The Most Awkward Boss's Day Gifts Ever Given (And What to Do Instead)

Boss's Day sounds easy enough – get your boss a nice gift, say a few words of thanks, maybe enjoy a bit of cake, then done! Everyone claps and proceeds to remember your success for years to come...and then you woke up. 

In reality, Boss’ Day is one of the trickiest gifting occasions in the workplace – getting it right requires a little more than winging it. Unlike birthdays, where almost anything goes, Boss's Day comes with a unique set of challenges: You want to show appreciation, but not look like you're trying to secure a promotion. You want to be thoughtful, but not too thoughtful so as to cross a line. And whatever you do, you definitely don't want to become office folklore because of a gift that missed the mark. 

Unfortunately, history suggests that's easier said than done. Let's take a look at some of the most awkward Boss's Day gifts – and how to do, well, anything other than that. 

1. The Self-Help Book You Definitely Didn't Mean As Feedback

Nothing passive-aggressive here…right? Right?!

"I saw this and thought of you!" – words nobody wants to hear when the gift in question is a book titled How to Listen Better.

Even if your intentions are pure, gifting a manager a book about communication, leadership, time management or emotional intelligence can accidentally come across as a performance review.

You think you're saying: "I know you're interested in leadership so you’ll appreciate this."

They hear: "Here’s where you’re falling flat."

What to do instead: A Boss’ Day group card lets people share appreciation without accidentally diagnosing someone's management style – now if you want to attach a Dymocks eGift Card for your bookworm boss, you’re really onto something. You could add a note in your card:

“We know how much you love leadership and reading, so we want you to have an unlimited selection of books to choose from!” 

Crisis averted. 

2. The "World's Best Boss" Mug

A workplace classic. Safe, right? Wrong. 

The problem is that every boss knows exactly what this gift means: We don’t know you, really.  Nobody genuinely believes they're receiving the first "World's Best Boss" mug ever produced – except maybe Michael Scott.

At best, it ends up in the office kitchen…at worst, it joins the other six in a cupboard somewhere. If this is sounding a little too familiar, it’s time for a change – step away from the mug. 

What to do instead: Skip the novelty gifts and focus on something personal, like messages from the team about moments that genuinely made a difference.

3. A Gift That's Weirdly Expensive

Every office has a different culture, but there's usually an invisible line when it comes to Boss's Day spending. Cross it and things get awkward – we’re talking about things like:

• A luxury watch
• Designer sunglasses
• A weekend getaway

Look, it all sounds great, we know, but we promise people aren't saying: "Impressive. What a thoughtful gift."

They're saying: "Wait...how much did that cost?"

Now you’ll notice the one and only Michael Scott comes up again on this list – a sign that the awkwardness is among us – and here we ask you to think about the iPod incident. No further comment.  

What to do instead: An eGift Card that the whole team has chipped in for spreads the cost and keeps things comfortable for everyone involved, regardless of financial situation. With GroupTogether, you can allow everyone to contribute an amount they can afford, rather than forcing everyone to fork over their savings. 

4. The eGift Card to a Place They Hate

eGift Cards seem foolproof – and they absolutely can be…until someone decides to pick a restrictive retailer like a coffee shop, a local restaurant or an adventure tours group. 

And then someone remembers the boss is 10 years sober. 

Or is terrified of snakes. 

Or has spent the last five years talking about how much they dislike that particular restaurant.

The problem isn't the eGift Card, the problem is pretending you know exactly what someone wants. 

What to do instead: Give them the freedom to choose – that is literally what the AnyCard was made for. It lets recipients decide where they'd like to spend their gift, removing the guesswork entirely.

5. The Office Joke That Escaped Containment

Inside jokes can be the best part of the work day. They can also be impossible to explain – particularly when they're printed on a physical gift. What felt hilarious during one Friday afternoon meeting can feel significantly less funny six months later when someone's partner asks:

"Why does this paperweight say ‘in memory of Dave's pants incident’?”

What to do instead: If you’d rather not cause a martial breakdown, put the jokes in a group card where they're part of the story rather than permanently engraved into an object without the much-needed context. 

6. Homemade Food From Someone Nobody Expected

There are two types of workplace baking: The first inspires confidence, while the second inspires questions…and concerns. 

Boss's Day is not necessarily the time to discover which category you fall into. 

What to do instead: A heartfelt message carries considerably less risk than mystery muffins.

7. The Plant That Became a Responsibility

Plants seem like a cute gift and the perfect way to add some colour to their desk. That is until they realise it was a fiddle-leaf fig that came with an extensive maintenance checklist including strict watering schedules, pruning and repotting. They already have a full-time job! 

Three months later, everyone is pretending not to notice the sad plant wilting in the corner. 

What to do instead: Okay, does this one really need to be said? Choose a gift that doesn't require watering schedules…so basically anything else. 

8. The Framed Team Photo Nobody Approved

There's always one person blinking…or even worse, the half blink! 

One person looking away.

One person staring at the cake on the desk. 

But you probably noticed the gift-giver is the only one sporting their best angle, while everyone wonders why this photo from the 2020 Christmas party is suddenly hanging in the office – masks and all. 

What to do instead: Collect photos, memories and messages digitally where everyone can enjoy them without committing to wall space or deciding on a single photo. A group card is the easiest way to do this, with GroupTogether allowing unlimited uploads.

9. The Gift That Accidentally Created Favouritism Allegations

Few things create workplace speculation faster than an unusually elaborate Boss's Day gift, particularly when one worker gives a card and another arrives with what appears to be a small yacht.

Nobody wants appreciation to turn into office gossip...except, well, the office gossip! 

What to do instead: Keep things inclusive and team-focused – instead of going for separate gifts, go for a team gift. It’s more affordable and it prevents comparison. 

What Bosses Remember on Boss’ Day

There’s a huge misunderstanding around gifting and showing appreciation – it’s not about money and it’s certainly not about being elaborate. Most managers don't even remember who bought the expensive gift. They remember the thoughtful messages, the funny stories, the note from a team member they helped years ago – yeah, they remember that time too. 

Chances are, if you’re keen to celebrate your boss, they’re one of the good ones who make work better for other people. And when it comes to recognising that impact, the most meaningful gift is often hearing about their dedication and showing them that you love and appreciate that about them. 

A Better Way to Celebrate Boss's Day: Group Card and The AnyCard

If your team wants to thank a great manager, a GroupTogether Boss’ Day group card is one of the easiest ways to do it – there’s no risk of awkwardness or line-crossing, but a 100% guarantee of happiness.

If you'd like to include a gift, the AnyCard allows the whole team to contribute towards a collection that your boss can actually choose how to spend – no accidentally offensive leadership books and no high-maintenance greenery. Just a portable reminder that their work has made a difference.

And unlike a "World's Best Boss" mug, they'll probably keep it.