More timeless, still-relevant information technology jokes

One of my most visited blog posts noted that certain IT jokes tend to come up again and again. That post covered four such familiar jokes, along with what I felt were some common themes uniting them: IT hubris, narrow perspective, self-righteousness. Each of those jokes contains a “grain of truth” to it that makes it funny, to IT and non-IT people alike.

Along those same lines, here are three more time-honored IT jokes, ones you’ve probably already heard if you’ve spent much time in the industry. Again, take a few moments to revisit them and consider what makes them timeless: how the common situations they describe seem to never quite go away. And then I’ll talk about what I think unites them thematically, and the resulting lessons for IT professionals.

1) Software sales vs. used car sales

What’s the difference between a used car salesman and a software salesman?

The answer is that the used car salesman knows when he’s lying.  

Highly successful salespeople (in any industry) can of course be inveterate truth-stretchers, exaggerating, embellishing, all for the sake of the sale. The world of software sales, however, is sufficiently complex, and the prospective customers often so sophisticated, that a salesman in that world can rapidly and unwittingly get out of his depth in describing the capabilities of the product he’s pitching.

Take a step back, though, and recognize that we IT executives are often in a “sales” position internally, in terms of describing to our peers or to the company at large our teams’ current projects, proposals, and approaches. Given that we don’t always have every detail at our fingertips, it’s certainly a danger that we, too, get out of our element and overpromise in situations where the facts won’t support us. Something to remember, even as we laugh at the joke: this could be us.

2) That was the demo

Bill Gates dies in a car accident. He finds himself in purgatory, being sized up by St. Peter. “Well, Bill, I’m not sure where to send you. I’m going to let you decide whether you want to go to Heaven or Hell.”

Bill replies, “Well, what’s the difference between the two?”

St. Peter: “I’m willing to let you visit both places briefly, if it will help your decision.”

“Okay,” says Bill, “Let’s try Hell first.”

So Bill goes to Hell. He finds a beautiful, clean, sandy beach with clear waters and lots of beautiful women running around, playing in the water, laughing and frolicking about. The sun is shining, the temperature perfect.

“This is great!” he tells St. Peter. “If this is hell, I REALLY want to see heaven!”

“Fine,” says St. Peter, and off they go.

Heaven is high in the clouds, with angels drifting about, playing harps and singing. It’s nice, but not as enticing as Hell he just visited. Bill thinks for a minute, and makes his decision.

“Hmmm. I think I’d prefer Hell,” he tells St. Peter.

“Fine,” retorts St. Peter, “as you desire.” So Bill Gates goes to Hell.

Two weeks later, St. Peter decides to check on the late billionaire to see how he’s doing in Hell. He finds Bill, shackled to a wall, screaming amongst hot flames in dark caves, being burned and tortured by demons. “How’s everything going?” he asks Bill.

Bill responds, his voice filled with anguish and disappointment, “This is awful! This is nothing like the Hell I visited two weeks ago! I can’t believe this is happening! What happened to that other place, with the gorgeous beaches and the beautiful women?”

“That was a demo,” replies St. Peter.

This joke has much in common with the first joke, in that it plays on something universally recognizable: the high-energy, enticing sales pitch (this time in the form of a glossy, seductive demo) that sets expectations that are of course invariably dashed by eventual delivery and harsh reality. The joke is made all the funnier, for many, by its featuring Bill Gates as its poster child. How many of us in IT raise expectations in this manner, only to see the disappointment that occurs after actual delivery?

3) Prepare three envelopes

An incoming CIO replaces a recently fired CIO. On his way out, the former CIO hands the new CIO three envelopes and tells him, “when you reach a crisis point, open these envelopes, one per crisis.”

Things go well for a while, but then along comes the first real crisis. The manager goes to the drawer where he keeps the three envelopes, and opens #1. It reads: “Blame your predecessor.” He does this, and the crisis is resolved.

More time passes and a crisis looms again, and the manager dutifully opens envelope #2. It reads, “reorganize.” Again, following his predecessor’s advice works like magic, and things settle down.

But sure enough, a few months later, troubles are mounting once again, more than ever. This time, though, the manager knows for sure that help is just an envelope away. So he turns to the drawer one last time and opens #3. It reads: “Prepare three envelopes.”

The degree to which that this joke mirrors actual, real-life situations is actually somewhat eerie. I’ve seen various organizations throughout my career, and a number of new IT executives in particular, where this exact pattern happened: first the blaming of the predecessor, then the reorganization, and then… well, floundering.

Let’s examine one common thread to these three jokes. Basically, it’s rank cynicism: cynicism about empty promises from IT in the first two jokes, topped in the third joke with some equally cynical gallows humor about both the classic hackneyed approaches and then the ultimate inexorable outcome for the hapless CIO.

But here’s a more succinct common thread that represents a key takeaway for those of us in IT: there are no easy answers. Instantly recognizable glibness (often stemming from spouting easy answers) on the part of the software salesman provides the humor in the first joke; easy and grotesquely misleading promises provide the humor in the second. And finally, in the third joke, looking for easy, bottled answers to crisis, such as blaming one’s predecessor or reorganizing, ends up not working very well or even backfiring.

So, the real moral of the stories here is pure homespun homily: Don’t overpromise or oversell. Deliver what you promise.  And don’t keep looking for a silver bullet to bail you out, instead of putting in the real, hard work that it takes to succeed over time.


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