20+ Hilarious Ways Boss-Employee Relationships Flourish - (2026)

Updated: 05/01/2026

My Boss And I Had An Ugly Sweater Competition

source

Every Year For Our Boss’s Birthday We Play Pranks And Gags On Him All Day. This Year One Prank Includes Switching Pictures Of His Kids With Photoshopped Versions Of His Employees

source

I Housesat And Watched My Boss’s Dog For A Month. So I Took These Pictures, Framed Them (Exactly How His Family Pictures Are Framed) And Hid Them Throughout His House. He Didn’t Notice For A Week

source

When You Request A Wall Clock For Your Office But Your Boss Is A D**k

source

My Boss And I Are In A Contest To Lose Weight. Today Is My Birthday. This Is What He Brought Me

source

My Boss Didn’t Like His Face Of The Group Picture And Asked Me To Photoshop It. Unfortunately, I Have Very Limited Gimp Skills

source

My Boss Was Just Gifted A Giant Classical Oil Painting Of Himself

source

A Friend Of Mine Faked A Doctor’s Note At Our Job. This Is My Boss’s Response

source

My Boss Has Talked To Me Several Times About Leaving A Note While I’m Away From My Desk. Today I Made This Convenient Slider

source

My Boss Installed An IP Camera At The Store To Spy On Us When He’s Away. I Retaliated With This Rig

source

Wise Words From The Boss

source

Friend Of Mine Is A Welder, Here’s His Present For His Boss

source

Ever Since My Boss Has Had A Daughter I’ve Received Diminishing Amounts Of Attention. But I’ll Be Damned If I’m Going To Let Her Artwork Be The Only Thing On Display In The Office!

source

So My Boss Calls Me To A Meeting On My Day Off, Then Asks Me To Arrange The Meeting Room

source

I Left This On The Security Cameras For The Boss In The Morning

source

My Boss Told Me To Find A Way To Keep Mice Out Of Our Cable Tray. I Think This Should Work

source

My Boss Censored My Cleavage At Work Yesterday

source

My Boss Insists On Using Webcams During Meetings. I Insist On Being A Wizard

source

My Boss Complained About My Coworkers Hair Being Too Long. So She Fixed The Problem

source

Won A Bet Against My Boss Nearly A Year Ago. Came Into Work To See That He Finally Paid Me… In Pennies

source

I’m A Lifeguard. My Boss Gave Me A Key To Open This Drawer, Then Started Laughing Hysterically When I Tried Unlocking It. I Didn’t Realize Why Until Now

source

My Coworker Is Coming Back From Burning Man Today, So My Boss Left This On His Desk… I Love My Job

source

My Boss Just Walked Up To Me, Completely Deadpan, And Slapped This Post-It Note On Me

source

I Work In Construction And Get Paid In Cash. My Boss Thinks He’s Funny

source

Boss’s Name Plate

source

Woke Up To This Snapchat From My Boss

source

Complained To My Boss And Received This Minutes Later

source

Get Your Sh*t Together, Cody

source

While My Boss Was On Vacay, I Switched The Pic Of His Gf And Him, With An Employee And Myself… Nailed It

source

My Girlfriend Got A New Job. Cake From Her Old Boss

source

My Boss Got This Ridiculous Excuse The Other Week And Decided It Needed To Be Hung Up

source

The Way My Boss Asked Me To Order Her More Pens Like This One. I’m Sure She’s Just Bluffing

source

My Boss Decided To Express His Opinion Of My Music Choice This Morning. He Is Not A Very Subtle Man

source

My Co-Workers And I Are Without A Boss Until The 14th, So We Improvised

source

My Boss Just Got Me These Socks For Christmas

source

Asked My Boss For A Standing Pad… This Is What I Got

source

My Boss Gave Me This During My Yearly Review

source

Asked My Boss For An iMac , Saw This When I Came This Morning

source

My Boss Slid This Under The Bathroom Door For Me

source

Walked In My Bosses Office And Saw This Sign

source

My Boss Just Learned A Thing

source

So I Bring A Pecan Pie To Work. By Noon It Was Missing. Found It A Few Hours Later In My Boss’s Office

source

Some Work Gloves My Boss Handed Me. Who Ever Came Up With The Product Label Is A Genius

source

My Mom Worked At City Hall In 1988. This Is How Her Boss Let Her Know He Wanted Candy

source

It’s The Boss’s 50th Birthday (Birthday 49a, According To Her). The Team Is Very Supportive

source

I Bought This For My Boss But He Didn’t Think HR Would Approve, So He Made It Hr Approvable

source

So, I Took My Boss’s Daughter Out Without Him Knowing. This Is The Note He Left A Few Days Later

source

My Manager Left For Vacation And He Left This Note

source

So We Got Into Work This Morning And Bosses Surprised Us With Brand New Company Cars

source

My Boss Hates Germaphobic A**holes

source

Read more: boredpanda.com

Relevant news