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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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 your 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.