Cool bosses aren’t just about authority—they inspire, support, and make work enjoyable. With a mix of leadership, humor, and empathy, they create a positive environment where employees thrive. They prove that a great boss doesn’t just lead, they lift everyone up.
"My Boss Lost A Bet"
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"Yesterday The Owner Of My Company Noticed That The Shoes I Had On Were Worn Through And The Jeans I Had On Had Holes In Them"
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"I was planning on getting a new pair of each on my next paycheck. Today he took me to Costco and bought me 2 new pairs of shoes, 4 new pairs of jeans, and some food.
I started in December of 2020 after being laid off/unemployed for a vast majority of the year. I’m still trying to get back on my feet financially and make ends meet. It was such an unbelievably nice gesture. I cried and gave him a hug. I can’t wait until I’m able to pay it forward."
"My Boss Got A Puppy And Brought Her Into The Office. Productivity Went Waaay Down"
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"Semi Load Of Water I Just Got To Donate"
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"I actually work for a company that cares. My boss gave me $10k to help wildfire victims, doesn’t care how it helps as long as it helps. Started with a semi load of bottled water. In 3 decades of work, I’ve never worked for good people until now. Been smiling for 2 days about this."
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"Someone Asked The Boss If We Were Going To Have Cake For Halloween, He Disappeared And Came Back With This"
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"Alli Had A Very Rough Day At The Animal Hospital - My Employer Found Out And Sent Her A Care Package"
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"Started A New Job 3 Days Ago And I Just Lost A Family Member. This Is How My New Boss Responded. I Couldn’t Be Happier With My Decision To Work For Him. Take Notes, Employers - This Is How It’s Done"
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"I Asked My Boss If We Could Pose With (Some) Of Our Prop Money At The End Of The Day; He Insisted We Use All Of It"
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"I'm The Only Gothic Person In The Office. Halloween Is My Favourite Time Of The Year. Came To Work To My Desk Decorated For The Day By My Managers"
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"It was also my birthday earlier this month, but I was on holiday (which is why the desk wasn't decorated to begin with) so they got me a Halloween themed cake! Don't think I've ever felt this special. Happy Halloween everyone!"
"Best Boss Ever"
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"Last week my boss asked me to go over some paperwork for a project, to which I said, I will make it a fun weekend activity to read through it with my son. For context, my wife and I have set a goal to read him 1000 books in 2024. We joked that the paperwork should count as 10 books, we chuckled and moved on. Today, I came in to work to find a couple books and this note with a couple books sitting at my desk. The fact that she cared enough to not only buy the books but to write this adorable note genuinely made me smile. It’s these small details that make her the best boss I have ever had."
"Boyfriend Lost His Serving Job Because Of Corona. Bosses Cleared Out The Kitchen To Provide Food For Employees And Intend On Making Them Weekly Care Packages"
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"The Manager At This Restaraunt Is Breaking Up The Lobster Shells For These Two Old Ladies Who Are Celebrating One Of Their Birthdays"
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"Been Battling Mental Health Struggles The Better Part Of My Life And Finally Had A Psychotic Break Last Night And Am Now Seeking Care. Was So Nervous To Text My Supervisor About It. This Was His Response :')"
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"My Boss Writes Notes On His Hand And Photocopies It For Later"
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"I Jokingly Told My Boss My Basement Level Office Needed A Sky Light. He Made It Happen"
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"These Were Given To Me By My Indian Boss As Part Of Diwali Celebrations. Sweet And Filled With Cashews"
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"My Boss Gave Me My Christmas Gift A Little Early This Year. A Set Of All-Clad Plus A Cuisinart Food Processor!"
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"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"