One of the owners of the company I work for is retiring. He always goes out of his way to be kind to people, and since I'm very shy I've always found very reassuring knowing he was in the company's management, although I have never worked in the department he was in charge of.

I'd love to be able to give him a book as a token of my appreciation, but I lack social abilities big time, and I'm not sure if being given books by random employees can be awkward for him (the last thing I want is to upset him).

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    – DarkCygnus
    Commented Sep 22, 2023 at 18:37
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    I really like the words you used in your question, and I suggest that you also use them when handing over the book. Personally, I'd be very flattered if someone told me "you always went out of your way to be kind to people. I've always found it very reassuring knowing that you are in the company's management, even though I have never worked directly in your department".
    – Heinzi
    Commented Sep 25, 2023 at 8:00
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    I think giving a book is a very good gesture, and will be fondly seen by the person you gift it to. However for this particular title ("the end of everything") isn't there a non-small chance that it could be linked to the idea of retiring? (even though the subject is cosmology, the title in itself seems a bit darker if one takes it as a parallel to what happens after the end of his carreer?) Commented Sep 25, 2023 at 10:18
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    (following) however if you think it will be enjoyed, it could be even better better. Otherwise, if you like science, some books that can be enjoyed both from people who know science or who doesn't: the biography of Richard Feynman "Surely you're joking mr Feynman" is a GREAT read. But of course offer a book that you know and enjoy and think that person will enjoy (which is probably ehat your choice was!) Commented Sep 25, 2023 at 10:25
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    If the person is someone dear to you or you simply just appreciate them, there is nothing wrong with a gift. Just consider getting something that you know they are interested in as it will make the gift feel more personal
    – CodeJunkie
    Commented Sep 25, 2023 at 12:01

5 Answers 5


I'm not sure if being given books by random employees can be awkward for him

Certainly not, I think it's a nice gesture if you want to give them a book, so I doubt it would be awkward or frowned upon.

Something along the lines of "Hello, Joe. I greatly appreciate your support during this time, it's been very valuable to me. I saw this book I think you'll like, and I decided to give it to you as a token of my gratitude."

Feel free to elaborate as much or as few as you want/feel like.

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    If you are awkward in person, I'd pre-write out what you want to say on a note or card (or on the inside of the book), so way you can properly communicate what you want to express when you're not under the stress of in-person communication. You can either leave the book, wrapped with a ribbon or in wrapping paper, with his secretary or on his desk, or hand it to him in person with a very short verbal exchange, e.g., "I hope you enjoy your retirement!" as you hand them the book, with your actual thoughts pre-written inside it or in a gift card on top of it (tied on with the ribbon).
    – Jamin Grey
    Commented Sep 24, 2023 at 2:21
  • @JaminGrey I'd hardly second to write this on the first blank page, I feel this is too rarely done nowadays, but books last longer than cards and are definitely more often picked up. I really enjoy finding old books that my parents gave me and be reminded of the occasion and warm words and if your boss likes the book, he'll have a beautiful personal touch to picking it up again after some years.
    – kopaka
    Commented Sep 25, 2023 at 9:55

The general rule is that gifts should flow down the organisation chart, and not up it. However, if someone is leaving or retiring, and it's someone who you care about then it's absolutely fine for you to give them a small gift - and I'm sure that they'll appreciate it. Don't make a big deal of it - just speak to them privately at some point, say that you've really appreciated them (or whatever), and give them the book.

Oh, and make sure it's not a book like "How to lose weight" or "How to be a better boss", unless you know them really, really well.

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    This randomly reminded me that when I finished grade 4, my teacher left the school and we made goodbye cards for her. Not understanding the concept of work, I taped a quarter in mine and wrote, "To help pay for your new job." Commented Sep 23, 2023 at 4:29
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    In what country is this the "general rule"? I've been in a fair few positions in the UK and I wouldn't think twice about getting a gift for someone more senior than me, whether it be a birthday gift or a leaving present. The idea that there is some "rule" around this I find quite chilling - are your organisations that rigid with hierarchy? Good bosses will treat you as equals and authority should only count where it's needed e.g. authorising business decisions, dealing with disciplinary matters etc.
    – roganjosh
    Commented Sep 23, 2023 at 7:41
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    @roganjosh it's a rule due to the power discrepancy. Yes, you could probably get somebody a gift for a special occasion even if they are "above" you but the general rule is there to not make this a habit. Because it is chilling of bosses expect to be showered with gifts on the implicit threat that those under them might suffer some sort of retaliation. This is what the power discrepancy is. It might never happen, sure, but there no way to ensure that one won't miss a promotion or be treated worse just because they haven't sent gifts. Therefore good bosses know not to set such expectations.
    – VLAZ
    Commented Sep 23, 2023 at 9:33
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    > Because it is chilling if bosses expect to be showered with gifts on the implicit threat that those under them might suffer some sort of retaliation... actually I would see this the other way: gifts to senior people can look like bribery for favours (hence things being relaxed for e.g. retirement gifts - see o.m.'s answer).
    – Lou Knee
    Commented Sep 23, 2023 at 10:31
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    @roganjosh you didn't. You asked why is the expectation for gifts to not go "up" the chain. That's the reason - because if done often it implicitly sets up the expectation that bosses should be given gifts.
    – VLAZ
    Commented Sep 23, 2023 at 14:58

Where I work, a mid-sized company in , it is common for co-workers to give signed cards and possibly small gifts to people who are leaving and especially to people who are retiring. Often the team joins efforts for a common gift and card with dozens of signatures.

Once someone is leaving, certain rules of propriety alter. It is considered OK to give a small gift to someone who is more senior, especially after a long and cordial relationship. Basically, one cannot bribe someone who has already handed over all management responsibilities, and the customary amounts are so low (single-digit € per contributor) that one does not think in these terms, anyway.

  • @Fattie, quite possible to add a box of chocolates, or something for a hobby, or something like that. But yes, the card is the starting point. With as many signatures and personal messages as possible.
    – o.m.
    Commented Sep 24, 2023 at 4:27

Some folks will find the concept of a boss who is also a friend unbelievable. But it does happen.

The main reason not to give a gift to a superior, assuming you would do so even if they weren't your boss, is because it might come across as an attempt to curry favor, "suck up", or otherwise purchase favorable treatment you wouldn't otherwise be entitled to.

But infrequent small gifts that you would give any other friend shouldn't be a problem. How you define occasional and small is a judgement call, but I'd say something on the order of picking up the lunch tab a few times a year is harmless, especially if they've been buying your lunch on occasion without submitting it as a business expense.

And in this case, where they're on their way out the door, it's pretty obvious that the gift is not a bribe or quid pro quo. So most of the concerns don't apply.

If it's something you would do if they were your peer rather than your boss, and it isn't so extravagant that it will be embarrassing, I'd say go for it. Maybe even talk to the rest of your team about whether folks might want to make it a group gift (with who contributed how much not being disclosed, and everyone invited to sign the card whether they contributed or not so there isn't pressure to get involved.)


One of the owners of the company I work for ...

I would honestly recommend a thank you card (ie, a "Hallmark" type card).

Any sort of gift is somewhat strange.

No matter how nice the person is, you're an employee and they're an owner.

Which means:

Say you worked there 10 years and were paid for example $1m in total. Through your work, the owner would have made tens of millions of dollars.

Once you realize that, the idea of gifting an owner, is both fatuous and bizarre, and indeed extremely misguided.

Keep things business-like.

To repeat:

No matter how nice the person is, you're an employee and they're an owner.

To repeat:

The owner would have made vastly more from your work than you were paid for your work.

Footnote about owners "retiring" ...

When an owner "retires" from a business, that means the business has "worked out" for the owner - to wit, the owner now continuously, forever, gets money weekly from the business and does nothing. IE the owner no longer needs to show up every day and now does nothing, continuously forever getting (a lot) of money due to the ongoing work of the employees.

Realizing this, you can see it's doubly-bizarre that an employee would give gifts to an owner.

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    While the attitude you describe may well fit many managers or owners, it 100% does not fit all of them. It doesn't fit me. I considered many of my staff friends and cared about many more of them. They were never cogs. You can be as cynical as you like -- it's your loss -- but when you present your cynicism as absolute truth and then base advice on it, I consider that bad advice. Commented Sep 23, 2023 at 22:04
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    Having worked for some scumbags, and for some good friends, and for entrepreneurs who made $millions, and for entrepreneurs who lost everything they put into their companies... I think this is a story in your head, not a fact.
    – Spike0xff
    Commented Sep 23, 2023 at 22:27
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    Do you somehow think I'm not an owner? Based on what, I wonder. You think I considered my staff all cogs. You're wrong and furthermore, cynical. But as I said already, that's your loss and doesn't affect my life or the way I feel about people who worked for me and helped me make or lose money while being paid fairly themselves. Commented Sep 24, 2023 at 16:38
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    -1 While the dynamic between owner and employee might be true to some extent, the answer massively fails to acknowledge risks on the side of the owners. If the company goes south, employees just walk out and get another job while owners have to deal with the failure and probably loss of money of the company. And overall, a bit of niceness and positivity goes a long way. Answer spreading negativity always need a -1.
    – user112367
    Commented Sep 25, 2023 at 6:20
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    @Fattie, why would it be it's sort of "oddball, weird and strange" ? A person is providing a small token of gratitude, maybe they appreciate something you did or you were simply nice. It is an interpersonal thing and not any kind of business based interaction. It does not matter who the person receiving the gift is. I am really wondering why your OG answer is obsessed with the financial gain ? You are viewing employees as tools to make money which is kinda, and no offense, sick.
    – CodeJunkie
    Commented Sep 25, 2023 at 12:48

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