I found real pain, but I still can’t get the first real user task completed

I’m building a small Windows app called Rootlize for local image workflows.

After talking with a lot of people who work with images, I’ve found some recurring pain around things like organizing batches, renaming, matching images to product or variant context, moving files, and repeating the same steps over and over.

So the problem itself feels real.

What I’m struggling with now is getting from “this sounds useful” to someone actually using Rootlize on one real task.

I’ve had people describe detailed workflows, show interest, and even download the prototype, but I still don’t have a clear case where someone used it to complete a real piece of work and then came back to use it again.

I think part of the mistake was asking people to “try the app” instead of asking them to try solving one specific task with me.

So I’m changing the approach to something smaller:

one real problem
one small real batch
one task
see where Rootlize helps and where it fails

For people who have been through this stage before, how did you get from early interest to the first few people actually using your product for real work?

I’m especially interested in what worked before you had much social proof or trust.