Redefining leadership and success with Deesha Dyer
From the Obama White House to bestselling author and social impact entrepreneur, Deesha Dyer has built a career defined by resilience, accountability, and authenticity. For eight years she worked in one of the most high-pressure environments in the world, eventually serving as White House Social Secretary under President Barack Obama. Today, she is an author, public speaker, and the founder of a company that helps businesses, entertainers, and organizations act more responsibly in their communities. Behind the achievements is a human story of self-doubt, growth, and a commitment to creating spaces where people feel seen and safe.
Leadership that owns mistakes
Asked what shaped her as a leader, Deesha points to accountability. As she puts it, “Oftentimes, when you’re a leader, sometimes you feel like you don’t want people to know that you’re wrong or that you did something bad.” Hearing hard feedback about micromanaging or trying to do everything herself became a turning point. She describes the work as taking criticism in, taking responsibility for it, and then changing behavior going forward. That is how trust takes root. Leadership is not a performance of perfection, it is the daily practice of owning decisions and making it safer for others to do the same.
Confidence and redefining success
Deesha is open about the invisible barriers that do not appear on a résumé. “So I’ll say that some of the invisible barriers that I’ve had to face have been my own confidence,” she says. During an intense period coordinating major events, the strain showed up physically through headaches, sleepless nights, and a constant stomach ache. That was the moment to reset. She began to anchor her worth in who she is, not only in what she has achieved. “But in the end, the beginning and the end, who I have is myself.” Her advice to her younger self follows the same line: “really to define success on your own terms.” Not meeting a prescribed timeline does not make anyone less worthy. What matters is pursuing the work that moves the needle in social impact and in the community.
Psychological safety in practice
Deesha’s view of psychologically safe workplaces is both empathetic and firm. “We are not numbers, we are not statistics. We, in a workplace, we are not just our productivity, we are actual people,” she says. Humanizing colleagues is the starting point, not the finish line. Safe environments also require follow through. In her words, “we have to have measures in place for accountability and consequences,” because people will not speak up if nothing happens when harm occurs. Real change looks like policies adjusted, values clarified, and behavior addressed. Anything less is lip service. Her grounding mantra supports this inner steadiness: “I am everything and I have everything.”
Women supporting women, and leadership that listens
When she looks ahead, Deesha is clear about what needs to change. “I think what I hope to see is other women supporting women.” She hopes more leaders choose grace over gatekeeping so that the next generation does not have to struggle in the same ways. She also calls for progress on age inclusion. “I really hope we get a grip on the ageism when it comes to women in the workplace,” she says, advocating for intergenerational leadership that values experience alongside fresh perspective. Her definition of leadership leaves room for others to lead too. As she says, “you also can be a follower and you need to be a follower at times.” Expertise can come from anywhere on the team, and missions move faster when leaders are willing to listen.
Deesha’s story reminds us that leadership is not a checklist. It is a way of showing up with integrity, supporting others, and remembering that worth is not earned by achievements. It is already present, and it grows when people feel safe to speak and contribute.
Deesha’s book, Undiplomatic: How My Attitude Created the Best Kind of Trouble, brings these lessons to life, weaving together behind-the-scenes moments from her eight years in the Obama White House with honest reflections on imposter syndrome, confidence, and health. It is available in print and as an audiobook, including on Audible and Spotify.
Written by Tudor Marinca