Same here. Unfortunately there are a lot of middlemen who want to get in between and filter that information. It’s a constant battle to be allowed to stay in touch with the actual users. It doesn’t help that a lot of devs don’t really want to interact with users feeding the stereotype that developers need to be told what to do.

I've done this too and it was great as so many things are usually left out of the spec while priority goes to things which are rarely or never actually done.

Yep. This should be step 1 to n of designing software for end users. Understand what the users problems and needs actually are by watching them do their actual job rather than working from a description of what a manager three levels up thinks their job is.

Really good point. I think this is why it’s easier to develop useful software if you are someone who ends up being a user of the software since you have the same problems. You automatically have all the needed empathy.

I can attest to this. As a Technical Director supporting artists the tools I create for them are more effective when I study their process thoroughly and also get my hands dirty. Then design and implement the tool and it becomes my job to manage the complexity. Designing for change is something I keep in mind as well.