Top Qs. for Idea Extraction for a new Product or New Feature : Product Management Tips

If you do not know how to ask the right question, you discover nothing. -- W. Edwards Deming

1. What's the most important area of your business? And do you have any pain associated with this activity?
2. Can you walk me through a typical day for you?
3. How do you know you’ve had a successful (day, month, year)?
4. What are you currently doing that frustrates you?
5. What tasks are you doing that you believe can be made easier or less tedious?
6. Is there any pain associated with that particular activity? What else?
7. What software have you been looking for but you just can't find a good solution?
8. What are some of the repetitive tasks that you have to do on a day to day basis?
9. What’s the most painful task you have day-to-day?
10. Who's responsible for those tasks?
11. How do you feel when you have to do those tasks?
12. If you could wave a magic wand related to that task, what would happen as a result?
13. What’s the most frustrating thing about the current solution/ feature?
14. What are the tasks that you do that take up the most time?
15. If you solve that problem, how much money will you save or make?
16. What problems are costing you the most money?
17. What current software out there have you been looking for, but can't find a good solution?
18. Have you ever tried to solve this problem in the past?” Try to know how much did they invested trying to solve the problem.
19. What problem costs you the most money?
20. What are some of the software programs that you use that make you want to punch your computer?
21. If this were available today would you buy/use it?
22. Where does solving this problem fall on your priority list?
23. Has our software/solution made you more awesome? How? 
24. Do you go to any conferences or trade shows? 
25. What websites or online communities do you use to stay current? How do you learn about your craft?    

References :

1.     What is Ideation – and How to Prepare for Ideation Sessions:

2.     Harvard i-lab | The Ideation Framework with Josh Wexler:

3.     Ideation technique: playing with the product:

4.     18 Best Idea Generation Techniques:

5.     12 Great Customer Interview Questions:

6.     4 Questions to Ask Users along the Customer Journey: