Who's going to pay for the project? Who's going to have to use it? Who will have veto power over the project? Whose bonus depends on the software working? Whose bonus depends on the successful delivery of the project?

What are you trying to accomplish? Where do you get the information you enter into the software? What do you do with the information you get out of the software? What changes to the software and how you work would make your life better? Can I sit with you for a day and observe you using the software in the course of your work day?

Most people want faster horses. A rare few can imagine the automobile that makes the horse redundant. Look for the few and treasure them. At one startup I was at, we had a lot of teachers who were grateful for anything more than what they previously had. But we had one school where they were clearly setting the pace for everyone else: we loved that school, and we implemented the bits of their needs and ambitions that'd scale to everyone.

That said, many projects are simply "do a better job of what the existing software does" and you aren't expected to invent the next Google in the course of the project.

A lot of what you ask sits in the product management and UX spaces. Marty Kagan's book "Inspired" on product management is a classic. You might also get good ideas from "Take Charge Product Management" (Greg Geraci). I don't have good UX recommendations, but I'm sure other HN commenters will.

You might also look to the customer development literature around lean startups. Steve Blank's "Four Steps to the Epiphany" and Eric Ries's classic "Lean Startup" would get you started in that direction. (And, of course, there are copious hits on Google for "customer development").