Subject: What to gift your boss

Cait here, ready to tackle this question for all you interns out there worried about gifting the wrong thing to the current most important person in your career. Whether it be a birthday or planning ahead for the holiday season or a leaving present, we got you.

When thinking office gifts, I always think you want to impress, but not be so “extra” as they say, to call too much attention. We’re not try-hards, we’re girl bosses, okay? Girl bosses don’t try hard, we work hard.

 First and foremost, be sure and plan ahead. The more time you give yourself to think about it in advance, the more you are setting yourself up for success.

Begin noticing what he/she may need the most, their feelings towards other gifts received, their personal likings, and your relationship you share with said boss.



If you notice that every time someone drops off a new notebook as a gift to your boss, it gets passed down to you or stacked in corner cabinet with a dozen others, avoid going back for the cute notebook you saw in the check-out line last week.


Pay attention to your boss’ conversations with you and other staff (respectfully).


Did they mention, or maybe you’ve noticed, how often they misplace their car keys and cell phone? Look into something like the Tile Tracker, which can be bought in a 1 pack or 4 pack and is a LIFE SAVER for people of my kind (the irresponsible kind). (ps. Unfortunately i’m not getting paid to say this by them)

If your boss has their initials printed on their favorite pen, calendar, bag, umbrella, and maybe stamped to their forehead, think about something you can personalize with their beloved monogram! If their favorite color is yellow, maybe do a theme basket of great yellow items like a lip balm, yellow candies, bananas, a notebook, etc. Just some useful things you think they’ll enjoy.

Think personal, practical, likable, and laughable.


ALWAYS consider the relationship you have with your boss during this process! If you’re new to the office, I think a great way to get noticed is to gift something personal, but very safe. Maybe you noticed they love a certain food or type of music or some personal preference of their, I would totally play on that just to say, “Hey look, I pay attention to you and remember this.”

 If you have a very close relationship with your boss and you know you share the same sense of humour, totally go for a laughable, but still practical gift.

In 2018, we have one thing to our advantage here. And that is the overabundance of GIFT BOXES in the world today!! Boxes for skin care, “treat-yo-self”, self-care boxes, maybe give them a free month or two of a subscription box like FabFitFun, BoxyCharm, or the oh-so-new and lovely Cosmopolitan subscription box. All of these should be chosen based on their personal likings and personality! There are also companies that have pre-made or customizable gift boxes.


Bonus: My favourite gift I have given in the office was a painting by a boss’ favourite local artist that I tracked down online and purchased at a semi-sketchy meet up in the city. She was so shocked at how thoughtful of a gift it was- especially when I told the retrieval story over lunch the next day!



I’d love to hear your creative gift ideas you’ve given, or answer questions or recommendations you might have!


Kind regards,



Caitlin LanningComment