I really, really didn’t want to. And it’s basically a trial run right now. But I had to switch to using Gmail for my personal email.

For the last five years my personal email site and email (www.michaelaffronti.com) has been running on Office 365. I have always loved it for a few main reasons:

(1) You get to run Outlook and OWA against it.

(2) Working at a company that uses the Office 365 stack for work (Microsoft) made it easy to do side-by-side things like overlay Work and Personal calendars.

(3) Windows Phone + Office 365 is the best way to do email and calendaring.

Since leaving Microsoft and joining Contactive I’ve had to take a very large technology plunge and immerse myself in the world of Macs, Google Apps, and my shiny new Android phone.

Why doesn’t Office 365 fit well with my new technology life?

(1) Office 365 email on Android sucks: no Conversation view in the native client and bad syncing (I’ve had two emails in my inbox that I can’t delete stuck there since December).

(2) No overlays: It’s way easier to overlay another Gmail calendar, in this case my Personal into my Work view, than trying to get my Office 365 calendar viewed in Gmail. 

After only three days I already miss a lot from Office 365: the UX and awesomeness of Outlook Web App, all the cool features that I love (and in some cases helped build) in Outlook 2013 like flagging, custom actions, and the calendar, and the general idea of staying within a single stack (I still love and use OneDrive, XBox Live, etc.).

I’m currently redirecting my email from Office 365 to my personal Gmail account. Like I said, it’s a trial. Seamless email and calendaring is critical for me (as with most folks) and so far the gains are outweighing the pains (and losses) of switching. 

I’ll update my feedback periodically as things progress.