With Skype, you aren't limited to simply chatting with your contacts. You can also send documents, songs and more. When you attempt to send a folder, however, you will encounter a problem; Skype forces you to open the folder and select an individual file rather than sending the whole folder. Fortunately, you can get around this problem and successfully send an entire folder to your contact.
Navigate to the folder which you want to send over Skype. Right-click this folder to bring up a list of options.
Hover your mouse over "Send to" in the list of options that appears. This brings up even more options; click "Compressed (zipped) folder" in this list. Wait a moment while your computer makes a zipped copy of this folder.
Open Skype. In the left panel of Skype's screen, click the name of the contact to whom you wish to send this folder.
Click the "Share" button that appears in the right portion of the screen, and then click "Send File" from the list of options. This opens a new window.
Navigate within this window to the compressed folder you created. Click the folder, then click "Open." This initiates the transfer, which your contact must then accept.