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 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 on Substack

Level up your leadership skills with Fort Light

Connect with Annie Riley

Connect with Dorothy Kilroy

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.

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(64)

Season 4 Wrap: What the Best Leaders Do Differently

After 50 episodes with some of the top leaders in startups and tech, Annie Riley takes a moment to reflect and share her top five leadership takeaways that surfaced again and again throughout the late...

24 Jun 21min

Rethinking Executive Presence with Scott Lamb

The stereotype of the hard-charging executive is hurting performance. Scott Lamb moved to NYC to pursue journalism, but ended up joining Buzzfeed when it was just five people and has been on the start...

17 Jun 54min

Self-Compassion Break for High Performers

The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael K...

10 Jun 55min

Speed to Signal with JZ - Laurel CPO

JZ has built product teams at Airbnb, Webflow, Dropbox (and now Laurel), and in this episode she shares her honest leadership playbook and lessons learned. JZ covers why conviction is really about spe...

3 Jun 48min

How "Temporary Permanent" Drives Progress

Don’t let perfectionist fantasies kill progress. Annie Riley sits down with Anna Randall, Director of Enterprise Sales at Curri and former VP of Sales at TigerEye, Autodesk, and PlanGrid, to explore t...

27 Mai 50min

Ex-Pinterest & Canva Exec: Curiosity As A Muscle

Work is not like school– there are no right answers, and if you’re looking to be “right” then you will always fall behind. Annie Riley sits down with Silvia Oviedo Lopez, Founder & CEO of Blomma AI an...

20 Mai 47min

Unblock Your Team with Powerful Questions

Better questions create better teams. Annie Riley sits down with Maayan Roth, Head of Engineering at Crux Climate, to unpack the skill most managers overlook: asking questions that actually move thing...

13 Mai 52min

Top CEO Coach On The Difficulty of Empathizing Up

Leadership is lonely. Most leaders don’t get enough support or positive feedback. And that includes our own boss too. Annie Riley and top executive coach Ed Batista break down why it’s so hard to empa...

6 Mai 49min