Get Yourself Some “Boast Bitches”

“Polite silence” is a silent killer on teams. Annie Riley sits down with Dorothy Kilroy, Chief Commercial Officer at Oura Ring and former Airbnb to talk about how to invite productive disagreement while fostering psychological safety and how to give direct feedback without making it personal. Plus: the career-changing power of building your own “Boast Bitches”—a trusted circle that advocates for you and helps you grow.TimeStamps:00:38 – Meet Dorothy Kilroy 03:20 – Storytelling, mission-driven work, and bringing your full self05:30 – The leadership shift: from having answers to building others06:44 – Vulnerability at work: not therapy, but a signal of self-awareness08:48 – Psychological safety + high standards 11:45 – “I believe in you”: the simplest, most powerful leadership tool17:59 – Inviting disagreement: how to avoid false harmony on your team21:54 – High standards without fear26:00 – Reflection as a system29:01 – Burnout, recovery, and building sustainable performance32:40 – Feedback that drives growth37:00 – “I” vs.“We”: balancing ownership and accountability38:06 – Get yourself some “Boast Bitches”: building your personal board of directorsJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Dorothy KilroyNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.