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

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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

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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/

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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

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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

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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

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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

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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

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

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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

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

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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

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