At my office we have this culture where there's no such things like 'a wall between manager and staff' or 'strict, polite formalities between co-workers', but it doesn't mean there's no respect here.

One of my bosses sent me an email regarding my finished task and cc'ed an other manager and director (all higher-ups in my office). After a while things started getting funny and seemed to get 'out of bounds', because the bosses started to joke around. I (as a staff member) don't have any idea how to interact with them.

Should I join the email conversation or simply watch how things go and reply only when prompted to?

  • 11
    Your bosses should probably learn the difference between "reply" and "reply all". ;)
    – Zibbobz
    Commented Jun 10, 2015 at 16:28
  • 17
    I learned very quickly that there is often a do as I say not as I do culture in many work environments when it comes to bosses engaging in "fun time" in front of employees. Barring being invited to join in I would simply observe. Commented Jun 10, 2015 at 16:28
  • 3
    Depends completely on the content of the emails and where you are, the former of which you cannot share with us. So, ask a colleague instead. Commented Jun 10, 2015 at 20:41
  • @AndrewWhatever The Boss is always right.
    – user15729
    Commented Jun 10, 2015 at 21:53

4 Answers 4


If you are not comfortable participating, don't participate. You shouldn't be asking us because you are the one best placed to make the determination as to whether you are welcome to participate.

I take the view that my bosses are my bosses but they are also fellow professionals. I defer to and respect their rank on work-related and business-related matters - I voice strong dissent with what they ask me to do when I disagree but the deference and respect for rank remain solidly in place. Having said that, I would participate in the joking around if I know enough of the company culture and of the management that my participation is more than welcome. Otherwise, I abstain because my participation may have a chilling effect on their banter.

If you are so uncertain that you have to ask a bunch of strangers who have no knowledge of your company culture and who therefore have no way of giving you a definite answer, then the safest course for you is to abstain from participating.

  • 8
    Yeah, third paragraph really nails it here...
    – enderland
    Commented Jun 10, 2015 at 19:25
  • I'm not sure you'd get "a chilling effect" lol. Otherwise spot on yeah Commented Jun 10, 2015 at 20:46

As an employee I would not join the fun.

The email conversation started with work-related topics and it is probably done using company email addresses. To be safe, consider all usage of company resources to be business related, not private. This includes usage of the company email system, which normally is not allowed to be used for private conversation.

If your boss and other people higher up mix work and private topics (like exchanging funny stuff) and use company resources for that, it is their decision. Perhaps they will not get into any trouble doing this (being the boss helps here). But as an employee it is better to be safe than sorry.

  • 6
    If you feel like commenting, comment to your own boss only -- among other things, to gently remind him that this is still being copied to many others.
    – keshlam
    Commented Jun 10, 2015 at 13:54
  • 4
    @keshlam - only if you feel like getting in trouble with your boss. You are assuming that s/he needs to be treated like a child. And that s/he doesn't know how to use email. Not going to be received well.
    – Pat
    Commented Jun 11, 2015 at 1:13
  • 2
    No, I am assuming that the boss is as human as I am, and makes the same mistakes. Forgetting to trim reply-to lists is universal. It does no harm and causes no offense to say "hey, do you folks really still want us all tracking/participating in this discussion? If so I've got an amusing story of my own i'd like to toss in." The answer may be "sure, join the fun" or "oops, we should get back on topic" or "yeah, we should probably take it offline rather than cluttering everyone's mailbox" ... but it's not an unreasonable question to ask
    – keshlam
    Commented Jun 11, 2015 at 4:23
  • 2
    @keshlam Sure. Try that out some time. The bosses that I know - myself include - would not be appreciative.
    – Pat
    Commented Jun 11, 2015 at 6:58
  • Out experience differs drastically, so I guess it's a good thing we aren't working together.
    – keshlam
    Commented Jun 11, 2015 at 14:54

Nobody really benefits from email conversations without content, especially when everybody is CC:ing everybody. Before you know it you can't distinguish the serious mails from the clutter, and you spend your working hours cleaning up your mailbox.

Let it die down.

  • Most boringly correct answer here. +1
    – OJFord
    Commented Jun 10, 2015 at 23:15

Another way to look at this is to ask yourself,

"What benefit will I receive if my joke is well received?"

"What harm will I receive if my joke is poorly received?"

Now consider this,

Written "humor" is subject to being misunderstood.

Written "humor" in email can easily be forwarded to HR and lawyers. Remember the 'e' in email is e for evidence.

Save the jokes for your friends outside of the workplace.

  • 2
    What about "humour"? Commented Jun 10, 2015 at 20:46
  • 2
    @LightnessRacesinOrbit Depending on location, that might be even more subject to misunderstanding. :P
    – reirab
    Commented Jun 10, 2015 at 22:00

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