Best Manager Ever

Annie Riley
  • 5.0 (31)
  • Careers
  • Updated Weekly

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.

  1. How "Temporary Permanent" Drives Progress

    3d ago

    How "Temporary Permanent" Drives Progress

    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.

    51 min
  2.  Ex-Pinterest & Canva Exec: Curiosity As A Muscle

    May 20

     Ex-Pinterest & Canva Exec: Curiosity As A Muscle

    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.

    48 min
  3. Unblock Your Team with Powerful Questions

    May 13

    Unblock Your Team with Powerful Questions

    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.

    53 min
  4. Top CEO Coach On The Difficulty of Empathizing Up

    May 6

    Top CEO Coach On The Difficulty of Empathizing Up

    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.

    50 min
  5. “Smart Rats”: Belief Boosts Performance

    Apr 29

    “Smart Rats”: Belief Boosts Performance

    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.

    52 min
  6. Be Champagne, Not Flat Soda

    Apr 22

    Be Champagne, Not Flat Soda

    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.

    37 min
  7. Get Yourself Some “Boast Bitches”

    Apr 15

    Get Yourself Some “Boast Bitches”

    “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.

    47 min
  8. Time Kills Follow-Up: Share Context Now

    Apr 8

    Time Kills Follow-Up: Share Context Now

    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.

    47 min
See All (60)

Trailer

5
out of 5
31 Ratings

About

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.

Information

  • Creator
    Annie Riley
  • Years Active
    2024 - 2026
  • Episodes
    60
  • Rating
    Explicit
  • Copyright
    © Annie Riley
  • Show Website
    Best Manager Ever

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