So I was always told the simplest ideas are the best but I want to know how do you go about cleverly finding people problems without asking them directly?
Lets break this down...
You are correct that the best ideas come from people's problems. As an entrepreneur, you don't need ideas. Shocking, I know. You need to actually reach out and chat with people either over the phone or in person.
Pick an industry and be very specific. For our example, I'll be using Real Estate Agents as my target customers. I have no idea what their problems are so I need to find them. I reach out and schedule either a phone call or an in person meeting over coffee.
My goal of these conversations is to ask the right questions and listen carefully. I may ask questions to better understand what they do on a daily basis and then focus more on which tasks are the most painful. If 10+ people have a common, painful problem, I have my business idea.
Now I want to validate that they will actually pay for a solution. I've already found a way to solve their problem (via SaaS app, Service etc..) so I ask them to pay for the solution. If it's painful enough, they will pay right there. If they won't, ask what it would take for them to pay you to solve their problem.
Repeat this process as many times as possible to find at least three paying customers before building your product or service.
Congratulations, you now have a profitable business!