How can I purchase an app already installed by another user?

We're using MacBooks in our business and I'm the new IT guy there. Basically I've discovered that due to lots of disregard by my predecessor (who is now my boss...>_>), people have apps installed on their computers that they don't "own" due to the fact his Apple ID is the one that they belong to. This presented a problem today when one of my coworkers tried to use Keynote, required an update to open a file, and was denied further progress due to needing my boss's Apple ID (eventually we just logged in as him and installed the update in order to keep things moving).
Is there some way to clear off apps that don't belong to a current user so that user can repurchase the app from the App Store with their own account and/or not be nagged by updates they can never complete due to Apple ID mismatches? Otherwise they just say "Installed" or "Update" and the users can't do a thing about it. I'd like to be able to reinstall Keynote to his machine under his Apple ID and also know how to fix this problem down the line when it's sure to happen again so people can reinstall apps/update apps already on their machines with their own Apple IDs.

You company has started a journey down the wrong road and you could have a mess of a future ahead.
Company Macs are not consumer Macs and should not be set up with personal Apple IDs. You should speak to the Volume Licensing division of Apple for advice on setting up Macs with company Apple IDs and volume licenses.
http://www.apple.com/business/vpp/

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