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I've been working on an app that involves making an application for a permit. Applicants typically need to upload 5-16 documents (drawings and specifications) before they submit their applications. Five of those documents are mandatory -- the others are optional.

We've been looking at creating "drop pads" for files to speed the upload process while allowing the user to categorize the files (architectural, structural, etc) at the same time. My questions:

Alternatives: Is there a better interaction approach than this?

Examples: Has anybody seen anything like this? Lots of "drop files" tools exist now, but I haven't seen anything that helps with the categorization part.

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Have you looked at Gmail's (or some other email clients') drag and drop file upload? You drag a bunch of files and drop it on your mail and it starts uploading them one at a time. –  rk. Apr 10 '13 at 16:44
    
Yes - nice example as well as flickrs and Basecamps's. The categorization part is the tricky thing. Is it logical to have 5 separate drop pads for five different types of documents? –  Dave Robertson Apr 10 '13 at 16:51
    

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I'm assuming it is required for the user to do the categorization because you need to be sure there is a file for each category to complete the application. Otherwise I'd say it would be nice if you could do the categorization for them.

It would be preferable to upload in step one and then be done with that and spend the rest of the time in the application. If you'd do 5 drop zones, a user would have to switch back and forth between your application and the desktop/explorer/finder for each zone. Not everyone has the screen real-estate to do that practically, and lots of people have everything full screen anyway.

After uploading a set of files, you could offer the categorization by drag and drop, or simply an overview where a category can be picked for each file.

You'll need to support additional uploads after the first set, and it'd be nice to support dropping right into a category, but I wouldn't recommend that as the primary flow of the application.

Also, I don't recommend using drag&drop as the only mode of uploading. It requires a certain level of motor skills that not all users will be able to deliver comfortably. Many of the applications I've designed offer drag and drop, but I find myself (pretty handy with a mouse) preferring to use the default upload dialog. That also doesn't require me to prepare my desktop or a finder window with the right files. One hand to support my head, the other just lazily clicking away: it's simply less effort than drag&drop :)

Same goes for drag and drop for categorization: it's a fun mode of interaction, but it isn't entirely natural using a mouse and you need to design it so that it's clear what the user has to do. But here it could make categorization (and checking completeness) a lot clearer than simply labeling items in a list.

mockup

download bmml source – Wireframes created with Balsamiq Mockups

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Great suggestions! Thanks for this, Koen! –  Dave Robertson Apr 10 '13 at 18:43

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