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Nov 02 • 4 min read

are you on a side quest


Designers get brought in at the 11th hour.

They talk craft while execs talk revenue. They defend the work in every review. Their wins never reach leadership.

Then the thing ships looking nothing like what they proposed.

🫠

We’ve all been there (me included).

The designer with the most influence wins. And almost no one teaches you how to get it.

Today, I got James Hsu on the show to talk it through.

He spent 18 years leading design at Disney, Live Nation, and Crunchyroll (his words: a corporate sellout). Now he runs Dark UX Academy, a mentorship and consulting business that helps designers close the influence gap.

We covered 3 things on the show:

1. Mapping the room, and who really holds power

James calls this a power audit.

Give everyone around your work a star rating. Senior leadership gets 5 stars. SVPs and VPs get 4. Keep going down.

You’re answering 2 questions: who makes the decisions, and who controls the resources.

If titles don’t make it obvious, watch the all-hands. Note who speaks. When there’s a restructure, note who breaks the news and in what order. That’s the inner circle.

(It’s also the room design that rarely gets a seat in.)

Next, read how each person communicates.

  • A direct communicator wants facts and figures, so open with your weekend and you’ve lost them.
  • A spirited, blue-sky thinker wants to talk about version 2, so facts-only makes you look like you’re not listening.

→ Try this: list the 5 to 10 people who touch your current project. Star them. Note how each one likes to be spoken to.

2. Speaking exec, and tying design to the business

James says design education trains us to take orders. Here are your materials, go make the thing. When the client says jump, we ask how high.

If execs can’t connect your design work to a business outcome, design becomes an afterthought.

His shortcut is 4 questions. Does the work:

  • Does it save time?
  • Does it make money?
  • Does it prevent something bad from happening?
  • Does it make us look good? (mostly ego and reputation, sometimes visuals)

His favourite example is Jared Spool’s $300 million button.

An e-commerce client had shoppers adding to cart and never checking out.

In testing, a user hit a forced registration screen and said (cleaned up for your inbox) “I don’t want a relationship with you, I just want to buy this thing.”

The fix was a guest checkout button. It added $300M in revenue in a year.

It ticks all 4.

James calls a project that ticks at least 1 box a main quest. Tick none and you’re on a side quest.

→ Try this: take the last thing you shipped and write 1 line for each of the 4 questions. If all 4 are blank, you’re on a side quest.

3. Visibility, and making your impact undeniable

Measure before you change anything. Without a baseline, you can’t show anyone what changed.

If you don’t tell the story, no one knows what you contributed.

Come restructure time, someone asks whether the company needs that many designers.

Same goes for interviews. When they ask how you measured success, “the client was happy” is a low competency signal, says James. Talk conversion, churn, CAC, and LTV.

If you can’t get the metrics, use a proxy. I added this one on the show: if an agency client signed another 6-month project, do the napkin maths on what they’re worth.

Early in your career, James says to make your manager look good. My add: be enthusiastic, and be enthusiastically useful.

As a manager, I found attitude was the hardest thing to train.

→ Try this: before your next project kicks off, write down the current number. You’ll need it later.

​

What James said that stuck with me:

"If you do not position yourself, you will be positioned."

Skip the politics, and someone else decides where you stand. (And which cliff you drive off by Friday.)

More from James:

  • ​Dark UX Academy → mentorship and consulting for designers who want more say in the room
  • ​His free newsletter → influence, org politics, promotions, and quantifying your impact
  • ​LinkedIn → where he’s most active, and he answers DMs
  • Tokyo workshop for design founders → November 13, in person only. DM James for an invite.

We also went deep on why “politics” feels icky, the Live Nation VP who taught James how to command a room, why AI makes curation the designer’s job (it never pushes back), and how Japan showed James his obsession with money was an obsession with safety.

Watch the full livestream ↓

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Our next livestream is How to design beyond AI tools on November 25th

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Catch ya soon.

— Chris
​rectangles.fm​

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