About this episode

Maya Rupert discusses the concept of authenticity in leadership and its implications for women and people of color.

What if the authenticity we keep demanding from leaders isn't actually a real, measurable thing? In this episode, I sit down with Maya Rupert , who managed Julián Castro's 2020 presidential campaign, becoming only the third Black woman in U.S. history to run a presidential campaign, and later served as a senior advisor to Elizabeth Warren. Today she's Executive Vice President at Blue State and the author of The Real Ones: How to Disrupt the Hidden Ways Racism Makes Us Less Authentic. Maya challenged something I hear constantly in the corporate world: that we can just "sense" when someone is or isn't authentic. She argues that judgment is mostly vibes, shaped by how many versions of "someone like them" we've seen before. Which means the narrower our reference points, the harder it is for women and people of color to ever be read as authentic, no matter how genuine they are. We get into how she defines real, self-reflective authenticity, what it was like running a campaign with no budget for message testing, why she asks every candidate to define winning beyond winning, and the one lesson from politics and movement work that business still hasn't learned about…

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