Regarding usability, Windows Live Messenger can learn from Skype chat.  In the past weeks, I have used Skype chat intensively.  There are several features that I miss in Messenger since I started using Skype chat as well.  Let’s take a look.

11 Examples of Skype Winning

#1: Contact List Interface

In Skype, you can set the main window (contact list) to include the conversation windows.  Everything is then in one place.  Might get messy at times, but looks nice.  An idea for Messenger?

#2: Aero Enhanced

Skype has two different display modes, Windows Classic (using your Windows theme), or Skype-look.  This looks like Windows Aero, but enhanced.  What do you like more, and why doesn’t Windows Live Messenger offer something similar?

#3: Chat history display

When opening a conversation window in Skype, you can choose to display the history for this contact, of yesterday, of 7 days, of 30 days or the complete history.  The messages are then shown directly in the chat window.  Messenger needs an extra window and manual date lookup.

#4: New messages when inactive

Imagine a conversation with your friend and you have to leave for a moment.  You minimize the chat window, but instead of still scrolling down when your friend sends a new message, the window will stop and just display some orange dots.  This way, when you return, you can continue to read what he sent without needing to scroll up first.

#5: Editing messages

How often did you send a message with a typo in it?  In Skype chat, you can press the [Up] key and edit your latest message.  As soon as you submit it, it will replace the original message, on the screen of your friend as well.  Using the context menu, you can edit older sent messages, too.

#6: Deleting messages

If you realize you sent a wrong message, or a text to the wrong recipient, right-click and remove it.  Messenger cannot do this at all.

#7: Messages order

You send message A, and after that, your connection drops.  You send message C.  In the meantime, your contact sent message B.  As soon as you reconnect, the messages will appear in the correct order.

#8: Signing in with no web connection

Skype has an offline mode.  You can sign in while you’re not connected to the Web.  This way, you can send offline messages when you are offline.  They get delivered when you connect.

#9: Copying messages

When you need to copy a larger chunk of chat messages, Skype auto-formats them and adds the date.  Everything looks fine when you paste your text for example into Notepad.

#10: Quoting messages

Do the test: In Skype, copy a message from a chat with contact A and paste it into the conversation with contact B.  You will see a fancy block quote—that looks really good.  And in Windows Live Messenger?

#11: Status icon

The Skype icon in the notification area tells how many contacts have unread events/messages.

A Remis—Both Do Well

#1: Multiple Points of Presence

Both Messengers support signing in at multiple endpoints.  Interesting!

#2: Extendability

Skype has an official API where third-party plugins can connect, while Messenger knows several good add-ons (Messenger Plus! Live and MessengerDiscovery being the most well-known ones).

Live Messenger Wins in Three Cases

I found three points that Messenger does better than Skype:

#1: Pasting images into the chat

Messenger will start a Photo Share or send the clipboard image as temporary JPEG image, but Skype simply ignores the paste.  Lame!

#2: Organizing contacts in categories

Correct me, but I haven’t found a way to sort my Skype contacts into categories.  The only group feature I found is for multi-way conversations.  Messenger does this job fantastically.

#3: Integration of social networking

Messenger connects successfully to Twitter, Facebook and YouTube, among zillion other What’s New feed providers.  Windows Live Wave 4 (Version 2010) will even enhance this, when Messenger directly connects to Twitter and more networks.

Windows Live Essentials 2010 can be expected for next spring.

Summary: Skype wins the race (bad for Messenger!)

13 points for Skype, 5 points for Messenger: a bad outcome.
Thus, in regards to usability and small interface tweaks, Skype makes the race.

What do you think?  What would your results be in a similar chat feature race?