There are two that tie for the worst:
#1. One of the tasks as a reservations manager at a Chicago hotel was to load sales contracts into the reservation system. This was back in the days of DOS, and it was a time-consuming process. The incoming contracts were kept in date-of-stay arrival order until loaded.
Unfortunately, a city-wide event was announced for a date almost a year away, so it was placed near the bottom of the pile. One of the sales reps booked a large block of rooms. By the time I got to that contract, most of the room inventory had already been booked. I was sick about it, and immediately went to the general manager and director of sales.
Fortunately, both were experienced and level-headed. The team brain-stormed on how to resolve the problem as quickly as possible. We got it rectified within a few weeks, but it took a tremendous amount of effort as well as a good dose of figurative self-flagellation from me.
The only positive aspect of this situation was working together with a plan so that it never occurred again. And it didn’t.
#2. When the company was sold almost a decade a go, a new president was brought in. He hired an outside company to do a thorough study on was was working, what wasn’t etc. Frankly, it was desperately needed.
The final result was that the dept. I worked for would probably keep the same amount of people, but be restructured. I would have stayed and taken a demotion, but a life-style change resulted in my accepting the severance package instead.
A co-worker and friend outside of work was informed that his dept. was to be eliminated. Since he had worked in my dept. before, he had a wife and two young children to support, and that I trusted him, I asked to meet with him. With the promise he would keep it a secret until officially announced, I gave him a heads-up on the opportunity.
A few days later, one of my direct reports came to me to ask if the rumor was true. My friend had told his direct report about the job opening in case he was interested. That guy ran into my employee over the weekend and asked her about it. I wasn’t about to lie to her; she was asked to keep it under wraps. Of course, the word got out quickly.
I had already told my supervisor what transpired. Her response was, “When a secret is shared with another, it is no longer a secret.” It was a valid life lesson.
It worked out alright during the few months I was asked to stay on. I just felt really bad for the four people who reported to me. Their jobs were secure and were ready to move to move on to reporting for their new supervisor (my boss, who accepted a demotion). Who wouldn’t?
While it sorted itself out, as it usually does, the frustration those employees went through wasn’t worth the risk in the name of an attempt to help out a friend.