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Here is a slight variation on your question. Instead of the craziest thing I said to my boss ... here is the craziest thing one of my bosses once said to me.
I was a sales assistant at the time and my boss was late for a meeting with some prospective clients from another country.
She called me on the phone and asked me to take care of them until she came in, which was going to be a while.
They only had a short time to meet with us because they had some other appointments that same day, and she didn't want them to get upset, so she asked me to start giving them the pitch until she came in.
So, I accompanied them into the conference room and began speaking with them. When my boss came in she first whispered into my ear and asked me, "Who did you tell them was the salesperson, me or you?"
Luckily, I played it legit and I told them I was the assistant.
Anonymous
I'd been at my job – PR Specialist at marketing firm MSCO in Rye Brook, NY – for less than a year. Long enough to have a sense of my boss' (Mark Stevens, president and CEO) personality, but not long enough to feel 'secure' in my new job.
On this day our biggest client at the time was scheduled to ring the bell of the New York Stock Exchange. It was a big to-do and we were all a little nervous, excited and anxious as we (3 staffers and the clients) made our way through security.
The president of the client went through the security checkpoint and was buzzed for something innocuous in his pocket. I went through next without a hitch. My boss came through third and again the buzzer sounded.
Security asked Mark if he had emptied pockets, he responded yes. It was then that my foot made its way to my mouth. An involuntary response that I would have done anything at the moment to take back: "It must be your nipple rings." (Of course he doesn't have any – that I am aware of, anyway.)
It suddenly felt as if the entire floor of the Exchange had gone silent. All eyes were on me – the client, my boss, the security guard, my horrified co-workers.
After the longest "moment" of my life, Mark left out a guffaw, which actually helped to relive the tension of the day. No, I didn't get fired. In fact, ten years later, I am still associated with the company!
Suzan French
MSCO
Most of my career life, I have been my own boss, but the one time I decided to leave the modeling industry to get a Wall Street "9 to 5", it was disappointingly not lucrative enough as my $20,000-$40,000/month modeling income. I enjoyed being around mostly men since I think like one (total alpha female) and hated having to deal with annoying female models at go-sees all day. My boss at 100 Wall Street hired me because he liked how aggressive I was in general and knew I could help him with the sales department. I did ... But after weeks of checks that were somewhat pathetic, I walked in to his office and simply said "I am going back to modeling. My Armani suit costs more than I earned all week here. Sorry." and he laughed, appreciated the honesty, and said he totally understood, even noting that if he could make the kind of money I'm used to, he'd put on high heels and a dress every day too.
Stephanie Adams
(Playboy's Miss November 1992)
I called out a VP on Core Values – I held them up and made him see how he was breaking them – it was ballsy – but he got it. Then I told him to build our brand we had to be willing to fire people who broke them. And I expected him to live them as much as we did.
Cameron Herold
Founder
BackPocket COO
As I left San Diego with IBM Sales to move to Rochester MN with IBM New Product Marketing my manager and I went for lunch.
(A week before he became my manager, had hit on my wife at the branch office Christmas Party, to indicate just what a jerk he was.)
At the beginning of lunch, he was going to pay.
As we sat and drank more, I said I'd pay.
Then, as we got a bit more trashed, desert arrived.
I said, "Not having you as a boss means I'll be quitting smoking cigarettes."
I crushed the tobacco in my practically full pack of Merit's all over his banana cream pie.
We split the bill.
Took a year, but I did quit.
Michael W. Frishberg
I once had a boss at American Express. He felt that I was hard to manage. We had a meeting one day and he started to lose his temper. I told him that if I had this type of impact on him that it was his problem and not mine. I did think he was going to have a heart attack. I did keep my job, however it did not make it a pleasant experience for me.
Kathy McShane
Ladies Who Launch
I run marketing at a tech startup in NYC.
The absolute craziest thing I've said to my boss was in early August at my Q2 performance review.
We were discussing the potential of me launching a new software tool, and I was skeptical of it being successful given a well-matched competitor who had more traffic, a higher reputation, etc. While debating how we could make the product a 'win,' I remarked "You should just fire me and acquire [competitor redacted] if you want to crush it."
I ended up getting a raise in the form of a commission on the new product's sales. My Q3 performance review is this week and I'm hopeful for a decent bonus!
Ryan Kulp
I said, "I speak truth to power."
He thought it was funny. Continued to be un-helpful. I quit the job.
Weeks later he emailed me to apologize. I asked "Why now?" Said he was just going through his spam file and saw all of the emails I had sent him, which he hadn't seen … because he was (deliberately) sending all of my emails to his spam file!
Mindy
Years ago I was an assistant manager at a grocery store (Publix chain in south Florida). My boss was an avid golfer and he could not understand why I did not play golf like the rest of the assistants he had worked with.
One day he casually asked me what I did on my day off. For some reason I thought it was a good idea to tell him that I took an airboat out into the Everglades and went alligator wrestling. I thought his head was actually going to split open and an alien pop out. I had never seen the man so angry. With spit flying out his mouth and his face burning the deepest shade of red he screamed at me that 1. He did not believe me, 2. He would fire me if I ever said or did something so unprofessional again, 3. I had the choice of playing golf or sitting at home reading a book on my days off but to never tell him something so outrageous again.
I was sworn to secrecy about the matter, so naturally everyone in the store found out about it anyway. There were alligator wrestling drawings in the bathrooms, gator jokes and much more for the next several years.
Of course the pressure was on me now since this originated as nothing more than a smart ass remark. With great hesitation I actually headed to the everglades and gave the guy at the Indian village $300 to show me how to wrestle. He made me sign a waiver on a napkin. "I aint gonna sue nobody if I dun get bit" is what he wrote and what I signed.
I actually wrestled gators about 5 times that day and made sure I had plenty of footage and photos. I was scared beyond words grabbing that 8 foot gator by the jaws but in the end I started to enjoy it.
The legend of John the Alligator Wrestler lived on for years at the store and as legends often do the gators got bigger and bigger with each retelling.
What started out as a mindless comment had taken on a life of its own and this former grocery store assistant now occasionally makes his way back to the Everglades and his gator friends.
John Olson - CEO Graystone Industries
www.graystonecreations.com
I left the job within a month after this communication. But I left on good terms. Because, to my mind, the reason my boss said, "You are so difficult" was that I had outgrown the job and we were experiencing increasing conflict due to a clash of roles. This was the snarky return I offered (and later published):
Woman
I am so difficult -
the way a jar of honey is difficult.
All that sweetness
gets stuck under the rim, makes your hands shake
they have to work so hard.
(source: http://us2.forward-to-friend.com/forward/preview?u=9e5e4dd4731a9649c1dd1cf58&id=2a66afef44
My former boss and I are still on good terms – made better by the fact that I went off to become a CEO of a different endeavor.
L. L. Barkat CEO
T.S. Poetry Press
This story's so bizarre that it's now part of my stand-up act (I left banking five years ago to become a stand-up comedian). When I was a banker I interviewed for a job at the New York branch of an Israeli bank. At the end of the interview the woman asked what I thought of Israelis. I said "They're the only people more obnoxious than New Yorkers …" And I got the job. Worked there for thirteen years before leaving for the stage.
Shaun Eli
Stand-up Comedian & Executive Director of The Ivy League of Comedy
www.BrainChampagne.com
I said, "I really hate the bathrooms here, can you let me make them more female friendly?"
Margo Schlossberg
When I first got divorced, I took a job at a furniture store because I was afraid I couldn't make it with just my intuitive abilities. My first day on the job, I got intuitively that the store was going to go bankrupt and I happened to mumble it without knowing the OWNER of the store was right behind me. He asked me, "What did you say?" I told him that I was just thinking out loud and that the sales manager was driving sales people out of the store, and without good sales people, there was no business. This is another one of my predictions that came true. I only stayed a few months and the store closed (bankruptcy) the next year.
Terri Jay, Intuitive, Medium and Pet Psychic
I think there's a lot to the idea of taking a calculated risk with the tone used when talking to superiors.
When being interviewed for my job, we were negotiating my role and compensation with the CEO and Chairman. When the chairman said we could pick up the conversation the next day as he had to be on the road in 40 minutes, I pulled out a bottle of fine scotch I was saving to celebrate with afterwards and slammed it on the table. I said, "This is the world's best scotch. If we make a deal in 30 minutes, we get to drink it." 29 minutes later my contract was written on a small piece of paper. The effect of this has been long term, as it established a cooperative power dynamic, demonstrated confidence, and, I assume, some manner of salesmanship (which related to my possible role.) It also started off the "welcome aboard" dialog over some drinks, and that never hurts.
Ben Feibleman
I worked for a company for five years. The owner, my boss asked me to trim his nose hairs. I told him "Not on your life." He laughed and said he didn't think I'd go for it. His wife was standing in the next room and heard it. She laughed so hard that she had tears in her eyes.
Myrna Lou Goldbaum
I worked for an Event Company in Denver – and the woman who ran it was the "biggest bitch." She was so nasty and condescending. We worked in a small office, with no walls or cubicles. One day, I got really tired of it.
I stood up, looked her in the eye and told her she was the "nastiest person I had ever met and that she could kiss my ass as I walk out the door ... oh and good luck with your million dollar event next week."
Ashley K.
Client quite angry with me over not sharing some information (as I'd repeatedly indicated I would not do) with another, outside contractor.
After meeting, client – angry. Lack of unhappiness level regarding my refusal to "share" made abundantly clear.
My response was,
"Well, if you're angry now, then you're really not going to happy with what I have to say next, which is you own a part of this as I have always made clear I would not be sharing specific information."
Wasn't fired. Still my favorite client.
However, my style – which is "No hype public relations" doesn't always travel well.
To a potential client running for office, I demonstrated his campaign had zero social media, although he was paying for it. Pointed out on several occasions those hired were clearly not engaging, including when comments were made on Twitter, that fairly well Begged for a response.
At our third meeting (this time with the chief strategist, potential client said,
"You always give me negative information."
My response was, "I am giving you factual information, which you choose to view negatively, rather than change."
Things went south after I remarked he was paying men to perform a task they were not, while asking women with expertise in the field, to "volunteer."
So we weren't a good fit. However, I wasted three meetings and hours of research to demonstrate what wasn't happening with the campaign, before throwing in the towel.
Bonnie Russell
PersonalPublicRelations.com
I was in the management training program at a national pizza chain when I was 19. I received a phone call from my best friend stating that she made a surprise visit to my babysitter to check on my eight month old daughter. She found my baby girl to be in distress and wanted to take her out of there, but the babysitter wouldn't allow her to take the baby. My friend told me my daughter was lying in a crib screaming and crying with curdled milk in her bottle and a fully soaked diaper. It appeared as if she hadn't changed her diaper or her bottle all day. I told my boss I had an emergency situation so I would have to leave for an hour to pick up my daughter and give her to my best friend. It was a slow time of day, with more personnel on the clock than was necessary for that time of day, so it wouldn't be a problem. My boss told me I could not leave. I explained that I wasn't asking his permission, rather just informing him of the situation. He told me if I left I would be fired. I looked him square in his face and said, "I am leaving, I will be back, and I will resume working." He said, "What's more important ... your child or your job?" I called him an idiot to his face, left to handle this situation, and came back to work in under an hour. He never said a word to me about it. I was expecting backlash, but it never came. Someone must have explained to him while I was gone how he was wrong to say such a thing. I don't know what happened after I left, I just know I had a responsibility to my child, and the guts to stand up for my right to continue working.
Kristen Brown
www.TheBigM.net
The craziest thing I ever said to a boss (the program director at a St. Louis-based oldies radio station) is, "So I see that you are concentrating on the pimple on the ass of a great event." I was the promotions director for the station. He had scheduled a meeting with the general manager and sales manager to lambaste me in front of them because the warm-up band for our oldies concert had played two '50s era songs in their set. His anger was surprising because 1) we regularly played '50s and '60s music on the station, 2) he had not mentioned before the concert that the band should only play '60s music and, 3) most importantly, the concert had been a huge success with a record-breaking number of ecstatic concert-goers, as well as happy clients who were literally dancing on the tables during the warm-up band's set. When I responded with the bit about it being a pimple on the ass of a great event, the general manager and sales manager high-fived each other, reminisced about how much fun they had at the VIP party and told Dave (the program director) to stop picking on me.
Kathy Bernard
Getajobtips.com
Years ago when I worked as a Personnel Assistant to a Director with a PhD in Industrial Psychology, I closed the door to my boss' office and told her:
"As somebody who cares about you very much, I need to tell you that you are drinking a little too much during lunchtime and when you talk to clients on the telephone during the afternoon, they are beginning to notice. You might consider professional help. This conversation will remain between us."
Bettina Seidman
SEIDBET Associates
www.seidbet.com
I don't know if I would define this as crazy, but most probably would; I told a boss that was always very demeaning to everyone, during my exit interview, that he was "not a good man." I said this calmly and sincerely, and it was obvious he was extremely uncomfortable. I had never seen him uncomfortable as he was very cozy being blatantly rude and nasty, but he was out of his element with a calm and collective genuine criticism that was heartfelt.
A boss I had prior to that, who was very shady, once asked me, "DON'T YOU TRUST ME?" in the middle of a situation that seemed a little shady to me, and I answered him, "No."
It was after a these two bad bosses that I realized I really needed to be self-employed. I had other good bosses, but these two solidified my desire to never have to deal with a bad boss again.
Ronny C. Jetmore
Principal
www.jetmoreinsurancegroup.com
I didn't actually say something – I did something – he wasn't my boss just a higher-up colleague moron who was saying that the organization was run by "old fat white guys" - so I held up a mirror to him.
Tina
When I started a new job some years back my boss traveled a lot, so I had been at the company probably a week or two before we had time to sit down and discuss specific responsibilities. Ultimately we got together so I joined him in his office and sat at a small conference table while he walked in circles around me listing things he wanted me to do.
In the middle of his inventory of issues, he stopped and said "You don't mind if I swear, do you?" He caught me completely off guard because he had not just sworn, nor did he seem to swear gratuitously (or even at all) during team phone conferences or individual calls. As such, it took me a few seconds to respond, and as I considered the question, I thought if he's going to ask, maybe I should go ahead and say what bothers me, so I did: "No, I don't mind if you swear, but it really bothers me when people say 'Jesus Christ!' as a swear. I'd rather just hear you say f***-f***-f***."
Apparently HE was caught off guard because he stopped his laps around the table and stared at me. Just as I was thinking "Uh-oh ... too far?!", he burst out laughing, saying he understood as he was raised similarly. Whew.
(Though that was among the longest few seconds in my career!)
Andrea
In an e-mail after he tried to make me look bad to other persons I work with, I asked him if he was ignorant, stated the facts of the incident, which I have in writing and called him contradictory and hypocritical. He fired me. I pointed out his own contact that required he give me 90 days' notice to let me go and my last day was this past Sunday. It boils down to my getting fired not because of me not doing my job but because he can't handle anyone talking bad about him.
Scott
I forwarded a series of emails relating to the actions of my boss to him by mistake. I had intended to forward them to my brother, and with the subject line "My boss is a mega arsehole". I kept my job, we had a discussion about it later that day (he had to pick my bonus that day – and was fair), and by keeping a lid on it and not telling anyone else, he saved face, he didn't fire me probably because he knew what he had done was wrong and he didn't want that to go public either. I ended up leaving the company on my own a year later – he was still a mega arsehole!
Greg
Greg Becker
Founder GetGuidance.com
I said 'No' to my previous boss more than once. It's really scary, but if you have their trust and respect, it makes you better.
Julia
Z Group PR
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