When Hank Gilman started his career, he aspired to be a great journalist. But just a few years later, he became an editor and suddenly found himself in charge of a slew of difficult reporters—without a clue how to manage them. Plenty of managers start out this way, never asking, expecting, or training to be responsible for others.

These accidental bosses often find that learning to manage is like learning to swim by being dropped into the deep end of the pool. Now the deputy managing editor at Fortune, Gilman learned the hard way about what makes a good boss. He shares his insights from the good, bad, ugly, entertaining, and sometimes just plain bizarre stories from more than two decades in the management trenches.