This AI Mistake Was Actually My Fault

Have you ever explained something to someone, watched them do the exact opposite of what you wanted, and thought:

“How did you misunderstand what I just said?”

I have.

Except recently, the “person” who misunderstood me was Athena, my AI employee.

And the annoying part?

She didn't misunderstand me at all.

I said the wrong thing.

Athena gives me a morning brief that keeps me updated on what’s happening across the business—projects, priorities, things that need my attention, things we're falling behind on.

Recently, she reminded me about work we needed to do for an in-person event scheduled for November.

There was just one problem.

We had canceled the event.

I knew that.

The people involved knew that.

But I had never told Athena.

So, of course, Athena still had the project plan. She still had the tasks. And as far as she knew, we needed to keep moving.

I replied to her in Slack:

“The November in-person event is a canceled event.”

Not exactly beautiful writing 😂, but she understood.

Then she did something important.

She started asking follow-up questions.

What happens to the partnership?

What happens to the existing deliverables?

What happens to the related relationships?

Good questions.

So I answered.

And that's where I screwed up.

There were two organizations involved, TrueMD and Jiffini.

What I meant to communicate was:

The partnership between TrueMD and Jiffini is dead.

What I actually wrote was:

“TrueMD and Jiffini are dead.”

Those are NOT the same instruction. 😂

Athena took me literally.

She started cleaning everything up.

She closed the board cards related to them. There were 25 items for TrueMD and another two for Jiffini.

Done.

Then she started asking me what she should do about some of the individual relationships connected to those organizations.

That's when I realized...

Oh crap.

That's not what I meant.

And here's the part I'm slightly embarrassed about.

My response was essentially:

“No, you misunderstood.”

Except...

she hadn't.

I misspoke.

That distinction matters a lot more than it seems.

Because Athena is AI.

She's not going home wondering whether the boss thinks she's incompetent.

She's not embarrassed.

She's not questioning whether she screwed something up.

She's not carrying that interaction into tomorrow.

But imagine I had done the exact same thing to a person on my team.

I give an unclear instruction.

They act on exactly what I said.

Then I tell them:

“You misunderstood me.”

Now I've taken my failure to communicate and quietly made it their failure to understand.

I've done that.

And I'm willing to bet you've probably done some version of it too.

That's actually one of the unexpected things I'm learning from building Athena.

Yes, she's helping us run the business.

Yes, she can keep track of projects, understand how one decision affects other work, ask follow-up questions, and clean things up when plans change.

But she's also becoming a pretty unforgiving mirror for how I lead.

Because AI can only work with the context and vision I give it.

And you know what?

So can people.

We talk a lot about leaders needing to set vision.

But vision isn't just the big speech about where the company is going.

Vision happens in tiny conversations too.

When you assign a task.

When priorities change.

When a project gets canceled.

When you tell someone what you need.

When you assume they understand something because you understand it.

That's where leadership communication actually gets tested.

I've started thinking about three things before I communicate something important:

What does this person already know?

What might they be assuming?

And, especially with another human:

How might they feel about what I'm telling them?

Because what I said, what I meant, and what someone else understood can be three very different things.

And when those don't match, my first question probably shouldn't be:

“Why didn't they understand me?”

It should be:

“What did I fail to communicate?”

That's a much less comfortable question.

But it's also a much better leadership question.

Can I ask you something? 🤔

When someone on your team gets an instruction wrong, what's your first instinct?

For me, I caught myself saying: “You misunderstood me.”

When the more accurate answer was: “I wasn't clear.”

What's the phrase you catch yourself saying?

💬 Hit reply and tell me in one sentence.

I'd genuinely like to hear it.

Want the full story? 👇

In the full video, I show the Slack conversation, what Athena did with my badly worded instruction, how she corrected everything once I clarified it, and what the whole thing taught me about communicating with AI and people.

For the physicians reading this 👨‍⚕️

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A few things worth checking out 👀

Just sharing a few things I've been exploring lately:

• 🤝 Let’s connect: I share more AI experiments and business lessons on LinkedIn.

• 📘 Book I keep thinking about: The Delegation Trap

• 🤖 What we’re building with AI: A look at what we’re working on with AI

• 📖 Currently reading: The book on my nightstand right now

• 🛠 Tool I’ve been using: GoHighLevel (GHL) — keeps the important stuff in one place.

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