“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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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

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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

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What if the secret to great leadership is actually learning to say no? Annie Riley sits down with Gautam Prabhu, VP of Engineering at Scribe AI and longtime startup operator, to unpack his lessons from 25+ years of building teams at PagerDuty, Zendesk, and Opentrons. Gautam talks through why leaders should treat every “yes” as a promise, how winning teams are built through systems (not heroics), why a bad decision is better than no decision at all, and how he builds trust through honesty and accountability.

Time Stamps:

00:00 Meet Gautam Prabhu

02:11 From engineer to accidental manager

05:04 Learning leadership the hard way

08:26 The two kinds of trust

12:03 Why intent matters first

15:42 Competence has to follow

19:18 Why great managers say no

23:57 A bad decision beats no decision

28:41 Startups can’t run on heroes forever

33:22 Building systems that scale

39:48 What great leadership really leaves behind

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What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role.

Timestamps:

00:00 Meet Karan Singh

04:30 Learning to manage on the fly

07:20 Winning people over

09:25 The mindset for surviving startup chaos

12:01 The j-curve of change

14:41 Speed vs. Space: giving teams time to process change

18:32 Healthy departures

22:24 Creating a “Next Play Plan”

26:49 Why you should re-recruit yourself

38:52 Rethinking PIPs: What most people get wrong

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Best Manager Ever shares hard-earned leadership lessons from the very best and most successful managers in startups and tech. But here’s the twist: Every guest is endorsed by their team as the “best manager ever.” We talk to the guest’s direct reports to learn how they *really* lead, and then unpack that feedback live with the guest.

This season we’re leveling up with world-class experts who have spent their careers studying the science of leadership, including professors, authors, and coaches.

Season 4 kicks off March 18th, with new episodes every Wednesday wherever you get podcasts.

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com

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In this special holiday spoof episode of Best Manager Ever, Annie Riley, host and founder of Fort Light, chats with the one and only Santa Claus!

Known for spreading holiday cheer and managing a diverse team at the North Pole, Santa gives a rare interview about life behind the scenes. His direct reports, including elves and reindeer, praise Santa for his leadership, though they note he's their only manager ever ;)

We will dive into Santa's leadership style, the secrets behind the naughty and nice lists, and the challenges of maintaining the Christmas spirit all year long. Join us for a fun-filled episode with laughter and insight into the man behind the magic.

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Connect with our hilarious Santa, Jason Gore

Listen to Jason’s podcast 108.9 The Hawk

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In this recap episode of Best Manager Ever, host Annie Riley reflects on standout lessons from Season 3.

Annie discusses the six things our top manager guests have in common: high standards, clear communication, strong relationships with peers, a relentless focus on their own growth, a unique view of career management, and a human-first perspective.

It’s a chance to pause, look back, and notice what makes our guests so exceptional— and then think about how to apply those lessons in your own work.

Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped our season.

Share your feedback and suggestions from the season in this super quick form, so we can make future episodes even better.

If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.com

Join us on Substack

Connect with Annie Riley

Check out Fort Light to level up your leadership skills

Connect with our show’s Producer, Alexis Ramdaou

Nominate your Best Manager Ever for the Podcast

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