Let me preface this by saying I do not recommend learning lessons the hard way. There's a wealth of human experience out there to learn from before you go off and make the same bone-headed mistakes. However, bone-headed mistakes will be made regardless of how cautious you are. In those cases, please go into it with a Fail-Fast, Kaizen mindset so that the mistake becomes a short-lived learning experience.
The Almighty PM
I've made a lot of mistakes in life, which means I've learned a lot of lessons “the hard way”. The one such lesson that has had the most impact on my current work life took place my senior year of college. I was in a capstone class where we were to organize ourselves into a real software team to develop a real-life application on top of a new API that we had Beta access to. We were given a little guidance, including how previous classes and many companies organize themselves, but told we could do whatever we wanted. We ended up with a very “traditional” model of a few Dev teams, a few Testing teams, an Architect, and the one Project Manager to rule them all.
I was eager to prove myself, so I went for the PM position (oddly enough, I didn't really have any competition from my obviously more self-aware classmates). The problem is Computer Science majors in their fourth (okay sixth) year of study haven't usually had any PM classes or experience. My architect laid out the architecture, lots of open source Java, wikis, subversion, etc, and the class was excited to get started. However, I was concerned about how to manage the work, as well as expectations. I started demanding individual Gantt charts up-front for the duration of the semester. I was asking each team lead to compile the Gantt for their team and report that to me so I could put it all together.
The Blind Leading the Competent
Basically, I was trying to command-and-control manage a team of part-time team members, all of whom were taking at least 12 hours that semester and had limited time to spend on this class. Of that limited time, I was asking an unreasonable amount of time on administrative work. My architect was an excellent “Yes Man”, which made it difficult for me to see what I was doing wrong. The tipping point came when we weren't getting the information we were asking for from the teams and we were way behind where we expected to be on the application. Our professor was pulled away for a class and gave me the option of keeping the class time or giving everyone the day off. My architect decided, with my blessing, to use that time to express our mutual disappointment with the team and shame them into getting their act together.
I knew it was all over when the architect started his oratory with something to the effect of “By the time I finish talking you should all be mad at me, and that's okay because I'm mad at you.” It was a horrible hour and ended with our organization in shambles. I was a broken, broken man who was certain I was going to fail the class.
A Lesson in Servant Leadership
Then one of the testing team leads asked if he could meet with me to talk through things. He kindly and patiently explained why what we did was so stupid and counter-productive. He told me that the teams needed a cheerleader, not a dictator. He asked me to spend time with the individuals on the teams. He wanted me to spend more time in face-to-face conversations instead of mass emails. He wanted me to understand how hard the class was working to accomplish a common goal so that I would stop wasting their time with unnecessary busy work. He wanted me to focus on listening and removing roadblocks. He is now, unsurprisingly, a manager at Amazon, and someone I still hold in high regard.
I didn't fail the class because the objective of the class wasn't to develop a fixed scope within fixed time and budget. My wise professor wanted us to experience real-world project work as best we could in an academic setting and learn from it. He saw me try to turn things around at the end and knew that I had seen the error of my ways. He knew that I had learned my lesson, albeit the hard way.
So what lesson did I learn? To be honest, I initially thought that the lesson I was supposed to learn was that I suck at Project Management. I could not be trusted with leading a project to completion. I could code well and kinda sorta test, but the realm of Project Management was beyond my grasp.
This lesson was reinforced when I entered the workforce a few months later and saw command-and-control PMs leading projects “correctly”. These were professionals who did not go on rants against their developers and testers. They were not perfect, but they did their best to make things work in alignment with the command-and-control, iron triangle, Waterfall-driven style they were trained to use. Despite their best efforts, I found myself in War Rooms quite frequently, and my wife learned to not expect to see me in the months surrounding a Production install. I didn't realize it at the time, but I was living through the hell that I had just put my classmates through.
Of course, that wasn't the PM's fault. As I said, they were doing the best they could, and we were doing the best we could. The problems were much deeper than any one individual. We had to change the way we work, starting by not only recognizing but emphasizing the human element of software development.
The real lesson is that command-and-control Project Management doesn't work. Had I taken the time to understand Lean/Agile development processes and practices, I could have done a decent job as a Scrum Master or Agile Servant Leader in my capstone class. I might have even done some coding and testing alongside my cross-functional Agile development team(s). Even before I learned that lesson, I learned the importance of being a cheerleader. I have always striven to let the teams I've worked with know what a great job they're doing and how much I appreciate them. I haven't always succeeded, but that pep talk I received my final year of college never left me.
Once I realized that what I was experiencing in corporate life was essentially the same as that capstone class, I vowed to change things. I delved into the world of Lean and Agile and brought the things I learned back to my area. To many people it looks like I've picked it up extremely quickly; in reality, I've been learning this lesson for at least six years. If anything, I'm ashamed it took this long to finally “click”.