Episodes

  • Episode 29 | Jason Averbook on 4 Forces Reshaping Work: Why AI Transformation Isn't About Technology
    Dec 19 2025
    🚀 Jason Averbook reveals the 4 forces creating the biggest change HR has ever seen—and why 95% of AI projects are failing. This isn't about technology; it's about trust, engagement, and fundamentally rethinking how work gets done. ⚡ THE 4 FORCES RESHAPING WORK: 1. Engagement is slipping (trust in companies at all-time lows) 2. Jobs and skills are changing rapidly 3. Early career on-ramp is broken 4. AI is being pushed into unprepared organizations 🔑 KEY INSIGHTS: - We're asking people to change while wearing "uniforms they don't trust" - AI transformation is a people problem, not a technology problem - Most companies are trapped in task optimization vs. workflow revolution - Early talent needs to challenge assumptions, not just fill roles - "Proof of work" beats "proof of education" in today's job market - Unlearning matters more than skill development 💡 FRAMEWORKS REVEALED: - Jason's 4 Sets: Mindset, Heart Set, Skill Set, Tool Set - Amy's AI Transformation Maturity Model - The FAFO Philosophy (Fool Around and Find Out) - AI Enablement Centers vs. traditional training 🎯 TACTICAL TAKEAWAYS: - Build proof of work without a job (18-year-old built 5 apps example) - Use LinkedIn to access networks, not just contact people - Start with workflows, then add technology (not the reverse) - Invest in unlearning before upskilling - Create "challenge partners" across age groups 🏢 THE PEOPLESOFT CONNECTION: Jason, Meg, and Amy share insights from their days as young professionals disrupting the status quo at PeopleSoft—and why today's organizations need that same fresh perspective. Jason Averbook is Senior Partner and Global Leader of Digital HR Strategy at Mercer, guiding 1,000+ organizations through transformation. This conversation bridges cutting-edge AI strategy with timeless leadership principles. ⏰ TIMESTAMPS: 00:00 Introduction & The 4 Forces Framework 07:55 Trust Crisis: Why Engagement Matters 17:00 AI Enablement Centers vs. Traditional Training 28:37 Early Career Crisis: Proof of Work vs. Education 41:09 Diversity Redefined: Age, Context & Experience 42:43 Amy's AI Transformation Maturity Model 44:45 Jason's 4 Sets Framework 47:40 Leadership Corner: Merging Dysfunctional Teams 🔗 CONNECT: Submit Leadership Questions: [EMAIL] The Meg and Amy Show: [LINKS] Jason Averbook: [LINKEDIN] #AITransformation #Leadership #HRStrategy #DigitalTransformation #FutureOfWork #EmployeeEngagement #EarlyCareers #WorkflowOptimization #MegAndAmyShow 📚 RESOURCES: Jason's Now to Next Podcast | https://open.spotify.com/show/1zrFUr0dBTUG2EUcK8ca5g How HR Took Over the World | https://www.economist.com/business/2025/11/10/how-hr-took-over-the-world The Palantir Model | https://blog.palantir.com/a-day-in-the-life-of-a-palantir-forward-deployed-software-engineer-45ef2de257b1Meg Bear on WTF Is a Forward-Deployed Engineer? by Thomas Otter | https://thomasotter.substack.com/p/wtf-is-a-forward-deployed-engineer/comment/110916540 Amy's Transformation Maturity Model | https://www.linkedin.com/pulse/ai-transformation-paradox-why-todays-innovation-tomorrows-amy-wilson-8adqf/ 🔗 CONNECT: Jason Averbook: https://www.linkedin.com/in/jasonaverbook/ Amy Wilson: https://www.linkedin.com/in/amy-wilson-insight/ Meg Bear: https://www.linkedin.com/in/megbear/ Instagram: @megandamyshow
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    54 mins
  • Episode 28 | HR Tech's Top Analyst John Sumser: AI Reality, Career Reinvention & What's Broken in HR
    Dec 12 2025
    🚀 FROM FOOD CRITIC TO KITCHEN: John Sumser, HR tech's leading independent analyst for over 20 years, reveals what happens when you step from the sidelines into operations—and why most of what we believe about AI, HR, and career success is wrong. Learn how to navigate uncertainty as opportunity, why "I don't know" is the most powerful thing a leader can say, and what the next 5 years hold for HR in this candid conversation about transformation and truth-telling. ⏰ TIMESTAMPS: 00:00 Teaser: The Best Clips 02:21 Welcome & Introduction 03:03 The Door-to-Door Santa Story 05:03 Polaroid's $100M Mistake: Old Problems, New Technology 10:00 Navigating Recession and Uncertainty 15:40 Comfort with Uncertainty as a Career Tool 18:00 From Food Critic to Kitchen: The Analyst Becomes an Operator 20:30 "I Don't Know" - The Most Powerful Leadership Tool 22:00 What Surprised Him About Being Inside 25:48 Re-igniting HR Examiner with Heather Bussing 28:00 AI's 80% Problem: Why Silicon Valley's $20 FUD is Working 31:55 Anthropomorphism: When AI Feels Like Your Friend 35:00 The Gigawatt Problem: AI's Energy Reality 40:00 Five Years Out: HR's Cracks Are Starting to Show 42:30 "What the Hell Do You Need Recruiters For?" 45:00 Strategy = Alignment (Not What HR Thinks It Means) 48:00 Leadership Corner: Caught Between Competing Executives 🔑 KEY INSIGHTS: - People take new technology and solve old problems without understanding what the new tech can do—this is how Polaroid failed, and it's exactly where we are with AI today - The difference between being a food critic and working in the kitchen: analysts imagine smooth stories, operators learn to wrap stories around chaos - "I don't know" is the most powerful thing you can say—it gives you a path out and creates space for improvisation - LLMs are 80-84% accurate, which means 1 out of every 5-10 words is wrong—and that makes them unusable for most HR applications - AI companies want you to anthropomorphize their tools so you'll lower your expectations and stay sticky with their product - In 5 years: People closer to the problem will solve it—recruiting shouldn't be centralized, it's a first-level supervisor's job - HR is an "ocean of exceptions to budget discipline" while every other function has rigorous budget management - The line from checkbook to productivity runs AROUND HR, not through it—and that has to change 📚 RESOURCES: HR Examiner: https://www.hrexaminer.com (John's analysis and commentary) John's Articles: 80% Isn't Very Good | https://www.hrexaminer.com/p/80-isnt-very-good Anti-Anthropomorphism Prompt | https://www.hrexaminer.com/p/anti-anthropomorphism-prompt Promptly Transparent | https://www.linkedin.com/pulse/promptly-transparent-john-sumser-qwjgc/? Sam Altman on AI's Energy Consumption | https://www.youtube.com/watch?v=Gnl833wXRz0 Democrats Seek New Relationship With Fossil Fuels | https://www.semafor.com/article/12/04/2025/democrats-seek-a-new-relationship-with-fossil-fuels 🔗 CONNECT: John Sumser: https://www.linkedin.com/in/johnsumser/ Amy Wilson: https://www.linkedin.com/in/amy-wilson-insight/ Meg Bear: https://www.linkedin.com/in/megbear/ Instagram: @megandamyshow This episode features one of the most provocative conversations we've had about the gap between AI hype and AI reality, why HR's current design is broken, and what happens when someone who's been watching for decades steps into the arena. John doesn't hold back—and neither do we. #AITransformation #HRTech #CareerReinvention #Leadership #FutureOfWork #MegAndAmyShow
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    52 mins
  • Episode 27 | Your Share of the Profits: Scott Santens on Why UBI Is Obvious, Not Radical
    Dec 5 2025
    Finland – Universal Basic Income Pilot🚀 THE CASE FOR GIVING PEOPLE MONEY: UBI expert Scott Santens reveals why the most radical idea in economics might be the simplest - just give people cash. Discover how Alaska has proven this works for 40+ years, why his crowdfunded basic income changed everything he thought about work, and what happens when we shift from survival mode to abundance thinking. ⏰ TIMESTAMPS: 00:00 Introduction: The Man Living UBI 02:33 How Scott Crowdfunded His Own Basic Income 07:32 What Universal Basic Income Actually Is 08:51 Why Work Requirements Don't Work 10:36 The Billionaire Question: Why Universal Matters 15:38 The Power to Say No 17:46 Reduced Stress Changes Everything 20:13 The Biggest Impact Is Always on Kids 22:28 Automation Since the 1970s: We're Already Living It 25:04 The Business Case for Consumption 27:57 Alaska: 40+ Years of Proof 36:29 Trust, Finland & the Rory Stewart Connection 46:44 Star Trek vs. Dystopia: Two Possible Futures 51:35 Amy's Aha Moment: The Dividend Concept 54:19 Where to Give Cash With No Strings Attached 57:17 We Have the Data - Time to Act 59:28 Leadership Corner: Moving from Full-Time to Portfolio 🔑 KEY INSIGHTS: - How living on crowdfunded UBI taught Scott about human potential - Why Alaska proves UBI works (and has for decades without inflation) - The hidden connection between stress reduction and crime prevention - Why cash beats free services every single time - How economic security literally rewires decision-making - The difference between surviving and thriving economies 📚 RESOURCES: Scott's UBI FAQ: scottsantens.com Basic Income Show: https://www.youtube.com/c/ScottSantens Income To Support All Foundation: itsafoundation.orgWhat If Everybody Didn't Have to Work to Get Paid? | https://www.theatlantic.com/business/archive/2015/05/what-if-everybody-didnt-have-to-work-to-get-paid/393428/Basic Income Grant (BIG) in Namibia | https://centreforpublicimpact.org/public-impact-fundamentals/basic-income-grant-big-in-namibia/Income Dividends and Subjective Survival in a Cherokee Indian Cohort | https://pmc.ncbi.nlm.nih.gov/articles/PMC7250001/How AI will impact the future of work with Kara Swisher and Betsey Stevenson | https://www.youtube.com/watch?v=hUrBYWQAcpECash Transfers and Child Welfare: Lessons from Alaska | https://www.nber.org/digest/202401/cash-transfers-and-child-welfare-lessons-alaska?page=1&perPage=50To End Extreme Poverty, Give Cash — Not Advice | Rory Stewart | TED | https://www.youtube.com/watch?v=tt0HOe7gf7IFinland – Universal Basic Income Pilot | https://weall.org/resource/finland-universal-basic-income-pilotManna: Two Visions of Humanity's Future Book | https://www.amazon.com/Manna-Two-Visions-Humanitys-Future-ebook/dp/B007HQH67UEverything is Figureoutable Book | https://amazn.so/5wcD9tFIkigai: The Japanese Secret to a Long and Happy Life | https://amazn.so/yNaA8GI Thanks to Laurie Ruettimann for the introduction! #UBI #UniversalBasicIncome #ScottSantens #AlaskaDividend #FutureOfWork #Economics #Alaska #Dividend #NegativeIncomeTax #MegAndAmyShow 🔗 CONNECT: Scott Santens: scottsantens.com Leadership Questions: amywilsonadvisor@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show
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    1 hr and 9 mins
  • 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 mins
  • 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 hr
  • 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 mins
  • Episode 23 | The Explorer CEO: Yamini Rangan on Inventing the AI-First Operating Model at HubSpot
    Oct 31 2025
    🚀 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: amywilsonadvisor@gmail.com 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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    1 hr and 12 mins
  • Episode 22 | Dr. Kirstin Ferguson on The Curse of Expertise in the AI Age
    Oct 17 2025
    🚀 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: amywilsonadvisor@gmail.com 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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    1 hr and 2 mins