A good interview lasts about 15 minutes. I schedule half an hour just in case but I don’t ask for more than 15 minutes.

Can you tell me about how you first started using (the product)?

This is one of my favourite opening questions. It gets straight to the heart of why they use the product but still conversational and warm.

If needed I will clarify that I am asking why they started using it not how they discovered the product, but the loose phrasing here usually encourages people to respond with a story rather than bullet points.

“Tell me about the last time you (used the product)?”

Once people establish their initial motivation for using the product then I try and understand if their current usage lines up with their initial motivation or how it has changed.

When needed, I have follow-up questions to help move the conversation towards the insight I am looking for.

  • What were you trying to accomplish?
  • Can you take me through what you did?
  • What was the context at the time?
  • What were you doing before that?
  • Why were you trying to achieve this?

I try not to ask these question when possible. Undirected, people are more likely to take the conversation to a place that matters.

I like to end conversations with:

“Is there anything else I should have asked?”

This is a great question because sometimes people understand what you’re trying to do but you haven’t given them an opening to say what they want to say. Other times you can sense that the conversation isn’t over yet and it’s because they have questions. Worst case scenario, they say no.


Other questions to ask yourself to improve your retention…

  1. Does your product make a clear promise?
  2. Do you know how often people have the problem you help them solve?
  3. Do you know what your product’s core action is?
  4. How many people continue to use your product six months after they sign up?
  5. Have you segmented your retention curve by the different types of users in your app?
  6. Do you know where the single biggest dropoff is in your current onboarding experience?
  7. Have you mapped out the number of times each person performed your core action last month?