Taste, Humility, Hutzpah: The Designer Hiring Lens
Hire for judgment, humility, and the courage to say 'not good enough' — tools and process you can teach.
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 90%
Katie Dill's screen for hiring designers, aimed specifically at non-designers (founders, PMs) who have to make the call. Tools and process are teachable; taste and character are not. She screens for three things — a demonstrated hit rate of great judgment and taste, humility (which drives attention to users and teammates), and hutzpah (the courage to propose something better on a blank page and to say 'this isn't good enough, let's do it again'), plus a structural recommendation for early-stage teams.
Origin
Katie Dill's own hiring lens, developed across design leadership at Airbnb, Lyft, and Stripe.
Core principles
- 01It's easier to teach tools and process than it is taste and character.
- 02Taste is contingent on context — a dense power tool for professionals should feel different from a sparse consumer app.
- 03Humility is what makes someone actually listen to users and to teammates.
- 04Creation is scary; courage is a job requirement, not a personality bonus.
- 05Early-stage teams need a doer, but still need the senior lens on how to build a user-focused organization.
How to run it
- 1
Assess hit rate for judgment and taste, not years of experience
Look at the candidate's track record of great judgment and taste and how they've honed it. Even with little experience, you can see whether the natural inclination for great things is there.
Pro tip Judge taste against the context of the product: dense, information-rich power tools and light, directive consumer products demand different aesthetics. Don't apply one universal bar.
Watch out Don't try to score taste against a generic 'good design' checklist or a single recommended book — it is contingent on what the thing is and what the user needs.
- 2
Probe with 'tell me the work you are most proud of'
Dill's favourite interview question. It reveals taste and judgment, what motivates them, what they consider a good outcome, what they like to do, and where their gravity naturally pulls them.
Pro tip Listen for what they call good — that is their bar, and it becomes your bar.
- 3
Screen hard for humility
People who are very good at what they do are not always humble. Humility drives respect and empathy for teammates, and — crucially — makes them pay more attention to what users are saying and stay curious about what's working and what isn't.
Pro tip Humility is the trait that connects the hire to your users, not just to your team.
Watch out High craft plus low humility produces a designer who cannot work in a multi-disciplinary team — which is where quality actually gets made.
- 4
Look for hutzpah
Design is the act of creation and it is scary — taking a blank page and proposing something better, and having the courage to say 'this is not good enough, we should do it again'. Look for someone with that fight-for-great instinct plus the hustle to execute rapidly.
Pro tip This trait is what supplies the 'courage' condition in the quality operating model — without it, quality has no defender inside the team.
- 5
For early-stage: pair a doer with a senior advisor
Early on you probably need a doer rather than a senior thinker/operator — but you still need the lens on how to build a user-focused organization from the start. Pair a full-time executor with a senior design advisor.
Pro tip This gets you strategy and execution without paying for a senior full-time leader you can't yet keep busy.
Watch out Hiring only a doer with no strategic lens bakes in an organization that isn't user-focused, which is expensive to unwind later.
In the wild
Rather than asking about process or tools, Dill asks candidates what work they are most proud of. The answer reveals their standard of good, their motivations, and the kind of problems their gravity pulls them toward.
→ A single question that simultaneously tests taste, judgment, motivation, and fit.
Dill points to Lenny's own stated bar — 'if it's not good we're not going to ship it' — as an example of the same courage she hires for: a small, repeated refusal to let bad work go out.
→ Each individual refusal compounds into a reliable quality expectation in the audience's mind.
Common mistakes
Hiring for tool and process fluency
Figma skill and process rigour are teachable. Taste and character are not — screening on the teachable thing wastes the interview.
Ignoring humility because the portfolio is dazzling
Great talent without humility won't listen to users or to teammates, and quality is a group effort. The portfolio is a poor predictor of team fit.
Applying one universal taste standard
Judging a B2B power-tool designer against consumer-app minimalism (or vice versa) will reject exactly the right hire. Taste is contingent on user need and context.
Is it for you?
Best for
Founders and product leaders who are not designers themselves and have to make their first (or first senior) design hire.
Not ideal for
Hiring for narrowly specialized execution roles (e.g. a production/localization designer) where tool depth genuinely is the job.
From the transcript
“than it is taste and character so I would certainly you know pay a lot of attention to that”
“you also want to find somebody that's humble”
“the last piece would just be you know hustle or or hutzpah”
“tell me what work you are most proud of”
“maybe a great way of doing that is kind of having like a more you know senior leader design advisor”
From the episode
Building beautiful products with Stripe’s Head of Design
Katie Dill (Stripe, Airbnb, Lyft)