalent of a presidential order being barked by the deputy to the deputy to the deputy chief of staff.

While I’m not sure of the solution here (that I will do better is a given), two things gave me heart as the week progressed. First, a series of in-person meetings at my company were interesting and productive, without a hint of anything other than colleagues working together (with humor!) to come to the best outcomes. And I read more articles about the emergence from the pandemic making workers appreciate the value of actually connecting with each other.

Nuance, irony, sarcasm, and all the things critical to interacting at a human level just don’t work via email or Slack, no matter how many emojis you toss in (and video calls are also a poor substitute, which is why companies are rushing to make them more like ... meeting in person). Every single issue I encountered in recent weeks would have been short-circuited and resolved if we were meeting in person, as opposed to failing to communicate effectively over email and group calls.

Anyway, it was most definitely one of those weeks, and a reminder we never stop learning or thinking. So, as I like to sometimes sign emails where things are squiffy or we’ve resolved an issue that matters not a whit in the grand scheme of life: Onwards!

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