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Allen Bailey
Allen Bailey

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I Stopped Expecting AI to Think Like Me — Results Improved

For a long time, I was quietly frustrated with AI.

Not because it was wrong—but because it wasn’t me.

It didn’t prioritize the way I would.
It didn’t notice what I noticed.
It didn’t frame problems with my instincts or context.

So I kept trying to fix it.

More detailed prompts.
More instructions.
More “do it like this.”

Ironically, my results only improved once I stopped expecting AI to think like me at all.

The Hidden Expectation I Didn’t Realize I Had

I was treating AI like a junior version of myself.

I expected it to:

Read between the lines

Understand what mattered most

Share my intuition

Anticipate my judgment

When it didn’t, I assumed the output was weak—or that I hadn’t prompted well enough.

But the problem wasn’t the AI.
It was my misplaced expectation.

AI doesn’t think like a person.
And it definitely doesn’t think like me.

Why That Expectation Was Holding Me Back

When I expected AI to mirror my thinking, I did two damaging things:

First, I over-corrected the tool.
I tried to force nuance, taste, and prioritization into prompts—things that only emerge through human judgment.

Second, I under-used my own role.
Instead of deciding, I kept refining instructions, hoping the next output would “finally get it.”

That wasn’t collaboration.
It was avoidance.

The Shift: Different Strengths, Different Roles

Everything changed when I reframed AI’s role completely.

I stopped asking it to think like me.
I started using it to think differently than me.

That meant:

Letting AI surface angles I wouldn’t naturally choose

Using it to challenge my assumptions

Asking it to argue against my instincts

Treating its outputs as contrast, not confirmation

AI stopped being a proxy for my thinking.
It became a pressure-testing tool.

My Judgment Got Sharper, Not Softer

Once I stopped expecting alignment, disagreement became useful.

When AI framed something differently, I asked:

Is this wrong—or just unfamiliar?

What am I dismissing too quickly?

What does this reveal about my bias?

Sometimes I changed my mind.
Often I didn’t.

But either way, the decision improved—because it survived contact with an alternative perspective.

That’s what I’d been missing.

The Outputs Improved Because the Process Did

The quality shift was immediate.

Fewer regenerations

Cleaner conclusions

Stronger recommendations

Less internal doubt

Not because AI got smarter—but because I stopped asking it to be something it isn’t.

AI handled breadth.
I handled judgment.

That division of labor worked.

The Lesson I Keep Now

AI is not a stand-in for my thinking.
It’s a counterweight to it.

The moment I stopped expecting alignment, I gained leverage.

AI didn’t need to think like me.
It needed to challenge me without ego.

And I needed to decide anyway.

The Quiet Advantage

When you stop asking AI to mirror you, you stop fighting it.
When you stop fighting it, you can finally use it well.

Results improve not when AI sounds more human—
but when humans stay fully responsible for judgment.

Build AI workflows that respect human judgment

Coursiv helps professionals learn to work with AI’s differences—so tools challenge thinking rather than replace it.

If AI feels useful but slightly off, that’s not a bug.

It’s the point.

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