Product Management in Practice, 2nd Edition

Chapter 14. A Manager Among Product Managers (The Product Leadership Chapter)

As ill-prepared as I was for the realities of product management, I was even worse prepared for the realities of product leadership. Which is not to say that I didn’t think I was prepared. After years of navigating the day-to-day indignities of product management, I was sure that I had learned just about everything there was to learn about how to run a product organization—or at least, everything there was to learn about how not to run a product organization. “I can’t believe the people in charge are making such obvious mistakes,” I would say to myself. “If I could just be promoted to the right position, I’d be able to fix this whole mess in no time.”

Several promotions later, the “whole mess” remained very much unfixed. And most of the steps I was taking to make it better—steps that had worked quite well when I was a product manager, thank you very much—seemed to be making it worse. Slowly but surely, I began to develop some empathy for the leaders who I had once badmouthed over after-work drinks.

Over time, I began to wonder if people were meeting up for after-work drinks to badmouth me. I wanted to be a “cool boss,” but I was also terrified that folks in my direct line of reporting would make mistakes that reflected poorly on me personally. When people came to me with problems, I fell back into old habits of commiseration: “I know, right, this company is SO MESSED UP!” Unsurprisingly, that line didn’t ...