“I look for whether they can define the real problem before they start solving it. At Facebook and Designer Fund, the designers who shipped things that mattered were the ones who asked sharper questions than everyone else, then proved their answers with users, not decks.”
“I look for whether someone learns by making: the best designers I know, including me, think with our hands, sketching and prototyping to discover what we actually think. Tool fluency matters, but idea fluency matters more.”
“I stopped hiring for portfolio polish years ago; the best people I brought into Thinkific could name the customer problem, the business constraint, and why their first idea was wrong. Watch whether they ask for research and facts before they start pushing pixels.”
“I look for whether they can explain why they made a choice, not just that it looks good. At the Timberwolves and Vox, the designers I trusted most could defend a type decision, a color call, or a layout in terms of what it was supposed to do.”
“I stopped trusting years of experience after seeing too many seniors who only assembled screens from Material components. For me, a good designer still needs taste, craft, and the ability to steer product decisions, not just follow a brief. I also watch how they present: a messy Figma file or a generic email tells me how they'll talk to clients later.”
“I look past the portfolio and ask how they know something worked: what changed for a patient, a customer, a business, because of what they made. The DBA awards taught me that evidence of impact separates good designers from polished ones.”
“I stopped trusting pretty portfolios once I saw too many designers who could nail spacing and color but couldn't ship. Now I look for what they actually got into the world: live products, messy iterations, and whether they can explain the business tradeoff behind a single button.”
“I look for the gap between taste and decision: can they explain why they broke a rule, not just that they followed one. At monday.com I watched designers with flawless craft stall because they couldn't defend a trade-off, while others shipped rougher work that moved the business because they owned the reasoning.”