40 Of The Best Bosses Ever That’ll Make You Wish You Worked For Them
The word “boss” doesn’t always come with warm fuzzies. It usually triggers memories of unread emails, awkward performance reviews, or someone taking credit for your work in a meeting. But then—just when you’re losing hope—you hear about that boss. The one who brings in surprise cupcakes for the night shift. The one who tells you to log off at 3 PM because you look tired. The one who not only notices you’re struggling—but steps in to help.
Grumpy Sharks rounded up 40 moments that prove good bosses aren’t just mythical creatures—they’re out there, quietly creating workplaces where people feel seen, supported, and, dare we say it… happy. These stories—from Reddit’s kindest corners and viral feel-good moments—will remind you that leadership isn’t about titles. It’s about trust, empathy, and showing up for people when it matters.
These aren’t micromanagers or buzzword lovers. They’re real humans doing their best to lead with heart—and making us all wish we worked for them.
#1. He’s the boss now
Source: Palifaith
#2. I quit my job. My Boss’s 10yrO daughter gave me this card. Yes, I did cry. She is the sweetest little girl and being the only female in my office, I would always ask how her day was to make sure she felt comfortable.
Source: Reddit User
#3. My boss at my internship was told by a coworker that I like to listen to music but don’t have headphones atm, so he gave me a headset!
Source: MrQuackalotOWO
#4. Wholesome Boss/Employee Relationship
Source: Cioki1000
#5. My boss lost his fishing buddy (his dad) a couple months ago, so I decided to take him out today and he showed me up with a nice smallie!
Source: Michael5825H
This heartwarming list pulls from r/MadeMeSmile, r/wholesome, and r/HumansBeingBros—subreddits known for spotlighting everyday goodness. Among the cat videos and feel-good rescues are incredible stories of bosses who go the extra mile—and then some.
Like the manager who bought an employee a car so she could get to work safely. Or the CEO who canceled a holiday party and donated the funds to cover staff medical bills. These aren’t stunts. They’re examples of leadership that prioritizes people over profit, relationships over rules.
Grumpy Sharks curated this list to celebrate the kinds of leaders who redefine what “boss” can mean—someone who builds you up, has your back, and knows your favorite snack.
#6. I have THE most amazing boss! I mean, who does stuff like this?? Faith in humanity restored.
Source: kveach
#7. Great boss.
Source: bilbofraginz
#8. This is my boss, running nearly a $200 million dollar company, emailing the whole company.
Source: reddit_dis_dik
#9. 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
Source: welcome2arbys
#10. Happened in Nigerian Bank A security man walked up to the bank manager and boldly told him that he is a graduate and would love to participate in the Aptitude test for the vacant position. The boss allowed him to write the test. He was ‘The Best Candidate’ and got the job.
Source: Reddit User
When a boss shows genuine care, it doesn’t just boost morale—it reshapes the entire workplace atmosphere. Studies have shown that supportive leadership leads to higher job satisfaction, lower turnover, and better health outcomes. But beyond the numbers? It simply feels good to be human at work.
Take the story of a shift supervisor who sent her employee home early with soup when she noticed they had the flu. Or the small business owner who drove 45 minutes to help a new hire with car trouble on their first day.
These moments don’t just improve retention—they restore faith in work itself.
#11. I recently had issues with ulcers and almost bled out, and in my recovery I’ve been very poor and unable to eat enough. I passed out recently due to malnourishment and my boss at my new job surprised me with this. I immediately started crying
Source: McDudles
#12. Our boss makes us breakfast every weds without fail. Really helps the morale.
Source: DatNick1988
#13. 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.
Source: jbrown132
#14. My girlfriend’s boss makes her healthy lunches because she has fainting spells
Source: Metallschleifer
#15. My job sucks, but my boss is great. This type of communication at work is very refreshing.
Source: theo1618
Years ago, I worked under a manager who never asked for more than she gave. She remembered birthdays. She learned everyone’s coffee order. And when I hit a wall during a hard season in life, she offered time off—no questions, no paperwork, just kindness.
When I came back, she’d reorganized my workload to ease me in. I’ve never forgotten it. Not because she saved the company—but because she saved me, quietly, kindly, without ever making it feel like a burden.
#16. Boss just handed me this bonus and said “Thanks for working over Christmas, I know you would’ve rather been with your family.” He’s not wrong, but he’s also the best boss I’ve ever had. Thanks Boss, see ya tomorrow👍
Source: Reddit User
#17. Encouraging email from my boss
Source: lonelyshoppingcarts
#18. Leaving for vacation tomorrow and my boss hands 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.
Source: Reddit User
#19. A compassionate boss
Source: jayy8143
#20. we all need that guy
Source: thefringeseanmachine
A 2018 Gallup study revealed that only 22% of employees strongly agree that their leaders have a clear direction and care about them as people. (source)
That’s why when we see a boss pick up a broom instead of assigning blame, or cry happy tears at a team member’s graduation, we stop and stare. Because it’s rare. Because it’s beautiful. Because it reminds us that workplaces can be driven by heart, not just KPIs.
#21. Being a real boss
Source: Kaos2018
#22. My boss’s response to me saying I wouldn’t be in work today due to ongoing mental health problems. I could honestly cry.
Source: Still-Waters-ASMR
#23. Birthday message from boss, after I called in sick (sick baby)…
Source: isabel_77
#24. Appreciation from my boss. (I work as a nanny)
Source: Ivymoon89
#25. My boss is a gem and leaves snacks and drinks for delivery drivers
Source: PizzaDatAss1738
Some bosses stay professional. Others become lifelines.
There’s the coffee shop manager who showed up at his barista’s mom’s funeral. The retail supervisor who covered a shift and left a grocery bag at an employee’s door with a note: “I know things are tough—no questions asked.”
These are the stories that go beyond job roles. They enter the realm of compassion. Because sometimes, what someone needs isn’t a schedule fix—it’s to know they’re not alone.
#26. This is how you boss
Source: PhenomenalPancake
#27. I injured my leg last weekend and am on crutches. Haven’t been able to make it into work all week with bad, icy weather. Got this text from my boss that he and my supervisor dropped by
I live alone and suffered an injury to my leg during a snowstorm leaving me unable to walk without crutches. Been trying all week to make it into work to no avail. I started at this company a year ago after leaving a horrible work environment. Feels like I found the right people.
Source: SawWhetOwl
#28. The best boss ever
Source: dianses
#29. My G/F just received this email from her boss. She works at a grocery store and they are taking care of her in the midst of this virus.
Source: snwbrdrmidget15
#30. The kind of boss everyone wants
Source: lowpaidsalaryman
Dr. Brené Brown, renowned researcher and author of Dare to Lead, says: “Clear is kind. Unclear is unkind. And empathy is not soft—it’s brave.”
Bosses who lead with empathy aren’t pushovers—they’re powerhouses. They foster trust, loyalty, and creativity. They make it safe to speak up, fail, and grow. And the result? Teams that thrive, not just survive.
#31. I work construction in the Midwest and my boss just delivered all of these food goodies to our home in time for the holidays!
Source: SoDakZak
#32. What i would do to have a boss like this
Source: masschock99
#33. Wish that was my boss
Source: Caterpillail91
#34. I’ve had terrible teeth my entire life. It’s been the bane of my existence. Today I got a $10,000 quote on the cost of what needs to be done, and it just made me feel even more helpless. My boss, mentor, literal angel, is taking care of this for me, free of charge.
Source: born2stab
#35. Some kind words from my boss during a hard time really made the difference
Source: superblank
You don’t have to run a company to lead with kindness. Whether you manage one intern or a full team—your attitude sets the tone.
We, Grumpy Sharks, believe the best bosses aren’t the loudest or most powerful. They’re the ones who ask how your weekend was—and actually listen. The ones who show up for your wins and stay present through your losses.
#36. His boss modified it to let him continue working
Source: winkysocks21
#37. Birthday surprise
Source: Snoo58499
#38. My boss being a total bro about spending time with family
Source: TheWardenOfFive
#39. My boyfriend told me to post this, came out to my bosses and expected to be fired. Slightly different response. Boss came in this morning and called me by my name, hugged me when I broke down crying
Source: lizertoast
#40. my boss and the frog
Source: grungeindiehipster
If your manager has ever made your life easier, listened when you needed to vent, or randomly dropped off snacks at your desk like an office fairy godparent—hold onto them. Bosses like the ones in this list aren’t just supervisors; they’re mood boosters, moral support systems, and occasional stand-up comedians all in one.
Now it’s your turn: Which boss moment made you laugh or go “Aww”? Ever had a manager who made your Mondays bearable? Share your favorite story in the comments or tag that one boss who deserves a raise (or at least this article link in their inbox).
