How do you find your clients' pain points?

When I managed a product at Microsoft I found a phenomenal source for understanding customer pain points was my Tech Support team. They live on the front lines helping customers directly. I always included their amazingly valuable feedback when considering what to include in my feature candidates list for upcoming development work. They were great at articulating important customer pain points.

The QA team was also incredible. It's amazing how often companies fail to value these uber users of their products.

Another great way we learned was to invite customers to use our software while observing them. We gave them a gift to show our appreciation. It was amazing to see how often the way our software was used was much different than what we anticipated. We provided scenarios, asked them to try to accomplish specific tasks, and then observed. We learned a tremendous amount about how to improve our design and what pain points we should address.

Finally, I'd say that you asking this question is a very good thing. Specifically articulating that you always include customer pain points in your planning will set you apart. You'd be amazed how often this is overlooked.

Kudos. Thanks!