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Best Manager Ever

Best Manager Ever

By: Annie Riley
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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.

Annie Riley
Career Success Economics Management Management & Leadership
Episodes
  • Rethinking Executive Presence with Scott Lamb
    Jun 17 2026

    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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    54 mins
  • Self-Compassion Break for High Performers
    Jun 10 2026

    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.

    Show More Show Less
    56 mins
  • Speed to Signal with JZ - Laurel CPO
    Jun 3 2026

    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.

    Show More Show Less
    48 mins
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