Get Yourself Some “Boast Bitches”

Get Yourself Some “Boast Bitches”

From Best Manager Ever by Annie Riley

April 15, 2026 · 47 min · Season 4 · Episode 5

About this episode

Annie Riley discusses the importance of psychological safety and productive disagreement with Dorothy Kilroy, emphasizing the value of having a supportive network for career growth.

“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 Join us…

People in this episode

Host: Annie Riley

Guest: Dorothy Kilroy

Topics covered

  • psychological safety
  • feedback
  • leadership
  • team dynamics
  • career development
  • vulnerability
  • disagreement

Keywords

  • Boast Bitches
  • psychological safety
  • feedback
  • leadership
  • team dynamics
  • career growth
  • vulnerability

Mentioned in this episode

Organizations: Oura Ring, Airbnb, Fort Light, Now It’s Hear, Substack

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