The Meg and Amy Show

• Episode 23 | The Explorer CEO: Yamini Rangan on Inventing the AI-First Operating Model at HubSpot

  🚀 INVENTING THE AI-FIRST OPERATING MODEL: HubSpot CEO Yamini Rangan reveals how she completely scrapped her $40B company's roadmap and rebuilt it AI-first. Learn how to pivot from volume to conversion, navigate the decline of SEO, and lead transformation when no one has the answers. ⏰ TIMESTAMPS: 00:00 Introduction: From Reading Every Book in the Library to CEO 05:00 Moving to the US: The Airport Story and Finding Her Voice 15:50 Immigration, Grit, and Tools for Navigating the Unknown 25:30 Customer Centricity: Sales is About Getting Customers Promoted 33:45 The 2023 AI Pivot: "When I Said Go, Nobody Went" 42:00 Change Management: Innovation Density vs Team Size 49:25 Board Role in AI Transformation 52:30 Marketing's Biggest Shift in Decades: SEO to AEO 57:00 3X Better Conversion: Volume Game vs Conversion Game 1:04:15 Leadership Corner: What mindset shifts do leaders need to make during times of huge change? 🔑 KEY INSIGHTS: - The mindset shift from "knowing" to "exploring" required for modern leadership - Sales isn't about closing deals - it's about getting your customers promoted - The shift from information to answers: People no longer want to search, they want well-researched answers - LLM queries average 23 words vs 5-word searches - showing much deeper, specific intent - Why LLM leads convert 3X better than traditional search leads - Why 8 out of 10 Google searches now result in zero clicks 📚 RESOURCES: Blindspotting: How to See What Others Miss | https://amazn.so/97uYE8w Yamini's Thought Leadership From INBOUND | https://www.linkedin.com/posts/yaminirangan_yesterday-at-inbound-i-had-the-pleasure-activity-7369750149276815360-RJC7?utm_source=share&utm_medium=member_desktop&rcm=ACoAAB5eYzoBji0hRFR25InbUtOYcrXhHjARevM Yamini on AEO vs. SEO | https://www.linkedin.com/posts/yaminirangan_its-been-a-week-since-we-launched-the-loop-activity-7371552819247759361-21_r?utm_source=share&utm_medium=member_desktop&rcm=ACoAAB5eYzoBji0hRFR25InbUtOYcrXhHjARevM **🔗 CONNECT:** Yamini's LinkedIn: https://www.linkedin.com/in/yaminirangan/ Yamini's Executive Bio: https://www.hubspot.com/company/management/yamini-rangan Leadership Questions: [email protected] Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #Blindspotting #Leadership #AI #IntellectualHumility #BusinessTransformation #HubSpot #MegAndAmyShow

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• Episode 22 | Dr. Kirstin Ferguson on The Curse of Expertise in the AI Age

  🚀 Why "I Don't Know Yet" Is the Most Valuable Leadership Skill in the AI Age: Dr. Kirstin Ferguson reveals how expertise becomes your biggest enemy and why intellectual humility beats certainty every time. ⏰ TIMESTAMPS: 00:00 Introduction & Antarctica Adventures 02:06 Welcome to Dr. Kirstin Ferguson 04:38 Why Travel Reduces Blindspots 05:49 The UK Post Office Scandal: When "The Computer Is Always Right" 08:44 How Success Becomes the Enemy of Adaptation 10:50 The Power & Authority Problem: Why People Won't Tell You You're Wrong 12:45 Why Leaders Are Trained to Have All the Answers (And Why It's Wrong) 20:13 Meg's SuccessFactors Story: Leading Through "I Don't Know" 26:32 What If the Post Office Had Been Curious Instead of Certain? 35:48 Meg's Oracle Epiphany: When Everyone's Pretending to Know 38:11 Reading the Room: When NOT to Say "I Don't Know Yet" 46:33 Kirstin's Work-From-Home Pivot: How to Change Your Mind Publicly 49:06 The Career Advice Blindspot: Why Parents Give Terrible Job Advice 51:50 The Three Practices: Be Honest, Be Curious, Be Flexible 53:22 Leadership Corner: Should You Pursue Leadership During Uncertain Times? 🔑 KEY INSIGHTS: - The "curse of expertise": Why being right makes you worse at knowing when to doubt yourself - How 900+ innocent people were prosecuted due to blind faith in technology - Why "I don't know yet" builds more trust than false certainty - The art of reading the room while admitting uncertainty - How to unlearn outdated expertise for the AI age 📚 RESOURCES: Blindspotting: How to See What Others Miss | https://amazn.so/97uYE8w Head & Heart | https://amazn.so/oOLPfL2 Dr. Kirstin Ferguson's weekly column "Got a Minute?" - Sydney Morning Herald/The Age How Travel Rewires Your Brain | https://superage.com/one-creativity-habit-nobel-scientists-swear-by/ SAP SuccessFactors Migration | https://news.sap.com/2023/02/sap-successfactors-next-generation-cloud-delivery/ Think Again, Adam Grant | https://amazn.so/wglEb5N **🔗 CONNECT:** Kirstin's LinkedIn: https://www.linkedin.com/in/kirstinferguson/ Kirstin's Website: https://www.kirstinferguson.com/ Leadership Questions: [email protected] Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #Blindspotting #Leadership #AI #IntellectualHumility #BusinessTransformation #MegAndAmyShow

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• Episode 21 | Female Leadership in a World Built for Men

  🚀 BREAKING OUT OF THE DEFAULT MALE WORLD: Meg and Amy reveal the hidden challenges of female leadership in a world designed by and for men. Learn how to navigate bias, own your power, and redefine what leadership looks like in the AI era in this raw and empowering conversation. ⏰ TIMESTAMPS: 00:00 Introduction to Female Leadership Challenges 05:55 WNBA Success and Equal Pay Movement 07:06 Fiji Simo's Historic OpenAI Appointment 08:09 AI Bias: ChatGPT Recommends Lower Salaries for Women 14:17 Invisible Women: The Default Male Design Problem 18:46 Power vs. Pleasant Language in Performance Reviews 24:42 Media Bias: Men Talk Money, Women Talk Culture 30:05 When Did You First Notice You Were "Other"? 33:49 From Mentee to Threat: How Power Changes Everything 42:42 "Everyone's Full of Shit" - Overcoming Imposter Syndrome 46:09 Hope for the Future: AI Era Leadership 48:50 Leadership Corner: New Mom Executive Concerns 🔑 KEY INSIGHTS: - Why AI systems perpetuate gender bias by recommending lower salaries for women - The "default male" problem affects everything from T-shirts to car safety systems - How women are described as "pleasant" while men get "powerful" language in reviews - The shift from welcomed mentee to perceived threat as women gain real power - Why balancing confidence with warmth is a uniquely female leadership challenge 📚 RESOURCES: - Kieran Snyder's LinkedIn Post: https://www.linkedin.com/posts/kieran-snyder_35-of-people-in-the-nerd-processor-survey-activity-7358858695188901888-Yd6-?utm_source=share&utm_medium=member_desktop&rcm=ACoAAB5eYzoBji0hRFR25InbUtOYcrXhHjARevM - Surface Fairness, Deep Bias: A Comparative Study of Bias in Language Models: https://arxiv.org/pdf/2506.10491 - Invisible Women by Caroline Criado Perez: https://amazn.so/Ie3mLd9 - Freakonomics: https://amazn.so/NeeOmhN - Likeable Badass by Alison Fragale: https://amazn.so/o1suXHW - Kieran's Interview Study: https://www.linkedin.com/posts/kieran-snyder_35-of-people-in-the-nerd-processor-survey-activity-7358858695188901888-Yd6-/?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAAVeN8BrXyqZRtd37eT9lCYDRykSAdLh5A - Jingjin Liu's Post on Diary of a CEO: https://www.linkedin.com/posts/jingjin-liu_ive-been-a-long-time-admirer-of-diary-activity-7341970108489093121-nlu_?utm_source=share&utm_medium=member_desktop&rcm=ACoAAB5eYzoBji0hRFR25InbUtOYcrXhHjARevM - Meg's Podcast with Charlotte Otter: https://open.spotify.com/episode/6jTHKO5ieg1PPErWb6BndQ - Amy's Podcast with Charlotte Otter: https://open.spotify.com/episode/164CQ4o14jqgRPWB40cKAC?si=Ytj7HsCeRQG8xGzhcUHT3ghttps://open.spotify.com/episode/164CQ4o14jqgRPWB40cKAC?si=Ytj7HsCeRQG8xGzhcUHT3g - Becoming by Michelle Obama: https://amazn.so/baf6fwF - The Insight Loop Newsletter: https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7357876676623544322 **🔗 CONNECT:** Leadership Questions: [email protected] Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #FemaleLeadership #WomenInTech #AIBias #LeadershipDevelopment #MegAndAmyShow

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• Episode 20 | Angela Le Mathon: Speaking the Language of Business – From Skills to AI ROI

  Angela Le Mathon reveals how HR leaders can move beyond the "skills data trap" to drive real business outcomes with AI. Learn how to speak the language of business, avoid the employee experience trap, and design AI-native organizations in this thought-provoking conversation on business transformation and leadership. **🔑 KEY INSIGHTS:** Skills data works for talent marketplaces but doesn't drive business outcomes HR must shift from talking about programs and platforms to speaking outcomes language Treat AI as experimental technology and focus on safe use cases first Employee experience initiatives need specific productivity unlocks, not general improvements Future organizations will be designed AI-native from the ground up **⏰ TIMESTAMPS:** 00:00 Introduction to Angela Le Mathon 02:05 Culture shock: Coming back to America 03:57 Angela's journey into analytics 07:29 Evolution from "what's happening" to "what's possible" 15:28 Building cross-functional analytics teams 16:50 Why everyone needs to become a unicorn 19:53 The analytics evolution moment 23:14 AI advisory tips for CHROs 26:31 The employee experience trap 42:46 AI native org design and workforce planning 45:30 Speaking the language of business 47:00 The skills data reality check 49:11 Final advice: Embrace experimentation 50:23 Leadership Corner: Getting senior colleagues to listen **📚 RESOURCES:** Angela's Guest Lecture at Stanford: https://www.linkedin.com/feed/update/urn:li:activity:7358923352830296065/ Everything is Figureoutable: https://amazn.so/mOs1fUJ Range: https://amazn.so/iUn324r **🔗 CONNECT:** Angela: https://www.linkedin.com/in/lemathon/ Leadership Questions: [email protected] Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #AILeadership #PeopleAnalytics #SkillsData #BusinessTransformation #HRStrategy #MegAndAmyShow

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• Episode 19 | Seth Wylie: Stop Training, Start Harvesting – The Grassroots AI Revolution

  🌐 Most companies are approaching AI adoption backwards. While executives push top-down strategies, the real innovation is happening in the trenches. Seth Wylie reveals why successful AI transformation starts with the people already experimenting - not training programs or executive mandates. **🔑 KEY INSIGHTS:** - Why mandatory AI training kills experimentation before it starts - The one question that gets everyone talking: "What have you been experimenting with this week?" - How to connect grassroots innovation to executive priorities - Why executives are disconnected from AI tools (and what to do about it) - Building "AI Clubs" that people actually want to join - Creating psychological safety for awkward first attempts **⚡ SETH'S APPROACH:** Find the experimenters already on your team → Create space for them to share → Let insights bubble up naturally → Then add training when there's momentum "Companies need to harvest the experimentation that's already happening, not mandate what should be happening." **⏰ TIMESTAMPS:** **01:00** - Meet Seth Wylie: AI Transformation Expert & Acapella Singer **08:32** - Finding Signal: How to Spot AI Innovation in Your Organization **10:45** - **The Magic Question: "What Have You Been Experimenting With This Week?"** **13:18** - Why Executives Are Disconnected from AI Tools **14:11** - What Companies Get Wrong: Training Before Mindset **18:08** - Leadership by Example: When CEOs Use AI for Poetry **19:26** - The Translation Problem: Executive vs. Individual Priorities **20:23** - Emergence Capital's Offsite Success Story **28:36** - Organizational Structure Changes for AI Transformation **32:22** - Creating Value Categories: ROI vs. Engagement vs. Innovation **34:48** - The Spreadsheet Story: How Leaders Kill Innovation and The Power of Executive Curiosity **37:10** - **Seth's Favorite Tool: AI for Self-Knowledge** **40:29** - Amy's Claude Projects Discovery (Life-Changing!) **42:19** - Wrap-up & Gratitude **💼 LEADERSHIP CORNER** **42:47** - Question: Should I Dive Into AI Tools or Let My People Mature First? **43:03** - Meg's Take: Get Context First, Model Curiosity Over Perfection **44:56** - The Learning Paradox: Being Bad at Things Builds Empathy **47:15** - Practical Advice for AI Leadership Balance **53:58** - Final Thanks & Sign-off 🎵 **BONUS:** Seth performs an acapella song live on the show! **📚 RESOURCES:** New York Times: CEOs Adopt AI: https://www.nytimes.com/2025/08/16/business/ceos-adopt-ai.html Meg's AI Fluency Blog: https://www.megbear.com/post/stop-wasting-time-on-ai-fluency-projects Emergence Capital Offsite: https://www.linkedin.com/posts/jakesaper_at-emergence-capitals-investment-team-offsite-activity-7328060051531747328-v3on/ Reshuffle Book: https://amazn.so/Rrd62oi **🔗 CONNECT:** Seth: https://www.linkedin.com/in/sethwylie/ Leadership Questions: [email protected] Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #AITransformation #BottomUpInnovation #AIStrategy #OrganizationalChange #Leadership #Innovation #AIAdoption #BusinessTransformation #WorkplaceInnovation #AIExperimentation

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