Best Manager Ever

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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Connect with Annie Riley
Connect with Silvia Oviedo Lopez
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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

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.

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.

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.

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.