I work at a small company of about 20 people. We have the owner/president, 2-3 managers (depending on how you look at it), and the rest of the people are employees. I'm one of the managers.

Each day we have a meeting to discuss what will happen during the day, but not everyone is there for each meeting, including the owner (my boss). Yesterday, while the owner wasn't there we had the meeting and I joked about him not using some daily tracking software that everyone is supposed to use, including him. It's typical to joke about everyone here. For example, there was an employee that had a few accidents at home and we joked that he needed a bubble suit.

Today, when we had the meeting my boss told me "I heard you have something to tell me from the meeting yesterday." I was confused and asked the room "Does anyone remember what it was?" He then said "I need to use the tracking software more?" I began chuckling because it was a joke, but he raised his voice and said "Do not ever disrespect me in front of the team again. I'm trying to make this company better. If you have a problem, you can talk to me directly." Even though I was in shock I said "Okay, I apologize."

The problem is that I think it's ironic that he thinks I disrespected him in front of everyone, but he did the same thing back to me. This is a small company, but I'm not sure who told him what I said yesterday. I'm not sure if they told him maliciously, meaning to get me in trouble or just as a joke that he took the wrong way.

My question:

This was embarrassing. I feel like my team looks down on me now. Would it be better to talk to my boss in private or just look for a new job?


I'd like to add that this tracking software I mentioned isn't very important overall to the business. It's not vital and most people don't use it very often. It's only purpose is so other employees can see where you are such as lunch or on a job site. When the software crashes there is a running joke around the office that goes along the lines of "oh no X software isn't working today, shut everything down!" I wouldn't have made a joke about my boss not using something more important such as an inventory system, especially if I actually had real criticism of him not using it.

  • 11
    Do you have any idea of how the owner came to hear about this in the first place? Someone told him and clearly either presented you in a dim light or at minimum left the door open for the boss to take what you describe as typically light banter as an attack. Also, working back through it, could what you meant as light have sounded darker than intended?
    – SemiGeek
    Commented Apr 12, 2019 at 16:52
  • 5
    Did your coworkers take it as a joke at first? If I was your coworker in that situation, and I saw this happen, I wouldn't be looking down on you. I'd be looking down on the boss for his behavior. Commented Apr 12, 2019 at 16:52
  • 1
    I think it depends on what's your goal. The answer will be different if you want to be sure that you keep your job, or feel comfortable. It's hard to tell whether the boss was misinformed and hurt, or took it personal and doesn't have distance.
    – luk32
    Commented Apr 12, 2019 at 19:07
  • Please review @SemiGeek's comment, they have a very important point. It's likely you have a saboteur/rat in your group that risked the wrath of your boss in order to rat on you. Keep your eyes out, maybe chat with your boss directly about who it was that brought the information to you and explain they may have presented the joke in a much darker light than you intended.
    – ldog
    Commented Jul 22, 2022 at 5:00

13 Answers 13


This was embarrassing. I feel like my team looks down on me now. Would it be better to talk to my boss in private or just look for a new job?

You have already publicly apologized but it wouldn't hurt to speak to your boss privately and apologize once again.

In the future, think twice before you decide to make jokes about or criticize your boss even if he is not present. It is obvious that someone will pass along that information to him and your boss seems to be sensitive about jokes/criticism.

  • 28
    Also, the idea that the boss owes you the same degree of respect an employee owes to him or her is impractical. It would be nice for everyone to be respectful, but companies are structured such that punching down is possible, and punching up is dangerous. And if an employee is disrespectful to the boss, it can easily come across as undermining them, which needs to be addressed. Being disrespectful, even unintentionally, really undoes a lot of the case that you, yourself are deserving of maximum respect.
    – Upper_Case
    Commented Apr 12, 2019 at 14:32
  • 38
    @Upper_Case respect is not a resource in limited supply, and leaders are supposed to lead. Managers should always treat their staff with respect - even when addressing problems or disciplining them. Commented Apr 12, 2019 at 15:01
  • 9
    ... especially if he is not present... Commented Apr 12, 2019 at 15:22
  • 76
    @Upper_Case I very, very, very strongly disagree with your comment, and I am quite frankly shocked that it’s received five upvotes. The boss owes you exactly as much respect as you owe him. The pecking order is not related to respect. If an employee is disrespectful to the boss, yes, that needs addressing; if the boss is disrespectful to an employee, that also needs addressing. Bosses can undermine employees just as much as the other way around. Everyone deserves respect in the workplace, not just those above you in the hierarchy. Commented Apr 12, 2019 at 15:36
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    @JanusBahsJacquet I'm not saying that disrespect is ever justified or desirable, but rather that an employee can't enforce respectful behavior in the same way that a boss can. That's why I used the word "impractical" rather than "appropriate". Some workplaces are flat, and some are hierarchical. In a hierarchical setting, undermining the hierarchy (through disrespect or any other means) is an additional harm beyond what disrespect already causes. And, in this case, the OP was already disrespectful towards the boss, which makes demanding respect from him problematic (though no less deserved).
    – Upper_Case
    Commented Apr 12, 2019 at 16:16

While I don't think your boss handled this in the best way - he certainly could (and should) have spoken with you privately rather than rebuking you in front of everyone else he does have legitimate cause to be annoyed with you. Bantering between employees is all well and good - but you have to be very careful with context. While I'm sure you didn't mean it maliciously your "joke" could easily come across as undermining/criticizing him over something explicitly work-related, this is not the same as ribbing an employee for their accident prone tendencies you're actually inferring that he's not doing a good job.

I'm not sure who told him what I said yesterday

It doesn't matter - if you say something in front of the team at large you have to work on the assumption that the boss may hear about it and that you aren't going to have any control of the context it gets relayed in.

This was embarrassing. I feel like my team looks down on me now. Would it be better to talk to my boss in private or just look for a new job?

Don't be a drama llama - as embarrassing as this felt for you it's hardly the end of the world. Move on with the work and it'll all blow over soon enough. If you want to say anything to your boss then perhaps approaching him privately and saying that you understand that what you did was inappropriate but that it wasn't malicious just an inappropriate joke. Obviously only do this if you genuinely believe this.

  • 4
    I think this answer hits the nail on the heal. You were joking but someone listening didn't hear a "joke" they heard "calling boss out for not following company process". Clearly he handled that situation poorly, but the correct response is to just be more mindful of how statements could be viewed - even clear jokes can be read as subtle criticisms. IMO a personal apology would go a long way to smoothing over any issues, and give a chance to reaffirm faith/support that the owner is being successful (assuming that's the truth and you have that relationship).
    – Vlad274
    Commented Apr 12, 2019 at 15:24
  • 3
    This is the correct answer. The only thing it's missing is a reference to the wholly incorrect "I think it's ironic that he thinks I disrespected him in front of everyone, but he did the same thing back to me" bit. One might disagree with the premise of the reprimand, but being reprimanded by the boss in front of the team is not at all analogous to taking the piss out of the boss in front of the team in the boss's absence.
    – Alex M
    Commented Apr 12, 2019 at 16:20
  • 4
    Don't be a drama llama - +1 :') I'm going to use that a lot from now on!
    – rkeet
    Commented Apr 16, 2019 at 10:05

Looking for a new job will not solve anything, as you will discover that the problem follows you.

The Problem

You attempted to bring about change by in others' behavior through an indirect method. In some cultures and/or workplaces this is acceptable.

You claim that you were joking, but did you actually want him to use the daily tracking software? Given that you say explicitly state in your question that everyone, including him, is "supposed" to use it, the answer is yes.

If others also prefer indirect communication, then those "jokes" are understood to be serious directives and so are followed. Everyone wins.

If others prefer direct communication, those jokes are ignored, and the desired change in behavior is not accomplished. In that case, the "joker" and the "jokee" lose. The "joker" loses because they were ineffective at achieving change. The "jokee" loses as others understood them to be criticized.

In this case, your boss understood you believed desired change in his behavior, and he does prefers direct communication. For him, you were giving conflicting information.

The solution

Given that you only told this "joke" to your subordinates, and yet your boss learned about it, that means at least one of your subordinates also understands that this is conflicting information and so understood your "joke" as a criticism of your boss's behavior.

As such, you have both a subordinate and a superior that prefers direct communication. This means your "joking" directives are not effective in your particular workplace.

I strongly suggest you refrain from making "jokes" when you actually desire change, otherwise this problem will repeat. Not just in this workplace, but in any future one with more than just a small handful employees.

Re-establish respect for yourself by taking responsibility

There is a difference between making a joke and saying something in a joking voice.

If someone claims something is a joke, that means they are not serious, and the contents of that joke should be ignored.

The bubble suit joke was clearly a joke, as you did not wish for that person to actually start wearing a bubble suit.

Given that you really wished your boss's behavior to be different, it is dishonest to claim what you said about him was a joke.

Do not hide behind calling your actions a "joke", you will only lose even more respect from your subordinates that prefer direct communication.

Apologize to your boss in private for how you communicated your desires. In addition, if you told any of your subordinates that "it was just a joke" then you need to retract that, apologize for being unclear, and re-iterate that you do wish everyone to use this tracking software.

Doing this will recover respect people have for you.

Update in response to Edit

Whether or not you actually wanted your boss to use the software in question doesn't really change the main point of my answer.

Someone in your company does want it used, else it wouldn't be a policy that it is "supposed" to be used. That person is either your boss, or it is someone whom your boss has empowered to make such policies.

As such, people will still be confused, as they cannot read your mind as to what is actually important, and they cannot know if you are actually saying to use it with your "jokes", or if you are just making an actual joke.

(And if you are just making a joke, that can be worse, as you are undermining your boss's authority, regarding the policy.)

In short, regardless of the usefulness of that software, you have learned that making jokes about an individual's compliance is not acceptable in your workplace, especially when that individual is your boss.

Your question involved your team looking down on you. Attempting to regain their respect by arguing that you didn't do anything wrong will only work by making your boss look unreasonable, thereby undermining him. Don't go that route.


  1. Apologize to your boss, explaining that you understand you were unclear in communicating directives (in this case, you didn't realize you were communicating a directive), and that it won't happen again.

  2. Make sure it doesn't happen again.

  • 5
    +1 because I strongly believe you spotted the problem, and this is precisely the kind of answer OP was looking for
    – Eugenio
    Commented Apr 12, 2019 at 16:34
  • 4
    And, above all, a joke is supposed to be hilarious. Very good deconstruction, welcome to the site.
    – kubanczyk
    Commented Apr 12, 2019 at 17:11

Just keep you head down for a week - it will all be forgotten. It is just a bump in the road.

  • 14
    I take it you've never had a superior that held a grudge?
    – Tibos
    Commented Apr 12, 2019 at 17:24
  • 2
    I know from experience: if the boss is THAT kind of guy, you can keep your head anywhere you want for years, not days, and it will still be like day 1.
    – virolino
    Commented Apr 15, 2019 at 10:41

I have to disagree with the majority of the other answers here.

Your a manager so part of your job is pushing for positive change throughout the organization and encouraging your team to both suggest improvements to the way they work and to hold each other to account when implementing these ideas.

You choose to highlight the importance of this tracking software by poking fun of the fact that the owner hadn't used this software and it had led to a problem. He then responded by undermining you (and consequently your message) publicly.

Those who you manage who took this in the light-hearted manner in which is was intended could now question the importance of what you said and in the worse case may consider the response by the owner disproportionate and be put off from raising similar issues in the future.

Those who you manage who saw this as you undermining your boss, have now had that view reinforced and are less likely to respect you as a team player and could work against you in future.

Your boss is in a position where he can help you overcome both of these issues by reinforcing your point on the importance of tracking software and showing you are on the same side.

I would recommend that you could meet with the owner and request that he help you regain the respect of your team by reinforcing the point your were trying to make around the use of the tracking software.

  • "any criticism of senior staff will be met with anger rather than an open ear." by which you surely mean to say 'any criticism of senior staff that is made widely, to the entire team, in that senior staff member's absence,' since that's what happened here? Surely?
    – Alex M
    Commented Apr 12, 2019 at 16:22
  • I admit that was not well worded. The key point I was trying to make was the impact this reaction has on the posters ability to manage there staff. If the posters joke was taken seriously it does two things, 1. Acknowledged that senior management are not using this tool. and 2. highlights the importance of its use by everyone. If OP is meant to ensure their staff use this software is he not undermined massively when the owner reacts as if it is unimportant?
    – Ryan
    Commented Apr 12, 2019 at 16:32
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    I don't grant that the owner reacted as if the tracking software is unimportant. I don't think the situation as described by OP tells us anything about the software, or about the owner's thoughts about using it or not. It tells us 1) somebody in the meeting reported to the owner that OP was taking the piss when he wasn't there, and that 2) the owner really doesn't want OP taking the piss when he's not there. That's it.
    – Alex M
    Commented Apr 12, 2019 at 16:36
  • 1
    fair enough, I feel my key point - that the owners reaction hurts the ability of OP to manage his staff and that this warrants action beyond simply ignoring the issue as many others here suggest. I will edit my response now to focus more on this point.
    – Ryan
    Commented Apr 12, 2019 at 16:40
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    The main thrust about enlisting the owner as the OP's ally is awesome. I would take out any request for the owner to apologize, though-- very few people are capable of apologizing, and that could turn into an ego battle; if there is an apology from the owner, it would have to be purely the owner's idea, and not to be expected.
    – Don Hatch
    Commented Apr 12, 2019 at 17:32

I'm going to disagree with most of the answers here. Assuming this all went down the way you say it did, your boss seems like an immature asshole. Moreover, it's not really very smart for a leader to castigate and demoralize people like this. It's self-defeating to undermine the authority of the people you delegate your authority to. He's also set a very clear precedent of fear-based leadership which is unlikely to go well in the long-run.

You should really figure out how much you want/need to stay in this job. Yes, it was embarrassing for you but he should be even more embarrassed. If I were observing this, the main thing I would take away from it is that the boss is really thin-skinned, silly person who will damage his own organization over an insignificant slight that he only heard about from a 3rd-party.

If you think it's worth continuing working for this person, I would suggest having a private conversation where you say something along the lines of "I was surprised in the meeting the other day. I didn't think that my comment would cause offense. Can you help me understand why you handled it that way." Make it clear that you don't care that he knows you said it because you didn't mean any offense. This is an opportunity to find out what exactly he was told and maybe who told him. Don't get defensive or argumentative about it. You are there to be enlightened. If he sticks with the line that what you said was unacceptable, apologize and tell him you will make sure it doesn't happen again.

One caveat: if you really need the job and don't feel you have a relationship with your boss that allows for this kind of frank conversation, probably the best option is to lay low while you find your next job.


Move on; lesson learned (even though I am not thrilled with it).

The entire thing is embarrassing, but the conclusion was your director telling you, "if you have a problem, you can talk to me directly."

You have learned (1) he takes things a little more personally than you anticipated, (2) he has opened his office door if you do have a "real" problem, and (3) you have learned that people gossip in the office.

None should make you feel unhappy at your job; if they continue to do so, speak directly to your supervisor and explain you had no problem but it was banter and it will not happen again (this seems to be your take from it).

I'm sorry there wasn't levity, but you can't know a person's internal thoughts or even the morning they've just had, but don't let it keep you up at night: you've duly apologized. I imagine your coworkers (well, most) were just as surprised as you were.

  • "if you have a problem, you can talk to me directly." If that was the message, the owner should take the employee aside and lead by example by actually saying just that. Instead the owner engaged in a tit-for-tat, "oh yeah, I'll show you" approach. The message that was given is pretty clearly "I'm an insecure fool with bad leadership skills who is easily manipulated by gossips and tattle-tales"
    – JimmyJames
    Commented Apr 12, 2019 at 20:09
  • @JimmyJames - agreed, (in where I say I am not thrilled with my answer.) In the end, however, there is a person with insecurities who happens to be the direct supervisor unfortunately.
    – Mikey
    Commented Apr 12, 2019 at 20:12
  • It's worse than that, He's not just the supervisor; he's the owner. Unlikely to be going anywhere.
    – JimmyJames
    Commented Apr 12, 2019 at 20:19

Beware of adversaries.

You should have spoken to your boss directly about him not using the software. It looks like you've learned that, and that's good.

There is another issue at hand though. On your team there is an adversary to you, and this event has revealed his presence. I don't think he relayed your joke to the boss in the way you intended. You must identify the adversary and watch them very closely. Even now they spread distrust towards you throughout the company. Make no mistake they will not rest until they have usurped you.

  • 2
    +1 for your last paragraph. I concur.
    – Lumberjack
    Commented Apr 12, 2019 at 19:58

First of all, that is one lesson why the workplace is different from a club or a bar. Irrespective of the size of the organization, a workplace is a workplace, try to maintain the decorum of a professional environment. Cracking jokes, let alone targeted jokes (at someone), is not at all a professional attitude.

This was embarrassing. I feel like my team looks down on me now. Would it be better to talk to my boss in private or just look for a new job?

Learn from it, and move on. You already said sorry, no need to stir it up once again.

Let it go, this time.

Do not make jokes at workplace. Focus on your work and keep it professional.

  • Exactly correct in all details - as usual! :)
    – Fattie
    Commented Apr 12, 2019 at 14:29
  • Reason for donwvote? Tips to "improve"? Commented Apr 12, 2019 at 14:40
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    I downvoted because your conclusion (Do not make jokes at workplace) is very culture dependent. I've seen employees take the "the workplace is for work, not jokes" attitude at companies with more laid back/casual work environments let go due to "not fitting in with work culture". In other words, depending on the office culture and management's mentality towards that culture, this attitude can lose you your job. On the other hand, OP evidently mis-read the office culture here, and I'd agree as a rule of thumb that you should always strive to be more formal than you think the culture expects.
    – Mayube
    Commented Apr 12, 2019 at 15:36
  • @Skidsdev I wrote "do not make jokes", but never said, do not understand them. OP mentioned, " It's typical to joke about everyone here.", however, ended up in the position they are in now. So, it's evident, go with the flow, enjoy the show, but do stay away from committing something which can cause problems for you. YMMV. Commented Apr 12, 2019 at 15:44
  • 1
    Jokes are indeed culture and context dependent, and yes, making a joke at someone's expense is bad idea. However humor in the form of jokes is absolutely a legitimate and useful form of communication. It can help people bond and empathize with each other in a workplace. It has a place in professional environments and people who can exercise a sense of humor effectively are rewarded for that in many ways. But yeah, it has to be done right and with some nuance and sensitivity or else it will backfire badly.
    – teego1967
    Commented Apr 12, 2019 at 21:43

If he needs to use the software, tell him he needs to use the software. Don't pull punches because the punches were jokes or frustrating.

The thing to remember is that he probably has done everything he can to make the company better. You have to keep in mind that you don't know what sort of day he was having too. People fall off sometimes. You just gotta do what you can to help them out and work with them.

Talk to him about it later and open with something along the lines of, "Hey, about that tracking software joke yesterday...." Make sure that when you finish he understands that it was just a typical joke and he does actually really need to use the tracking software like everyone else. Also, apologize again for offending. You don't get a be rude free card simply because your observation is factually correct.


Every boss is afraid of being ignored. If he says something, he expects people to jump and not question him. If he loses the patina of he must be obeyed, then he's afraid people will ignore what he says and just go off and do what they feel like.

In most cases, if you talk with a boss privately, you can pretty much say whatever you want. You may change his mind on something, but in the end you have to do what he says. If you contradict him in a one-on-one meeting, you don't threaten his air of authority.

That may not be what's best for the rest of us, but that's the way it is.


Yesterday, while the owner wasn't there we had the meeting and I joked about him not using some daily tracking software that everyone is supposed to use, including him. It's typical to joke about everyone here. For example, there was an employee that had a few accidents at home and we joked that he needed a bubble suit.

You need to fine tune your sense of humor. These two instances are completely different for a multitude of reasons:

  • A bubble suit is obviously an exaggeration
  • It was not work related
  • I suppose the person was in the room. I can joke with colleagues but not about them without them present (or, if so, in a rather small circle)

I feel like my team looks down on me now.

No matter how chummy you are with your coworkers there is an infinitesimally small number of people that would willingly want to be publically associated with the person that upset the head honcho, period.

They are probably avoiding you to dissuade any notion of siding with you about the incident. You don't control their paycheck, the boss does, and anyone willing to jeopardize their source of income for you in this situation would be properly labeled a fool.

Company culture stems from the top and don't you ever forget it.

It sounds like a few days have passed since this incident so it would be wise for you to request audience with your boss and personally apologize in a meaningful way. Do not try to defend what you said; just admit that it was in bad taste.

The team looks down on you because they are mimicking the big boss. If the big boss stops looking down on you then you can expect everyone else to follow suit, eventually...

The situation doesn't sound morbidly unrecoverable so good luck to you.

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