Provoking thought

It Doesn't Matter What You Say

An exercise:

Stand in front of a group, and say something meaningful on a topic the audience cares about.

No, no, that’s not all, here comes the hard part:

Now, look around the room (realistically: zoom room). Hopefully you see familiar faces. Now do this exercise in empathic listening: for each audience member, mentally put yourself in their shoes, or ears, or whatever. Mentally recreate their context: their history in the company, their role, their hopes and dreams, their frustration, everything you know about them including their mood that day. Now replay what you just said. Got that? Now, what did this person just hear?

Sanity check sidebar: If, when you do this, you just hear your own words echoed back to you — I’m sorry, but you’re not ready. In that case, repeat the exercise, but remove the “putting yourself in their shoes part” and literally ask the people in the room: can you paraphrase what I just said?

Heard something different now? Good, let’s get back to the main program.

“Crap. That's not what I intended at all...”

“Luckily,” you may think, “technically that's not what I said, claimed, or stated so: haha — I would win that court case!”

You’re absolutely right. However, unless you're willing to fight every individual’s interpretation of what you say in court, here's your reality:

It doesn't matter what you say, the only thing that matters is what people hear.

Welcome to wondrous world of leadership communication! A world in which you basically cannot win, but, on the flip side, you can always attempt to get better.

In various places I’ve gotten into the habit of writing a weekly update that is visible to anybody in the company. The purpose of this weekly update evolved over time. It started as a type of status email, but eventually I started to use it as a channel to openly talk about challenges I see in the company and how I think about solving them.

I think it’s healthy to acknowledge problems that exist, and ideally give people some sense we’re either:

  1. actively addressing them, or
  2. there’s a plan to address them, or
  3. we’re actively asking people to help us address them, or
  4. we’ve explicitly decided not to address them (for now)

All of the above (in my mind) are better than seemingly ignoring the stampede of elephants in the room.

I feel there’s a lot of value in trying to be more transparent as a company this way. Nevertheless, it’s super duper hard to do well, and the more contentious the topic, the more slippery the slope.

Why? Because for me to do this perfectly, I need to run the exercise we started this post with, not with a few people in a room, but with potentially hundreds, thousands of people in a company — many of which I’ve never met, and many of which don’t me. If I want to push it, it’s even wise to consider what would happen if this type of message “leaks” outside the company.

Obviously, it’s not practically possible to this perfectly, but we can approximate by classifying our audience into clusters and then performing an exercise in empathic reading.

Here’s my process:

I start with an initial draft, then I attempt to read the message putting myself in shoes of various shapes and sizes:

  • How would somebody completely new to the company read this? Is there a risk of “oh my god, this place is a mess, where is the exit!?”
  • How would somebody who previously was completely ignorant of this challenge take this? “I was very happy before, but now that you pointed to this problem, yikes!”
  • How would somebody who’s in the middle of this challenge take this? “You’re completely missing the point!” “That’s actually not a good representation of what the problem is.” “I never said that!”
  • Could anybody think I’m specifically calling them out (without name of course), even though I’m not? “Dude, if you got a problem with me, just talk to me, don’t broadcast this to the company!”
  • How would my boss’ boss’ boss take this? “Wow, it seems like there’s quite some challenges over there, should I be worried?” How would somebody who is borderline toxic take this? In other words: what is the most negative interpretation of this message?
  • How would the outside world read this if this message were to “leak”? Over time I built up a “pool” of people that have had strong responses to my messages in this past (good or bad), so I usually consider them specifically.

Now that I revealed my process, you may think it’s completely bonkers to put this much effort into it, but hey — this is what I do.

I’ve been doing this for a good number of months now, and so far I’d classify the result as worth it. Mostly I get appreciation for the effort. And it’s a useful exercise in structuring thoughts for myself.

However, every week or two, there’s a bit of a blow up. Somebody interpreted something in a way I had not anticipated in my 10x rereads attempting to take all my audience “personas” in mind. Perhaps I hadn’t considered this particular person, or perhaps I had just not anticipated how this person could take it accurately. It sucks every time this happens, there are a few relationships that have suffered as a result.

Realistically, this is unavoidable and likely just the cost of the game. However, this is also where the learning starts: I do try to take each such case seriously, and think how to avoid them in the future (if possible).

Here’s one of the learnings: sometimes I'm quite proud of a clever way of phrasing something. Something I write hints at something, but technically without making any concrete promises. Noice!


In practice, this is often the root cause of these blow outs. “But... in this update you wrote X!” With my retort: “haha! — well, technically...”

It doesn’t matter what you write, the only thing that matters is what people read.

While it’s sometimes hard to predict how a message lands, it doesn’t mean the “sender” is less responsible for the crash. Or, phrased more to the point:

If people don’t hear what you intended to say — tough cookies — this is on you.