Key questions you should be asking
1. Describe your typical daily workflow. What are the biggest pain points in it and how do you work around them?
You want to walk through your customers’ process and note where blockers pop up to slow down their efforts. As you compile their responses, you can see trends develop and begin to understand how your software can solve their major problems with new feature releases as soon as possible. You’ll also know which features your customers can wait for in the mid-term, as well as the ones that you can safely put on a back burner for a while.
Make sure you also pay attention to the methods your customers say they use to get around their obstacles. Those descriptions can also help inform new feature development.
2. Let’s say you’ve solved all your pain points and you no longer need any workarounds. What would you do with the extra time?
This question can help you understand what’s on your customers’ roadmaps for their businesses. They likely have endeavors they’d like to undertake, if they had some extra time to work on them, so knowing what they are can give you pointers toward future features for your service.
3. Who do you work with, both on your team and outside it, during a typical workday? What are their job functions and how do you interact with them?
The answer to this question will help you understand how your software fits into the bigger picture at your customers’ workplaces. You might discover not only ideas for new features but also opportunities where you could get your sales team involved.
4. How do you measure success at your company?
The KPIs (key performance indicators) your customers use as yardsticks to determine how well they’re doing from month to month and year to year can help you understand how your solution supports the work done to achieve those goals. You may discover that your software maps nicely to those measurements, or you could learn that your offering misses the mark in important ways.
5. Let’s pretend you have to slash your budget and eliminate some software in the process. On a scale of 1 to 10, with 1 being “cut this first” and 10 being “this is crucial,” how would you rate our software and why? Who’s ahead of us in your ranking and what software is behind us?
This one requires brutal honesty from your interviewee, but it’s important to understand exactly what your customers think of your software. Is it truly something they could live without? The “why” part of their answers, as well as how they rank you compared to the other tools they use, will help you understand where you should improve your offering so it becomes indispensable to your customers’ daily workflows. You may want to schedule time for some competitive research afterward.
6. How do you describe our software to new employees on day one?
This question offers a good way to deconstruct your software and understand how your customers view its basic functionality. New employees likely won’t receive an in-depth tutorial on the product during their first day at work, so those simple “We tell them that your software does X, Y, and Z” responses will give you a sense of how your software fits into your customers’ businesses. You may be surprised by what they say.
7. What’s the one thing you wish our software could do right now?
If you want to know how to prioritize your features wish list, this question will give you plenty of guidance. Hopefully, one or two similar answers will emerge and you can go back to your engineering team with a clear idea of what they need to work on next.