40 Of The Best Bosses Ever That’ll Make You Wish You Worked For Them
Let’s face it—finding a great boss is like finding a unicorn that offers PTO, listens, and brings donuts. Most of us have crossed paths with managers who think “teamwork” means watching you do all the work. But every now and then, the universe tosses in a boss who actually makes work enjoyable. The kind of boss who sends memes instead of passive-aggressive emails, or surprises you with a cake just because it’s a Thursday.
This article is a cheerful collection of 40 legendary bosses who went above and beyond, cracked jokes, spread joy, and turned their workplaces into unexpectedly wholesome spaces. Whether it’s standing up for employees, celebrating the small wins, or just giving the kind of pep talks you didn’t know you needed, these bosses have earned their gold stars—and then some. Scroll on to restore your faith in workplace leadership (and maybe send a gentle nudge to your own manager).
#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
#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
#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
#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
#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
#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
#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
#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).
