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For a systems administrator, one of the advantages of working in a startup environment is the distinct lack of ancient (in computer terms) legacy equipment that needs to be kept on technical life-support because “our whole company is connected” to that wheezing box in the closet. And, being a smallish outfit of developers and creative types, there is ready acceptance of not being bound to the prevailing Corporate Style here in the center of the Financial District.

MacBook Pros for all.
Open Source Software backend.
Exchange Server [not].

Not that our email service was anything special – outsourced to a provider somewhere in New York. OK for cheap small-scale email hosting, but definitely becoming a support liability as we have grown. Time for a capable in-house solution, with all the features that users have come to expect – messaging, contacts, calendars, etc. Just a couple years ago that would have meant an Exchange Server, as there basically wasn’t anything else out there with the whole package of services and administration.

I’ve done Exchange Server. While it is certainly able to do the job, the experience was rarely pretty. And more often it was something far worse than having white hot steel needles shoved through my eyes. Thankfully, today there are a number of very capable solutions available in many server flavors. We looked them over, tried a couple, and settled on the Zimbra Collaboration Suite – I suppose you really can’t get just an “email server” anymore. I won’t pester you with the technical details or feature descriptions because you can get all that elsewhere. What was interesting to me was observing the human element as we went through the process of changing email systems on the fly.

Up to now I’ve performed one major replacement and literally countless minor surgeries on email backends and there is easily no other technical task fraught with such potential for open weeping, wailing and gnashing of teeth…and that’s just from the user end. Like it or not, email has apparently become the Super Glue of our cultural and commercial fabric. Fire, Flood, or Famine – no sweat…is the email server down? They don’t call them CrackBerries for nothing. So we headed down this road with as much caution, courage, and preparation as possible.

The challenge here is not to eliminate chaos, but attempt to mitigate its effects through every step of the process…keep the Fear at arm’s length and stay on the balls of your feet. Several rounds of user beta testing, extensive step by step instructions (love those screenshots!), and multiple dry runs on various test machines. Then E-Day arrives and the troops hit the beaches…

“Oh, I thought you were going to make the switch on Tuesday evening.”
“Yes, we did, and this is Wednesday morning.”

Styles of Personal Digital Organization:
– one inbox, 8000 messages and growing
– one inbox, 4 messages, but 80-something subject folders
– four inboxes, shared subject folders, and a labyrinth of rules
– “huh, where did those come from?”

Cryptic error blues.
Character bounds exceeded.
  /   in folder name.

Forget spam…25MB PowerPoint attachments are the cholesterol of the Internet.

“The instructions for Outlook transition don’t work”
“Aren’t you on a Mac?”
“Yes”
“There is no such thing as Outlook for the Mac.”
“No, really, I’ve always used Outlook.”

And so on….

Soon enough the Ripples will smooth out, the Fuzzy Blue Blankies will get dry-cleaned, and we can all move to the next project on the List. As email transitions go, this wasn’t too bad. But you contribute to your own Karma in this biz, and there is no substitute for keeping the Wheels of Progress well-greased with careful consideration and adaptable attitude.

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