How to Ask the Right Question

Have you ever wrapped up a user interview feeling like you didn't really learn what you needed?  The key to great interviews isn't technique alone – it's asking the right questions. I've spent years refining how I approach user interviews. I’d like to discuss common pitfalls – and what you can do to ensure your interviews get you the information crucial to your decisions.

Before an interview, define your core goal. What critical information do you need? Who will ultimately use those findings?  Interviews meant to aid sales differ vastly from those meant to guide product design. Having a clear purpose leads to asking better questions.

When I did a recent project with Moment Technologies to shape product strategy, we had to revise our initial questions substantially.  Our first questions were likely to lead users to give us misleading answers. Let's break down some common pitfalls:

Overly specific questions

Sometimes, we have a feature or a product direction in mind when we’re starting interviews. Asking about those specific features is not likely to work. Asking hypothetical questions – “would you pay for this feature"? – rarely gives meaningful answers. Users aren't great at predicting their future selves, and you and your interviewee almost definitely have different ideas of what a product with that feature might look like. 

For a better approach, reframe the conversation around pain points. If you know what your product is meant to help with, you can learn how users interact with that problem. For Moment, we started exploring the concept of  "toil" –  DevOps lingo for those annoying manual tasks that aren’t quite worth automating. We learned a lot about our users' daily challenges, which let us start figuring out how to tune our tool for their work.

Confirmation Bias and Leading Questions

Beware the trap of asking what you want to hear – and then hearing what you expect! Our preconceived ideas can seriously derail interviews. Maybe you're hoping for positive feedback on a pet feature,  so you accidentally phrase questions to steer users that way. It's surprisingly easy to slip into without even realizing it. These sneaky biases mess with your results. 

I’ve been happiest with the results of studies where any answer is a surprise. It’s hard to steer users wrong when you genuinely just want to know what they think.

Using Your Own Vocabulary

Watch out for that jargon! In the interviews I carried out with Moment, after stewing in terms like "toil" and "automatable" for a week, we nearly forgot those are our internal lingo. Turns out, some users had totally different definitions, which started to skew our results. We were able to get back on track, but it’s important to look out for this one. Try to understand the world from your users' point of view. What language do they use to describe their day-to-day problems?

Overly personal personas

Persona methods can get us into our users’ heads and can give a rich sense of how your product can fit into their work. Some persona presentations go deep on rich and descriptive persona examples: “Jill lives on a homestead farm with three chickens”. The trap is when teams dive too deep into irrelevant questions. Before you ask Jill about her egg-laying situation, focus on how work fits into her life. Is she at home or office-bound? Does she have set hours, or does her work come at irregular intervals?

Let me share a story from my time at Honeycomb. We wanted to understand our users’ work schedules and when they picked up the product. We did get some stories about people’s personal lives — but mainly because they were explaining how they’d used the product on a plane or while picking up groceries. The real insight of our interviews was that we found two distinct core behaviors: people who used Honeycomb actively during the development process and those who turned to it only after something broke. These were very different mindsets – and they sparked some great conversations about what features could support each work mode. 

Wrapping It Up

Interviewing users can be tricky, but the payoff is huge! Everyone loves talking about their work – and you might be surprised at the gold you uncover, leading to products people genuinely love.

Transforming those raw insights into a product roadmap is another skill. Do you need help crafting an impactful, data-driven strategy? That's where I come in! Drop me a line, and let's see how user interviews can supercharge your next project.

Speaking of those Moment interviews – the next step is to organize the raw material I pulled out of those conversations into insights. In the next blog, I'll dive deep into applying analysis methods to turn those interviews into powerful actions!