I think that a personality is what a lot of programs need. The biggest problem is coordinating personalities between applications. Microsoft's Agent has the biggest potential for Personality, and yet, since the user can control which Agent shows up, or which are even available, and there are so many possible applications that use Agent that it is hard to keep up a running dialogue or illusion of personality.

The same thing applies to Office Helpers (a subset of Agent). They all say the same things, because they aren't differentiated between, and it might be a nightmare to write lots of dialogue for each... But, Agent/Office Helper do at least provide some personality in the animations, which typical voice programs can't do. For instance, in Office, although like most people I don't like Clippy, I like Links, the orange cat. Links doesn't dance around as much or tap your screen, he/she generally just sleeps in the corner. As for Agents, Peedy has become one of my favorites, because he seems slightly more courteous in animation, without being overly humble like Genie. But also, less servitor, more "emotional" of a charactor than Merlin or Robbie.