One Brief, Two Designers

Step 1

See what's broken

Click "Get started free" on Bitwarden's homepage and you land on a pricing page. The free plan you were promised isn't visible, and the biggest button says "Create Premium Account." The first thing a new user feels is a bait and switch.

Then it asks you to install the extension before you have any reason to want it. After that comes a tooltip tour and an empty vault, with importing your passwords left as step two of a checklist. It asks for money, then trust, then commitment, and saves the payoff for homework.

Step 2

Redesign it by hand first

First I cut the pricing wall. Instead of "pick a plan," one question: how are you planning to use this? Server region became two plain cards that spell out the difference. And the structural change that matters most: import comes before the extension.

I still made people verify their email before continuing. Hold onto that. It comes back.

Step 3

Give Claude the same brief

I dropped all nineteen original screens into Paper, connected Claude to it, and gave it the same five goals I'd set for myself.

Lead with value: does this screen earn its place by giving something?
Personalize early: do we know who we're talking to before we shape the flow around them?
Cut friction: is every step actually necessary, or have we just accepted it?
Show, don't tell: does the user feel the value, or are we just describing it?
End with a habit: does the last screen make coming back feel automatic?

Step 4

Read AI's three directions

A couple of minutes later it came back with three fully-formed directions.

Option A, Value-First Story: open with a breach check. The hook is fear. Option B, Do-It-Now Sandbox: a working password generator before you make an account. Option C, Concierge Path: a "who are we protecting?" question that tailors the rest of the flow.

Step 5

Make the call yourself

A is a trap. Bitwarden's pitch is privacy, and asking a stranger for their email up front contradicts it. B isn't the front door. An IT director rolling it out to five hundred people wants compliance and admin controls. C wins because it works for both ends of the market.

AI also caught me: it pushed back on email verification, and it was right. But it missed the freelancer, a business of one. "My company" implies SSO and a five-seat minimum they'll never touch. So I added a fourth path, Solo Business.

Step 6

Ship the rebuilt flow

It starts with four cards: just me, my family, solo business or my company. The plan screen became two columns. And you click "Start importing" and Chrome's export page opens in a new tab. When you switch back, the screen is already a drop zone waiting for the file.

The moment your passwords come in, Bitwarden flags the weak and reused ones. Only then does it bring up the extension. You've felt the payoff, so the big ask makes sense.

Gut check

Which user segment did AI miss entirely?

Honest verdict

Who won?

Use AI for

Three strategic directions in minutes, and catching constraints you've stopped questioning, like email-gating the flow.

Don't hand it

The call. It couldn't tell which direction fit a product serving both families and enterprise, or that Option A contradicts a privacy brand.

Careful with

Edge cases outside the brief. The solo business owner fell through every path.

Take it to work

Your Monday checklist

Ask these five questions at every screen. If a screen can't answer at least one, it probably doesn't belong in the flow.

“Email this to myself” opens your own email app with a link back to this cheat sheet. Nothing is sent from this site.

Workflow done.

No streaks and no guilt. Come back whenever you have ten minutes.