40 Awesome Bosses Who Show You Can Be Kind And Still Run A Successful Business

In a world where tales of terrible bosses often steal the limelight, it’s refreshing to shine a spotlight on those at the helm who lead with kindness and compassion. These aren’t just leaders; they’re game-changers, proving that you don’t have to choose between a kind heart and a sharp mind.

This compilation showcases 40 awesome, wholesome bosses who have seamlessly blended empathy with excellence, demonstrating that success isn’t just about the bottom line—it’s about lifting everyone up along the way.

Dive in and be inspired by leaders who are rewriting the narrative, one act of kindness at a time.

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2. My Dog Goes To Work With Me Every Day And My Bosses Gave Him A Christmas Bonus

3. Our Boss Makes Us Breakfast Every Wednesday Without Fail. It Really Helps With The Morale

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6. I Confided In My New Manager How Much I’m Struggling Mentally With My New Job. I Also Commented On How Much I Loved Her Pin Badges. This Was On My Desk This Morning

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8. My Boss Encouraged Me To Paint At Work Since It’s Been So Quiet

9. My Boss Stood By Me The Whole Time I Had Cancer Treatment, So For Christmas, I Made Him This

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13. My Boss Recently Rescued An Injured Hummingbird. It Loves Being Fed Sugar Water Through An Eye Dropper

14. I Had Mentioned That We Were Having Financial Difficulties At Work To My Boss. I Didn’t Expect This At All And Almost Went Full Cry Mode At Work

15. My Boss Is A Gem And Leaves Snacks And Drinks For Delivery Drivers

16. My Boyfriend’s Boss Had This Helmet Made For Him While Working In Egypt

17. My Awesome Boss Went To America For A Month. I Got A Month Off With A Pay, And She Brought Back These For Me

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20. I Have To Work On Christmas Day, So My Employer Has Given Everyone Who’s Working Today A Christmas Hamper With Goods

21. My Boss Gave My Coworker A New Monitor. He Didn’t Get Caught Doing Anything, He’s Just Blind As Hell

22. My Boss Mailed Me This After Two Years At My Newest Job. Complete 180 From The Last Job I Was At

23. Today, I Got A $10,000 Quote On The Cost Of What Needs To Be Done To My Teeth. It Made Me Feel Even More Helpless. But My Boss Is Taking Care Of This For Me, Free Of Charge

24. My Boss Handed Me My Paycheck With This Included. He Continually Goes Above And Beyond For Me, And I’ve Only Been Employed With Him For Just Under A Year. He’s A Good Man

25. My Boss Rushed Out To Get Me A Last Minute Birthday Present. He Came Back With This. I Was Not Disappointed

26. My Boss Sent These Cookies To Me During The Lockdown

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31. I Work At Construction, And My Boss Gave Another Meat Platter This Year In Time For The Holidays

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34. I Had To Quit My Delivery Job Today Due To Depression, And This Is How My Manager Responded

35. Further Evidence That My Wife’s Boss Has A Sense Of Humor. This Is Her Christmas Card

36. This Is My Boss, Running Nearly A $200 Million Dollar Company, Emailing The Whole Company

37. “Made Some Care Packages For The Employees. They Are Coming In From 12-2 To Pick Up, And Then We Are Going To Have A Movie Night Tonight On Netflix Party”

38. I Was Having A Rough Day At Work So My Manager Brought Me A Bouquet

39. I’m An Intern At A Fashion Magazine. My Boss Asked If I Liked Lipsticks And Handed Me A Bag Of Free Samples

40. My Boss Cured And Smoked Some Meat For Him And His Family. He Gave Me This Today At Work. What A Legend

Mike

Mike Primavera

Mike Primavera is a Chicago-based comedy writer even though he doesn't HAVE to work. He lives comfortably off of his family's pasta fortune. Follow him on all social media at @primawesome