10 Most Cringe-Worthy Career Mistakes

If you’re like most people, you’ve had some truly cringe-worthy moments in your career, where you did something so clueless or embarrassing that you still shudder when you think about it today. I recently asked readers to share their most embarrassing career mistakes, and here are the top 10 they shared.

1. Asked the boss for his salary

In my previous career in advertising, I asked my boss how much he made while our whole department was out at a social gathering. Everyone stopped talking and stared at me, and I didn’t realize till then that it was a major faux pas. My boss just said, “We don’t talk about that.”

2. Beanbags and puppies

I was interviewing for a job at a small publishing house. I was still in college and had never had an interview beyond “Can you wait tables? Good. You’re hired.”  The interviewer asked me what kind of office environment I preferred to work in. I said something like “Oh…my dream office environment would have bean bags instead of chairs, lap desks that we could use on the floor, and office dogs to play with.” I remember there was a silence, and then the rest of the interview moved surprisingly quickly. It was on the way home that I realized that my idea of “office environment” probably wasn’t what they were looking for. D’oh.

3. Name confusion

I had a coworker named Joaquin. At the time, I spoke zero Spanish, and didn’t know how to pronounce it. I didn’t make the connection when other co-workers talked about “Wakeen.” For months, I honestly thought I had two different co-workers, Joaquin (pronounced JOE-a-kwin) and Wakeen. In my head, I assigned them different personalities and areas of responsibility and everything. I sent emails saying, “We should get Wakeen to look into this” and talked about what Joe-a-kwin had been working on, and no one said anything, including poor Joaquin. I wanted to die when I finally put it together.

4. Mistimed flatulence

I was only in my job for about a year when I had to present a marketing plan to all my colleagues in my department. Near the end of the presentation, I was cruising along when someone made a joke and we all laughed.
 Then I farted. And everyone started to laugh as if I would laugh it off, but I didn’t. I just pretended it was my shoe squeaking. Then came the red face, the stammering speech, the rush to finish things and the long, awkward silence for the rest of the presentation.

5. Locked in the office

One day, a coworker came into my office, told a dramatic story, slammed the door to illustrate some point in the story…and apparently slammed it so hard it broke the lock and we couldn’t get out. I was due to present an important report to my boss but I was too embarrassed to confess to her that I was locked in my office, so we spent a good half an hour trying to figure it out from the inside, and then called building security, who basically had to take the lock apart from the outside. When my boss finally came by to find out where the report, my coworker, and I were, the whole thing was revealed.

Fortunately, she thought it was hilarious, but did say several times, “Um, you could have just called me and we probably would have gotten you out of there sooner.”

6. Outsourcing your own job

My boss had asked me to do some follow-up phone calls, inviting donors to a gala for a client of ours. I felt awkward making these phone calls, and after a few, I was over it. I asked my friend (who had recently lost her job) if she wanted to make the calls, pretending to be me. I offered to pay her and take her out to dinner. I headed to the pool and took a secret day off.

She called one donor who was actually a close family friend of mine. I didn’t realize he was on the list. They small talked for about five minutes, him thinking it was me. When my friend eventually ask if he and his wife could come to the gala, he got confused – his wife had recently passed away. I even went to the funeral! My friend acted as if she just found out, saying she was so sorry to hear about his loss. I was absolutely mortified when she filled me in later.

7. Slightly too comfortable

I was fresh out of college and was unbelievably green. I had to moved to San Francisco and was hunting for a job. I interviewed with an incredibly cool advertising agency for an admin position. They loved me and invited me back for a second interview to meet the whole office. I showed up in the early 90′s version of skinny jeans tucked into soft-sided “slouch” cowboy boots, chewing gum, and put my feet up on the conference table. (Gads, I’m cringing just remembering it).

8. “Any great ideas?”

At my first job after college, I knew nothing but was full of enthusiasm. I attended a meeting where the sales team spoke in a slew of acronyms and things I didn’t understand, but I was too shy to ask anyone for clarification. The CEO then stops me in the break room after the meeting, and asked, “Get some great ideas at the meeting?” and I responded with an enthusiastic “Yes!” As he waited for me to elaborate on what those ideas actually were, I froze. The voice in my head kept saying “say SOMETHING” but I couldn’t think of a thing. He waited a few minutes, then sighed and shuffled out of the break room. I ran into him a few years later, after I’d long left that job, and he said “Hey, E.R., have any ideas from that meeting?!” Yes, it really was as bad as I had remembered.

9. Several extra zeros

At my very first job, I had to put in an order for color/glossy/laminated/everything-you-can-think-of copies at a copy store. My manager asked for 300 — I ordered 30,000. And I didn’t realize the error until I went into the store to pick up and the person handed me several boxes filled with paper. And then the bill confirmed it.

Resigned to my fate, I paid with my own debit card and severely overdrew my account. I took all the boxes to a nearby alleyway and then had a complete breakdown, where I called my mom and begged her to help me cover for some of the cost. Thankfully, she did (though I had to pay her back over time, obviously) and I dumped all but 300 of the papers in the dumpster. Wiped off my face, pulled myself together, and went back into the store – where I asked if there was anyway we could separate out 300 of the orders on a new receipt for “expense purposes.” Ultimately, my boss was never the wiser. But wow, do I still get paranoid about quantities.

10. Wrong answer

I was in my early 20′s and working with a placement agency to find that perfect job that would take me out of food service. My agency contact had set up an interview for me for my dream job, the day after my birthday. Being young and not much of a responsible drinker, I partied like it was 1999. I showed up at the interview not just hung over but still drunk. The person conducting the interview asked me if I was sick, and if I was we could reschedule. I answered, “Nope, not sick, drunk.”

I did mention that I had gone out for my birthday the night before and rambled about how great my party was.
I was not hired. My placement agency stopped returning my calls and I do believe that the other agencies in town also had me on their do-not-deal-with list.
I burned a lot of bridges that day.

Do any of these mistakes remind you of ones you’ve made over the years?

Alison Green

Alison Green writes the popular Ask a Manager blog where she dispenses advice on career, job search, and management issues. She's also the co-author of Managing to Change the World: The Nonprofit Manager's Guide to Getting Results and former chief of staff of a successful nonprofit organization, where she oversaw day-to-day staff management, hiring, firing, and employee development.

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  • Anne

    Hilarious list. :)

    In the introduction, though, I think you mean “shudder”, not “shutter”. :)


  • Wren

    “If you’re like most people, you’ve had some truly cringe-worthy moments in your career, where you did something so clueless or embarrassing that you still shutter when you think about it today.” The word is SHUDDER. Shutters go on windows.


    Alison Green - Ask a Manager Reply:

    A cringe-worthy mistake in itself! Fixed :)


  • Bethany

    In my first fresh-out-of college job, I had a great, female manager. She was a mentor and someone I felt close to. I woke up one morning feeling a little ill, and made an early morning appointment with my doctor. I let my manger know I was sick, but had a doctor visit scheduled. After the doctor confirmed my suspicions, I went into work, arriving around 10am. I think she was surprised to see me in so early, and she sent me an email to see if I was feeling ok. I didn’t want her to think I was playing hooky, so I replied with “Yes, I’m feeling much better, just a UTI!”. As soon as I hit send, I immediately regretted it. I still cringe when thinking about this today, a simple “yes, I got a prescription and am on the mend” would have sufficed.


  • The Other Dawn

    Wow, these are funny! And I’m embarrassed for these people. I’ve definitely made a couple cringe-worthy mistakes myself though.


  • Lindsay

    I just pulled a number 10 today. I was supposed to meet my boss and a coworker at 7AM today, to travel to a site for training. I stayed up very late last night partying, and wound up blacking out at the end of the night and didn’t set an alarm.

    I woke up 30 minutes after I was supposed to be there with two text messages (one from boss and one from coworker) asking if I was there yet. I throw on my uniform and call and ask what I should do – get told that I’m too late and should stay home. Then I text my boss an apology which includes the information that I was blackout drunk.

    I don’t want to go to work tomorrow.


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  • Shinosha

    Your idea of an office environment sounds pretty cool.


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