Do you give your boss a holiday gift?

I work for a large company and technically have a number of bosses. Pre-covid, we used to get the boss solely over our team a gift, but he also usually got us something as well.
 
The department that I am in currently we just did a "Secret Santa" thing... supervisors were also included. That's perfectly fine with me.

In my old department, they would shake us down to all "chip in" for a Christmas gift for the boss. I grudgingly donated every Christmas until we got a boss that I absolutely loathed. I just told the little minion that was collecting NO WAY.

I remember when I was a teacher, they would have some little minion running around collecting for the principal. That always griped me because the school got us NOTHING and the principals always made a lot more than us, and they expected us to cough up like $20 for the "good of the cause". One year I finally had enough of it (and I really did not care for that principal), I printed one of those George Costanza things that said "A donation in your name has been made to the Human Fund" and gave it to that little minion who was collecting. She was like, I'm gonna tell him you did this", I was like OK cool. :rotfl2:
 

I have in the past given my boss a small gift. It is usually a card with candy or one of my homemade ornaments. Now that I work fully remote and live on the other side of the country from my boss, I do not give anything. I don't even have her actual address to send something so that complicates it a bit. I did get a cute desk calendar from her last week (although it came via amazon with no note or name - found out during a team meeting - I was not the only one trying to figure out that mystery).
 
There was a situation at my work a number of years ago where people started chipping in for a gift for the team lead. It was not much money, but some people felt uncomfortable, especially as the team leads received large stipends. Several years later HR said that we were not to do this.
 
I was part of the management team for many years. Some of those years I had people who directly reported to me, others I did not. I never gave my boss a gift unless it was a secret santa thing or I was giving several people (like the rest of the managers) something and that was generally something liked baked goods or one year I bought my direct reports and the management team chocolates made in my home town. I did on occasion receive a small gift from an employee.
 
No. In the legal world gifts flow down, not up. Its okay to give gifts laterally to work friends, but not to your direct boss. My secretary/paralegal always receives something nice from me.
 
Op. I thought I’d update on what happened to my coworker. Her team went out for a holiday brunch (everyone to pay their own check). Gave boss the gift - she said boss was embarrassed and in turn the boss felt she needed to pick up the tab. My coworker said she felt bad for the boss
 













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