“What are you trying to get better at?”
From Kathy Sierra · Author of Badass: Making Users Awesome
Why it works
Sierra's central argument in Badass is that sustainable products succeed by enabling user mastery in a 'bigger, cooler context' that sits above the product itself. The question forces the answer into that larger domain — a photographer says 'capture moments that actually feel alive,' not 'get better at your photo editor.' That gap between what they say and what your UI rewards is the product gap. A blunter question like 'what features matter most?' keeps the conversation trapped inside the product boundary and surfaces only feature requests, never the unreached aspiration driving them. This phrasing also bypasses social desirability: people freely name an aspirational skill because it reflects well on them, giving you unfiltered signal about their real goal.
When to ask
Early in discovery, before you have locked in a feature roadmap. Ask it whenever you sense the team is optimizing for engagement with the tool rather than outcomes in the user's real-world domain.
Good follow-ups
- What does doing that really well look like to you — what would you be able to do that you can't do now?
- What's getting in the way of improving at that right now?
- Who do you know who's already great at it, and what do they do differently?
Watch out for
The most common failure is confirming you already knew the answer and moving on. When a user names a domain you didn't anticipate ('I'm trying to get better at staying calm under pressure' for what you thought was a productivity app), resist the urge to redirect. That unexpected answer is the highest-signal data in the conversation — press into it before returning to your prepared questions.
Where to ask
- User interviewgreat
Native habitat — the answer opens a thread about the user's aspirational domain, not your product, which is exactly what you need to hear early.
- In-product surveyworkable
Works as an onboarding or post-activation survey question; keep it open-ended and resist the urge to pre-populate a dropdown of your feature categories.
- Long-form surveyworkable
Useful as the first question in a longer research instrument to anchor the rest around the user's actual goal rather than product usage.
Stage: Get value · A question popularized by Kathy Sierra