Everything But the Kitchen Sync

“We just re-synced the account, so you should be all set now.”

“You what?”

“The techs said they re-synced the account and, when they did, they saw a few issues were resolved. I don’t think you’re going to have a problem anymore.”

“Really?” I asked, “Because I’ve called about this problem many, many times and this is the first time I’ve heard anything about ‘re-syncing.’ Can you tell me what problems were resolved?”

“Not really. That’s all the techs told me.”

“Well, ok. If my emails stop disappearing, then I’m happy.’”

Having that “I just talked with my manager” feeling people get at a used car dealership, I was very skeptical that anything had really been done to resolve my problem. And, sure enough, between when I went to bed and got up in the morning, some emails had disappeared from my account.

When I started healthsystemCIO.com almost four years ago, I knew the first thing I had to do was secure the domain, and I always thought Go Daddy was the best place to register a URL. After that, I figured I might as well use them for our email. In fact, I never considered any other option. For a long time, things were just fine, but then emails started disappearing from my inbox after they were a few days old.

When I called Go Daddy, they immediately blamed “one of the devices or applications that was synced with the account” — Outlook or my iPhone. “Something tied to the account was deleting email off the server after a certain number of days,” they said.

Ok, I thought, let’s start with the iPhone. At the suggestion of a Go Daddy support rep, I changed the password on my iPhone that allowed it to interact with my Go Daddy email. “That will break the connection,” he said.

But emails still disappeared — it wasn’t the iPhone.

Then I became convinced that Outlook 2013, which I had just upgraded to, was the culprit. I spent lots and lots of time on the phone with a very nice support rep who first rebuilt my whole profile, then installed Outlook 2010 when I insisted that it must be a bug with their new product.

Ok, no good … emails still disappeared. Perhaps both versions of Outlook had this strange bug. Let’s think this through, I said to myself: My use of Outlook is not through an Exchange server. The thing is just sitting on my desktop, which means that when the computer is off, Outlook isn’t doing anything.

With the iPhone connection to Go Daddy broken, and my computer off, I checked my email using the Go Daddy iPhone app, noting how many there were before I went to bed. In the AM, the old emails were gone, gone, gone.

The next day, I called Go Daddy and had the above conversation. That night, after the mysterious re-syncing, they were gone again.

I was done. Finished. It was time to break up.

And where else to go, but Google Apps for Business? At first, I told the team they’d still be able to use the Outlook 2010 both had been running. But after dipping my toe into the Gmail waters, I had a better idea.

Let’s try to quit our Outlook addiction, I suggested.

Why? Because Outlook was essentially created to put a nice mask on ugly webmail; to provide functionality with calendar, contacts and tasks that webmail could not offer. Also, back when Outlook was created, working directly on the web was slow and painful. Now, with super-fast internet service everywhere, it’s a whole new ballgame. It seemed to me that the underlying face had become pretty enough that the mask was no longer necessary.

In fact, the mask was a snapshot in time (2010, or the 2003 I recently graduated from) while the face (Gmail) constituted the best that could be offered right up to the current minute. I liked no longer having to think about whether technology was passing us by. Now it couldn’t — we were on board.

Just like any transition (think docs to EMRs), moving email programs is a painful one; quitting Outlook after working in it for one’s entire career is a big and tough change, but I’m absolutely convinced that it’s the right thing to do.

There are a few lessons here, such as why Go Daddy and Outlook (Microsoft) have lost, and why Google has won. The former had unreliable product performance and inconsistent customer support (you might get someone savvy or a newbie) and seemingly no methodology for escalating frustrated users to senior service managers. The latter lost because the problem it was solving ceased to exist, leaving it irrelevant and quite replaceable. It’s worthwhile to ensure that you, your department, and/or your business never wind up with either of those problems.