The Interview Question That Tells You Everything
Most user interview frameworks are designed around what users want next. What features would you add? What’s the most frustrating thing? What would make this perfect?
These are fine questions. They generate reasonable answers. They rarely generate useful ones.
The question I keep coming back to: What were you using before this?
It’s the simplest question in the room and it contains everything.
What it surfaces that other questions don’t
When someone tells you what they used before your product, they’re telling you:
- What problem actually made them look. Not the abstract version they’d give in a survey. The real version — “I was stuck doing this in a spreadsheet and sending it to three different people and losing track of which version was live.”
- Who you actually beat. Not a category. A specific tool, workflow, or even a person. “My old agency.” “My own brain.” “A combination of Airtable and a Slack thread I could never find again.”
- What the switching cost was. If they came from a complex, established system, they were motivated. If they came from nothing — from doing it manually — the bar was much lower. Both tell you something about how defensible your position is.
The before tells you more than the after.
Why founders avoid asking it
Most founders skip this question because the answer can be uncomfortable. “We were using your competitor and switched because their support was terrible” is fine. But “we were just… not solving this problem at all” — that means you’re not displacing anything. You’re creating a new habit. And that’s harder.
Or they find out they’re winning on price. Not value. That’s also uncomfortable.
Uncomfortable findings are the useful ones. The interview that leaves you feeling good is the interview that confirmed what you already believed.
The follow-up that does the real work
Once you have the before, there’s one follow-up worth asking: What pushed you to actually look for something new?
Not when. Not how. What.
The trigger is where the buyer’s psychology lives. “My team doubled and the old system broke.” “I lost a client because we didn’t have a proper process.” “I saw someone mention this in a Slack group and spent an hour reading the website at midnight.”
That last one tells you about the emotional context, the urgency, the time of night someone was spending their attention on this problem. You can’t write a better sales page or design better onboarding without knowing that.
The practical version
If you’re running user interviews — even informally, even just calling ten people who signed up last month — start here:
- What were you using before this?
- What made you start looking for something different?
- What almost made you not switch?
That’s a better first fifteen minutes than any NPS question or feature request prompt.
The “jobs to be done” framework talks about the old solution as the thing you’re really competing against. That’s useful framing. But the actual question is simpler.
What were you using before? Say it out loud. Wait. The answer is the map.
You already know what users want to do. The before tells you what they were willing to put up with before they found you — and that gap is your real value proposition.