#12: Say it, Bob. Say it!

An 80/20 tip for instantly communicating better asynchronously

Hey folks,

Long time. Some headwinds on the 1 thought per day (1TPD) experiment lately for various personal reasons, but we’re back now and that’s what counts. I hope you’ve been keeping well since the last post.

Today’s thought is about communication.


Comms is something I care a lot about. When I learned about ChatGPT’s custom instructions feature, for example, I wrote the following as part of mine:

I care a lot about communicating clearly and kindly.

Please always reply with clarifying questions if there are ambiguities instead of making assumptions. And whenever you're making assumptions about my intent or what I'm saying, please state those assumptions clearly. This helps us avoid misunderstandings.

This kind of custom instruction gets obeyed as a system prompt by the AI, so I get exactly what I ask for.

But I can’t go around prompting humans to respect my communication preferences, even if some of those preferences are just basic courtesies…

As someone who notices these things, I’ve collected many instances of “this could have been communicated 80% better with 20% more effort” in my notebook.

Here’s an example:

Bobs be bob-ing… (Image: re-enactment in Notion)
Bob: (highlights text and writes an inline comment in Notion)
Bob (10 hours ago): Should probably only allow edits, not deletes.
Nick (2 minutes ago): Why do you think so? Wouldn’t that make us look bad?

In this case, Bob is communicating poorly in an asynchronous work environment. He asserted himself without explaining himself. I always frown when I see people communicating like that.

How could it have been better?

Simple: always accompany assertions with explanations.

From what I can tell, this happens a lot more with people higher up in the corporate hierarchy. Perhaps they have to be brief because they’re busy. Perhaps they like brevity a little too much because it makes them sound like they know something others don’t. Perhaps they don’t know much of substance, preferring merely to spout talking points and hide behind their authority, to camouflage a knowledge deficit.

So in this example, we can see that Nick shouldn’t need to ask this question. Bob, as an adult, should anticipate that other adults wouldn’t simply accept what he says without reason.

What happened in that case afterwards was Bob having to explain himself, 12 hours since his initial assertion. How ridiculous! He managed to waste his time and that of Nick’s, because the following happened since his first message:

  1. Nick gets notified of Bob’s reply by email
  2. Nick pauses what he is doing to open the message 10 hours later
  3. Nick reads the message
  4. Nick wonders, wtf, why
  5. Nick writes politely, wtf, why
  6. Bob gets notified of Nick’s reply by email
  7. Bob pauses what he is doing to open the message 2 more hours later
  8. Bob reads the message
  9. Bob thinks hard to recall why he made that original assertion
  10. Bob writes a reply
  11. Nick gets notified of Bob’s reply by email
  12. Nick reads the message
  13. Nick contemplates Bob’s reasoning…
  14. Nick replies to Bob

All of that could — should, ethically speaking — have been compressed into:

  1. Nick gets notified of Bob’s reply by email
  2. Nick contemplates Bob’s reasoning…
  3. Nick replies to Bob

That’s 14 steps instead of 3. If you do the math, that’s a 78% improvement in terms of steps count. It’s at least a 10000% improvement in terms of time to understanding.

With how much more effort in this case? Zero… because Bob had to explain himself eventually. I might argue he could have saved 20% of his effort if he had done it upfront when his brain was already holding the context and reasoning behind his assertion.

You know what’s the worst part of all of this? 99% of people will not call out this kind of behaviour in their workplace. Giving feedback makes people uneasy. Most think giving feedback is a kind of confrontation, and I guess they’re not wrong because some people react negatively to feedback. And so… 99% don’t call it out.

The result is that the Bobs of our workplaces continue to communicate poorly, wasting everybody’s time and thoroughly annoying those who see it for what it is.

The next time you encounter a Bob in your workplace, feel free to send this post to them.

If you’re Bob, and you’re reading this, know that I believe you can do better. For yourself and all of us.

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