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Heart-warming Stories About Best Bosses Ever

Last Update: May 4, 2020

I really like my boss, he’s the best! How many times have you heard this? I bet so rarely that you can count them on the fingers of one hand. It seems like it’s much easier to find someone who thinks their boss is awful than finding someone who genuinely likes their boss. It makes you think if good or best bosses are just mythical creatures that exist only in theory? Well, no. That’s not the case. We went on Reddit to prove our point, and we’re sharing with you some of the best stories about best bosses out there.
Yes, they are real.

Best Bosses: The boss who brought drinks and snacks

dannyr, Reddit

I once had a boss called Rusty. Rusty was the most unassuming person you’d ever see running an ISP Call Centre in the early 2000’s. Rusty wasn’t technical at all (he was only there because he couldn’t find another job as a Supermarket Manager, where he’d spent the last 20 years) and didn’t know a modem from his a***ole.

HOWEVER, what Rusty did have are awesome staff management skills. Every day he’d bring in an esky/cooler full of drinks and snacks for the staff. He kept a lolly jar on his desk full of our favorite sweets, and he always, always backed us up in front of customers.

Management would often send through directives that Rusty would send on and go “yeah, do whatever they want…unless you think it’s wrong…then do whatever you think you should – just keep me informed”.

We always got our work done for Rusty because we wanted to keep him around. Eventually, he was made redundant when the company got bought out (in 2 years at the same company I got made redundant 5 times and never moved desk – I AM A DOT COM BOOM SURVIVOR) and is now the state manager for one of the largest supermarket chains here in Australia.

Man, I miss Rusty.

A boss who trusts his employees’ judgment

One of the best bosses ever..trusted my judgment even if I didn’t always deserve it. After my mother’s death, I drank every day for six months. I called him one evening, drunk & crying. Instead of being horrified, he hooked me up with our employee assistance folks…which eventually got me back on track.

He was good to all staff members, not just me. The company was lucky to have him too. They got their money’s worth, both from the boss and his staff. I would have given him my left arm.

The boss who trusts his employees' judgment


The best boss for many reasons

Considering I worked at a store that had more than a hundred employees and one boss per department (not all could be listed as best bosses), about seven for cashiers (was a cashier), then the store manager, and three assistant store manager, I’ll still say the store manager, Floyd, was awesome.

He was an awesome guy, always willing to help out with questions, didn’t really hide in his office, would come to the front of the store and jump on a register if we needed another cashier, he never minded helping out a customer if there was nobody else around that could answer a question they had (since cashiers knew very little about the store and where things were located).

About thirty minutes after the store opened there would always be a brief opening meeting with all employees that never involved cashiers, and there was always some kind of food brought for employees (usually donuts or breakfast tacos) that he always made sure cashiers who couldn’t leave their registers got some. He never cared about cashiers eating at the registers (it was typically candy or chips, but sometimes donuts or a taco in the morning) or having drinks there. He bought a Keurig coffee maker for the break room instead of the generic cheap one that they give the stores. There would often be several ice chests sitting in the break room full of cans of soda that we didn’t have to pay for, occasionally there’d be a cake or something.

Every now and there’d be a massive barbecue that he’d personally oversee and it would make the back of the store smell absolutely amazing, and even if people weren’t working enough hours (at least seven) to earn a separate lunch break he’d make sure everybody got the chance to get something to eat if they wanted, even excusing people running over their fifteen minute breaks so they’d have a chance to eat.

I left after a year there because I was moving for school and even though I hadn’t talked to him very much, my dad (who goes in fairly often) texted me one day saying, “Was just in the store and ran into Floyd. He asked me how you were doing and said you were a great employee.” something like three or four months after I’d stopped working there. The fact that he remembered somebody after so long was pretty damn cool and that he recognized my dad as my dad (my dad did come in sometimes when I was working to either buy stuff or occasionally drop off my water bottle or something at home by accident and we’d talk for a minute or two if I wasn’t busy and I would tell other cashiers who asked that it was my dad but I don’t think I’d ever said that around Floyd.) was awesome.

The awesome boss for many reasons

The enthusiastic boss

Not my current boss but I did have one of the best bosses before I had to leave (location and pay reasons).

The main reason was that he loved our work, everytime he explained something he was genuinely enthusiastic about it and it is also the only company I have worked at that seemed to actually care about giving good customer service. After working there a few months I got to know a lot of customers by name and our office (admittedly only 4 people and a dog) was generally a friendly, relaxed environment all because of him being a very friendly, upbeat person.

He also taught me some very good habits when it came to telephone/email conversations, the police alphabet (alpha, bravo, charlie) and a habit that has helped me in every job since – keeping a notebook and meticulously writing down everything from phone calls and meetings to how I solved a problem on the server or something.

Bonus – he would often pop by the local shops to buy his lunch and bring in a pack of cookies or something that “fell in my basket” for us to share.

Other best bosses ever

L.T. Neal. He encouraged people to do things their own way as long as they got the work done. He saw to it that people had the chance to learn new things that got them opportunities for better jobs.

If you screwed up he let you know clearly what you did wrong, what you needed to do to fix it & how to avoid it in the future. When people complained about his people he always assumed they had something wrong & his people were not at fault until it was proven otherwise. He was a good guy.

My current one, he’s a geek! We talk a lot about movies, Star Wars, he worries about his employees, and sometimes he brings donuts! I do wish he could pay us more, or at least get a good coffee maker…

I’m 22 and have had the same employer since I was 15. They treat me well and in turn I’ve been a hardworking, loyal worker who’s advanced from being a groundskeeper to being in charge of access control to the property (a luxury condo) most evenings.

Some of the comments have been censored or edited for grammar.


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