Best Manager Ever

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 RileyNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 matters02:07 — Scott’s leadership style04:08 — Joining BuzzFeed at five people06:13 — Management is a skill08:47 — The problem with “executive presence”10:02 — Visibility vs. impact13:21 — Directness over aggression17:20 — Tough conversations done well19:42 — Leading through layoffs22:19 — Avoiding emotional dumping24:56 — How to fire someone clearly29:29 — The power of “say more”37:22 — Listening and accountability43:04 — Why humor matters at work48:06 — Reps over perfectionJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Scott LambNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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 leaders06:30 – Understanding the threat system11:15 – The antidote to constant stress13:00 – The striver's trap18:00 – Why kindness doesn't kill ambition20:15 – The self-compassion break29:00 – Mindfulness, resistance, and suffering33:00 – Responding instead of reacting37:00 – Working with your inner critic41:00 – Bringing compassion into the workplace43:00 – Building a sustainable practice49:00 – A better edge than self-criticismJoin us on Substack Level up your leadership skills with Fort Light Connect with Annie RileyConnect with Micheal KleinNominate Your Best Manager EverBest Manager Ever is a Production of Fort Light and Now It’s Hear

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

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