Sending a gift to your boss

Hey Savages,


I am thinking about sending a gift to two people but want to get your thoughts on how it might be received, especially for the second case.


1st Case: When I was at shitty, terrible shit hole of a company (Read "Series A War A Stories" for more context) I reached to the top sales leader at one of the fastest growing start ups in the past few years. He got back to me and offered to refer me but wanted to have a quick chat with me first.


We met 2 weeks after... at that point, I already had 3 offers, so, instead of referring me, we had a great convo about life and business and he helped me choose between the offers I had.


We have stayed in touch since that and he's been super cool and really appreciate his help and the advise he has given me. So, I want to send him a book that i think he would enjoy, it is about one of the topics he enjoys the most and it reminds me of him based on the few interactions we have had.


Would this be a good idea? Just tying to stay in touch with him and show I appreciate his time. I dont know his address so Im guessing I can send it as a gift card and send the book as a suggestion, I imagine this is possible, right? I'd send like a $50-$100 Gift Card but want to show the book as the purpose of it to make it more personal rather than a gift card which I am sure he doesn't need.


Any thoughts?



2nd Case: My Boss' Boss, who manages the managers and is in charge of the whole team, just had a newborn and thought I'd send her something for the baby, any specific ideas?


But, she is my current boss and wouldn't want to make her think that I am just looking to get promoted quicker or something like that... of course I'd like to get promoted but that wouldn't be the whole goal of it. I am genuinely super happy at my current company and she was the one who made the final decision to hire me and want to show my appreciation while also stand out in a positive way.


What do you savages think? If you are in a leadership position... what would you think of getting a gift from someone in your team?

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11
Sunbunny31
Politicker
4
Sr Sales Executive 🐰
Both cases are fine and very thoughtful.

1 - if you don't know the address, then maybe either an Amazon or B&N gift card in the amount of the book + shipping with a note stating that you thought the book would be something he would enjoy.

2 - gifts when a baby is born are very appropriate and thoughtful. It doesn't need to be big. A couple of ideas: gift certificate to local favorite restaurant for the parents, who might enjoy a night out after a few months; gift card to Target for any baby supplies she might want/be missing. Unless you know her super well and/or find something absolutely irresistible, I'd avoid infant/baby clothing. Odds are pretty good she has too many of some things and not enough of others, and nobody but the parents know which. However, I'll give you an example of an exception: some years ago, Costco had infant/baby sets that had an aviator theme, down to a faux leather jacket and infant hat that looked like an old time helmet with googles. It was really cute, and I knew my brother and his wife would really enjoy it, so I bought it and sent it to them. So my message is: the exception is if you see something absolutely adorable, odds are pretty good they'll find it adorable too. Pro-tip - if the baby is a newborn, you're buying at smallest 3-6 mos, probably better 6-9 mos size. You could also get 12 mos for later. Kids only get bigger.
CuriousFox
WR Officer
3
🦊
All of this, yes. You could also approach the team and see if they would like to chip in together for a baby gift.
DevSomeBiz
Valued Contributor
2
Senior B2B Sales Guy.
I'd be good with both. I've sent Christmas gifts to management, they are always well accepted.
Diablo
Politicker
2
Sr. AE
I like GV as no one ever says no
antiASKHOLE
Tycoon
2
Bravado's Resident Asshole
I think the thoughtfulness and the occasions have every right to be just that. Nothing for an ulterior motive.
Kosta_Konfucius
Politicker
1
Sales Rep
1st case: I think a book would be perfect

2nd: Hard to anything about gift outside of a gift card. I would honestly ask your current boss for ideas. This keeps them in the know and avoid the idea of going over her head. Plus she probably knows her better which will lead to a better recommendation on gifts
Pachacuti
Politicker
1
They call me Daddy, Sales Daddy
1 - send the book. No money.
2- send a small gift from both you and your spouse (assuming you're married) or from the Team if you're not (but make sure she knows you're behind it in some way). Don't make it about you.
jefe
Arsonist
1
🍁
I think reasonable gifts to someone you appreciate/with whom you have a good relationship are a good thing and will be well received.

If you start sending gold or diamonds then you might come off as trying to get ahead, but something thoughtful and not super expensive is a good idea.
SaasSlingin
Politicker
1
Sr AE
I like the book idea! The 2nd can be something along the lines of handy usable stuff they’ll probably end up buying anyway. Maybe crack a joke in the card and leave it at that.

Seems like you really like your gig.. curious what industry, size, role etc
Mobi85
Politicker
0
Regional Sales Manager
1st one good

2nd one, I would do a small gift basket and would go a gift for the baby like a warm hat with their name on it because it is starting to get closer to cooler temps. If they have other kids a really small gift for the other kids so they don’t get jealous and cause more stress on the mom and a bottle of wine or Starbucks/local coffee shop gift card for her because damn kids are a handful and she deserves something.
CallMeMaybe
Opinionated
0
Director of Sales
Never gifted a book only because you dont know if they already read it. Go to Baby gift idea: Piggy Bank
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