Why Your Team Doesn't See You as Authentic (And What to Do About It) with Maya Rupert
Why "Just Be Yourself" Is Bad Leadership Advice
Authenticity is treated as a baseline requirement for leadership, yet almost nobody defines it. That gap is the problem. When something matters this much but stays undefined, we judge it on gut feel, and gut feel is trained on the leaders we have already seen.
My guest Maya Rupert has watched this play out at the highest level. She managed Julián Castro's 2020 presidential campaign, becoming only the third Black woman in US history to run a presidential campaign, and served as senior advisor to Elizabeth Warren. Today she is Executive Vice President at Blue State and author of The Real Ones: How to Disrupt the Hidden Ways Racism Makes Us Less Authentic.
Her argument matters for anyone stepping into an executive role where few people share their background: the fewer versions of "someone like you" the room has seen in a leadership seat, the more likely you are to be read as inauthentic, no matter how genuine you are. Technical leaders moving into influence roles feel a version of this too. You are being measured against a template you had no part in creating.
How to Tell Real Authenticity from Performed Authenticity
Rupert separates two kinds of authenticity, and the distinction changes how you should think about your leadership presence.
Self-reflective authenticity is an internal audit. Look at the choices you have made and ask whether each one is true to you or adapted for a setting. Adaptation is not automatically inauthentic. It is information about your story and your values.
Perceived authenticity is the version other people assign to you, and Rupert argues it does not actually exist as a measurable thing. Two people can call the same leader inauthentic and mean entirely different things. Her sharpest framing from the episode: authenticity isn't writing a book, it's defending a dissertation. The audience always gets a vote, and the audience brings its bias.
Why Some Leaders Are Never Read as Authentic
In 2020, a historically large and diverse candidate field narrowed to two older white men who were consistently described as authentic. Rupert's diagnosis: we assess authenticity against a mental library of prior examples. Some leaders have thousands of reference points working in their favor. Everyone else has a handful, so any deviation registers as incongruence.
The takeaway for executives: when you feel pressure to perform a leadership style that is not yours, the meter being applied to you may be miscalibrated. Your job is the internal audit, not the performance.
How to Define Winning Beyond the Scoreboard
Before taking on any campaign, Rupert asks the candidate one question: assume you don't win the office, what does winning look like then? Leaders who can answer that build more committed teams and survive setbacks intact. The same question applies to your product launch, your reorg, and your promotion cycle.
How to Build Team Ownership: The Lesson Business Hasn't Learned
People commit when they see the whole board. From her early career in corporate law, Rupert saw how handing someone a task without the larger picture guarantees hired-hand energy. Reading in even the most junior person on the full mission produces ownership, and the second question that actually moves work forward.
Key Takeaways & Timestamps
04:01 Self-reflective authenticity defined: audit your choices, not your image
05:54 The vibes-based authenticity test and why it fails leaders who don't fit the mold
09:49 How bias shapes who gets called authentic and who gets called "too rehearsed"
14:46 The paradox of measuring your own authenticity through other people's perceptions
18:55 The question every leader should answer: what does winning look like beyond winning?
22:51 Why reading in junior team members on the big picture creates real ownership
30:53 The one change Rupert would make overnight
32:32 Bring joy to your hustle: the reconnection habit that shrinks big problems
Ready to Lead as Yourself Instead of a Performance?
If you are a leader trying to figure out which parts of your style are truly yours and which are adaptations that no longer serve you, that is exactly the work I do with executives. Start at coachfulcoaching.com.
📕 Maya's book, The Real Ones, is out now wherever you get books. Find her at mayarupert.com, @MayaRupert on X, and maya.rupert on Instagram and Bluesky.