Fred Brooks, the man who managed the development of IBM’s System/360 family of computers knows a thing or two about good judgment, he wrote the book on it. Brooks wrote about his experiences managing systems development at IBM in the book The Mythical Man-Month: Essays on Software Engineering.
The book coined what is known as “Brook’s law,” which states that “Adding manpower to a late software project makes it later.” Brooks discovered this law when he himself added more programmers to a project falling behind schedule, then concluded that it delayed the project even further. Using this and other examples of what he learned in his career, Brooks is quoted as saying, “Good judgment comes from experience and experience comes from bad judgment.”
What are you doing to prepare yourself for leadership? Making some mistakes on your own is inevitable and one way to learn; but learning from the mistakes of others is the easier route. Are you reading books? Do you have a mentor?