stories of the greatest bosses of all time

There’s no shortage of stories about bad bosses out there – get any group of workers together and you’re sure to hear some horror stories. But it’s rarer that we get to hear about the good bosses – but there are plenty of them too, and it’s time they got their turn in the spotlight.

I recently asked readers about the best boss they ever had. Here are eight of the most impressive stories you shared.

1. Taught me office politics

“My first boss was amazing. She would often say, ‘Hey come in here and listen to this phone call.’ Then she’d explain the politics of what happened and I’d be expected to handle the next one. Each situation and project she gave me, she prepped me for but expected me to handle on my own as well. She supported me but demanded that I produce results.
 The job had moments that were extremely frustrating and she gave me resources to help understand what I was doing wrong and alter my strategies.”

2. Even fired employees liked her

“My best boss was one from early in my career. She was reasonable about workloads, provided insightful feedback and suggestions, and was always polite and professional in dealing with employees, colleagues, outside professionals, and clients. We knew she had our backs but also would deal with problem employees with empathy and professionalism.

I once ran into an employee she had fired who told me that they admired and respected this supervisor and felt their performance deficiencies had been dealt with respectfully and professionally. The person said she was given every opportunity to be successful including extra training and mentoring but ultimately lacked the skills needed to do the job. How many people would say that after being fired?

Every manager should take lessons from my former boss. I would work with or for her again in a heartbeat.”

3. Helped me move on

“My boss was the one who advocated for a promotion for me and when my employer overlooked me, she helped me to grow and understand that it might be time to move on. When I put in my two weeks, her exact words were ‘I am so incredibly proud of you,’ which was just the right response.”

4. Fair decision-making

“I really appreciate both of my current bosses because of how they handle making decisions that don’t make everyone happy. There are times in any organization where, no matter what you decide, some people will wish you’d decided differently. But these two women are both good at getting input from all the relevant contingents before making big decisions; being candid and open about the decision process when possible, and upfront about not being open when it’s not possible (e.g. confidentiality issues); communicating the decision clearly, acknowledging that people might disagree but still being firm that this is the decision; being open to feedback and revisiting decisions down the line if something changes; not taking things personally or trying to prove their authority. It creates a culture where it’s safe to voice dissenting opinions, but where decisions do get made and things get done.”

5. Foul-mouthed but pushed me to achieve

“I had a boss who was an angry little man and had the most foul mouth. The first time I upset him, he almost reduced me to tears. He was so mean. He used cuss words that I had to research what they meant. Yet he was the best boss ever. I always knew where I stood with him. No BS. No trying to decipher the message. If I screwed up, I knew it loud and clear.

If you messed with me or one of his other reports, you got an even meaner version of him. Nobody was allowed to be mean to us except him. We all wanted to genuinely make him proud. I don’t know if it was avoidance or what, but I always went the extra mile for him. We were always so happy when we did something that exceeded his extremely high expectations. He once gave me kudos in a town hall for a project that I had led. It still ranks as one of my proudest professional achievements. And not because I got recognized in front of peers, but because I had left such a positive impression on him.

Come bonus time, he fought tooth and nail and got his team some of the highest percentages in the firm.”

6. Taught me to be a pro – and to drive stick

“When I started out, I was both afraid of making decisions and had the fiscal perspective of a college student — which is to say, I’d agonize endlessly over spending $75 of the company’s money over the wrong pipe fitting. My boss did a lot of work to teach me a more realistic perspective over this sort of thing, particularly as it related to cost of labor — that is to say, my time and his time.

He also was very up-front about the concept that if I ran into something I didn’t know yet, then the next step was that I was going to learn that something and apply it. Even over little things, like learning to drive stick on the company trucks. This was something that I was already on-board with as a matter of personal preference, but as far as being in an environment that unquestionably supported me in the process of pushing those boundaries to go from ‘a person who does not do X’ to ‘a person who does X’… not necessarily so. That experience actually gave me some really important tools for my professional and personal life. (It’s also down to him that I don’t own an automatic transmission vehicle anymore.)”

7. A great take on mistakes

“My best boss was an attorney at a non-profit legal services firm. My second day on the job, I made some random mistake, like printed the wrong agreement or something minor like that, and when I gave it to him I realized that it was not what he was looking for so I apologized profusely.

I wish I could remember his response verbatim, but it was something like how he believes mistakes are made because of poor instructions, not poor employees, thereby taking the guilt I had for messing up and instead turning it onto himself, that his instructions were not clear enough. I really respected him, not just for that, there are a million other little things that made him a great manager, and a great person. I have worked for many other attorneys since then, and none have earned my respect the way he did.”

8. I’d give him a kidney

“My first boss wanted to surround himself with what he felt were great people. He was there for guidance, but he let you run with your strengths regardless of whether or not something was in your job description. Working for him you just felt more capable, smarter, part of a team.

Not everyone liked him – he was polarizing. But without exception, the higher performing people loved him for the opportunities and those just trying to do as little as possible would have burned him in effigy.

But he had this magic where he could just make you feel like you could do absolutely anything. He instilled confidence like no one I’ve ever known. There is a lot of lip service every day to team players – but at the risk of sounding like a cliché, he really had a way of making you feel like you were part of a team. You knew what you did mattered. It mattered to the company and it mattered to him.

I don’t have any idea how he did it. No effusive compliments, no empty praise, no weekly luncheons or gift cards. When he said ‘thank you, I couldn’t have done it without you,’ you just knew he meant it. There was never a question that he had your back. He engendered a loyalty that’s rare. I haven’t worked for him in years, but if he needed a kidney, I’d see if I was a match.”

{ 28 comments… read them below }

    1. Cruciatus

      She means #2. The fired employee still liked the boss even though she had fired her. The fired employee felt that the supervisor had been more than fair.

  1. LQ

    These best boss stories are really nice to read. We see so many bad bosses, bad leadership and management. It’s great to see some positives.

    (And my best boss ever totally made the cut because she is!)

    I’d love to see great coworker stories but I’m not sure they’d be quite as relevant.

    1. Not So NewReader

      Agreeing about the best bosses stories, and the coworker stories. I think that those stories could be inspiring, too. Not all of us are bosses, but most of us are a coworker to someone else. (How many have had a good boss, but a coworker that was so nasty you had to leave the job in spite of having a good boss?)

  2. AnotherAlison

    I didn’t comment on this topic in the original thread, but while most of my bosses have been average, with one or two who were great, I certainly didn’t appreciate ANY of them like I should have. I feel like I owe them all apology letters. Maybe it was just me, but I think a lot of us are jerks in our 20s (even if you aren’t what society would consider a jerk, by the standard set by your 35 y.o. self, your 25 y.o. self was probably more self-centered and jerky). Managers who deal with a lot of younger employees deserve a lot of recognition.

    1. Not So NewReader

      Am chuckling. I think it is a safe bet that most people look at their younger selves and think “yikes”. That’s pretty healthy, that means we have grown.

      In fairness, I must say that there are older workers that can be very challenging for a boss, also- set in their ways or deciding that they know better than the boss does. ugh.

      A good boss knows how to pick her battles and knows when things should not even become a battle. So she is able to carry on in a manner that reduces the outbreaks in skirmishes.

    2. Annie O

      It’s funny you mention this. A couple months ago I had an opportunity to thank my former manager for all he had done for me. When I worked for him, I just had no idea how much he was doing to protect his people from some internal drama. When I got a new boss, it was like being pushed out into a tsunami of crazy and I realized I should have been more grateful for the cover old boss had been providing! I’m glad I did get a chance to thank him and acknowledge that I should have been more grateful at the time.

    3. louise

      I lost touch with one of my former bosses: he was a mentor before he was my boss and when I had a hard time my sophomore year of college (undiagnosed depression and anxiety), he and his wife invited me to move in with them to get some space from the dorms. This couple provided the perfect balance of space and guidance and I don’t think I could have re-enrolled in college without them.

      While living there, he watched me work two jobs and run myself ragged. He convinced me I could make more money if I came to work for him, so I did. I learned so much, but mainly because he gave me the tools to figure things out myself.

      However, I still regret a handful of the things I said to him in those years. I can’t believe how I treated him. For years I’ve wanted to apologize, but I had heard he’d moved away and I had no idea where to. This year, out of the blue, I got a Christmas card from them and based on the note he included, I gathered his health may be failing. I grabbed a notecard right then and wrote out what I wished I’d done differently and how his guidance has influenced my career.

      I felt like a million bucks when I sent that. 31 yo me thinks 21 yo me was really stupid and I’m so grateful he and his wife just chalked it up to immaturity instead of assuming the worst of me.

  3. Snargulfuss

    I’m currently reading The Confidence Code and have been thinking a lot about women and leadership. When I first started reading Alison’s article I was struck that the bosses mentioned were all women (as I read on I saw that the bosses mentioned in the latter half of the article were men). So now I’m curious: Alison, did you make a conscious decision to choose stories that featured male and female bosses equally or is that just the way it worked out.

    1. Annie O

      It’s also possible that pronouns were deliberately changed – by Alison or by the commenters.

  4. Adam

    I wouldn’t say he’s the best manager ever, but I respect my current manager because he was honest enough to be like #3. He can tell I’m not at all jazzed about my current position and there’s not a lot he can do about it, so I think he’s just appreciative of the work I do while I’m still here while waiting for the inevitable day when I hand in my notice.

    When a possible opening did open up in another department within the company he specifically warned me away from it, not because he doubted me, but because he knew the environment would be a fast track to misery-ville for me. So he looks out for me even if he only has minimal influence on what goes on around the office.

  5. Wonderlander

    My favorite boss was my first ever boss, at my first ever job at Dairy Queen when I was 16. He loved everything about his job and showed it. Once, when he had asked me to go out back and hose down/scrub out a trash can, I remember complaining about it. His response? “I promise, you won’t ever have to do something that I wouldnt do or havent already done here.” That seriously stuck with me. Because you know, cleaning up ice cream is not all that glamorous haha.

  6. JM

    I missed the original post which I shouldn’t have I guess.

    My first manager taught me that most project crunch times are due to the inefficiency of project management team. It is just that they pass the blame on to the worker bees to save their face.

    The best manager taught me to think twice before responding to a not-so-happy client/colleague or an email from a subordinate who fails to understand something in spite of explaining it umpteen times. He taught to empathize and look at it from the other person’s perspective. Also learnt to control emotions from him. I have never heard him blame another person, never seen him stressed and panicky. And the best of all with all due respect to work, he made sure that his team had a perfect work-life balance.

  7. lachevious

    I loved reading everyone’s stories, this was such an uplifting post. And…I must add that I am giddy over the fact that my entry was included.

    I’ll shall tweet this to him and embarrass him!

  8. Loni Ashley

    Well boss 5 would not have been on my list, respect is more important to me than money. To each his own. That said, I’ve had so many great bosses it would be hard to mention all of them. I didn’t stay long with the couple that weren’t. I learned from those situations to really investigate and interview your company during the interview process. Since then, I never started a job with a bad boss again. Alison’s advice for interviewing boss’ right back is spot on too.

  9. Clever Name

    I love this post. As others above said, very uplifting.

    My first boss was a great boss, and so far my best boss. I was fresh out of graduate school and practically taught me everything I know about my industry. He was an amazing guide and mentor. He kept me and my counterpart in the loop and he fought tooth-and-nail to get us good raises, knowing that we were both underpaid. At one point when I was pulled into some political nonsense he explicitly told me that he would fall on his own sword to protect me and my job if it came to that.

    A really amazing guy. He still, over 7 years after I’ve moved on (relocated to another state) sends me a Christmas card every year.

  10. MR

    One thing that I have noticed – maybe it’s something, maybe it’s nothing – is that so many people’s first boss (either as a high school type job or their first job out of school), are either the best or worst boss that they ever had.

    My first boss out of grad school was amazing. I knew it at the time, but once she moved on to another position, it was even more evident at how good she was just based on the next couple of managers that came after her.

    Am I the only one that notices the good boss/bad boss dynamic? Is it maybe because we generally have so few other reference points, and that future bosses help solidify that opinion?

Comments are closed.