Most epic professional fails

We all make mistakes in life, don’t we? Especially when we’re at work.

Photo of eraser gum with inscription 'errare humanum est'

Here’s my personal top-10 of professional fails (so far), carefully collected over the years. They range from slightly reckless behaviour and laughably embarrassing situations, to outright unforgivable actions.


#10. Driving 180 km/h with a harddisk full of data

More than twenty years ago, when I was still in my twenties and therefore immortal, a customer of ours needed to urgently launch a massive website containing tens of thousands of pre-generated pages.

Too much data to send over the wire or by avian carrier, so we went for the highway. Never was I driven faster from Brussels to Luxemburg than on that particular day.

The website went online alright, but I swore to never do that again.

Good: Made the deadline
Bad: Almost made the deadline

#9. Stomach problems on an intercontinental flight

What do you get when you combine a week of jetlag and lack of sleep with a chicken curry inflight meal, and a glass of port?

A big mess, a lot of hassle and a plastic bag full of clothes. Plus complimentary pajamas carrying the British Airways logo — a real collector’s item!

Good: deep respect for flight attendants and airport paramedics
Bad: embarrassing walk in BA pajamas through Heathrow transit zone

#8. Not checking company-critical backup tapes

This is a classic.

When I was working at one of Belgium’s first web development shops in the mid-nineties, the external SCSI disk containing half of all our managed websites suddenly decided to stop working. To make matters worse, the backup tape also seemed corrupt.

Just when I was about to take the blame and write my resignation letter, the disk came up again, and the company was saved. As was my job.

A few weeks later, we got our state-of-the-art automated backup system, and a rack full of fault-tolerant RAID disks.

Good: never waste a good crisis
Bad: heart rate and blood pressure

#7. Firing a key person in the team, and then quitting

At that same startup, I had to let go an important team member, knowing that I might resign myself a week later. Which I did, once I got the green light from my new employer.

Every so often, timing is everything.

Good: the company survived, of course, at least for a while
Bad: there’s little fun in dealing with ethical dilemmas

#6. Agreeing to get paid half in money, half in shares

In the mid-noughties, when I was a freelancer building speech-driven phone applications, I was called in to program the one and only Beavis & Butthead Hotline. The New York startup I was working for didn’t have a lot of cash, so I agreed to be paid in equity for half of my work.

No need to say that this assignment was by far the funniest thing I’ve ever worked on. But also the least well paid.

Oh, never mind!

Good: It was damned COOL heh hehheh heheheheh heh heh
Bad: I never met Beavis & Butthead in person

So, what else did I suck at?

#5. Telling political jokes to foreign co-workers

Over lunch at work, I once jokingly made a comment to a French project partner about “Hirochirac” — the nickname given to the then French president Jacques Chirac. There was no laughter: apparemment, ce n’était pas très marrant.

Years later, when I should have known better, I wanted to display my knowledge about the Po Valley to Italian colleagues we were visiting. To do so, I innocently used the word Padania, which turned out to have acquired a strong political connotation. A few colleagues choked on their espressos and cappuccinos.

Don’t. Just don’t.

Good: Follow the international news
Bad: Discuss it with locals

#4. Not putting all contractual clauses on paper

When joining a Belgian company that had just been acquired by a very well funded Silicon Valley startup, I was promised a sizeable amount of stock options. Alas, I was gullible and naïve enough to settle for a gentleman’s agreement with the local boss.

One year later, the daughter company went bankrupt. Stock options were nowhere to be seen, of course.

Six years later, the mother company was sold to Microsoft for a bit less than a billion dollars. A small part of which could have been mine.

Since then, everything is on paper. Always.

Good: I could have made some decent money
Bad: I didn’t

#3. Agreeing to split an R&D team in R and D subteams

A couple of years ago, my boss wanted to make sure that the R&D team I was leading would spend enough time on innovative research, next to the more operational work of developing models. He wanted to achieve this by splitting the team in two virtual subteams, along these lines.

Intuitively, I knew this was a very bad idea: most R&D people — especially the ones with a PhD — prefer to see themselves as … researchers. Nevertheless, against my own will and intuition, I gave in and complied with my boss’ wish.

It didn’t take a day for the team to lose its internal coherence, and fall apart in two camps: the “winners” (researchers) and the “losers” (developers).

Next time: just say no.

Good: I had been loyal to the chief
Bad: I was squeezed as a middle manager

#2. Telling truth to CEO, bypassing local boss

The daughter company from item #4 was in dire straits, so the mother company CEO decided to cut his losses and pull the plug. Because I had —rightly so — lost all confidence in our boss to represent, let alone defend his local staff, I sent a mail directly to the CEO with my version of the truth, pleading for a reversal of his decision. To no avail, of course.

A few hours later, I got one of the most unpleasant phone calls in my life. A few weeks later, I was fired, together with a couple of other people. A few months later, everyone was fired.

That is, except for the local boss, who parked the exit funds meant for the turnaround of the daughter company in his personal Luxemburg holding. He lived happily ever after, I think. I never checked.

Good: Keep your self-respect by staying loyal to your own beliefs
Bad: Be prepared to take the bullet

#1. Send blame mail to team member for assumed lack of motivation, with whole team in Cc:

A project team member wrote to the team that she was unable to perform a certain task by a certain deadline, giving a reason that I deemed bogus. In a moment of weakness, anger and frustration, I sent a not-so-friendly reply mail, clearly singling her out. Three seconds after pushing the Send button, I fully realized how stupid I had been.

Written and oral apologies followed to the team member, her boss and the team. It took a couple of days to be on speaking terms again.

Good: I assumed responsibility and apologized
Bad: Everything else

Morale of the story

Next time you’re acting stupidly, know that you’re not alone. There’s quite some competition out there.