Best Manager Ever

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 empathize up— and how simple shifts like checking in or offering genuine positive feedback can change the dynamic, because sometimes the most powerful move is truly seeing the person behind the role.Time Stamps:00:00 Meet Ed Batista02:36 Why empathizing up is so hard03:48 The myth of the “invulnerable” leader05:11 How to actually start empathizing up06:45 Why your boss isn’t getting enough positive feedback08:39 Empathizing up vs. managing up09:56 Empathy does not mean agreement12:03 What to do when your boss shuts you down16:34 It’s probably not about you20:07 Intent vs. impact 24:50 Leaders as shock absorbers31:49 Pain is mandatory. Suffering is optional.33:50 The danger of overvaluing feelings at work39:07 Is the story you’re telling serving you?41:52 Leadership is intuition, not a formulaJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Ed BatistaNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

You don’t become a great manager by regurgitating frameworks. Management is a craft and a skillset that gets built over time.  Annie Riley sits down with Maura Church, VP of Product & Engineering at Two Chairs, to talk about how a manager’s mindset impacts team performance. From the “Smart Rats” theory to balancing tough feedback with real belief, Maura breaks down how to coach growth, build confidence, and unlock better results.TimeStamps:00:00 — Meet Maura Church02:54 — Management is a craft, not a side job04:49 — Why startups can’t afford bad management07:14 — “No one is coming to save us”10:09 — The trap of managing by checklist13:07 — Giving feedback without making it personal19:06 — “Smart Rats”: belief as a performance levers25:13 — Turning “non-technical” skills into strengths38:55 — Clear expectations make feedback easier41:39 — Psychological safety is built, not assumed45:10 — Rewriting the rules as your team evolves47:15 — There’s no one “right” way to manageJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Maura ChurchNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

Building a strong network is a skill. Annie Riley sits down with Whitnie Narcisse, former First Round Capital Partner, to unpack how she has built one of the best networks in Silicon Valley. Whitnie breaks down how to be memorable and build connections that last using her FACE framework (Factual, Authentic, Credible, and Engaging). Plus: why most networking advice falls flat, how to design rooms people want to be in, and the biggest networking mistake most people make. Time Stamps:00:00 – Whitnie's 3 biggest career inflection points05:50 - How Whitnie got to First Round06:50 – Agency in networking09:30 – What actually gets a response11:30 – Async networking and respecting people’s time13:30 – Why most networking formats don’t work 15:30 – Building a high-value community and ecosystem18:30 – The secret to great events21:00 – How to create meaningful connections 23:30 – The FACE framework: how to be memorable 29:00 – The follow-up gap: why networking really starts after the handshake31:00 – Generosity, authenticity, and playing the long gameJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Whitnie Narcisse Nominate Your 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