dnsk

You're thinking about using AI for design work. Maybe you already started. Someone told you it's the future, and they're probably right, but let me tell you what nobody mentions.

I spent six months in 2025 using AI tools daily. Made me faster. Also made me worse. By June, I couldn't defend my own design decisions anymore. Wrote a book about it: Looks Good to Me: On AI Sycophancy, Context Loss, and Inverted Baselines (Apple Books). It's free. This is what I'd tell you if we were having coffee.

You know how this goes.

Three weeks on the portfolio. Rewrote the case study twice. Rebuilt the layout because something felt off at midnight on a Wednesday. Sent it to two designer friends who said it was strong. Found the right contact on LinkedIn, personalized the message, attached the link.

Three days later: automated rejection. No subject line variation. Thank you for applying.

Different company, same month. A referral came through – someone you’d worked with two years ago, mentioned your name in a Slack message to someone they knew. You sent a portfolio link you hadn’t touched in weeks.

First-round interview confirmed within 48 hours.

I wrote this book without AI. Every chapter, every argument, every edit. Four months, a notebook, and no tool that would tell me my drafts were compelling.

The most predictable version of this project: run the manuscript through ChatGPT, get told each section is “well-structured and insightful,” ship it. A book about AI sycophancy, produced with the help of a sycophantic AI. The irony would have been neat. The argument less so.

Anyone who’s tried it knows what happens. You get agreement. You get polish. You get “great point – you might also want to consider…” followed by something you already said, reworded. Occasionally it suggests adding an executive summary. The book has no executive.

What you don’t get is resistance. Not real resistance. Building a sustained argument requires something pushing back – saying a thing, testing it, finding where it breaks, deciding whether the break invalidates the claim or sharpens it. That process needs a counterforce. AI is not a counterforce. It’s a mirror with better vocabulary than you.

The book is called “Looks Good to Me.”

That’s what the mirror says.

A UX strategist is supposed to bridge business goals and user needs through high-level planning. They’re meant to answer questions like “Should we build this?” and “Which problems matter most?” before anyone opens Figma.

In practice, most I’ve worked with excel at one thing: not committing to answers.

“Should we prioritize mobile or desktop?” “It depends on your user base.”

“Which feature should we ship first?” “It depends on your business goals.”

“When should we launch?” “It depends on market conditions.”

Every answer buys them more time to conduct another research phase, run another workshop, build another framework. They become professional question-deflectors who get paid to suggest you need more information before making any decision.

And here’s the thing – they’re not wrong. Everything in product development genuinely does depend on context. But when “it depends” becomes the primary output of someone earning $120-180 per hour, you’re not getting strategy. You’re getting expensive procrastination.

I’ve made pricing pages I was quietly proud of. Clean grids. Calm colours. A monthly/annual toggle that felt clever until it pushed the CTA just enough to break the fold on Safari. In screenshots, they looked convincing. In practice, they behaved like polite doormen who never actually opened the door.

This is the personal version of what I learned the hard way.

Five years ago, I hired a UX designer with exceptional soft skills. Articulate in meetings. Diplomatic with stakeholders. Created beautiful presentation decks. Responded to Slack within minutes with encouragement and emoji.

Three months later, the project failed because they’d agreed to every terrible idea anyone suggested.

Seventeen stakeholder requests. Fourteen contradictory features. Zero pushback.

The product launched as a compromise nobody wanted, designed by a committee nobody asked for.

Their soft skills were outstanding. Their design judgment was invisible.

That’s when I realized “great soft skills” in a job description usually means “won’t challenge us when we’re wrong.”

Which is exactly what clients don’t need but desperately want.

(Like hiring a doctor who agrees with your self-diagnosis.)

Now I hire differently.