Zian comments on Hold Off On Proposing Solutions - Less Wrong
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In my experience as a programmer (who wore all the software-related hats), I found that even when I understood the domain quite well, inquired about the purpose multiple times, and wrote little stories illustrating my interpretation of the users' desires, I could walk away from early usability tests with major changes to the project.
In one particularly memorable instance, I got all the way through making paper prototypes and making pretend e-mails. Then, I convinced my manager to try out the system. The process started in a pre-existing e-mail package and then routed stuff to the proposed custom software. He sat down, opened up the pretend e-mail, and started to save the attached files. At that point, we discovered that there was no need for the custom software and killed the entire project.