Asking this set of questions across even a small pool of people — ten or less — will show you clear, recurring themes and patterns that can be used to validate user needs:
1. How do you define a successful work day? What has to happen in order for you to feel good when you leave?
2. Does that definition of success (and your stated goals) change from day to day — or from week to week? Are there certain times of year where what you need to accomplish changes?
3. What are the top three things standing in the way of you accomplishing your goals or having a successful workday?
4. What are the biggest problems, obstacles or inefficiencies you deal with? Why do you think these things happen?
5. Did you do have this same role at other organizations you’ve worked for? Was it better, worse or different – and why (or how)?
6. Did you perform these tasks in the same way at any of these other organizations? Was it better, worse or different – and why (or how)?
7. What frustrates you most about this? Why?
(1) The full article provides the rationale for each question.
(2) The first two questions probe what users are trying to achieve, what defines success for your users. In other words, they help you investigate the Job To Be Done. The third and fourth questions probe the context and challenges. As a result, these questions are helpful in completing a Job Outline.
(3) See also How to interview customers to get great product insights and How to learn about your customers.