Thanks to KC Lemson for spurring me to finish and post this!

I’ve been outside of Microsoft for 3 months, and am now leading a medium sized social venture.  The outside world is different.  I suspect the assumptions born and lived inside of Redmond lead to all kinds of bad decisions.    If the below is obvious to you, please ignore.   If, like me, you’ve lived the last 10 years inside the all-encompassing embrace of the Redmond domain and Exchange servers, read on…

  • eMail is important, but not for personal or work communications.   Inside of the Redmond domain, your friends and colleagues are all on one email system with a convenient address book and contacts.   This means email is very important, probably your primary communications channel.   Outside, your inbox (see mine below) is used for mostly commercial emails – receipts, junk mail subscriptions, and such.   As a result, email is much less central to me.   I often check email one or two times a day, not multiple times per hour as I did while at Microsoft, because there’s just not that much that’s interesting to me.



  • Nobody has solved for calendaring outside of the enterprise.   I miss Exchange scheduling.   Calendars aren’t well solved by gMail or Google apps, where I can’t see free/busy well.   I did migrate my entire Microsoft address book to my Google account before I left, so there’s that.   But generally, my email communications are pretty hodge-podgy now.
  • Outlook + Gmail doesn’t really work on the PC.   My new company uses Google apps for email, but setting it up to work with Outlook is painful.   And then, it doesn’t do calendaring?!   But webmail with multiple accounts drives me crazy.  Outlook needs to embrace Gmail and vice versa.  At Microsoft, everyone has a well managed Exchange system.   Outside, I’m gradually being dragged to the Mac, where the calendar and email clients aren’t relentlessly trying to drive me to the linked email service as Gmail and Outlook do.  This is a huge missed opportunity for both Google and Microsoft.
  • Gmail doesn’t work well in the native iOS app.   No real push?   Silly.
  • My most important address books are LinkedIn and Facebook, and messaging on these is my most important channel.   Friends and family are all on SMS or iMessage so you use that.   But LinkedIn and Facebook are where my contacts are, constantly updated, and everyone else now appears to check for messages routinely.   It works very well.
  • With coworkers, messaging is crucial.   I’ve now become President of a small/medium sized social venture, and my team members are heterogeneous as hell about communications.   Few use email for work communications.   Many use text messaging.  Others use a wide variety of messaging services, from WhatsApp to Google hangouts to facebook messenger.     This creates a real mess of different services and apps I must install.
  • iOS and Chrome tie everything together.   Thank goodness there’s one set of channels for notifications for all these damned services.   The most important for me are iOS notifications (so there’s one service that reminds me when one of a dozen channels has a new message) and Chrome browser notifications on my PC.
  • I still haven’t made Slack work.   At Microsoft I tried to get my teams to use Slack – everyone said it was awesome.   It didn’t work for us since everyone uses and loves email.   Now I’ve tried getting Interconnection to try it out, but it’s just not sticking.   Perhaps it’s me, but it feels like just another damned messaging app.  Which leads us to….
  • There are too many damned messaging apps.   Seriously, it’s a pain.   Thank goodness for Chrome and iOS – they make the situation tolerable – but seriously, I wish everyone but one would just die already.    Of course that won’t happen so I think we’re stuck.

William Gibson said that the future is already here, it’s just not evenly distributed.   I think this is a great example of that phenomena.   I wonder if it’s just Microsoft or all Microsoft-centric enterprises that live and die on Exchange?   I also wonder if the new employees joining Microsoft experience things differently, or if once they’re pulled into the Redmond Domain they experience the same warm embrace of email?   Let me know.