The Cloud

72 Hours of Technology Hell

For the past 30 years, technology has thrilled and tortured us. It still does. Never turn your back on IT. The more you know, the riskier it gets. ...
Susan CrammOctober 26, 2012

New technology brings with it new possibilities. It also brings pain and disappointment.

The latest installment in this life lesson involved my recent iPhone upgrade.  After the announcement that a new, improved iPhone was ready, I jumped on the site and placed my order. Shortly thereafter I received confirmation that my wonderful new slice of technology  whiter, slimmer, lighter, faster, sharper, and smarter than ever before  was winging its way around the world to me and was scheduled to arrive on a Friday. 

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Every day, like a child waiting for Christmas, I checked the UPS tracking site. On Thursday I awoke to discover that my new iPhone 5 was on the truck! I’d be getting a whole lot cooler a whole day earlier! Little did I realize that the end of my iPhone’s journey would be the start of my journey into technology hell.

I should have known better. I’d had problems before. But this time, I reasoned, would be different. I was standardizing on Apple  both hardware and software  and surely the elegance of its engineering would mask all the underlying complexity and transform my world into one where I could manage my business on any of my devices, with data automatically synching in the background.

The first 24 hours of hell involved an operating system upgrade. In order to use all the latest, greatest iCloud features, I upgraded my OS to Mountain Lion. I didn’t need to, but optimism overcame wisdom. Just as I clicked the “Download” button, my husband came home, saw what I was doing, and lovingly asked, “Are you crazy?”

Yes, apparently, I was. After I restarted my computer, some kind of mysterious background process started that consumed more than 90% of my CPU capacity for the next 12 hours. A new day brought normal CPU utilization levels and with them a renewed sense of (misplaced) optimism.

Day two of techno hell involved the iCloud. Sporadically, I would get some kind of a server error message with a bunch of meaningless (to me) letters and numbers. After spending an hour with an Apple genius (at the Apple Store), I was referred to Apple’s iCloud team. My (virtual) appointment was for 6:00 a.m. sharp the following morning. Before I was fully awake, I learned that I had exceeded the calendar data limits on iCloud, and there was no way to archive a portion of my old calendar entries. I was left with the option of 1) not using iCloud or 2) wiping out my calendar. Since I don’t really ponder the past all that much, I decided to start my life over.

In addition to the weird server error, I also was unable to invite attendees to a meeting using Apple’s Calendar application. Surely a user error, right? Unfortunately, no. The genius who replicated my problem couldn’t fix it, and referred the issue to the Apple engineering team.

At this point, I knew I was stuck. A long career in IT has taught me that nothing good ever comes quickly once an issue escalates to engineering. It was time to jump off the Apple bandwagon. I called in a favor with an in-house IT guru and we agreed that it was time to go back to Microsoft Outlook and use a product like Office 365 to synch up my devices.

The third (and final) day of hell involved getting back on the Microsoft bandwagon. The Outlook installation was a breeze. All my years of meetings magically appeared, as did my e-mail history. That was a relief. I didn’t have to start my life over from scratch.

I checked out a few options for hosted Microsoft Exchange and decided to go with Office 365. Ordering and installation looked pretty easy. Well, of course. It always does.

Without the benefit of comprehensive installation instructions, I was left to surf the Net, visiting chat rooms and watching YouTube videos. My desktop and Office 365 started to synch, but my iPhone was playing hard to get. As a last resort, I submitted an online support request to Microsoft. And believe it or not, Microsoft (via Mumbai) called me 15 minutes later and whispered the magic words necessary to get my iPhone synching with Office 365.

For the past 30-plus years, technology has tortured us. It’s always too little, too late, and costs too much. In the anticipation and excitement of the new, it’s easy to forget the past. Don’t. Never forgive. Never forget. Stand on my shoulders and keep these lessons in mind:

  • Lesson #1: Make sure the gain is worth the pain. Wait to upgrade existing technology until you can hardly stand it.
  • Lesson #2:  Always stay away from the latest version. There is no reason to be the first to implement anything. Ever.
  • Lesson #3:  Don’t trust the hype. There is no such thing as a single vendor solution. This is why you need your own IT people. They’re skilled at integration. Your vendors aren’t in the business of making it easier for you to buy other vendor’s products.
  • Lesson #4:  Get your hands dirty. Unless you’re engaged with the tools, it’s impossible to understand the trade-offs and make the right decisions when problems arise.
  • Lesson #5:  In the end, it will be good enough, but it won’t be perfect. For example, yesterday I realized that the calendar on my phone was missing a couple of meetings. Yikes!

Still, I’m loving my new technology. I just don’t want any more  for a long, long time. . . .

Susan Cramm is an executive coach and president of Valuedance, an executive-coaching and leadership-development firm specializing in information technology. She is a former CIO and CFO, and is the author of The 8 Things We Hate About IT: How to Move Beyond the Frustrations to Form a New Partnership with IT (Harvard Press). Susan can be reached at