Best Manager Ever

“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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Level up your leadership skills with Fort Light 

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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 

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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.

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

Join us on Substack 

Level up your leadership skills with Fort Light 

Connect with Annie Riley

Connect with Gautam Prabhu

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.

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 

Join us on Substack 

Level up your leadership skills with Fort Light 

Connect with Annie Riley

Connect with Karan Singh

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.

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: [email protected]

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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

This is a Production of Fort Light and Now it’s Hear

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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.

Connect with Annie Riley

Connect with our hilarious Santa, Jason Gore

Listen to Jason’s podcast 108.9 The Hawk

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

This is a Production of Fort Light and Now it’s Hear

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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:  [email protected]

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

This is a Production of Fort Light and Now it’s Hear

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

Jared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice rising from a solo designer pulling all-nighters in the early days, to leading a 50-person design organization and serving as GM across product and GTM as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health. Jared is known for his design mentorship and community-building, and is an active advisor and angel investor. 

Jared brings a calm, steady presence, especially during challenging times, always seeing the long view and providing unwavering support. His team appreciates his high standards, attention to detail, and commitment to craft, but also noted that he balances intensity with humor and approachability.

In this episode, show creator and Fort Light founder Annie Riley sits down with Jared, and they discuss:

• Why all managers should master selective transparency
• The right way to communicate destabilizing intel 
• How to recondition your mindset for “hard mode” leadership
• How to build a bench of resources to support yourself  
• The best way to recruit exceptional talent 
• Why managing your own mindset is the ultimate leadership unlock 

If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  [email protected]

Join us on Substack 

Connect with Jared Erondu

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

This is a Production of Fort Light and Now it’s Hear

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

Dana Lawson is the CTO of Netlify. She’s been a technologist for decades, and was previously the VP of Engineering at Github and the Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, and served in the military. 

Dana's direct reports praise her for building confidence, providing autonomy support, for bringing honesty and compassion, and for sponsorship that goes beyond mentorship. 

In this episode, show creator and Fort Light founder Annie Riley sits down with Dana, and they discuss:

• How imposter shows up at senior levels– and how to handle it  
• How to deal with interpersonal conflicts
• What it takes to be an effective sponsor
• The importance of embracing change

If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  [email protected]

Join us on Substack 

Connect with Dana Lawson

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

This is a Production of Fort Light and Now it’s Hear

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