The following is a tale from the annals of “Things That Can Go Wrong in IT, but That Didn’t Actually Happen” … but its message is no less real. Read on.

I remember that day all too clearly. I was sitting at my desk one crisp autumn morning in Boston, Massachusetts. A fresh, steaming, hot Dunkin Donuts coffee in one hand and a toasted muffin in the other. I hadn’t been logged into my computer for more than 5 minutes when the familiar Skype for Business message alert sounded.


Cindy: “Sean, this is Cindy from HR.”

Me: “Good morning Cindy. How the heck are ya?” Even in instant messaging I try to use the ol’ Irish charm.

Cindy: “Can you come to my office please?”

That’s when my muffin and coffee suddenly became unappetizing as a roiling, bilious ball of anxiety grew in the pit of my stomach. We all know that sudden and abrupt visits to the folks in Human Resources are rarely good things. I did a quick rundown of any inappropriate behavior I may have exhibited lately. Nothing of significance came to mind. I placed the Styrofoam cup and wax paper bag on my desk and bounded up the stairs to the 3rd floor.

As I approached Cindy’s office, I noticed that it was unusually dim, illuminated only by a single lamp on her otherwise barren desk. I knocked on her open door and saw that she was not alone. Sitting at her small, round meeting table was Karl Stanfield, our Chief Security Officer. Cindy sat, looking down at a pad of yellow lined paper, pen in her left hand, her right hand nervously flicking some invisible dust from her fingers. Karl sat stone-faced next to her. As I walked across the floor, suddenly very mindful of my every step—like a driver undergoing a field sobriety test—I could sense Karl examining me like a cop from an old 1980’s TV drama.

Cindy: “Take a seat Sean. This won’t take but a minute.”

Uh – oh, I thought … are firings normally a quick action?

“Do you recall losing a laptop on the tram in Amsterdam last month?” she continued.

“Yes, of course I do. I was devastated at my carelessness. I can’t imagine where my head was at that I could have forgotten my bag on that seat.”

I felt my face flush with embarrassment. This is it, I thought. A bead of sweat made its betrayal from the top of my brow.

“Yes, that was a curious lapse in judgement.” She said as she scribbled some notes on her legal pad.

Suddenly Karl unclasped his hands and asked, “What kind of data did you keep on that laptop?”

Relief rushed through my body like a shot of cold air. I nearly burst from my seat with confidence as I gleefully replied, “Aha! None. I am all cloud storage, baby. All files, folders, spreadsheets, intellectual property is all secured in our cloud file share.”

I don’t think Karl appreciated my cockiness because he just kept staring at me.

“I see,” he replied, lacing his fingers back together like the serrated teeth of a bear trap prematurely sprung on its targeted prey. “And what about Skype for Business?”

“What about it?” I asked still high on a cocktail of adrenaline and arrogance.

Do you realize that if you run Skype for Business local on your laptop and leave all the settings at their default that every letter, word, sentence and emoticon are stored in log files, locally? Every file you transfer in a meeting is also cached local to that laptop?

There was that boiling, roiling angst in my stomach again.

“That laptop you treated like a disposable camera fell into our competitor’s hands and they now have details on our customers, deal sizes, deployment details and even discounting. All your contacts were also stored locally. Oh, and they also have the functional spec for ‘Project Pink Flamingo’.” He gave a menacing grin and continued, “You remember ‘Pink Flamingo’, don’t you?”

If my tragedy has left you wanting to learn more on the ways you can avoid sitting across from “Karl the Security Officer,” then I encourage you to attend this insightful webinar.

Oh, and about that muffin I had left on my desk that fateful day? Of course I ate it. It was chocolate chip after all.

Watch the webinar on-demand: “Skype for Business? Yes, the fastest growing unified communication system just got even more secure.”

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