About a hundred times a day I find reason to send a file to someone I am in contact with. Just sending the file directly to that other person using Skype File Transfers works very well for me.
In this post I wanted to point out some of the ways you can do this:

1. Click on the Send File button inside Skype:

2. Open a chat with your Skype contact. Click the Send File button or drag the file into the chat. Works also on multi-chats also, of course.

View demo

2. Right-click on any file in Windows Explorer and choose
Send To - Skype


View demo

3. Download and install the Skype Toolbar for MS Office from http://www.skype.com/download/skypeofficetoolbar/. With that installed you get an extra toolbar in Ms Word, Excel, PowerPoint, Access, Visio and Project that allows you to send the file you are currently working on. Note that this application is in BETA, though!
View demo

4. Transfer file that you get in emails from within the Skype Email Toolbar. Works in MS Outlook, MS Outlook Express and Thunderbird. Download from http://www.skype.com/download/skypeemailtoolbar/. Note that this is application is still in BETA.
View demo

5. Of course a lot of partners applications can also do Skype File Transfers. My personal favorit is SnagIt. Read Jim Courtney's blog post about that here:
http://www.skypejournal.com/cgi-bin/mt/mt-henshall-tb.cgi/2424

A few things to consider:

* You can only send files to people who are on your contact list and those people must authorize first.

* The person you are sending to needs to authorize each file transfer.

* When you recieve a file from someone else, make sure to run it through an updated virus checker before opening the file.

* Regretfully it is not possible to send folders - only files at this time.

Hope you find these techiques as useful as I do