When Frameworks Fail and Gut Feelings Take Over

By Hannah Baker

Dear Reader,

You know that moment when the data looks clear, the framework is airtight, and yet something in your stomach says, don’t do it?

That’s judgment, the quiet, inconvenient voice that shows up when the evidence has already spoken.

It’s also the thing most of us struggle to explain, even though our careers depend on it.

Businesses love reasoning.

We build frameworks to make decisions look rational, dashboards to make them measurable, and now AI tools to make them automated.

But if reasoning were enough, every junior with access to ChatGPT would be a design visionary

They’re not, because good design still depends on something slower, messier, and more human: judgment.

So what is judgment, and how do we keep growing it?

The Rabbit Hole of Judgment

To unpack this, I went down a small rabbit hole of psychology and philosophy.

Three thinkers, in particular, helped me see why judgment feels so different from reasoning, and why it refuses to be automated.

Of course, these three didn’t always agree: Kahneman saw intuition as bias-prone, Gigerenzer saw it as wisdom, and Dreyfus saw it as embodied skill. But together, they sketch the full arc of judgment. From cognition to intuition to embodiment.

Kahneman: The Two Speeds of Thinking

Psychologist Daniel Kahneman once described our minds as having two systems:

System 1: fast, intuitive, automatic.
System 2: slow, deliberate, analytical.

Most of the time, they work in tandem.

You notice something feels off in a design review (System 1) and then reason through why (System 2).

Judgment lives in that switch between the two, in knowing when to trust instinct and when to slow down and analyze.

That balance takes years to develop. It’s why experience matters: it teaches you when speed helps and when it hurts.

AI, by contrast, runs entirely on logic without lived context. It can simulate the output of reasoning, but it doesn’t feel what’s at stake.

Kahneman showed us the mechanics, the gears that make judgment possible.

He warned us about intuition’s biases, but stopped short of explaining why, in some domains, intuition becomes sharper and more trustworthy with experience.

That question led another psychologist, Gerd Gigerenzer, to look closer at the mysterious thing we call “gut feeling.”

Gigerenzer: Intuition as Compressed Experience

Intuition has always had an image problem; we’ve been trained to treat it like a bias we should correct.

Gigerenzer saw it differently.

He found that in uncertain, real-world environments, people who follow simple rules of thumb often outperform those who analyze everything.

He called it ecological rationality, the idea that our gut feelings aren’t random; they’re contextual intelligence shaped by experience.

Think about it: every project you’ve run, every critique you’ve endured, every time you said “this doesn’t feel right”, all of it becomes data your brain quietly stores and reuses.

Judgment grows through those moments, not by avoiding them.

That’s why there’s no shortcut to it. You earn judgment the same way you earn scar tissue: by living through the consequences.

Dreyfus: From Rules to Responsiveness

If Gigerenzer rescued intuition, philosopher Hubert Dreyfus gave it a body.

He argued that true expertise isn’t about following more rules; it’s about no longer needing to think about them consciously.

A novice follows the checklist.
An expert reads the situation.

That’s what he called embodied skill.

A seasoned facilitator doesn’t just run a workshop; they sense when the energy dips and pivot instinctively.

That responsiveness—subtle, sensory, social—is judgment.

It lives in our embodied attunement to the situation, not in the slide deck.

And yet, in most companies, we still trust spreadsheets over sensing.

The Trouble with Data

The irony is that most workplaces don’t reward judgment; they reward justification. “Data-driven” has become the safest phrase in any meeting.

It sounds objective, responsible, even noble. But data doesn’t make decisions, people do.

Numbers can tell you what happened; they can’t tell you what matters.

Judgment bridges that gap, interpreting what the data means in context and deciding which trade-offs are worth making.

The best leaders I’ve seen aren’t anti-data. They know that data can inform a choice, but it can’t own it.

Because the moment you decide what to build, what to cut, what to ignore, you’ve moved from the realm of information to the realm of values.

And now, we’ve built machines to reason for us, to find patterns faster, summarize better, and fill our meetings with confidence.

But even the most advanced AI can’t decide what should matter.

It can calculate, but it can’t care.

Why AI Still Feels Like an Intern

Here’s the simplest way to see the difference. AI is like an incredibly well-read intern.

It can read every research report your company has ever written, summarize the insights, and quote the right framework.

If you asked that intern what to do next, they’d probably pause, because they know they don’t have the experience yet.

AI won’t pause. It will give you an answer, instantly, confidently, and without any sense of what’s at stake.

That’s the difference.

Judgment isn’t about having the right answer.

It’s about understanding the weight of deciding at all.

Because judgment isn’t about information, it’s about discernment born from experience, knowing the cost of being wrong, the nuance of timing, the unspoken signals in a room.

Reasoning can be automated. Judgment has to be grown.