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50 Wholesome And Funny Bosses Who Put Their Employees First (New Pics)
Wholesome WorldDEC 10, 2024

50 Wholesome And Funny Bosses Who Put Their Employees First (New Pics)

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There's this trope that most people hate their boss. The Internet is ripe with pictures of bosses micromanaging, refusing to give raises, and just being plain jerks. Yet the reality might be different. According to a Pew survey, 55% of Americans have an excellent relationship with their boss, with 26% describing their relationship as "good."
This list might just be the proof that there are funny and wholesome bosses around. We've gathered the best examples of bosses who aren't afraid to be whimsical and nice to their employees and have earned the title of "Good Boss." Want proof that not everyone's boss is an insufferable jerk? Scroll away!
Bored Panda reached out to Robyn L Garrett, author of Happy At Work and CEO at Beamably, to chat about what it takes to be a great boss. She told us more about what the younger generation expects from their bosses and how important personal connections are for employer-employee relationships. Read her expert insights below!

#21 What A Perfect Response

Text message from a supportive boss, offering empathy and playlist creation to cheer up an employee.
90points

Just as listed in the Pew survey, a good boss, according to Carnachan, also gives feedback on an employee's performance, sets clear goals and direction, has high expectations for themselves and their team, doesn't shy away from difficult conversations, and isn't afraid to admit when they've made mistakes. "These are people who are not only respected, they often are role models for future leaders," Carnachan explained.

#22 My Boss Gifted Me My Dream Car

Person posing happily beside a black car, capturing a moment of joy.
The Outback has always been my dream car for the last 10 years. Started out with an Impreza that ended up breaking my heart when the CVT died and I wasn’t in a position to get it fixed. I’d given my wants up to time, if I get it, awesome. If I don’t, I still have a vehicle.

I moved 2k+ miles with just my kitties from the state I grew up in 2021. Will be at my firm 2 years on 04/25. I had a car after the Impreza died, which happened 10 months after I moved, but the Volkswagen had been stolen (then returned 12 hrs later with 7 suitcases and fentanyl in it) and it was really janky and would break down a lot.

My boss saw I had a need and only out of the goodness of his heart fully paid for my ‘21 Outback. No strings. No payments to him. However he is an attorney and made me get an insane 1M policy. But I don’t complain about that at all. I got incredibly lucky as the amazing dealer found one with 1 owner who leased it so, it only had around 18k on it. I have my dream car. 5 months later I still can’t believe it. Absolutely floored. Hard work pays off in other ways than money or promotions.

I’m so eternally grateful for the people the Universe has put in my life. Words can’t explain my appreciation and safety knowing people I have no relation to has my back. And it gives me comfort to know that my closest friends and family to think of me in such a way to see me happy.
89points

#23 My Boss Lost A Bet

Boss in a funny dog costume standing in an office.
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88points

#24 My Boss Gave Me My Christmas Gift A Little Early This Year. A Set Of All-Clad Plus A Cuisinart Food Processor!

Shiny kitchen pots and pans on a countertop next to a blender.
88points

A good boss also needs to constantly ask themselves: "Am I a good boss?" As Linda A. Hill and Kent Lineback write for the Harvard Business Review, "as they settle in and lose their fear of imminent failure, they often grow complacent. Every organization has its ways of doing things—policies, standard practices, and unspoken guidelines, such as 'promote by seniority' and 'avoid conflict.' Once they're learned, managers often use them to get by—to 'manage' in the worst sense of the word."

#25 Two Years Ago, The Company I Was Working For Was Bought Out And I Lost My Job. My Manager Sent Me This Hand Forged Knife As A Goodbye Present Because He Knew I Collected Knives. It's One Of The Kindes Gestures I've Ever Received

Hand holding a small knife with a white handle next to a brown leather sheath, suitable for a good-funny-bosses theme.
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87points

#26 My British Boss Is Pretty Pleased With His 4th Of July Outfit

Man in wolf shirt and American flag shorts, embodying good funny bosses with a cheerful pose.
85points

#27 Gift From The Boss

Tattooed hand holding a novelty lightsaber resembling a flashlight, capturing the essence of good fun with funny bosses.
I was joking with one of my bosses that when he went to Disney that he should bring me back a lightsaber. He jokingly told me one of the owners is a huge Star Wars guy himself and goes several times a year himself. I started joking with him that he should get me one next time he goes. Turns out he came back yesterday and he gifted me this bad boy today. I offered to throw him money for it but he insisted that I just have it for free. Definitely extremely grateful to my boss for this!
83points

A good boss also faces conflict head-on, although most tend to avoid it. "'I hate company politics!' they say. 'Just let me do my job,'" Hill and Lineback write. "But effective managers know they cannot turn away. Instead, with integrity and for good ends, they proactively engage the organization to create the conditions for their success."

#28 Last Day At Work, Boss Got Me A Cake

Cake with humorous message "Knock Knock Who's There Not Jade," featuring colorful balloon decorations.
81points

#29 We Made Our Own Valentine's Day Boxes For Work. This Is My Boss

Funny boss at desk with a large, humorous face cutout and playful desk decorations.
76points

#30 I Don’t Drink Coffee And This Morning My Boss Gave Me A Strange Beverage Simply Labeled As “Ocean” And Now My Brain Feels Like It Has 800 Hp And I Can Also See God

Large cup labeled "ocean" with dark blue drink and pink straw held in hand. Good-funny-bosses moment.
74points

Who wouldn't wish to have a boss like the ones on this list? What about you, Pandas, what's your relationship with your boss like? Let us know some feel-good, wholesome boss stories in the comments! And if you're looking for something similar to this list, check out our two previous articles in this series here and here!

#31 Boss Surprised Me With Vegan Cupcakes For My Birthday

Box of vegan cupcakes with "Happy Birthday" written on the lid, showcasing a good-funny-bosses vibe.
73points

#32 If You've Ever Felt Like An Idiot, There Are Two Managers On This Planet Who Were Tasked With Buying A Sofa For Their Office, And They Ordered It From A Doll Shop

Person holding a miniature white sofa, illustrating a good-funny-bosses moment.
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71points

#33 23 Years Ago, My Boss Gave Me This Ornament Because I Loved To Eat Hot Dogs For Lunch At Work

Funny hot dog ornament with a smiling face, hanging on a Christmas tree, representing good-funny-bosses humor.
71points

#34 My “Boss” Just Sent Me This

Text message exchange about receiving a Dunkin' E-Gift, showcasing a thoughtful, funny boss interaction.
I’ve been helping this girl out by doing chores at her apartment, caring for her pets, organizing, etc. since she is too busy because she is about to take her bar exam. I’m OBSESSED with dunkin refreshers, and I’ve shown up with one almost every week. I go over there this morning, and she sent me this literally could cry. She was paying attention, I see. It’s the little things. It really is.
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71points

#35 I’d Like One Please

Cart filled with old telephones and calculators, showcasing a humorous boss's request.
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69points

#36 I Started My First Full Time Job Recently, And My New Supervisor Bought Me These

LEGO figures of funny bosses displayed on a wooden shelf, featuring various characters in a creative setting.
66points

#37 My Boss’s Response When Asking To Come In Late To Finish An Essay For College

Chat exchange showing a supportive and understanding boss, highlighting good-funny-bosses vibes.
He is literally one of the best managers I’ve worked with. He is always working with me when I need time off or I’m sick, and when I’m overloaded with school. Wanted to post to show there are still good bosses out there.
62points

#38 Me: - I Have A Small Stapler, Do You Have A Bigger One? Boss: - Yes, Here You Go

Small stapler on a desk next to a large stapler; a funny office comparison highlighting good-funny-bosses.
62points

#39 My Boss Bought A Display Shelf For My Mocs

Display case of toy fire trucks and a large fire truck, highlighting good-funny-bosses with a playful approach to emergency vehicles.
I got into vehicle procurement at the Fire Department (Berliner Feuerwehr) after I built a MOC of the first electric fire engine (2nd from the top, Rosenbauer RT) and brought it to their booth at a huge fire/rescue trade show 2 years ago.
Since then, I’ve accumulated quite a number of trucks, and the last time I brought one in my boss said that’s enough we need a display shelf (and I needed some space at home tbh).
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60points

#40 Rate My Outfit (This Was The Manager's Punishment For Being 30 Minutes Late)

Person in a funny bunny costume taking a mirror selfie, showcasing good humor in a workplace setting.
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59points
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