Recently, at a Sharepoint conference in early March, Microsoft co-founder and chairman made the following comments regarding Google:

“In terms of Google, not to overstate it, but they really don’t understand the special needs of business. Today, their economic model is based on consumer search. They have done an incredible job there and obviously we’re investing in challenging them in that space …

Gates's point is that going from consumer to enterprise is non-trivial and that while Google has executed very well in the consumer search space, they have not executed very well in the enterprise space.  Of course, the same could be said for Microsoft which for years has done well in enterprise but has only recently made moves into the consumer space.  In fact, now that I think about it, there aren't too many tech companies that have done well in both (Apple doesn't count... they are still more into consumer than enterprise).

While I can't comment on things like Office applications or Sharepoint, this is definitely true in the email space.  Hotmail's spam filter is Smartscreen and we use it in our own filtering.  However, the behavior in each is quite different.  Hotmail has requirements that are either too lax for us or too restrictive.  Hotmail is willing to put up with a higher false positive rate than we will, but they will also add IPs to a safelist that we would never consider putting on.  The transition from Consumer (Hotmail) to Enterprise (Exchange Hosted Services) is so different that I would say that we have a long way to go before we can make use of Smartscreen's full capacity.  Enterprise and Consumer are just so different.