“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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Connect with Dorothy Kilroy

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Best Manager Ever is a Production of Fort Light and Now It’s Hear

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Speed beats perfection every time. Annie Riley dives in with Junan Pang, VP of Customer Success at Intercom, to unpack how he gives direct reports the context they need to act independently. He talks through why most leaders under-share, and how quick, imperfect updates unlock better decisions– without drowning the team in meetings or messages.

Timestamps:

00:00 Meet Junan Pang

01:58 Learning as a mindset

05:28 Taking intentional steps back

08:48 Growth through manager & IC zigzags

14:32 Building authentic, long-term relationships

18:08 Being in the problem

22:32 Fast, imperfect context sharing

31:35 Learning through osmosis

37:26 Feedback as a daily practice

Join us on Substack

Level up your leadership skills with Fort Light

Connect with Annie Riley

Connect with Junan Pang

Nominate Your Best Manager Ever

Best Manager Ever is a Production of Fort Light and Now It’s Hear

Hosted on Acast. See acast.com/privacy for more information.

Meetings can be a real problem when they’re not run well or have the wrong people in them. Julia Bernstein, COO at Brightside Health joins Annie Riley to break down how she audits, redesigns, and even “dress rehearses” meetings to make them actually useful. From cutting unnecessary attendees to auditing recurring meetings regularly, Julia shares her no-BS approach to protecting time and driving results.

Timestamps:

00:00 – Meet Julia Bernstein

02:00 – Translating business into people-first leadership

04:50 – Influencing without authority

06:30 – Managing diverse teams

07:15 – Building career ladders from day one

16:20 – Being involved vs informed

20:50 – The meeting audit: cutting what doesn’t work

24:50 – Designing better meetings

26:40 – Giving your team real ownership

27:20 – No one will set your boundaries for you

33:15 – Weekly rituals that keep teams aligned, human, and performing

Join us on Substack

Level up your leadership skills with Fort Light

Connect with Annie Riley

Connect with Julia Bernstein

Nominate Your Best Manager Ever

Best Manager Ever is a Production of Fort Light and Now It’s Hear

Hosted on Acast. See acast.com/privacy for more information.