Best Manager Ever

Speed to Signal with JZ - Laurel CPO 03.06.2026 48分

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 speed to signal, how to move fast without creating chaos, and why great leaders should share uncertainty instead of performing conviction. JZ also shares hot takes about 1:1 meetings, asking for help, and scrapping work that isn’t going in the right direction. This conversation between JZ and Annie Riley is packed with practical frameworks for managers and startup operators who want to move faster and build teams that thrive in ambiguity.TimeStamps:00:00 — Meet JZ03:03 — The “fast-moving river” analogy05:38 — Getting people to jump in07:22 — Hiring for curiosity and urgency10:11 — What “speed to signal” means12:43 — Building through fast feedback16:16 — The 3 leadership traps20:41 — Operating at 120%23:54 — Sharing unfinished work early27:14 — Open sourcing strategy and workflows31:34 — Knowing when to stop34:16 — Graduating out of one-on-ones36:23 — Asking for help effectively40:23 — Trust, communication, and speed43:41 — Ownership, introspection, and timeJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with JZNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s HearThis episode is sponsored by Blomma, the AI career coach built to help people grow with more clarity, accountability, and insight over time. Use code MANAGER for a free month and early access: https://www.blomma.com/  Hosted on Acast. See acast.com/privacy for more information.

How "Temporary Permanent" Drives Progress 27.05.2026 50分

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 the power of “temporary permanent” thinking. They break down why the best teams prioritize momentum over precision, normalize imperfect solutions, and keep moving when the path changes. Plus: why the traditional “lone wolf” sales mentality is a bad thing, and the best leaders win as a pack. Time Stamps:00:00 Meet Anna Randall02:16 Startup vs enterprise: autonomy, control, and team dynamics04:38 Grit builds excellence: repetition over talent06:23 Navigating early-stage chaos in real time09:52 “Standing on the sun” + embracing uncertainty10:24 “Temporary permanent”13:31 The limits of grit:16:21 The pack mentality: why lone wolves lose21:07 Connecting team performance to the bigger “why”23:19 Rethinking one-on-ones: making them actually valuable27:38 Building trust through human connection30:22 Saying the hard thing33:29 Negotiation as trade-offs and “cards”38:53 Managing expectations43:35 Choosing the pack over selfJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Anna RandallNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

Ex-Pinterest & Canva Exec: Curiosity As A Muscle 20.05.2026 47分

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 and former Canva and Pinterest leader, to unpack how the best leaders train curiosity, learn in real time, and see hard questions as a gift.Time Stamps: 00:00 — Meet Silvia Oviedo Lopez03:48 — How to Position Yourself for Growth05:25 — Be Someone Who Brings Clarity09:28 — Fast Learning Loops10:44 — Pattern Matching vs. Fresh Thinking12:34 — Curiosity Is a Muscle16:16 — Coaching Without “Right vs. Wrong”18:18 — Let Go and Keep Moving27:05 — Scaling as a Leader33:15 — Building Complementary Teams36:57 — Leading People Smarter Than You41:04 — What Are You Hearing From Your Team?42:33 — Curiosity as a Leadership Superpower43:16 — Flexibility in a Changing WorldJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Silvia Oviedo LopezApp StoreUse code MANAGER for early access at blomma.comNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

Unblock Your Team with Powerful Questions 13.05.2026 52分

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 things forward. Maayan shares how to use curiosity to uncover what’s really going on and guide conversations without controlling them. Plus: the traps new managers fall into, the difference between coaching and interrogating, and the simple question that turns hesitation into action.TimeStamps:00:00 – Meet Maayan Roth 02:53 – Startup leadership: building everything from scratch05:27 – Why asking better questions is a leadership superpower06:16 – Open vs. closed questions 08:28 – The “Socratic trap” and fake curiosity10:09 – Letting go of having the answer12:03 – Why leaders should speak last14:17 – Go-to questions to unblock your team18:58 – How to know if you’re asking the right questions23:39 – Common traps: not listening, fake coaching, dead ends31:23 – When coaching doesn’t work (and switching styles)32:20 – What coaching actually means as a manager39:31 – Growth should feel uncomfortable43:46 – Hard lesson: stop doing everything so your team can step up47:07 – There’s no “easy mode” in leadership + finding your peopleJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Maayan RothNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

Top CEO Coach On The Difficulty of Empathizing Up 06.05.2026 49分

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

“Smart Rats”: Belief Boosts Performance 29.04.2026 52分

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

Be Champagne, Not Flat Soda 22.04.2026 36分

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

Get Yourself Some “Boast Bitches” 15.04.2026 47分

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

Time Kills Follow-Up: Share Context Now 08.04.2026 47分

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

Bad Meetings Are Disrespectful 01.04.2026 49分

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

A Manager’s Word Has To Mean Something 25.03.2026 54分

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

COO of Headspace: Why You Should Re-Recruit Yourself 18.03.2026 49分

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

Welcome to Season 4 11.03.2026 1分

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

Best Manager Ever: Santa 24.12.2025 13分

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

Best Manager Ever: Top Takeaways From Season 3 17.12.2025 20分

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

Best Manager Ever: Jared Erondu – Hard Mode Leadership 10.12.2025 52分

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

Best Manager Ever: Dana Lawson - Conquering Imposter Syndrome and Fostering Team Resilience 03.12.2025 43分

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 conflictsWhat it takes to be an effective sponsorThe importance of embracing changeIf you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Dana LawsonConnect 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 Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever: Amit Shah - Building Trust Through Gratitude 26.11.2025 48分

Amit Shah is the COO of Virta Health, where he’s built the company from ~30 team members to over 800 colleagues working to reverse obesity and diabetes. Amit has 10+ years of experience in building and scaling entrepreneurial and high-growth healthcare organizations, with a focus on delivering financial and operational results while aligning on mission and values.Amit’s direct reports praise his ability to balance the needs of Virta’s members, business, and staff, describing him as incredibly kind, caring, driven, and a fierce protector of his team. He is celebrated for his passion, structured thinking, dedication to his own growth and development, and continuous improvement in leadership.In this episode, show creator and Fort Light founder Annie Riley sits down with Amit,and they cover:How to build a gratitude practice that supports your team – and yourselfThe importance of emotional awareness and regulation in leadership Energy management habits and practices   A process to take charge of feedback, learning, and growth The relationship between execution and strategy in startups If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Amit Shah 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 Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever: Patrick Reynolds - Creating the Conditions for Success 19.11.2025 39分

Patrick Reynolds is the Co-Founder and Head of Product at Office Hours, an expert marketplace. Patrick started his career as a software engineer, before becoming a self-taught product designer and making the leap into product leadership. He has worked at an array of tech companies and startups including Affirm, Sweep, and Adobe. Patrick's direct reports praise him for his exceptional thoughtfulness, noting his ability to remember personal details and small, meaningful actions that remove friction and boost morale. They describe him as a natural coach who not only sets high standards but also provides the necessary support and resources to achieve them. In this episode, show creator and Fort Light founder Annie Riley sits down with Patrick, and they discuss:The difference between leadership and management  How to prime yourself so it’s easy to spot opportunities to support your team The difference between a culture that inspires ambition vs. enforces it How to consume content for maximum ROI The best way to spot (and stop!) perfectionism If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Patrick ReynoldsConnect 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 Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever: Sophie Ruddock – Showing Up for Your Team During Crisis 12.11.2025 40分

Sophie Ruddock brings deep expertise in scaling mission-driven tech companies, and is now the COO at Empathy. Sophie was an early employee at Multiverse, where she grew with the company and ultimately became their global COO leading through rapid growth and market expansion. Sophie’s direct reports praise her empowering leadership style, her commitment to their development, and her unwavering advocacy. She hires people for their unique expertise and encourages them to bring their full selves to work, and reminds them of their value even in moments of self-doubt.In this episode, show creator and Fort Light founder Annie Riley sits down with Sophie, and they discuss:What a “founder mindset” really means for employees How to earn the right to dissent How to lead when someone on the team has an unexpected crisis The mindset shift that enabled Sophie to go from managing 3 to 600+ people If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Sophie RuddockConnect 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 Hosted on Acast. See acast.com/privacy for more information.