Best Manager Ever

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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Connect with Micheal Klein
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Best Manager Ever is a Production of Fort Light and Now It’s Hear
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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

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.

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.

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.

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.