I like “personality” in a web app.  It helps users form an emotional connection — a relationship — and that’s good for the user and the app.  The trick is to treat interactions between app and user the way you’d treat interactions between people.  Then, build your app with the “people” personality of someone everyone likes — charming, polite, a little bit funny even.

There are a few things to consider:

• Your audience.  The personality of BOOMj (social network for baby boomers) should be different than Nymbler (naming wizard for expecting parents).
• Your purpose.  Sites like Mixx and Twitter can afford to have amusing error pages because the state-of-mind of the user is rarely too serious.
• Your experience.  What is the user experience as they interact with your app?  Just as you would in the “real” world, communicate with your users in a way that takes into account the experience they’re having at that moment.

The advent of widgets, which allows a part of an app to be “plugged” into a larger site, creates a new challenge.  The personality of the widget needs to conform to the site it’s wrapped in. 

This morning, I was reading a very serious article on cnn.com about the assassination of Benazir Bhutto.  I was intrigued by the option to continue reading about the topic with the “From The Blogs” feature, provided by Sphere.  My state-of-mind was somber — this wasn’t an amusing topic.  When I clicked on the widget, I got this loading message:

“Sit tight, we’re getting to the good stuff” sounds good if I’m reading about the foul-mouthed posthumous tipper (how is this news, by the way?) but given what I had been reading, it stopped me cold, like someone telling a joke at a funeral.  I wasn’t in the mood for “cute.”

The technical solution to this issue is simple — it just takes planning.  The best web apps will increasingly offer highly-personalized user experiences where every interaction is more and more human (and charming).  If you’re building one, build this in.