The current goings-on at a friend’s place of employment, and the bad luck this friend seems to have with employers, has caused me to reflect upon my own employment history. When I think back, I realize I’ve had good bosses, and mostly good working environments.

My first real professional job after college was probably my worst. I was on my own in a small town in northern Ohio, working for a small company where everyone knew almost everyone else. I took the job because it was the first one offered to me, and I felt at the time that it was a good stepping stone to something better. In many ways it was: I learned a lot professionally and personally, but the job itself was remarkably unsatisfying. My boss was an interesting person, and I find myself having mixed opinions about that person now. I learned a lot, but I think the largest take-away from that experience was “what not to do”. I do lament the fact that I didn’t keep in touch with my peers after I left: they were a neat group of people, and I would like to be able to talk with them again some time.

After that, I moved back to Columbus and worked for the local branch of a national computer consulting company. A friend got me into the company, and we were put on the same assignment together for awhile. There was a lot of travel involved, which at the time I liked – especially when I was put on an international project that took me throughout Europe! I earned my Microsoft Certified Systems Engineer certificate while working here, and I was excited about the doors that I thought that piece of paper would open. I was eager to start working on servers and advanced client networks, but my immediate supervisors were content to keep assigning me to simple desktop support contracts. I rarely interacted with my immediate supervisors, instead reporting to the assignment’s project manager or client. It was from these gentlemen that I learned a lot about how to execute a successful project; the importance of a strong finish; and the value of teamwork.

The one strong memory I have of my direct supervisor at the time (I went through several, as the company cycled through management teams) was during a performance review. He used a scale of 1 through 4, much like an academic point system. He told me that he never ever gave anyone a four, because a four was perfection and no one was perfect. There’s always room for improvement. I thought at the time – and still think – that it was pretty stupid to spend so much time explaining to me why I’d never get the best possible score. A better use of time would have been to talk to me about ways I could improve, and to celebrate what I had been doing well all along.

After the consulting company, I took a position at a small non-profit agency focusing on mental health for children. My job was to build a computer network for them, from top to bottom. It was, in many ways, a dream job. I got to select and implement the solutions I felt were most appropriate for the organization. Looking back, I see that many of my decisions were affected by hubris, and what I built, while functional, was not as good as it could have been. Nonetheless, I was very proud of the work I did there, and it was an exciting time for me. It was also very motivating to know that the work I did directly helped the mental health professionals provide long-term care to kids in crisis.

My boss at this organization was probably the most influential in terms of my professional development. Very early on in my time there, my boss explained to me that he wanted me to fail. I was shocked at first, but as the conversation unfolded, I learned what he meant. He wanted me to experiment, and try wacky things, and generally take risks in order to develop the best possible solution. Each failure I experienced was a lesson learned, and would result in that much better of a product at the end. If I got it all right the first time, I was either playing it too safe, or just getting lucky: neither of which would prepare me to deal with unexpected problems down the road. (I was reminded of this sage advice as I read J.K. Rowling’s commencement address to Harvard.) My boss’s job was to promote an environment in which it was safe for me to take risks and to fail.

My boss never once took credit for anything I did. He encouraged me to go home early after a couple of long days of work. He encouraged me to take long lunches (usually with him!) to brainstorm new ideas and look for ways to tackle long-standing problems. He supported me 100%. He was exactly the kind of boss I needed at that point in my life, and I’m eternally grateful that we got to work together for as long as we did.

After (almost) everything was put in place, it was agreed that we needed another person to help with the day-to-day support issues. We hired from within, and transitioned one of the clinical staff to an IT support role. I was made this person’s supervisor. This was my first real experience with being a boss. Frankly, I was terrible at it. Even with a terrific role model to follow like my own boss, I was an ineffectual supervisor, a poor motivator, and worst of all not very patient. I’m not sure why the guy stuck around as long as he did, but he seemed to take it all in stride.

I was, unfortunately, let go from that organization. My boss and I had a great working relationship, but my relationship with the CEO of the organization was not as robust. (In fact, no one had a particularly positive working relationship with the CEO.) The CEO quickly hired a friend of his wife’s to replace me. I stayed in contact with my former boss, meeting him for lunch on a monthly basis, and got updates about the goings-on since my departure. All the work I had done to build their network was ripped out and re-implemented from scratch by the new guy. That’s pretty common in IT: it’s easier to build it up your way than learn how your predecessor did things. Unfortunately for the organization, the transition was both expensive and complicated, and there was a major interruption in business continuity.

After several months on unemployment, I finally found another job. My first day was on September 12, 2001. As you might expect, things were more than a little hectic around the office, and it wasn’t a particularly fun time to start a new job. I wasn’t particularly thrilled about the specific job, but I was thrilled to be working again: unemployment sucked for me. This was probably the hardest job I had, because it was in an industry about which I knew nothing. I had to do an awful lot of on-the-job training while trying to keep operations up and running.

My boss was a programmer, who worked from his home several states away. He would fly into Columbus once every couple of months to meet with the users and management, and sometimes clients. He was an extremely challenging boss to work for, for me, because he was, without a doubt, one of the smartest people I’ve ever met. He would almost instantly see short-comings in solutions I proposed, and he constantly pushed me to provide better service than what I had done to date. It was also hard because the casual communication over lunch I had grown so used to at my last job was absent. Instead, we communicated most through email, and the occasional telephone call. I had to be very precise when describing my work to him, because he wasn’t there day-to-day to see me doing it.

Although I was at times resentful, I grew professionally an awful lot under his supervision. Where my previous boss had helped me be a better person, this one helped me be a better employee, something which I absolutely needed. I regret that I let my attitude get in the way, and that my relationship with him was strained more than it needed to be. I liked him a lot as a person, and truthfully enjoyed working with him.

My current boss is very much a blend of my last two. He’s demanding and driven, but balanced and supportive. We have a very positive working relationship, and we like each other personally, too. We share the same goals with respect to our jobs, and he helps me stay focused and on-task when I might otherwise wander off into less important projects. He protects me from a lot of the political goings-on, and ardently advocates for me and my counterpart at every opportunity.

I’ve been extremely fortunate to have such good bosses. I’ve learned a lot from each of them; and although I’m not yet ready to make the transition into any kind of supervisory capacity, I know I’ll have a lot of excellent advice and experience on which to draw when I need it!

home / about / archive / RSS