Sharing files on Skype is easy, tracking what you may have sent is impossible for there is no history on what files and names were sent or received on Skype. That may be fine for sharing the odd photo with friends however for the 30% that are using Skype for freqent business use it actually becomes a problem.
Over the last few weeks we've been running a couple of different projects. Much of our file sharing is done in real time. When the notes are recorded in chat session and files sent back and forth it's a shame that there is no way to record which files and sometimes versions were sent when. I know there are better ways of synchonizing documentation. Still most of us are luddites and we amend a document and usually change the name (version number or date slightly) and share it yet again. It's got to the point where I've left files ready to send to offline individuals to return the next morning, the screen is blank. Did they get the file? How does one know? Plus I need something like the VM that suggests a received file share is still not opened.
If you have received 10 files at once it's easy to find that later you haven't opened them. Plus I'm now sharing so many that just dumping them into "My Skype Received Files" is way to primitive.
I believe I'd like an option, that duplicates the behavior I have in email. When I send a file I need a shortcut to the file saved to a folder. The folder is Skype File Transfers with sub-folders by log-in name for everyone that I've shared files with. In fact I think I'd like the sent and received files in the same folder. Where sent to multiple recipients I'd just have multiple shortcuts filed under each name. Even now on the receiving end I realize I could become more disciplined. I've typically filed them by project however that doesn't provide a record of who the file was from.
In all of these projects our email volume has been very low. Almost all arrangements are done via chat messages and that's where I need additional information recorded. The chat archive doesn't record when files are sent. Plus multichats are close to impossible to save. I need a feature that asks me when I leave a multichat whether I would like to save it to a Topic archive. It may also be important to enable all chats such that when I click leave, if I haven't provided a topic, it asks me whether I want to close the chat and save it to a topic file. While I can bookmark multi-chats that's not the solution. I may also want to save it under a topic that is not the chat topic.
To add to the list of additions. I also want a record of when voice mails were sent. Thus the chat record needs to become a time or lifestream record of the exchanges I've had with a buddy. I should also be able to save a copy of sent voice mails. It's nuts that I lose the instruction after it is sent. In fact all voice mails should be saved in my Skype Files / Buddy Records. This could be by default or alternatively by choice. As the VM is ready for despatch.. do you want to save a copy etc.
These are little things that are really big things. Add this data into the API and the Skype exchanges could be recorded into Outlook or another program.
. Nov 7-9. San Francisco. 
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