Improving Outlook is no easy feat given that it's notoriously anti-social when it comes to social networking. The free Outlook plug-in iLook Social and Outlook tries to make Microsoft's ubiquitous e-mail client a bit more sociable by including souped-up searching and filtering, Skype integration, e-mail controls, content and attachment exporting, and Facebook support.
For a sidebar pane, it's a good list of features with an interface that integrates smoothly into Outlook 2007. Desktop e-mail clients are going to have to adapt to social networking far better than they have to survive, especially if the future of e-mail is Google Wave. Postbox does a decent job of remixing Thunderbird for social networking, but it's still in beta and lacks the calendaring you can get in Thunderbird using the Lightning plug-in. While iLook's features are worthwhile, their execution leaves plenty of room for improvement.
The search and Skype features are the strongest, but could still be better. Boolean searches are not supported, nor are cross-folder queries, and the nature of Outlook requires you to manually create a new search results folder that iLook doesn't address. Basically, that means you've got to figure out where your search results are going to go before you see what they are--it's counter-intuitive.
The Skype support is strong, with decent chat quality, contact list support, and other Skype features. Like any third-party Skype plug-in, though, it requires Skype to be running, and iLook wouldn't load if Skype was running before Outlook loaded. The Facebook support was far less convenient than it should've been to convince users to utilize it in iLook. Attachment exporting worked well, but that was more of an alternate path up the mountain than introducing a whole new geography to Outlook.
Making use of the entire iLook experience, unfortunately, will put you in for a bumpy ride. Although Outlook itself isn't known for its speed, this plug-in definitely slows it down. Switching between its features often causes error messages, and it's hard to tell if or how those errors affect either iLook or Outlook. The features that iLook Social and Outlook provides are smart choices, but the end experience is buggy and needs to be tightened before it can be considered for daily use.