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The Meg and Amy Show

The Meg and Amy Show

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Join best friends Meg Bear and Amy Wilson on The Meg and Amy Show – a podcast for big-picture thinkers who are ready to challenge the status quo. As former tech executives and seasoned business leaders, Meg and Amy have spent decades leading through change. Now, they’re joining forces to break down the trends they’ve lived and helped shape.All rights reserved by WRKdefined Economía Exito Profesional
Episodios
  • Episode 26 | From Scarcity to Abundance: How Childhood Shaped Our Leadership Styles

    Episode 26 | From Scarcity to Abundance: How Childhood Shaped Our Leadership Styles
    Nov 21 2025
    🔄 What happens when two leaders with completely different upbringings join forces? In this deeply personal episode, Amy and Meg explore how their vastly different childhoods - one marked by stability and support, the other by constant change and scarcity - shaped their leadership styles, decision-making approaches, and the way they navigate challenges today. ⏰ TIMESTAMPS: 00:00 Introduction & Banter including Meg's Vietnam travels, The Gist Project and Sangeet's Provocative post 13:13 Main topic introduction - Scarcity to abundance 14:13 Meg's two realities - Evangelical vs working class 25:38 Amy's stable childhood - The complete opposite 30:10 Risk tolerance and planning styles analysis 37:17 Decision-making patterns and communication styles 46:03 How they help each other see blind spots 50:13 The "plums trauma" - Amy's childhood story 51:05 Leadership Corner - Building resilient team culture 55:33 Closing thoughts on gratitude and community 🔑 KEY INSIGHTS: - How childhood experiences of scarcity vs. stability create different leadership superpowers and shadows - Why "nobody's gonna save you" became Meg's greatest adult strength - The difference between direct and diplomatic communication styles - How Amy's "it'll all work out" philosophy transforms team dynamics - Why protecting each other's hearts is crucial for leadership partnerships - The psychology behind why some leaders plan everything in advance 📚 RESOURCES: The Gist Project with Marne and Chrissy: https://www.youtube.com/@UCM3-PP9OqIJDRcWFE-s9TxQ https://open.spotify.com/show/3Ct5MqBunjMNRgC1EBNwhf Sangeet Paul Choudary's LinkedIn Post: https://www.linkedin.com/posts/sangeetpaul_theres-a-strange-idea-going-around-that-activity-7395005212517867520-cRig?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAAYiVkBNGvG88w_XozNSZSs3tmPrlwlqZA Sangeet Paul Choudary's Episode: https://www.youtube.com/watch?v=eaSZhRkk2NU The Insight Loop Newsletter | Meg's Personal Story: https://www.linkedin.com/pulse/meg-amy-show-newsletter-issue-9-the-meg-amy-show-wggbc/?trackingId=0zitkl3iQBCekr1X9EFjyw%3D%3D 🔗 CONNECT: Leadership Questions: amywilsonadvisor@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #Leadership #ChildhoodTrauma #Resilience #LeadershipDevelopment #Scarcity #Abundance #MegAndAmyShow
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    58 m
  • Episode 25: Maksim Ovsyannikov, CPO SugarCRM - Building The Product Org That Doesn't Exist Yet

    Episode 25: Maksim Ovsyannikov, CPO SugarCRM - Building The Product Org That Doesn't Exist Yet
    Nov 14 2025
    What would you build if you were creating a product organization from scratch in 2030? SugarCRM Chief Product Officer Maksim Ovsyannikov joins Amy and Meg to explore how AI is fundamentally reshaping product development, design thinking, and organizational structures. From "very little user experience" as a value proposition to why QA is more critical than ever in probabilistic systems, this conversation challenges everything you think you know about building products in the AI era. ⏰ TIMESTAMPS: 00:00 Introduction: Three types of software companies 08:20 Why "very little UX" is the future value proposition 10:48 Why every dashboard is broken and what to build instead 15:46 The AI context problem: smart LLMs need smarter humans 22:04 Hiring explorers vs. map readers in product roles 24:16 The tool explosion problem for product managers 25:56 Building for jobs that won't exist tomorrow 31:20 Legacy company transformation: additive AI strategy 32:51 Turn AI into your customer intelligence superpower 41:19 Why QA becomes make-or-break in agentic enterprise 46:21 Product operations: the expanding role you need 48:23 Leadership Corner: Networking tips for introverts 56:30 The optimistic view: jobs getting more interesting 57:44 The messy middle: AI's awkward transition phase 🔑 KEY INSIGHTS: - How to hire product managers who focus on outcomes over features - Why dashboards are broken and what to build instead - The context problem: keeping AI relevant in fast-changing businesses - Additive AI strategies for legacy companies - QA challenges in probabilistic vs. deterministic systems - Why your existing skills matter more dramatically now 📚 RESOURCES: SugarCRM Precision Selling Platform: https://www.sugarcrm.com Mostly Growth Podcast with CJ & Kyle: https://www.youtube.com/@MostlyGrowth M&A Show, Episode 22 | Dr. Kirstin Ferguson: https://www.youtube.com/watch?v=lceHtsbNAcs M&A Show, Episode 23 | Yamini Rangan: https://www.youtube.com/watch?v=ca_zbuD6IYI 🔗 CONNECT: Maksim Ovsyannikov: https://linkedin.com/in/movsyannikov Leadership Questions: amywilsonadvisor@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #ProductManagement #AI #ProductStrategy #FutureOfWork #SoftwareDevelopment #Leadership #MegAndAmyShow
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    1 h
  • Episode 24 | 24 Episodes of Learning: Our AI Transformation Framework for Getting Ahead

    Episode 24 | 24 Episodes of Learning: Our AI Transformation Framework for Getting Ahead
    Nov 7 2025
    🚀 After 24 episodes and conversations with 20+ transformation leaders, Amy reveals the AI Transformation Maturity Model that synthesizes everything we've learned. Discover how to get ahead of AI transformation instead of being a victim of change, why this moment offers the biggest career opportunity in decades, and how to build the change agility that separates thriving organizations from struggling ones. This episode weaves together insights from Sangeet Choudary (constraints thinking), Yamini Rangan (grassroots experimentation), Jen Morrow (strategic transformation), John Wookey (customer conversations), Angela Le Mathon (generalist advantage), Usman Sheikh (new co vs legacy co innovation), Kieran Snyder (organizational transformation), and more into a practical framework for navigating AI transformation. ⏰ TIMESTAMPS: 00:00 Introduction to the AI Transformation Maturity Model 05:30 The Race to the Bottom: Why Task Optimization Fails 12:01 Feature Factory vs Strategic Innovation Parallel 15:24 The Constraints Breakthrough: Thinking Beyond Tasks 18:25 Customer Conversations and Real-World Examples 20:01 The Generalist Advantage in AI Transformation 21:20 Grassroots Innovation: Why Collaboration Beats Top-Down 26:53 Why Specialization Has a Low Shelf Life 28:13 The Career Opportunity: Everyone's Back at Baseline 30:09 Why These Skills Are Now Crucial, Not Just Nice-to-Have 30:58 The Software Coordination Revolution 34:18 Scale Challenges: From 50 to 3000 People 37:00 The Context Switch Problem 39:06 The Looping Process of Organizational Reinvention 40:00 Building Change Agility vs. Fear-Based Culture 42:18 Community Input and Next Steps 🔑 BREAKTHROUGH INSIGHTS: - Why most companies get stuck optimizing tasks when they should be reimagining systems - The career reset happening right now (and how to capitalize on it) - How to build organizations that thrive on continuous change - Why grassroots experimentation beats top-down AI training - The coordination breakthrough that could finally fix software development This isn't just another AI episode—it's the culmination of everything we've learned about transformation, synthesized into actionable insights for leaders who want to get ahead of change instead of being overwhelmed by it. 📚 RESOURCES: NYT Vietnam Article: https://www.nytimes.com/2025/10/27/world/asia/vietnam-russia-relations.html Meg's Blog 'The Future is Interdisciplinary' | https://www.megbear.com/post/the-future-is-interdisciplinary AI Transformation Maturity Model: https://www.linkedin.com/pulse/ai-transformation-paradox-why-todays-innovation-tomorrows-amy-wilson-8adqf/ Amy's Product Transformation Story at SAP SuccessFactors: https://www.linkedin.com/pulse/my-product-transformation-story-sap-successfactors-what-amy-wilson-djk9c/ Sangeet Paul Choudary's "Reshuffle": https://www.amazon.com/Reshuffle-wins-restacks-knowledge-economy-ebook/dp/B0DTKW6NQV 🔗 CONNECT: Leadership Questions: amywilsonadvisor@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #AITransformation #BusinessTransformation #MegAndAmyShow #ChangeManagement #FutureOfWork
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    57 m
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