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After 50 episodes with some of the top leaders in startups and tech, Annie Riley takes a moment to reflect and share her top five leadership takeaways that surfaced again and again throughout the latest season.  Annie also reflects on the current moment—from the rapid rise of AI to the growing need for authentic human connection—and why those realities have only strengthened her commitment to building a show that is honest, practical, and deeply human. Plus, she shares what's next for Best Manager Ever as the team heads into a summer of experimentation, new formats, and fresh ways to support leaders navigating the messy middle of company building. Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley 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.

The stereotype of the hard-charging executive is hurting performance. Scott Lamb moved to NYC to pursue journalism, but ended up joining Buzzfeed when it was just five people and has been on the startup path ever since. In this episode, Scott sits down with Annie Riley to explore a different model for leadership– one rooted in curiosity, steadiness, psychological safety, and real human connection. They discuss what’s really behind vague feedback about “executive presence”, how management is a learnable craft, and how to have hard conversations that don’t FEEL bad.  Time Stamps: 00:00 — Why management matters 02:07 — Scott’s leadership style 04:08 — Joining BuzzFeed at five people 06:13 — Management is a skill 08:47 — The problem with “executive presence” 10:02 — Visibility vs. impact 13:21 — Directness over aggression 17:20 — Tough conversations done well 19:42 — Leading through layoffs 22:19 — Avoiding emotional dumping 24:56 — How to fire someone clearly 29:29 — The power of “say more” 37:22 — Listening and accountability 43:04 — Why humor matters at work 48:06 — Reps over perfection Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Scott Lamb 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.

The voice pushing you forward is also holding you back, and your inner critic is costing you more than you think. Annie Riley talks with clinical psychologist and self-compassion teacher Dr. Michael Klein to explore the psychology behind ambition, achievement, and the never-ending pursuit of "more." They discuss why success doesn't automatically lead to happiness, how striving and self-criticism can narrow creativity and reduce judgment. And they explore practical self compassion tools to help high-achieving leaders become more resilient, focused, creative, and effective. Time Stamps: 00:00 – Introduction  01:00 – Why self-compassion matters for leaders 06:30 – Understanding the threat system 11:15 – The antidote to constant stress 13:00 – The striver's trap 18:00 – Why kindness doesn't kill ambition 20:15 – The self-compassion break 29:00 – Mindfulness, resistance, and suffering 33:00 – Responding instead of reacting 37:00 – Working with your inner critic 41:00 – Bringing compassion into the workplace 43:00 – Building a sustainable practice 49:00 – A better edge than self-criticism Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Micheal Klein 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.

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 JZ 03:03 — The “fast-moving river” analogy 05:38 — Getting people to jump in 07:22 — Hiring for curiosity and urgency 10:11 — What “speed to signal” means 12:43 — Building through fast feedback 16:16 — The 3 leadership traps 20:41 — Operating at 120% 23:54 — Sharing unfinished work early 27:14 — Open sourcing strategy and workflows 31:34 — Knowing when to stop 34:16 — Graduating out of one-on-ones 36:23 — Asking for help effectively 40:23 — Trust, communication, and speed 43:41 — Ownership, introspection, and time Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with JZ Nominate Your Best Manager Ever Best Manager Ever is a Production of Fort Light and Now It’s Hear This 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.

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 Randall 02:16 Startup vs enterprise: autonomy, control, and team dynamics 04:38 Grit builds excellence: repetition over talent 06:23 Navigating early-stage chaos in real time 09:52 “Standing on the sun” + embracing uncertainty 10:24 “Temporary permanent” 13:31 The limits of grit: 16:21 The pack mentality: why lone wolves lose 21:07 Connecting team performance to the bigger “why” 23:19 Rethinking one-on-ones: making them actually valuable 27:38 Building trust through human connection 30:22 Saying the hard thing 33:29 Negotiation as trade-offs and “cards” 38:53 Managing expectations 43:35 Choosing the pack over self Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Anna Randall 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.

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 Lopez 03:48 — How to Position Yourself for Growth 05:25 — Be Someone Who Brings Clarity 09:28 — Fast Learning Loops 10:44 — Pattern Matching vs. Fresh Thinking 12:34 — Curiosity Is a Muscle 16:16 — Coaching Without “Right vs. Wrong” 18:18 — Let Go and Keep Moving 27:05 — Scaling as a Leader 33:15 — Building Complementary Teams 36:57 — Leading People Smarter Than You 41:04 — What Are You Hearing From Your Team? 42:33 — Curiosity as a Leadership Superpower 43:16 — Flexibility in a Changing World Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Silvia Oviedo Lopez App Store Use code MANAGER for early access at blomma.com 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.

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 scratch 05:27 – Why asking better questions is a leadership superpower 06:16 – Open vs. closed questions  08:28 – The “Socratic trap” and fake curiosity 10:09 – Letting go of having the answer 12:03 – Why leaders should speak last 14:17 – Go-to questions to unblock your team 18:58 – How to know if you’re asking the right questions 23:39 – Common traps: not listening, fake coaching, dead ends 31:23 – When coaching doesn’t work (and switching styles) 32:20 – What coaching actually means as a manager 39:31 – Growth should feel uncomfortable 43:46 – Hard lesson: stop doing everything so your team can step up 47:07 – There’s no “easy mode” in leadership + finding your people Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Maayan Roth 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.

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 Batista 02:36 Why empathizing up is so hard 03:48 The myth of the “invulnerable” leader 05:11 How to actually start empathizing up 06:45 Why your boss isn’t getting enough positive feedback 08:39 Empathizing up vs. managing up 09:56 Empathy does not mean agreement 12:03 What to do when your boss shuts you down 16:34 It’s probably not about you 20:07 Intent vs. impact  24:50 Leaders as shock absorbers 31:49 Pain is mandatory. Suffering is optional. 33:50 The danger of overvaluing feelings at work 39:07 Is the story you’re telling serving you? 41:52 Leadership is intuition, not a formula Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Ed Batista 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.

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 Church 02:54 — Management is a craft, not a side job 04:49 — Why startups can’t afford bad management 07:14 — “No one is coming to save us” 10:09 — The trap of managing by checklist 13:07 — Giving feedback without making it personal 19:06 — “Smart Rats”: belief as a performance levers 25:13 — Turning “non-technical” skills into strengths 38:55 — Clear expectations make feedback easier 41:39 — Psychological safety is built, not assumed 45:10 — Rewriting the rules as your team evolves 47:15 — There’s no one “right” way to manage Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Maura Church 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.

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 points 05:50 - How Whitnie got to First Round 06:50 – Agency in networking 09:30 – What actually gets a response 11:30 – Async networking and respecting people’s time 13:30 – Why most networking formats don’t work  15:30 – Building a high-value community and ecosystem 18:30 – The secret to great events 21:00 – 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 handshake 31:00 – Generosity, authenticity, and playing the long game Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Whitnie Narcisse  Nominate Your Best Manager Ever Hosted on Acast. See acast.com/privacy for more information.

“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 Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Dorothy Kilroy 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.

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  Connect with Annie Riley 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.