Upfront tips:

• The aim is to get your interviewee to speak freely and openly. ‘Yes’ or ‘no’ answers aren’t desirable. The more they speak, the more you can learn about the words they use (language/market fit)
• You don’t need to follow a rigid interview guide. It’s best to let the conversation flow naturally. You’re looking for what pushed the interviewee away from their previous solution (alternative), what pulled them toward yours, what anxieties they needed to overcome to give you a try and what habits they needed to break.
• If you struggle to get your interviewee to elaborate, it can help to paraphrase in an incorrect way (”So does that mean you never do xyz at all?”)
• Focus your research efforts on speaking with recurring, or even power users that are paying for your product. These are the type of people you want to tailor your product to!

Notwithstanding the above (no need to use a rigid interview guide), below are a few questions that can help you get inspired:

1. How would you describe yourself? / What’s your job title - and beyond that, your role at the company?

(Profiling, identifying personas)

1. How do you use (Product) in your work life? What part of your job are you doing with it?

(Look for the main job, and a start of a job map.“Walk me through this as detailed as possible” - ask them to outline each step and what they’re trying to achieve with that step)

1. Can you think back about the time before (Product): What was difficult or frustrating about (that part of the job)? Which moments were the most frustrating?

   (Look for the pain, struggles, trigger moment, and the alternatives your customers were using - useful for messaging and understanding the competitive landscape)

2. What stood out about (Product) that made you interested in trying it?

   (Look for motivation. An often-occurring answer should be displayed front & center on your website, and delivered on quickly within your product/service)

3. Once you started using (Product), at which stage did you realize it was the right product for you? what happened that made you feel that way?

   (Look for ‘aha moment’, motivations - drive new users to this moment!)

4. Now that you’re using (Product) regularly, what are you able to do that you weren’t before? How does (Product) make things easier?

   (Look for desired outcomes for messaging (customer acquisition, activation) and product decision-making, drive new users to this ‘eureka’ moment. Look for the core-value of the product for this segment.)

5. What’s the best feature?

   (Inspiration for your messaging and product tour)

6. What can we do to improve (Product) for you? What’s the #1 thing?