Building empathy in the terminal

What empathy means in product work

Not feeling for someone. Indi Young calls the useful kind cognitive empathy: understanding how another person thinks. In A New Way to Listen, she asks people to recall what went through their mind during something they did, and listens for the whys, not their opinions. Her line for the listener: “It’s her mind, and you’re the tourist.”

So empathy isn’t how sure you feel about your users. It’s how much you know about how they think, and how much of that came from them.

That’s also why AI can’t do it for you. When Nielsen Norman Group compared synthetic and real users, the synthetic answers clustered around the average and lost the unusual ones, which is often where the real problem is. And personas, AI-made or not, can’t be checked for accuracy. So dwic’s first rule: never invent a user, a quote or an interview.

How it’s meant to work, and how it actually goes

In the textbook version, you listen to people first, find the patterns, then design, then test with people again. Building with an AI tool skips all of it. You’re often the designer, researcher and developer at once, with no notes and no users yet. Who it’s for is whatever was in your head when you typed the prompt.

My first version assumed the textbook: it organised interview notes most people don’t have. What I wanted was something that helps you build empathy from wherever you are. Then I noticed everyone does have evidence of one thing: what they believe about their users. It’s in their code.

Your code already says who you think your users are

We don’t read our own code as claims about people, because we wrote it. That’s the curse of knowledge. In a Stanford study, people tapping famous songs expected listeners to name half; listeners named about 1 in 40 (Heath and Heath, HBR). Designers reading their own forms are the tappers.

<input name="phone" required />

const STEPS = [5 steps]
// all required before first invoice

"You entered an invalid phone number."

That’s what /design-empathy does with you. Point it at one flow and it lists what the code assumes about people, with the file and line, then asks you about the riskiest three.

Questioning yourself without wearing yourself out

Being questioned about your assumptions is useful and tiring. Advait Sarkar warns in AI Should Challenge, Not Obey that an AI that keeps challenging you wears you out. So dwic asks three questions, each narrower than the last and each about a moment that already happened, since people are poor at predicting their own behaviour. Then it stops:

If there’s still no real person after three, it says so and records the belief as an assumption. And every question carries one line explaining why it asked, so you learn to ask it yourself.

Say how you know what you know

What would make me wince is Claude Code inventing users or quotes, calling it evidence, and recording it without anyone confirming. So dwic proposes, and you decide what gets written.

And every point is labelled by how it’s known, a habit worth stealing for any research doc:

“Recalled” matters most. A real moment you remember is more than a guess, but nobody can check it. Without its own label, memories quietly become evidence.

The why belongs to the user

Knowing what someone did is half of it. The why decides what you build:

But as a builder you usually don’t know the why, and pushing you would only produce a guess. So dwic asks once, “Did she say why?” If not, it records why: unknown and turns it into Young’s question for the real person: what was going through your mind?

Why do this in the terminal, with dwic

You could do all of this with a notebook. In practice, few of us do. dwic helps because:

• It shows assumptions you can’t see in your own code, with the file and line.
• It asks the follow-ups you’d skip on yourself, and stops after three.
• It won’t let a guess pass as a fact, and writes nothing until you say yes.
• It works before you have users. It can search public reviews and forums for what real people say, check each quote is on its page, and label it public. That runs on your own Claude account, so it asks first.
• What you learn gets used: dwic’s copy and form commands read .dwic/EMPATHY.md.

dwic is free as a Claude Code plugin:

/plugin marketplace add imsaif/design-with-claude
/plugin install design-with-claude@design-with-claude
/reload-plugins

Then run /design-with-claude:design-empathy the signup flow. If you try it, I’d like to hear where it felt wrong.