How do you know whether the brave move is to go for it or plant your feet? 

CMOs are making that call with short runways, incomplete information, and teams being asked to adapt fast. Comfort can delay the hard decision. Pressure can push leaders toward false certainty or speed for speed’s sake. Brave leadership is more measured, and it gets stronger with practice. 

In this episode, Drew talks with Todd Henry, author of The Brave Habit, about building that practice into leadership. Todd shows how clarity and agency help teams move when the path ahead is still taking shape. The superhero cape can stay home. This is bravery with judgment, habit, and a much better read on what makes your team tick. 

Three Ways Leaders Get Bravery Wrong: 

1. Trying to manufacture certainty in an uncertain moment
2. Equating bravery with action
3. Motivating the team through the leader’s own lens

What You’ll Learn: 

• How to turn brave leadership into a weekly habit
• Why separating true risk from perceived risk matters
• Why AI works best when it amplifies expert thinking

Listen in for how CMOs can build bravery into their leadership, lead with clarity through uncertainty, and give their teams the agency to move.