Best Manager Ever

Best Manager Ever reveals the secrets of successful management and empowers leaders to build winning teams. Join a community dedicated to sharing insights and stories from the most successful and beloved leaders in the startup world. All guests have been nominated as the “best manager ever” by a recent direct report. Before each interview, we go behind the guest’s back to collect feedback and stories from their team about what they’re *actually* like to work for. Then we sit down with the guest to unpack that feedback and to dig into their leadership playbook and lessons learned. Tune in, learn from the experts, and enhance your management skills while building meaningful connections throughout your career. Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever is a business podcast hosted by Annie Riley, with 64 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Annie Riley hosts Best Manager Ever, a business show with 64 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #15

  Season 4 Wrap: What the Best Leaders Do Differently

  Jun 24, 202622 minS4

  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.

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  Episode #14

  Rethinking Executive Presence with Scott Lamb

  Jun 17, 202654 minS4

  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.

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  Episode #13

  Self-Compassion Break for High Performers

  Jun 10, 202656 minS4

  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.

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  Episode #12

  Speed to Signal with JZ - Laurel CPO

  Jun 3, 202648 minS4

  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.

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  Episode #11

  How "Temporary Permanent" Drives Progress

  May 27, 202651 minS4

  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.

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