“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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