Enterprise users aren’t easy to switch over. On the plane to New York I saw a guy using Windows 2000 with an older version of Lotus Notes. I felt sorry for the guy. But his usage is typical of those in many enterprises. CTOs don’t like to invest in new stuff when the old stuff is working just fine.

So, you try being a Google salesperson and trying to get the CTO to rip out old stuff (er, Microsoft Office and all of Microsoft’s servers like Sharepoint and Exchange) and switch to your newer stuff (like Google’s Docs and Spreadsheets, Gmail, and Google Calendar).

I’m going through that move myself and I can tell you it isn’t easy. And I’m one guy who can make up my own mind. Imagine the momentum a big company with, say, 100,000 seats has to go through. Next time you’re at Hertz rental car you can see that momentum in action: they are still using a character-mode app on their front line machines.

But the early adopters have already moved. When I ask audiences what they are using now, I see more and more Google customers.

I can’t think of a situation where the enterprise didn’t eventually follow the early adopter crowd. It might have taken years, but they do follow eventually.

Today we are seeing new signs of life in Google’s strategy and the help didn’t come from within Google itself.

It comes from a small company named Cemaphore. They just announced “MailShadow for Google Apps.”

What does it do? It synchronizes email and calendar items between Microsoft Outlook and Exchange and Gmail/Google Calendar.

Sounds really boring, right? Hey, didn’t Google just ship its own synchronizer?

Yes, and yes.

But Google’s synchronizer sucks compared to Cemaphore’s. It’s slow and buggy. Earlier in the week I got a demo of Cemaphore’s new offering from Tyrone Pike, Cemaphore’s CEO and President.

I saw that, thanks to Cemaphore, when I enter a calendar item in Microsoft Outlook it instantly appeared in Google Calendar.

He repeated the demo with reading and sending email from both Exchange and Gmail. Again, synched within seconds.

My own tests with Google’s sync technology showed that items wouldn’t sync for hours, and sometimes, never, if you screwed up and loaded two separate synching products like I did.

So, why is this important?

Because it lets Enterprises slowly introduce Google’s Enterprise products in.

Enterprises will never move wholesale over to Gmail and Google’s other offerings. Users just don’t like that kind of change. There would be revolt at work, if CTOs tried to force it. But this way a CTO can let his/her employees use whatever systems they want and still have them synchronized. And there ARE major reasons to move to Gmail: Cost, for one. I also am hearing that Gmail’s email servers use far less electricity per mail than Exchange’s do. Environmentalism anyone? You think that’s not important for CTOs? It sure is. Both are going to be major drivers that will get Google’s offerings paid attention to.

Anyway, I’m hearing rumblings that Google will follow this announcement up with several of its own over the next couple of months.

It’ll be interesting to see what CTOs think of this and it’ll be interesting to see if it does, indeed, take five years for Google to make major inroads into the Enterprise like I think it will.

What do you think?