What You Say vs. What They Hear

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Communication is super important within any organization, but it’s particularly vital in remote work. At Automattic, we use the phrase “Communication is oxygen.”

The take-home message—building something amazing is impossible if everyone isn’t on the same page.

Any communication is better than silence, but aspects like clarity, actionable next steps, and an understanding of how everything “fits” can take a message from mediocre to “Hell yeah…let’s do this!”

A few weeks back, I was able to catch dinner with my buddy Chuck, and we were chatting about leadership and communication. I mentioned one communication error in particular that I was trying to address—reconciling what you’re saying with what “they” are hearing. This harmony is imperative for great communication, but I/we so often walk away from a conversation thinking “Oh yeah, made that totally clear” only to revisit the same idea two weeks later and find out we’re on different pages.

For example, let’s say that you have someone on your team named Tony. Your little donut shop is slammed with customers today. So, you bump into Tony and tell him:

We’re swamped out there! If everyone could make 50 more donuts, that would be a huge help.

In my head, it’s easy to think I’ve set a clear expectation for Tony—make 50 more donuts. In his head, that expectation is more of a suggestion. When I tell Tony I’m disappointed he hasn’t done 50 more donuts, he’s probably going to be confused for several reasons.

First, I used the word “everyone” instead of directing the request at Tony in particular. In Tony’s mind, it’s easy to brush it off as someone else’s problem.

Second, I used weak words. Things like “If you could…” softens the demand. I feel less like an asshole. The “ask” though now feels more like a “Hey, if you have time…” and less like a “I’ll hold you accountable for this later.”

Lastly, (and this is a bit ridiculous in context) I’m assuming Tony understands the importance of making more donuts. I’m assuming he understands the larger plan here and how this particular action fits in with the mission of our donut shop.

I’ve avoided feeling like an ass, but Tony and I aren’t on the same page.

Enough with the donuts. What can we do about it?

I’m still figuring this piece out. If you’re looking for answers, I don’t have them. I can share how I’m trying to approach the issue.

Whenever there’s an objective measure of success, make that clear from the start.

Part of the issue is born out of a desire to not sound like a demanding asshole. So, we instead switch over to the other side of the spectrum and drown out our message with weak words. This ultimately does a disservice to the listener. How can they possibly meet our expectations if we’re not setting those expectations clearly?

We assume that others are averse to statements like:

Tony, please do 50 more donuts by 2pm today. We’re really drowning here.

In the right context though (assuming Tony doesn’t already think you’re an ass), these kinds of statements inspire direct action. They leave no room for ambiguity. Next steps are obvious.

Repeat the “Why” like a broken record.

Consequently, a great leader is one that continues to beat the same drum, repeat the vision of the company day-in and day-out. To the leader, it might eventually feel and sound rote but the reality is that it’s not – we all need to hear the life-giving words that help us, remind us, about the “why” in what we’re doing.

— via John Saddington

If you’re leading a team or organization, this equation is crystal clear in your head:

Daily Work * Days = Team/Company goals

From someone else’s perspective, the math is murkier. It’s not always obvious how daily actions roll up into BHAGs yet it’s crucial for motivation. If you’re making a request, include the why. If you can’t think up the why, it’s probably not worth doing.

The goal is to make the leap from:

I need to make 10 widgets today.


It’s important for me to make 10 widgets today because we’re really behind on widget production, and ultimately, this will help us achieve our vision of delivering widgets to the world.

Repeat through text.

Whereas voice conversations can carry ambiguity, text leaves a smaller window for misinterpretation.

Every month we have a meeting for Drink for Pink to discuss next steps. We toss out all kinds of crazy ideas and hundreds of “We should do this!” suggestions. When we’re wrapping up, I forget 99% of what I’ve agreed to do. So, we have a 5 minute recap that outlines the deliverables for each person at the table. Then, those same deliverables are reiterated in an email recap sent afterwards.

This kind of immediate, unambiguous recap gets ahead of misunderstandings. After a one-on-one, I’ll send a Slack ping with:

I can hold you accountable for:

– Thing 1

– Thing 2

You can hold me accountable for:

– Thing 3

– Thing 4

If I’ve misunderstood or left something off my list, we can correct it right then and there.


I definitely don’t have the issue figured out, but the steps above feel like the right direction. The overall goal is to make sure our lovable Tony and I are on the same page.

If you’ve ever run into this communication issue before, I’d be interested in hearing how you handled it!

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