Hey Shrikar,
Luckily, this question has a simple answer and it's two pronged. You've probably heard of User Research. In User Research we use 2 things to uncover peoples' pain points.
- 1. SHADOWING; following participants over a period of time and recording observations. It's a free-flow method and the researcher can probe where he/she feels they need more information. These session usually take between an hour to a full day and vary based on the complexity of the app and the research goals. The data collected is usually super reliable.
- 2. USER INTERVIEWS; this is basically conducting one-on-one question answer sessions whether directed or not is upto the needs of the projects, goals and context of user. So far I've conducted, Field Interviews, Phone Interviews, Skype Interviews, Street Interviews and done hundreds of hours in recordings. The data is usually very good especially for directed interviews. But the interview questions must be tried and tested but more importantly, designed for the target audience.
I am more than willing to introduce and coach you on the lean and "mean" variations of the two methods that uncover awesome insights.
Looking forward to hearing from you.