questions product managers should ask customersA few well-phrased questions can yield fantastic customer insights. But asking the right questions during customer conversations and win-loss interviews takes a lot of practice and a healthy dose of curiosity.

Here are ten open-ended questions I have in my arsenal that have worked well for me over the years when engaging with prospects and customers on products including ProductPlan. Asking a few of these questions can make a difference in the features you decide to include on your product roadmap.

  1. “Why?” This is by far the most powerful question you can ask, so ask it often. Product managers should rarely accept a customer’s first response and move on. By asking “why” as a follow-up question you can often extract a more enlightening response and get to the crux of their issue. For example, when I interviewed people about the product concept that became Citrix GoToMyPC we spent less time talking about remote access features and more time asking why their life would be better with our solution. As a result we uncovered a stronger value proposition for the product.
  2. “How do you do that today?” This is a great question when a customer asks you for a specific feature. Rather than taking their feature request at face value, dig in to really understand how they are accomplishing the job today. If you can, have them show you their process or how they are using their current product. This line of questioning proved particularly useful for ProductPlan when we interviewed product managers to understand how they were building and communicating their product roadmap.
  3. “How do you know you’ve had a successful (year, month, day)?” This is a good question for business products, where you are trying to uncover metrics and customer goals. If your product can help your customer achieve their goals or help make them successful, you are well on your way to a valuable product.
  4. “How do you feel about (the current solution)?” This one is good for understanding opportunities to differentiate your product from competitors, especially during win-loss interviews. Good follow-up questions might be “Where does your current solution provide the most benefit? What do you like best about it?”
  5. “What is the most frustrating thing about (the current solution, a feature, your day, etc.)?” This is a great multi-purpose open-ended question that you can use to open up conversations and discover pain.
  6. “What do you wish you could do with (a product, a task, etc.) that you can’t do today?” This is a variation on the “If you could wave a magic wand…” question asked by many product managers. I’ve found that questions like these work well for very specific features or use cases. Be careful about asking this question in too general a fashion or too early as it can lead to ambiguous results or a blank stare.
  7. “How would your (day, job, task) be different if you had this?” I use variations of this question depending on the circumstances, but the objective is the same: understanding how your solution or feature solves a problem and what type of value a customer would place on solving that problem.
  8. “Can you give me an example?” This is another great general-purpose question that can give you a goldmine of supporting evidence for your new product or feature.
  9. “If this were available today, would you buy/use it?” This question in itself may not result in an accurate answer (and can often lead to false positives). It’s what you do after this question that counts: Ask this question and then be quiet. Listening to their response for 60 seconds can give you insight into their decision process and the value they place on your product or feature. Make sure to follow-up with detailed questions such as “Would you walk me through the purchase process?”
  10. “Why would you recommend our solution to others?” You can use variations of this “ultimate question” to gauge satisfaction with your solution and then ask follow-up questions.

Try a few of these questions with customers or prospects during your next interviews. Some are better suited for new product development, but most will work well for your ongoing feature validation and win-loss interviews. Of course, great questions aren’t worth much unless you listen closely, read between the lines and then ask deeper follow-up questions.

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