No matter what bosses you've had, I hope you learn from them. What best practices do you observe that you can adopt for your own management style? What bad habits do you notice that you should avoid?
In this light, I'd like to reflect on several managers I've had over my career, both good and bad. I'll use first names only, for the sake of privacy.
My first job after university was systems administrator for a small geographics company. We made custom maps. I had a great boss! I've mentioned Gwen a few times on this blog; she was an inspiration to me. She helped me through some tough first experiences at work, like the first time I made a mistake on one of our Unix servers. From Gwen, I learned that while it may feel like this the first time anyone has done this (such as when you're facing a mistake, or stuck on a problem) others have probably done something similar before. Don't be an island; don't go it alone. Instead, be a peninsula; attach yourself to someone who has been there before, and get their help.
My next job was at a small company owned by a law firm, scanning and processing legal documents. We helped law firms sort through mountains of paper, an especially valuable service as part of "electronic production and discovery." My boss here was not that great. Jerry seemed supportive, but when the chips were down he only looked after himself. I learned to be careful of him when we went to meetings together. I also learned to watch my back. And along the way, I learned how to read upside-down; Jerry often left planning memos laying on his desk when we met, and these accidental previews were often my only warning to what changes were coming.
I then moved into higher education, leading a web production team at the University of Minnesota. I would stay in higher education for the next seventeen years. My first boss there was Mike. From Mike, I learned the importance of meeting with people, of building coalitions to work together. I also learned that relationships matter, especially with people who don't see eye-to-eye with you. You can leverage the relationship to work past difficulties and get things done.
Technically, Bob wasn't my boss; he was an outside contract project manager we hired to uplift our web registration system. But my real boss, Mike, realized the political importance of the web registration upgrade, so he assigned me and my team to work with Bob and deliver the new system. Bob and I got along pretty well. I didn't take my day-to-day direction from Bob, but we would often meet anyway to plan what was coming up. I learned to always plan for the future, and to always have a plan "B" ready to go. And by watching Bob in difficult meetings, I learned that you should always know who your friends are before you walk into an argument.
Kari took over for Mike after he left the U of M, so I reported to her for several years. Kari was great to work with. She had an innate understanding of the importance of play. We had a chessboard in one corner of the office, and developers and database administrators would sometimes take breaks to challenge each other in chess. I was wary at first, but the opportunity to step away from a problem and to apply their minds in a different way often lead to discovery and new solutions.
After the U of M realigned its technology units, I was moved to the Central Computing Operations, part of the Office of Information Technology. CCO supported the enterprise systems across the U of M. My new boss, Nick, taught me how to on-board new staff, especially as I transitioned to my new role. Nick brought me to meetings and exposed me to executive-level briefings. With Nick, I learned the only way to tackle large projects (we supported PeopleSoft and the registration systems for the U of M) was to have confidence in your team members to do the right thing, and in return the manager needed to be there to support the team members and remove obstacles.
I later moved into a senior manager role within the Office of Information Technology. For a time, I reported directly to the Deputy CIO. Scott was a great manager, and I learned from him that people grow best when you give them responsibilities that are just outside their current capabilities. Watch them, make sure they are supported, but leave them to take on the larger role. Under Scott, I grew quickly. It wasn't uncommon to be in a leadership meeting, discussing some problem that needed fixing, and hear "let's form a working group on this, and Jim can lead it." And somehow I always managed to get the team to pull together and figure it out.
By watching Doug, I learned several lessons about what not to do, how not to act. For example, model the behavior that you want reflected in the organization (Doug modeled poor behavior). But I did learn one or two good things from Doug. For his faults as a leader and manager of people, Doug was a very good project manager. By working with Doug, I learned how to manage projects more effectively, including how to develop and leverage an effort-based workplan.
I moved to the U of M Morris as the campus CIO, and worked under Lowell, one of our vice chancellors. Lowell was a very supportive manager, and an insightful leader. He also delegated well. When we met to discuss issues and plan projects, he always left the technology leadership to me. "Jim, I hired you to lead the IT, this one's yours." Lowell also helped me reach out to the campus, and coached me as I navigated a minefield of campus issues.
I'll call him Butthead so I don't have to use his name. Technically, all the campus CIOs and collegiate IT directors had a dotted-line to Butthead through an organizational alignment. I reported directly to Lowell for day-to-day and most strategic planning at Morris, and had a dotted-line to Butthead for certain strategic items for system campus planning. Butthead liked to play the role of benevolent mentor, but in reality he was petty, childish, immature, and manipulative. But I did learn one lesson: good organizations eventually recognize and reject these bad actors. Technically, he wasn't fired, but the news reported his resignation was accepted "effective immediately," so you can draw your own conclusion there.
After seventeen years in higher education, I moved to local government. I work for a great boss. Johanna provides great coaching. While higher education and government are very similar (we have the same governance, structures, org charts, processes, committees, etc—they're just labelled differently) there are a few differences here and there, and it's good to have someone to help me out when I need it. Johanna was my predecessor in my position, so I can always go to her to ask advice or to seek background context on a situation. But she never gets in my way; she doesn't try to be the CIO. Johanna leaves IT decisions to me, and she takes care of the larger issues for our section of the organization. That makes for a successful partnership.