Best Manager Ever

Annie Riley
  • 5.0 (29)
  • 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. Top CEO Coach On The Difficulty of Empathizing Up

    1D AGO

    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
  2. “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
  3. 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
  4. 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
  5. 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
  6. Bad Meetings Are Disrespectful

    APR 1

    Bad Meetings Are Disrespectful

    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.

    49 min
  7. A Manager’s Word Has To Mean Something

    MAR 25

    A Manager’s Word Has To Mean Something

    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.

    55 min
  8. COO of Headspace: Why You Should Re-Recruit Yourself

    MAR 18

    COO of Headspace: Why You Should Re-Recruit Yourself

    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.

    50 min
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Trailer

5
out of 5
29 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
    57
  • Rating
    Explicit
  • Copyright
    © Annie Riley
  • Show Website
    Best Manager Ever

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