TL;DR: Shared reality was always an illusion. But because AI customizes everything to us personally, we're finally being forced to see it. Learning to navigate the gap between your world and someone else's is about to become your most important leadership skill.
Miscommunication is a reminder that everyone is living in a slightly different version of the world.
When it happens, you feel it before you understand it. A tightening in your chest. A flash of frustration. The sudden sense of being lost in a conversation you thought you were having together.
Here's an example most of us have lived:
Person A: When will you be able to finish the project?
Person B: We'll finish it as soon as we decide the objective.
Person A: What do you think the objective is?
Person B: That's what I've been wondering. Is now a good time to discuss?
Person A: We have a lot to accomplish today.
Two people. One conversation. Two completely different realities underneath it. Neither is wrong. Neither is listening poorly. They're just living in different versions of the same situation — and neither has named it. And nowadays, maybe their viewpoints have been solidified by engaging with their AI chatbots on the sidelines.
I grew up in the 90s, when everyone watched the same TV, read the same newspapers, absorbed the same cultural references. It felt like a common world. Then the internet arrived, and suddenly every subculture, every marginalized voice, every alternative narrative had access to distribution. Some of it has been disorienting. Some of it was long overdue.
Now AI is doing something more significant. While social media showed you content made by other humans, AI generates content tuned to you, in real time, every time. You're no longer choosing from a buffet. The buffet is being cooked to your exact palette.
Daniel, a security researcher and AI systems builder, put it plainly in a recent talk: when everyone has their own AI filtering their interface to the world, they're getting different news and different ideas. His example: you tell your neighbor about a K-pop video you've watched 95 times. They look at you and say, "You still believe Korea is real?"
He was joking. Mostly.
Miscommunication isn't going away. It's going to increase. This is important to know because strong leaders will know how to move through it, by surfacing what’s hiding beneath the surface, so for a mutual purpose, they can find common ground to move forward together.
Here's how to manage miscommunication:
1. Feel it before you speak.
When miscommunication hits, the impulse is to fix it immediately — to explain yourself, go quiet, or go on the offensive. Before you do any of that, notice what's happening inside you. Anger. Frustration. The disorienting feeling of being lost. Start there.
That urge to fix it quickly? It's the desire to restore a shared reality that may never have existed. Notice it. Don't act from it.
2. Talk about the miscommunication openly.
Name the gap as a shared problem. Not yours, not theirs.
It might sound like: "I think we're working from different assumptions. Can we surface them?"
Get curious about their version of reality. Not to agree with it, but to understand it. Ask what they assumed, what they expected, what success looks like to them. Then ask if they'd like to hear your perspective.
The goal isn't to persuade them to see it your way. The goal is to recognize that two different realities are in the room, and that's okay.
3. Recognize what you can and can't change.
Most people in power don't examine their assumptions. Not because they're malicious, but because they don't have to. When your reality is the default, it's invisible to you.
Some miscommunications aren't fixable through better conversation. They're structural. What you can do is see it clearly. People reveal their assumptions in what they reward, what they ignore, what they never think to explain. Pay attention. Not to change them, but to decide whether you want to keep operating inside their version of the world.
As my AI agent Wisp, who co-wrote this article with me, puts it in a clear, concise way using a contrasting statment: "That's not cynicism. That's discernment, Michael."
In a world where the illusion of a shared reality is fracturing faster than ever, knowing whose reality you're willing to inhabit, and whose you're not, might be the most important leadership skill you develop.

Michael Shehane is the founder of InStride Leadership, helping tech executives build the communication skills to lead through complexity, ambiguity, and now, a world where shared reality is no longer guaranteed. Contact me at [email protected] and visit leadinstride.com to learn more.


