Employee cancels supervisor's hotel reservation on business conference to Hawaii after supervisor uses his rank to secure a spot on the trip: ‘He had to stay at a motel’

Author image for Bar Mor Hazut
Bar Mor Hazut • Senior Editor
Jan 3, 2026 4:00 PM EST

How would you react if a manager in your workplace, whom you generally cannot stand, decided to join you on your annual business trip to Hawaii?

Technically speaking, it's clear that if a supervisor who outranks you in everything, like the one in the story below, decides to tag along to a business conference, there's not much you can do to stop him. That doesn't make the experience less annoying, though, especially if he joins by taking the place of a coworker you actually wanted as your companion.

Most people would have accepted their fate and readied themselves for a week in Hawaii with a supervisor they cannot stand. That is not what happened with the employee who wrote the story below. No, they found out that their supervisor had pulled rank to take someone else's place in the conference, and they decided to ensure that the supervisor regretted it.

How did they pull that off, you ask?

Well, it started when they called the airline to change Tom, the supervisor's, flight to a different date. When Tom got to the airport, the only way he could board the original flight was by agreeing to an economy seat in the middle of a 5-seat row, instead of his original Business Class seat. Already an annoying start to the trip for Tom.

Then, when Tom arrived at the Hawaiian resort, he discovered that his reservation had also been cancelled, and we think you can guess who was behind that little trick. Tom was then forced to take a room at a motel 10 minutes away from the conference, and the employee got to have some distance from his entitled supervisor during the week-long trip.

Next time, Tom might think twice about shoving his nose into events that are none of his business, or else the employee might have a few more tricks up their sleeve…

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  • Hawaiian Resort

    I worked at a company for almost 15 years, in the 90s and early 2000s. Toward the end of my time there, we hired a supervisor.
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  • Business Professionals Walking in Modern Architecture
    via Aflo Images

    Image is representative only and does not depict the actual subjects of the story.

  • I didn't report to him, but he would read documents on my desk when I wasn't there, and would sometimes make copies of my product and give it to his subordinates, telling them to modify it to fit what they were working on.
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  • To be honest I didn't care, since we all worked for the same company, but it was the sneakiness, and doing it behind my back that irritated me.
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  • He was also an obnoxious person, blowing his own horn and basking in the success of his "guys" way too much.
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  • He was not well- liked. A coworker (Bert) and I had been attending a conference in Hawaii every year.
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  • We were good friends and hung out together with others from the conference that we met once a year.
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  • It was a reward for doing our jobs. The conference was at a resort hotel in Waikiki Beach, but the rooms were limited, and would be sold out by the time the conference began.
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  • If you didn't make your reservations in advance, you'd have to stay somewhere else. Tom, the supervisor, saw the travel authorization form on my desk that I had to submit for the conference, and then filled one out for himself to go.
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  • He was told that there was only funding to send two people, so he went up the management chain to get approval for himself.
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  • Because he out ranked me and my coworker, one of us had to withdraw our paperwork to ao.
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  • We literally flipped a coin, and I won. I travelled frequently, and had accumulated lots of frequent flyer miles.
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  • Because the flight time was over a certain number of hours, from the east coast to Honolulu, we were authorized to travel in Business Class, a huge benefit.
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  • I did not want to sit next to Tom, so I used miles to upgrade from Business Class to First Class.
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  • I did not tell Tom about my upgrade. Our travel agent was able to get reservations for both of us at the resort hotel.
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  • Tom, being Tom, let everyone in the office know that he was going to Hawaii, bragging about flying in Business Class, and staying at a "Hawaiian Resort".
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  • He also told me that I was expected to introduce him to the conference regulars, take him to the best restaurants, and show him a good time.
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  • It got to be too much, and I intended to avoid him as much as possible while we were there.
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  • businessman in a hotel room
    via GeorgeRudy

    Image is representative only and does not depict the actual subjects of the story.

  • We were flying out on Sunday, and flying back on an overnight flight the next Saturday.
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  • Saturday afternoon I called to confirm my airline reservation, something I had learned to do over my years of frequent travel.
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  • Asking about seats, I was told that there were no Business Class or First Class seats available, but Coach still had some.
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  • That got me thinking. I called from a pay phone later that day and changed Tom's reservation to a Business Class flight on Monday, I then called the hotel and cancelled his room.
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  • I checked in at the airport Sunday morning and then went to the First Class lounge to wait for my flight to be called.
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  • When the announcement came over the loud speakers, I grabbed my stuff and went to the gate.
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  • They were boarding the First Class passengers as I arrived there, so I got on the plane, found my seat, and ordered a drink.
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  • When most of the plane was boarded, Tom came through the Jetway looking furious. Seeing me, he stopped and started ranting about the airline fucking up his reservation.
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  • The flight attendant quickly told him that he needed to be seated. He asked her if there were any empty seat other than Coach, and she apologized, but the premier cabins were full.
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  • Twice during the flight, he came up to my seat to complain some more. The agent at the counter was able to change his ticket to this flight, but could only get him a seat in Coach.
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  • He was assigned the middle seat in a center row of five seats, and couldn't get comfortable.
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  • He ranted on, even asking if I would switch with him for the last half of the flight.
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  • I politely declined, and didn't see him again until we were at the luggage carousel to get our bags.
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  • We took the courtesy shuttle to the hotel, and waited in line to check in. He was at the check in next to me when he learned that he had no reservation at the sold out "Hawaiian Resort".
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  • He went ballistic. A manager was summoned, and took him to another computer station about 20 feet away.
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  • I didn't stick around, and went up to my room. My room phone rang about 15 minutes later, and it was Tom, pitching a fit.
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  • He told me that he needed to share my room with me, since it was where the conference was.
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  • He complained that the manager was only able to secure a room for him at a motel, about a ten-minute walk away.
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  • Although I had two Queen Sized beds, I told him my room only had one bed.
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  • I didn't mention the balcony with the ocean view or the separate living room area. I saw Tom during all of the sessions.
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  • I took pity on him and he hung out with me at the cocktail social after the first day of sessions, and tagged along with me and my companions for dinner.
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  • We flew back Saturday evening, and since he was in Business Class, he didn't come up to complain.
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  • I did confess to Bert at lunch a few days after returning, and he said it kinda made up for not being able to travel with me.
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  • We fully believe it's really brave to teach someone who outranks you at work a lesson, and we love how this employee was able to pull that off.

    Could you ever do something like that as revenge for a misjustice at work? Scroll down to the comments and let us know your thoughts!

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boss employee hotel manager job tales-from-the-workplace business trip hotel room supervisor overworked-employees workplace company
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