Why Your Team Doesn’t See You as Authentic (And What to Do About It) with Maya Rupert

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 getting people to truly own their work.If you've ever been told to "just be yourself" and wondered whose self they meant, this one's for you.🎧 Chapters00:00 Welcome and Maya's introduction (plus a guest appearance from Crispin the cat)01:45 Maya's path and why she wrote The Real Ones04:01 How do you actually define authenticity?05:54 The vibes-based test we use to judge leaders09:49 What the 2020 campaign cycle revealed11:48 Inside a presidential campaign: likability is "squishy"14:46 The irony of measuring your own authenticity18:21 When there's only one winner: redefining what winning means20:25 The values Maya looks for in the leaders she backs22:39 What business still needs to learn from movement work26:38 What worries Maya most right now30:43 The one thing she'd fix overnight31:56 Bring joy to your hustle35:17 Where to find Maya and The Real Ones📕 Maya's book, The Real Ones, is out now wherever you get your books.Find Maya online: @MayaRupert on X, maya.rupert on Instagram and Bluesky