Check Your Context

I didn’t much like Wally from the first time I met him. We worked in the same circles, but not on the same projects. I was aware of his work, but not involved or dependent on it. My initial reaction to Wally, “Complains. Nitpicks. Doesn’t act.” I made this judgment in a moment.

Months passed, and none of Wally’s observed actions changed this initial perspective. In conversation, he was the guy who pedantically and exhaustively pointed out flaws, but did not suggest the means by which we address the flaws. My impression was unchanged: “He believes identifying the problem magically fixes the problem.”

Several years after we first met, Wally and I were paired on the same project. I was the technical lead, and he was one of three engineers contributing. From the moment it was announced that we were on the project, I knew there would be a Wally situation.

To his credit, Wally didn’t Wally for almost six months. I figured there was something about the project or the team structure that prevented the endless critique, but I was wrong. Seven months in, the project went sideways, and the Wally flood began. The good news is that I’d been preparing my speech for him for just under a year. I know what I wanted to say, and the moment the debate became unhelpful, I took him aside and executed on my speech.

“Wally, it’s clear that you care about this project. So do I. It’s why they put this on the effort. You have experience. You work hard. You listen to the team, but when it comes to solving hard problems, you… endlessly analyze. You scratch at that problem itch way past the point of uselessness. Yes, we need to understand problems, but the understanding should begin to reveal solutions. Please help us find solutions faster.”

From that moment on, Wally and I got along famously. Problem solved.

I am not joking even a little; I am, however, lying quite a bit.

A Vacuum Full of Fear

I’ve never actually met Wally. Yes, we had a tremendous amount of interaction over the years, but the entirety of our interaction has been text-based; it was online. We never worked together. All of my impressions were real, and, yes, we did end up co-contributing on a volunteer project virtually. And, yes, the Wally talk did finally occur, and it did fix our relationship, but the situation had very little to do with Wally and everything to do with me.

The rule is: “In the absence of information, humans will fill the vacuum with their worst fears.” The reason I lied to you is that I’m wondering: Did your perspective change when I told you I’d never met Wally in person?

Without a doubt, I know that a distributed company can work. I’ve helped build several and watched them work. We can communicate well in a virtual environment. However, if someone is sitting on the other side of Slack, everyone is missing context. A look here. A sideways glance there. Perhaps a critical pause.

What is aggregated with these small bits of missing information is an increasing vacuum. In that vacuum, you do what all humans do: you make an educated guess on how to fill the vacuum. Well, she responded to the message slowly, so I guess she doesn’t care that much about the project. His written answers are always so terse, I guess he’s mad… about something. He keeps typing and typing about the problem. I don’t think he’s that strategic.

Wally is strategic. I’d trust Wally to handle any curveball these days because I have… and he does. Wally isn’t the problem. I’m the problem. From his first few communications, I defined my Wally judgement and hung on for dear life. I never rechecked my assumptions.

Relative to me, the core issue with text communication is that I have decades of senior leadership experience and a truly impressive short attention span. These have served me well, but in order to read the room, I require a physical room populated with real, live humans. I need to see where you’re looking when you’re speaking. I understand more when I hear the length of your pause before you answer the question. I see discomfort as well as I see joy — you don’t have to say a thing.1

The skills you develop as a senior leader over decades in the room soup tasting have given me the impression that I am good at leaping to judgment or inferring intent quickly based on the vibes in the room. The room is not confident in what this person is saying, I will ask questions. No one is asking any questions about any of this presentation? What are they scared of? I will ask others to speak. He didn’t answer my question. I will ask again.

In a remote or virtual set-up, context vanishes. The amount of correct information you have about this person, their true thoughts about this topic, and others’ impressions drops significantly.

The written word gives you a powerful medium to define and refine your thoughts. Continued practice will improve the quality of your writing. However, you are the writer, not the reader. What publishing hundreds of articles and several books has taught me is that the reader plops themselves in the middle of your narrative and reads the story they want to hear. You shape their perspective, but you do not own it; they do.

Check your context. If you rely on written communication on a team: mail, Slack, messaging, the burden is on everyone involved, not just to read, but to understand. My belief: you’re missing 50% (probably more) of the context in the first draft of short-form written communication.

Check your context:

Any question you have, however small, is worth asking. Ask them. Ask them again. Ask until you are satisfied you understand.

In text, your impression of the emotion behind their words is your emotions speaking, not theirs. Clarify — do you mean this? I am reading your feelings as that? The incorrect snap judgment on emotion is a sure-fire way to point your understanding in the wrong direction.

If the writing seems clear, if the conclusions are reasonable, and you believe you understand, great. Does this thought lead us to a high-risk decision? Can you sense enormous consequences if we head down their suggested path? Repeat their thought in your words or use theirs. Watch what happens.

The One Conversation

In person, you are swimming in context. You’re so used to it that you take it for granted. The murmur of agreement — that’s good. The complete silence after the key point — that’s bad. Frank, nodding in the corner when she finishes speaking, Frank never nods unless he’s super on board, and Frank is never on board.

The reason the Wally conversation “fixed” my relationship was it was the first time I took time to give Wally feedback. Lunacy on my part. I know. I was sitting there hiding behind my keyboard, thinking Wally could infer my poorly informed judgment from my silence, from my lack of sharing context.

I find great comfort in the written word. It gives me satisfaction to translate the mess in my head into occasional helpful words and phrases. If you and your team are heavily relying on written communication to get the work done, you, the reader, have extra work to find the errors in their thinking and ask them questions to gauge the substance of what they write.

And, sorry again, Wally. You’re aces. And you already know that because I told you and you heard me.

Here’s the thing. The problem isn’t senior leaders who are being thrust into distributed environments where they need to rely on their writing skills and reading comprehension ability. The problem is that even to be able to deduce intent from written communication, you need to spend months, nay years, of your life in the room with other humans. It’s how you build a mental model for how other humans work. If you haven’t built this model, if you’ve spent your career typing versus talking with humans, then the above advice won’t resonate because you’ll believe the way to interact with the humans is via short, pithy statements via the keyboard. It’s not. You stopped reading in the first paragraph. This footnote didn’t stand a chance. ↩