My boss uses agile development so he doesn't has to think about use cases he wants to be covered by the application.

He's just throwing in a "design" (an image that is probably created with Paint) without any further specifications and inconsistent elements, let the developer work two days on it, see the outcome, complains why it's not how he wanted it to be and then starts thinking how the feature should be integrated in the app and notices that his "requirements" from the image could not provide any advantage or usage at all for the user of the application. Asking for clarification before starting to work just leads to spongy statements or silence when he notices that he didn't think through to the end.

Sad is that this has not happened only once but is usually the way a new feature is developed...