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My Best Boss - Stories of the Greatest Bosses of All Time

Written By: Alison Green
June 5, 2014
7 min read

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 managers they talked about. (Have you had a boss who measured up to the ones here? Leave your own accounts below!)

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.

Written By: Alison Green
Alison Green writes the popular Ask a Manager blog where she dispenses advice on career, job search, and management issues. She's also the co-author of Managing to Change the World: The Nonprofit Manager's Guide to Getting Results and former chief of staff of a successful nonprofit organization, where she oversaw day-to-day staff management, hiring, firing, and employee development.