Bad Boss – Good Boss: Learning from Both Kinds

Gary Magenta
Sr. Vice President of Client Solutions,
Root Inc.

I’ve always been fascinated with the things that distinguish a good boss from a bad boss. Just what is it that makes a good boss good and a bad boss bad? As I’ve been working on a book on management techniques, I’ve been asking people for their experiences with managers who stand out to them in negative or positive ways. See if you can relate to any of these horror stories – and success stories.

Thella F. Bowens
Thella F. Bowens
President and CEO,
San Diego County Regional Airport Authority
San Diego County Regional Airport Authority

The absolute worst boss I ever had was a bully – not just to me, but to everyone in the organization. He had all of the classic problems of a bad boss. He never gave a compliment. He looked for things to be wrong. He was a control freak and made changes to our work without consulting us. But he did teach me fortitude. He taught me to be thorough and to look at things strategically. His “nitpicking” attitude led me to watch out for things that could leave me vulnerable.

On the other hand, I once had an extraordinarily bright boss – the type of person who could sit with kings and hobos. He had a great sense of humor, didn’t take himself too seriously, and had very high performance standards. He pushed us to excel. People told me I wouldn’t like him because they perceived his demanding standards to be harsh. But I did like him. He was charismatic, and he taught me things. When I wrote my first report for him, he said, “This (expletive) report sounds like you’re trying to write a novel!” I had written, “My feelings are…” and he started to sing the song “Feelings”! Then he sat with me and, sentence-by-sentence, showed me how to better structure it and better convey my thoughts. He continued to help me hone my writing skills. One day, I submitted writing to him and never heard back. I asked his secretary for his comments, and she said he’d signed off on it with no changes! She assured me that he had never done that before. This boss challenged me to think, and he challenged me to challenge him. He gave me courage to say what I thought without feeling stupid. And I still take pride in my writing skills.

Another good boss nurtured me and challenged me to stretch without “telling” me. He put me in charge of new things and let me figure them out. He was available when I had questions. Once, a high-ranking political official called my boss to get him to change my mind on an issue. My boss let me make my own decision. I knew he had my back, which made it easy to make the right decision. Because of what I learned from him, I want to help others gain visibility and new opportunities as well.

Adrian Kurre
Global Head,
Hilton Garden Inn
Hilton Garden Inn Logo

The best manager I ever had was – lucky for me – the first manager I ever had. Curt Johnson owned a service station in a small town in Minnesota. This was one of the old-time gas stations where you actually got “service,” like cleaning windows and checking tire pressure. Curt was firm, fair and consistent. He told me exactly what he wanted me to do, watched me do it, and gave me feedback. He was continually patient about teaching me how I could avoid repeating mistakes.

Here’s an example: When I had proven my excellent customer service skills to Curt, he decided to let me drive the bulk delivery truck to construction sites. Despite never having driven a stick-shift truck, I drove the big rig to fill up some equipment. The first tanks had regular fuel, and the last had diesel fuel. You can probably guess what happened. I put 100 gallons of regular gas into a diesel engine. When I realized this, I briefly wondered if I could get away with this error, but I knew I had to tell the truth. The construction boss was not exactly happy, as it took 8 hours to drain the tank, clean it out, and get it working again. When I got back to the station, Curt calmly sat me down and told me that I’d screwed up. And without losing his temper, he asked what I had learned that day. He didn’t fire me and he didn’t even yell. He told me in a fair and honest way that I had messed up, but that I had made an honest mistake, I’d admitted it, and I’d become wiser.

Curt’s management skills were tested again just a couple of months later when I drove the bulk truck a half-mile with the emergency brake on. This caused a grease fire under the truck filled with gasoline. The fire truck, Curt, and I arrived at the fire at the same time. Curt smiled, but the next day, we had another chat about what I’d learned.

The greatest thing Curt did for me was to be consistent all the way. He knew the difference between being plain stupid and making an honest mistake. He taught me that it’s best to hire good people, explain what they’re supposed to do, and let them do their job in whatever way they like best. I remembered all he had taught me and developed them into habits for being a good leader. Whenever my team gets good results, I give the credit to Curt.

And this is Gary’s story…
I was already in my 30s when took my first corporate job. I’d had my own business and had worked with my family, so I’d never really had a true manager. When I sold my business and accepted a corporate position, the plan was to work remotely for nine months, and then relocate to take on a newly created position.

The man who would become my manager was an affable, tenured vice president with a gift of gab. Once I started with the company, however, I never heard from him. Never. I told myself that he was really busy, and I’d have plenty of time to talk with him later. When I relocated, I was bursting with enthusiasm as I walked into my manager’s office on my first day there.

“What are you doing here?” he said. “Is this the week you’re starting? I forgot. Ask my secretary to find you a place to sit.” The only thing worse than his welcome was his negative reaction as he reviewed the raise I was supposed to get. This was my first day in my new office, the beginning of a new position, and I was already having doubts.

Whenever I had the chance to meet with my manager, he talked from the start of the meeting until the very end. He was always multi-tasking – talking, typing, and answering his phone at the same time. He never once asked me a question.

I was frustrated. I wanted his input, feedback, recognition, and counsel. After about five months, I confronted him about my frustration. I said that I didn’t feel I was being heard, and that I had a lot to offer. That’s when he told me he was leaving the company for another job!

This was the end of my first experience with a “manager.” While I believed, and still do, that he wasn’t a very good manager or role model, he did start me thinking about what kind of a manager I’d been in the past, what kind of manager I wanted to become, and how I would like my future managers to engage me.

I decided that I wanted to have a manager – and be a manager – who treated people with respect, who valued them as real people with meaningful lives and valuable experiences that extended beyond the halls of business.

What did you learn from your best and worst managers? Let us know! Email your stories to greatmanagers@rootlearning.com.