“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 self
05:30 – The leadership shift: from having answers to building others
06:44 – Vulnerability at work: not therapy, but a signal of self-awareness
08:48 – Psychological safety + high standards
11:45 – “I believe in you”: the simplest, most powerful leadership tool
17:59 – Inviting disagreement: how to avoid false harmony on your team
21:54 – High standards without fear
26:00 – Reflection as a system
29:01 – Burnout, recovery, and building sustainable performance
32:40 – Feedback that drives growth
37:00 – “I” vs.“We”: balancing ownership and accountability
38:06 – Get yourself some “Boast Bitches”: building your personal board of directors
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