Since I wouldn't like to get caught naked by my boss (well... in both senses of the term!), I recommend the fine article from ZDNet: A checkpoint on Web 2.0 in the enterprise by Dion Hinchcliffe.
For sake of discussion, I'm including two charts from the full article. Although long, I strongly recommend it (I already said that, did I?).
"Web 2.0 is an underlying set of principles... that have reached a tipping point that’s enabling brand new business models, unleashing a wave of innovative products, influencing public behavior on a large scale, and in particular, resulting in entirely new types of online businesses."
"... like SOA or SaaS, the ideas represented by Web 2.0 will take years for the majority of the world to embrace and make effective use of. ... Many of these will require serious soul-searching in business, not to mention overcoming the Innovator’s Dilemma, the latter which raises the interesting question of how do you adopt a new way of business that is at odds with your current way of doing business?"In short, Web 2.0, just like the Web about 15 years ago, is challenging several aspects of the business functions, including IT. It shouldn't be dismissed by fear of the unknown or hiding behind a comfortable status quo that is bound to haunt us for the coming years. The best approach might be to pick a few quick wins, explore and learn even if its only for sake of initiating discussion and sparkling a cultural change... Which would already be something interesting for companies that have a conservative culture.