SURVEY SAYS – What's Your Most Awkward Boss Discussion?

October 2, 2009 ( - I was struck by the recent CareerBuilder survey on awkward workplace moments.

I was particularly intrigued by the differences in circumstances when people said they would bring something to the attention of a coworker, but perhaps not their boss (see  Awkward Workplace Disclosures ).

This week I asked readers to share the most awkward thing they had ever had to tell your boss about his/her personal behavior/appearance.

“Laugh” Tracked

Now, there is no real way to effectively tabulate these – so, you just enjoy them as they were submitted – but these three made me laugh:

I still have not told him he eats with his mouth open. I am also surprised nothing has fallen back out given how large the opening is.


Last year, during a Benefits Committee meeting, I was sitting next to my boss’s boss. Halfway through the meeting I noticed we were both drinking from the same bottle of water. I whispered to her, “Stop drinking the water.” She had to ask why, and I had to tell her. She laughed and announced it to the entire room. I was embarrassed. However, at the end of the meeting I stood up and let those in attendance know that since she and I had drank from the same bottle, I was going to leave so I could get a tetanus shot just to be safe. I try not to sit next to her anymore.


Our receptionist has many tasks that take her away from the front desk. We leave a bell on the desk so guests or delivery people do not need to yell for help or stand around waiting. The finance staff are closest to the reception area so they usually assist any visitors when the receptionist is absent. Our President developed a habit of ringing the bell every time he walked past — usually on his way to/from the restroom. It was driving the finance staff crazy. Several of them were always getting up to check and when they reached the reception area either no one was there and/or the receptionist was busily working and mentioned the President had rung the bell. This was getting quite disruptive, so I finally needed to tell him to control his impulse to hit the bell every time he walked by. He is the kind of guy one normally does not want to criticize, but he took it well and has stopped ringing the bell.

Not that these weren't also interesting:

  • Wear a bra
  • Boss 1 - that we knew about his "relationship" with his very much younger secretary, who also complained, and the baby and that he was no longer employed. Boss 2 - that smoking in his office was illegal. He didn't care, so he put in a very expensive vent system we couldn't afford which didn't work, so we called the authorities and told him we did. He didn't care. So his personal fine was pretty high... we didn't care.
  • Just the normal stuff - spinach in teeth, flys down, toilet paper on shoe, skirt stuffed in top of stockings, etc.
  • His polo shirt was on wrong side out
  • My boss was always late for meetings with people, her staff as well as others. Sometimes she didn't even show up at all if she get held up in another meeting. Apart from those of us who worked for her thinking this was rude and that she didn't value our time, I started hearing other people saying the same thing.
  • So I finally got up my courage and told her the reputation that she was getting - that she thought her time was more important than other people's time, and that people perceived this as being very rude.
  • While she knew that she often ran late, she had no idea how this was perceived, and really made an effort to better manage her calendar and time.
  • My boss came into the office in a blazer that smelled incredibly musty from hanging in a damp closet. I knew he had a meeting with a client in a few hours, and there was no way he could sit in a meeting with someone the way the jacket smelled, the odor could be smelled from across the room. Surprisingly, he was grateful and we fixed the problem with some Fabreze and fresh air.
  • I have always figured that I'd rather tell someone they had toilet paper stuck on the bottom of their shoe or dragging from under their skirt than let them walk around that way, so haven't found that too awkward. I have had a situation where I told someone else's boss that she had mustard on the end of her nose... just before the board meeting (of which I was a member) at 4:00 in the afternoon. Much to her chagrin, she had had a hotdog at lunch and had been in several meetings since then during which time no one had bothered to tell her that they had stared at her mustard nose the entire time!
  • As head of HR, I had to talk to him about anger management and the professional expectations of a C- level exec. Not fun, but he has only slipped up twice since that conversation. I would rather have had the zipper or bad breath conversation!
  • Are you kidding. Once my boss was loudly complaining she didn't understand something I wrote; I asked her to close my door for privacy and she started stuttering, she was so surprised. I'm not telling her anything else.
  • I have had only one boss that I felt someone needed to offer advice about his behavior. Only one person in the office could talk to him and not have fear of repercussions. When he really got out of hand, we would go to her and she would take him to lunch and unload on him. They had worked together for years and she could get away with it. He would calm down for a few months after their talk but always reverted to past behavior. He had no tact in dealing with others and would tear you down without focusing on the issue and how to handle it better next time. He was eventually asked to leave the company because no one wanted to work with him.
  • I have had to tell my former boss to go in her office and shut her door and not answer her phone. She came back from a business lunch having had one too many "crystal yumyums" (martinis) and was pretty much incapable of doing anything more than sleeping! Oh, for the good old days of 2 (and more) cocktail business lunches when it was still (politically) correct and expected to have them! (And we had not yet heard the term "politically correct!)
  • Telling my boss that I didn't care to know why she preferred a specific type of underwear and that I really didn't care where and when she bought them. She must have been really proud because she later informed another employee of her preferences.
  • One of my bosses wore a perfume that I was extremely allergic to. The perfume triggered an allergy migraine. She would put so much of this scent on, that I mused that she must have used a bottle per week. I could deal with the scent in most circumstances, but our department's weekly meeting in a small conference was a challenge. I took to dosing myself with allergy meds pre-meeting and sitting as far away from her in the meetings. This was a workable procedure and kept the migraines to a minimum. One week a new employee was sitting in my usual space when I went to the meeting. My boss was already there. I had to oust the new guy from "my seat" by politely explaining that I was severely allergic to our boss's perfume and that I sat in this particular seat to minimize the migraines that the perfume gave me. I'm sure she heard my comments. I seemed to notice that after that meeting that the dose of perfume that she dove into on a daily basis was smaller and less wafting.
  • I had to tell my boss to quit passing her terminating clients to me.
  • Something hanging out of her nose...I tried to discreetly hand her a tissue, but she didn't know why I was doing it (we were in a meeting where she and I were presenting)
  • That he had something hanging out of his nose!!
  • After spending the first part of the morning looking and wondering ... I finally mentioned that he had on two different shoes: one brown tie shoe and one black loafer. I thought the awkwardness of that moment would mitigate the same in a client facing moment.
  • My boss would charge into my office. pass my desk and come right up close to me when he needs something and even sometimes told me to do certain things against to rules but he refuses to put anthing in writing. Needless to say, he was not happy when I told him to back off and authorize exceptions in writing. I think it will come back to bite me later.
  • He walks into work right by his secretary and on some days doesn't even speak to her. I'm used to it since he is all the way next door in the next office, but she sits right outside his door. I told him he needs to be more considerate of others and at least "speak"
  • In a mostly smoke free environment it was "suggested" by HR that I tell him he is not allowed to smoke while camped out in the "JOHN".Some one unknown had ratted on him to HR. Wed, Sep 30, 2009 4:14 PM Find...
  • I've never been in a position to need to tell a boss of mine something like this before. I can't wait to read others' stories, though. (However, my boss pointed out to me once that she had gotten dressed in the dark, not wanting to wake her sleeping husband, and inadvertently put on two different shoes. She spent most of the day hiding in her cubicle so no one would notice.)
  • I had to tell my boss that he had offended me with a comment he made. It was not the message, but the delivery that was offensive.
  • A former boss had the practice of sitting down on my desk to talk with me. It wouldn't have been so offensive if she would clear a space. However, she just sat on whatever project that I was working on! She continued this practice even after I spoke with her. Even our staff attorney called the behavior to her attention without success. I decided she didn't think enough of my work and finally left!
  • I had a female boss who had small children and was always a wreck by the time she arrived. Finally one day I had to say something about the food stains on her clothes and the hem that was hanging on her dress. She acted horrified, but continued to wear the same outfit for months and never took it to the cleaners! Or any of her other food stained clothes! And this was a formal business environment. Ew.
  • My boss was going into an important meeting when I noticed a significantly long nose hair sticking out of his nose that I thought would be embarrassing for him - at least it was for me. So I held up a mirror in front of his face and then pointed at my own nose - that's how I told him. He seemed appreciative.
  • Guess I'm lucky and haven't had it happen. The closest to that would be interviewing someone who's fly was open. I didn't comment on it, because I didn't want to add additional stress. We hired him, and he's now corporate vice president, but he still doesn't know about his transgression.
  • Well, I haven't actually had the courage to tell her (she doesn't take criticism well)...but what I'd LIKE to say is that her angry outbursts over relatively trivial things make the entire department uneasy. Some things just aren't worth getting so worked up over.
  • I told a boss once that she sounded "shrill" whenever she talked with someone...that basically, no matter what she was saying, it sounded like she was berating us. She appropriately responded in the shrill voice, "What do you mean!!!???" Point was proven, but she still didn't get it.
  • In a key meeting I noticed that the tail of his shirt was sticking out of the zipper of his pants just as we started to enter the conference room. At the same time I told him my binder of papers slipped and papers went all over the floor. This distraction allowed him to step back outside the door and make the necessary adjustments.
  • A former department head used to unbuckle his belt and loosen his pants after lunch, making it a bit awkward to pop into his office. Even worse, when he thought the staff had gone for the day (although many of us were working away at our desks long past 5:00), he would remove his socks and clip his toenails! But the ultimate was that he would often "cut the cheese", not realizing we could ALL hear him!!p.s. - nobody told him, but we really got some good laughs out of it.
  • A female director was wearing a decent, but close to being low-cut blouse during an informal meeting in her office. In and of itself, the blouse was not a problem. She was leaning forward and gesturing with her hands during our conversation, and one of her buttons got caught on her desk drawer and the blouse came open and completely off of her right bosom, completely exposing half of her colorful, leopard-print brassiere. She did not notice it and continued talking for about 20 - 30 seconds. Myself and others in the room were speechless, as we were trying to maintain eye contact and decorum while she finished her sentence. It appeared that no one else was going to tell her, so I calmly pointed to her chest and said, " I think you need to fix your blouse before we continue this conversation." Needless to say, she was quite embarrassed and she left the room in a hurry. She did not reconvene the meeting until the next day!
  • I had a boss once that was as rude as ever. One night while out partying at a local night club, here he came up to my table of friends and acted like he was my best friend. I confronted him the next day and told him to NEVER do that again. Proceeded to call him two-faced. I was very young but haven't forgotten I had done that.
  • I had to tell the owner that if he did what he did again I would personally report him to the EEOC. I was quite surprised but I kept my job.

Thanks to EVERYONE who participated in this week's bonus survey!