Ann Howard, product and technology leader, talks about how leaders need to share information widely and make decisions publicly. Ann says leaders are charged with predicting the future. She lays out her method for making decisions, knowing that there are very few decisions that are irreversible. Ann describes how to scale decisions down, test them, and get information about risks, describes the differences between leadership and management, and how she builds teams that are accountable to each other. Tom and Ann spend some time talking about what makes for bad leaders. Ann talks about when people are drawn to leadership for the wrong reasons, and why you can't be a leader alone. Ann tells why she admires Ray Dalio's idea of hyper realism and the difference between kindness and niceness. Tom asks Ann who is the best leader she ever worked for and why. Tom and Ann talk about raising kids as a test of letting people fail and dig their way out. Tom asks Ann why she doesn’t think of herself much when she's leading. Ann talks about how her personal story informs her desire to lead. After Ann tells a story about her daughter on the playground, Tom asks how things have changed for women since Ann was a kid.