Best Manager Ever

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/ 

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

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

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

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