Picture this: You’re in a room filled with very smart, very talented, very knowledgeable individuals. You’re teaching them about the latest in Enteprise 2.0 tools – wikis, blogs, RSS, social bookmarking, social networking. You’re explaining the advent of “Web 2.0,” the rise of the prosumer, and how all these tools have changed the way people interact and the way we capture and retrieve knowledge. You get head nods, some skeptical looks, and some glassy-eyed individuals who, as you get into the technical how-to of the first tool asks…

“What’s a URL?”

Oh, OK, so you’re not familiar with web technology (that’s over a decade old)… I can explain that…

“Exactly what does a ‘web browser’ do?”

Hmm, now I’m getting a bit worried. You’re not familiar with what a web browser is? OK, deep breaths, we’ll get through this together...

“What’s a right-click?”

<groan> Uh-oh. Better step back and take this a little more s-l-o-w-l-y.

That’s the position I was in recently. Working with obviously smart folks who had been so consumed by their areas of of expertise (or management), that the world of technology had passed them going 100MPH. For some, that happened five years ago, for others, ten. These are folks who still think one wrong keystroke is going to crash their computer, that computers are “scary” and fragile, and hard to use. These is the digital immigrant crowd which is a far cry from the four digital natives I come home to (ages 8 mos to 6 yrs) who, in a matter of minutes, learned how to use my iPod Touch as well as me.

I’ve watched as the browser has become the key (or only) “application” you need to launch, as more applications move to the web, and as user interfaces for these various systems becomes more intuitive, friendly, and consistent. But I’ve been watching. The students in my classes haven’t.

And so it was with relief when the lightbulb went off that I needed to create an 3 hour introductory hands-on web workshop to help students become familiar with what many of those reading this post would consider mainstream or even passe. This would help them understand the nature and capabilities of the collaborative tools on the intranet.

Because the very nature of the Web is that of an ebb and flow, deciding which sites to highlight is difficult and has changed frequently in the short time I’ve taught the class. So I need your input…

What are the absolute, essential, can-not-miss web sites/applications you feel an “Internet N00b” should be familiar with? I’m not talking the latest-and-greatest (though services like Google’s Buzz could be considered). Below, I’ve listed the ones we currently teach to, but I encourage you to critique this list in the comments.

Social and Collaborative Web Sites for the Internet Neophyte

• Gmail. Arguably, the most popular and best email service on the web.
  • Key points: ISP-independent email address; integration with other Google Apps (one account, many sites); lightweight
• Google Maps. Once a rival to Mapquest, has become the de facto standard for getting directions.
  • Key points: Free maps, integrated with Android mobile operating system, allows users to add photos, create custom maps, and recommend changes.
• Google Docs. Online creation and storage of common files. Don’t worry, we’re just getting warmed up with this Google fan-boy love.
  • Key points: Creating sharable documents, spreadsheets, and presentations; work collaboratively with other authors; create web-based forms that feed data in Excel-exportable spreadsheets.
• Wikipedia. Accuracy arguments notwithstanding, this pinnacle of crowdsourcing is still enviable.
  • Key points: Anyone can edit, uses MediaWiki which is open sourced, grew bigger and faster than its predecessor Nupedia.
• Flickr. The go-to photo sharing site for many.
  • Key points: Anyone can upload photos; tags link photos with similar photos; users can subscribe to get updates from users or albums.
• YouTube. Like Flickr, but for videos…
  • Key points: Similar to Flickr, anyone can upload; tags help you find similar videos; users can subscribe to other users, tags, channels; videos can be embedded in blog posts.
• Google Reader. The power of RSS and subscribing to web content so it “comes to you.”
  • Key points: So much new content, RSS helps you filter and “dial in” the information you want to get; integrated with Google Translate, which automatically translates web sites in foreign languages.
• Twitter. Still the king of microblogging/messaging.
  • Key points: Used to transmit links, thoughts, “lifestreaming”; unlike Facebook, Twitter is asymmetrical; can use GPS location data; integrated with Google Translate to convert “tweets” into your language; URL shorteners are handy, but you need to exercise caution lest a rogue user (or hacked account) links to a malware site.
• Facebook. The monster of social networking sites for the US, despite changing privacy settings recently and removing…privacy.
  • Key points: A quick way to connect and maintain “weak ties”; set your privacy settings appropriately; be careful of what you share and who you friend.
• Delicious. Store all your web bookmarks on a web site instead of inside your browser.
  • Key points: Allows you to access from work, home, anywhere!; tags provide more flexibility than folders; tags provide for maximum discovery; use RSS to keep track of all new bookmarks saved by  another user or saved to a tag.

Your turn! Which of these should I dump or replace and which ones need to go on the agenda?