Ask Don't Tell

The Questions That Change Leaders with Beth Masterman | #19


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The Questions That Change Leaders with Beth Masterman

In this episode, Oscar sits down with executive coach Beth Masterman, whose winding career through law, politics, psychology, and prosecution shaped her into the rare kind of coach who can walk with clients through the most complex corners of leadership. Beth shares how she helps high-level executives navigate toxic workplaces, difficult conversations, self-doubt, and the human experience behind every professional challenge.

Hear Beth break down the coaching strategies she's refined over decades — including how to turn "why" into "what," how silence becomes a leadership tool, and why the best solutions are the ones people discover for themselves.

Key themes:

  • How to use smarter questions to unlock better leadership
  • Why difficult conversations fail — and Beth's repeatable formula for getting them right
  • The difference between listening and really listening
  • How our past careers silently shape our superpowers

By the end, you'll see leadership (and yourself) differently — and feel inspired to ask the questions that move your life forward.

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Ask Don't TellBy Oscar Subirats