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 self05:30 – The leadership shift: from having answers to building others06:44 – Vulnerability at work: not therapy, but a signal of self-awareness08:48 – Psychological safety + high standards 11:45 – “I believe in you”: the simplest, most powerful leadership tool17:59 – Inviting disagreement: how to avoid false harmony on your team21:54 – High standards without fear26:00 – Reflection as a system29:01 – Burnout, recovery, and building sustainable performance32:40 – Feedback that drives growth37:00 – “I” vs.“We”: balancing ownership and accountability38:06 – Get yourself some “Boast Bitches”: building your personal board of directorsJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Dorothy KilroyNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 Pang01:58 Learning as a mindset05:28 Taking intentional steps back08:48 Growth through manager & IC zigzags14:32 Building authentic, long-term relationships18:08 Being in the problem22:32 Fast, imperfect context sharing 31:35 Learning through osmosis 37:26 Feedback as a daily practiceJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Junan PangNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 Bernstein02:00 – Translating business into people-first leadership04:50 – Influencing without authority06:30 – Managing diverse teams 07:15 – Building career ladders from day one16:20 – Being involved vs informed20:50 – The meeting audit: cutting what doesn’t work24:50 – Designing better meetings 26:40 – Giving your team real ownership27:20 – No one will set your boundaries for you33:15 – Weekly rituals that keep teams aligned, human, and performingJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Julia BernsteinNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 Prabhu02:11 From engineer to accidental manager05:04 Learning leadership the hard way08:26 The two kinds of trust12:03 Why intent matters first15:42 Competence has to follow19:18 Why great managers say no23:57 A bad decision beats no decision28:41 Startups can’t run on heroes forever33:22 Building systems that scale39:48 What great leadership really leaves behindJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Gautam PrabhuNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 Singh04:30 Learning to manage on the fly07:20 Winning people over09:25 The mindset for surviving startup chaos12:01 The j-curve of change14:41 Speed vs. Space: giving teams time to process change18:32 Healthy departures 22:24 Creating a “Next Play Plan” 26:49 Why you should re-recruit yourself38:52 Rethinking PIPs: What most people get wrong Join us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Karan SinghNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear

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 RileyConnect with our hilarious Santa, Jason GoreListen to Jason’s podcast 108.9 The HawkCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear

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.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear

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 transparencyThe right way to communicate destabilizing intel How to recondition your mindset for “hard mode” leadershipHow 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:  sponsor@fortlight.comJoin us on Substack Connect with Jared EronduConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear