It depends on the type of book on the Kobo. And where the Kindle App is.
Firstly, you can add a book from the device to calibre. With the device connected, go to the device list and find the book you want to add. Select and right click on them and select "Add to library". Calibre will copy the book from the device to the library.
There are two problems with this. One, is DRM and the other is kepubs. If the books have DRM, adding to the calibre library won't help unless you remove this as well. And "kepub" is Kobo's format and uses their DRM. A kepub will probably get added to calibre as an epub unless it has DRM. In that case, I don't think it will get added (it's been a while since I tried).
To get to the Kindle app depends on where it is. If it is on an iPad or iPhone, you need the iOS reader applications. It will allow you to send to the Kindle app. I haven't dealt with Android, so I don't know how it works.
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