• What Every Executive Woman Should Know About Perimenopause
    Oct 16 2026
    What Every Executive Woman Should Know About Perimenopause with Dr. Jessica Kassis OB-GYN Dr. Jessica Kassis missed her own perimenopause for a year - until her primary care doctor caught it. She joins Meg and Amy to explain why high-performing women miss the signs at work, how to talk to your doctor, and what actually helps with brain fog, rage, sleep, and burnout. We cover #perimenopauseatwork , #brainfogperimenopause , hormone stabilization vs replacement, birth control in early perimenopause, advocating for care, leaving a hospital system to build Radiant Women's Health at 46, plus Leadership Corner on leading with candor when a strong performer slips. Featuring Dr. Jessica Kassis, OB-GYN and co-founder of Radiant Women's Health, with hosts Meg Bear and Amy Wilson. Timestamps: 00:00 Intro to Dr. Jessica Kassis 02:25 Her personal perimenopause story as a GYN 05:58 Why doctors avoid menopause care - RVUs and 20-minute visits 07:52 I don't feel like myself - the key symptom 10:29 Brain fog, estrogen receptors and sleep 1 3:34 Early vs later perimenopause explained 16:25 Stabilizing vs adding - birth control pill option 20:09 Rage, misophonia and hormones 26:12 Finding care beyond concierge - telehealth options 28:28 How to advocate with your doctor 31:33 Leaving the system - burnout and loss of empathy 37:27 Energy alignment and North Star 39:27 Building Radiant Women's Health and partnership 44:01 Growth, marketing and community 47:21 Leadership Corner - when a high performer slips Subscribe to The Meg and Amy Show for weekly conversations on AI, leadership and the future of work. Full episode out Friday. #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #WomenInLeadership #LeadershipWellness
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    1 hr and 1 min
  • HubSpot Layoff Memo: What She Got Right and Wrong
    Oct 13 2026
    HubSpot CEO Yamini Rangan shared a layoff memo for 660 employees. As longtime operators, Meg and Amy break down what she got right (and wrong) about leading with clarity, humanity, and accountability in a hard moment, and what other leaders can learn from it. What we cover: - Why this memo stood out from most layoff announcements - What Yamini got right on principles, focus, and severance - What was missed on market pressure, cost structure, and investing better Timestamps: 00:00 Why this HubSpot memo stood out 00:56 What Yamini got right up front 01:44 It's not about AI - but it is about AI 02:34 First principles before cuts 04:01 Flattening and the leadership bar 06:46 Severance transparency 08:17 What she got wrong and close About The Meg and Amy Show: Former tech executives Meg Bear and Amy Wilson share bold takes and real expertise on AI, leadership, and the future of work. #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #WomenInLeadership #ChangeManagement
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    12 mins
  • AI Won't Fix a Broken Process: Stacey Harris Shares Survey Data
    Oct 9 2026
    AI won't fix a broken process — it makes outcomes worse. Stacey Harris shares new results from the 29th Annual HR Systems Survey on what actually drives better outcomes. Former tech executives Meg Bear and Amy Wilson sit down with Stacey Harris, Chief Research Officer at Sapien Insights Group, to break down 29 years of HR tech data and what it means for leaders working on AI, HR tech, and the future of work. Stacey explains why companies that fix processes and HR data first see better business outcomes, why less than 50% of enterprises have an enterprise integration strategy for HR data, why HR is uniquely equipped to lead AI oversight, and why putting a chief AI officer in charge lowers HR's strategic standing and hurts results. Plus practical advice on how to raise burnout and cost pressure without sounding anti-AI. Timestamps: 00:00 Intro with Stacey Harris 01:11 Why 29 years of survey data matters 11:15 Why AI won't fix a broken process 15:01 Less than half have an HR data plan 30:14 Why a chief AI officer hurts outcomes 32:14 Why HR must lead AI oversight 33:14 Treat AI like employees? 38:58 Agent costs and rehiring after AI layoffs 53:36 Leadership Corner: Raising burnout without sounding anti-AI 65:14 Closing 📚 RESOURCES: Sapient Insights Group: https://sapientinsights.com/ Stacey's HR Tech 2026 session, 29th Annual HR Systems Survey key findings: https://www.hrtechnologyconference.com/seminar-programme-2026/voice-customer-sapient-insights-group-29th-annual-hr-systems-survey-key-findings "Introduction to HR Technologies" by Stacey Harris: https://sapientinsights.com/introduction-to-hr-technologies-book/ "Introduction to HR Technologies" on Amazon: https://a.co/d/060S7PXs Lexy Martin, founder of the HR Systems Survey: https://www.linkedin.com/in/lexymartin/ Josh Bersin: https://www.linkedin.com/in/bersin/ Leighanne Levensaler: https://www.linkedin.com/in/leighannelevensaler/ Aashna Kircher: https://www.linkedin.com/in/aashna-kircher-75657b34/ W. Edwards Deming: https://en.wikipedia.org/wiki/W._Edwards_Deming Meta to record employee keystrokes to train AI (TechCrunch): https://techcrunch.com/2026/04/21/meta-will-record-employees-keystrokes-and-use-it-to-train-its-ai-models/ Our AI transformation framework (Ep 24): https://wrkdefined.com/podcast/the-meg-and-amy-show/episode/episode-24-24-episodes-of-learning-our-ai-transformation-framework-for-getting-ahead "You Can't Redesign Work With a Team You Haven't Designed" (Amy): https://www.themegandamyshow.com/p/you-can-t-redesign-work-with-a-team-you-haven-t-designed "The End of the World Is Just the Beginning" by Peter Zeihan: https://a.co/d/0gEr0JTC HR Tech 2026: https://www.hrtechnologyconference.com/ HR Tech taps WRKdefined as official podcast network: https://www.globenewswire.com/news-release/2026/09/29/3370653/0/en/hr-tech-taps-wrkdefined-as-official-podcast-network-for-next-month-s-event.html 🔗 CONNECT: Stacey Harris: https://www.linkedin.com/in/staceyharris/ Website: https://www.themegandamyshow.com/ Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show https://www.linkedin.com/in/megbear/ https://www.linkedin.com/in/amy-wilson-insight/ About The Meg and Amy Show: Former tech executives Meg Bear and Amy Wilson share bold takes and executive expertise on AI leadership, HR tech, and the future of work. #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #HRTech
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    1 hr and 5 mins
  • The Future of People Analytics Isn't About (Just) People
    Oct 2 2026
    People analytics has spent years analyzing people. Now it needs to analyze the work. Recorded live at People Analytics World, Meg Bear and Amy Wilson make the case that as AI changes how work gets done, the function has to move past studying humans and start studying the system of work itself: how humans and AI share it, where it gets stuck and how it should be designed. They also discuss why the bottleneck in software was never the code, and why AI should change how the whole engineering organization works, not just the engineers. They also cover why "learn it, train it, deploy it" breaks down when AI keeps improving this fast, and why leaders need to keep learning too. From there, they get into what it takes to lead right now. It takes a special person who's willing to unlearn and relearn, and a special organization around them. They talk about why the manager job just got a lot harder and is likely to be split into separate roles. And they make the case that you can't start a movement alone. If you work in people analytics, lead teams or design how work gets done, this conversation is about the questions you'll face next. Subscribe for more from The Meg and Amy Show. TIMESTAMPS: 00:00 Welcome: Live from People Analytics World 02:14 David Green Keynote: A Teams vs B, C, D Teams 04:17 AI Use Cases Still Stuck in HR Topics 05:09 Work Design Goes Mainstream: From Evangelism to Urgency 06:44 DRI vs Dynamic Team: Prasad Setty and Amy's Debate 09:20 Why Committees Fail and Movements Need Co-Creators 10:40 Intel's Kelsey Klein: Real Work Redesign Use Cases 12:04 Changing the Organisation vs Changing the Individual 13:26 Software Dev Bottlenecks Are Not the Code 17:49 Bundling and Unbundling: Roles, AI Tasks and the Manager 20:06 Jack Dorsey's Model as an Extreme Provocation 22:12 Human-AI Systems: Measuring What Makes Humans Better 25:35 The Special Person and the Special Organisation 28:36 The Future of the People Analytics Role 30:56 Context Engines, Strategy Alignment and Sense-Making 34:25 Storytelling as a Core Analytics Skill 35:33 Dashboards Are Dead, Long Live Interactive Data Spaces 📚 RESOURCES: People Analytics World: https://home.paworld365.com/ PAWorld26 New York: https://home.paworld365.com/events/26nyc/ Ikona Analytics, our podcast stage host: https://www.ikonaanalytics.com/ Richard Rosenow: https://www.linkedin.com/in/richardrosenow/ "The End of People Analytics As We Knew It" (Ikona): https://www.ikonaanalytics.com/insights/the-end-of-people-analytics "Context Is All You Need" (Ikona): https://www.ikonaanalytics.com/insights/context-is-all-you-need Insight222 People Analytics Trends 2025/26 (David Green): https://go.insight222.com/insight222-people-analytics-trends-report-2025/26 Prasad Setty: https://www.gsb.stanford.edu/faculty-research/faculty/prasad-setty Siobhan Savage, Reejig: https://www.reejig.com/company/siobhan-savage "You Can't Redesign Work With a Team You Haven't Designed" (Amy): https://www.themegandamyshow.com/p/you-can-t-redesign-work-with-a-team-you-haven-t-designed "From Hierarchy to Intelligence" (Jack Dorsey & Roelof Botha): https://sequoiacap.com/article/from-hierarchy-to-intelligence Jaya Gupta on unbundling intelligence: https://x.com/JayaGup10/status/2101799427145183571 Our episode with Jason Cohen: https://wrkdefined.com/podcast/the-meg-and-amy-show/episode/hidden-ways-to-grow-without-more-hires-or-funding-jason-cohen Kieran Snyder: https://www.linkedin.com/in/kieran-snyder-60572987/ Morgan Depenbusch: https://www.linkedin.com/in/morgandepenbusch/ Bill and Morgan's Dashboard Confessionals: https://creators.spotify.com/pod/profile/bill-yost/ 🔗 CONNECT: Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show https://www.linkedin.com/in/megbear/ https://www.linkedin.com/in/amy-wilson-insight/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #HRTech #AIStrategy
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    37 mins
  • Why Conway's Law Matters More in the Age of AI
    Sep 30 2026
    Why do Sales, Customer Success, and Engineering keep hitting the same friction? In this hot take, Meg Bear and Amy Wilson break down Conway's Law — the idea that your org structure shows up in how work gets done. From DRIs as a band-aid to why aligned incentives and shared goals matter more than boxes and roles, plus the Oracle story and why AI makes this urgent now. Subscribe for bold, exec-level takes on AI, leadership, and the future of work with The Meg and Amy Show. #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #ChangeManagement #AIStrategy
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    8 mins
  • Hidden Ways to Grow Without More Hires or Funding | Jason Cohen
    Sep 25 2026
    Serial founder Jason Cohen shares hidden ways to grow without more hires or funding from his book Hidden Multipliers. Meg Bear and Amy Wilson dig into why negative reviews boost sales, the math behind keeping customers, and how to make frameworks actually fit your team. In this episode, Jason breaks down practical ideas leaders can use right away: - Why showing negative reviews builds trust, increases sales, and lowers returns - The churn math most teams miss — why keeping customers beats chasing new ones - How to make faster decisions with Fermi estimation - Who your best customer really is, and why the bottom 10% can drain profit - How to keep customer love as you scale, from Southwest to Workday - Why frameworks should fit like clothes — start off-the-rack, then tailor Jason Cohen is a serial entrepreneur and author of Hidden Multipliers. Meg Bear and Amy Wilson are former tech executives hosting The Meg and Amy Show on AI, leadership, and the future of work. TIMESTAMPS 00:00 Cold Open: Logo Churn Is Death 00:28 Introducing Jason Cohen 01:40 Engineering Mindset vs Strategic Thinking 03:09 A Smart Bear: Fermi Estimation and the Power of Ten 06:53 How Fermi Estimation Beats Scoring Rubrics 11:38 Why Jason Wrote Hidden Multipliers 14:24 Carol: The Ideal Customer Profile 16:51 Bazaarvoice Data: Negative Reviews Increase Sales 19:52 Strengths Are Proclivities: Context Changes Everything 25:36 The Workday Case Study: Love, Drift, and Disruption 28:03 Can You Scale and Keep Customer Love? 30:13 Culture, Founders, and Succession 36:37 Why Culture Cannot Live in One Person 38:55 The Math of Retention vs Net New Acquisition 40:55 Why Cancellation Is the Most Important Number 44:23 Customer Discovery: Hypothesis Before Interviews 50:30 Frameworks Are Clothes: Try, Tailor, or Reject 56:53 Closing Reflections 👉 Subscribe for weekly sharp takes for busy execs 👉 Tell us in comments: which multiplier will you try first? Links: https://andertoons.com/ https://en.wikipedia.org/wiki/Philip_E._Tetlock https://en.wikipedia.org/wiki/Law_of_trivialityhttps://longform.asmartbear.com/roi-rubric/ https://longform.asmartbear.com/https://skills.asmartbear.com/skills/asb-willingness-to-pay/ https://en.wikipedia.org/wiki/Enrico_Fermi https://www.linkedin.com/in/chanofernandez/ https://www.linkedin.com/in/hbrunner/ https://www.linkedin.com/in/reidhoffman/ https://www.linkedin.com/in/aneelbhusri/ https://www.linkedin.com/in/pattyazzarello/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #CareerAdvice
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    59 mins
  • Why AI Fails Without a New Operating Model with Kelley Steven-Waiss
    Sep 18 2026
    Your AI tools aren't broken. Your operating model is. Meg Bear and Amy Wilson sit down with Kelley Steven-Waiss, Founder of Novaworks, former CHRO, founder of Hitch (acquired by ServiceNow), and author of Valley Girls, to explain why so many AI pilots stall — and what great leaders do differently. Kelley shares why adding new tech on top of old ways of working leads to poor results, how to design a system of work that includes people, agents, and robots, and why she believes the CHRO role should evolve into Chief Work Officer. In this episode, you’ll learn: * Why AI fails when the operating model stays the same * How to map strategy to work before you add new tools * What strong AI leadership looks like in practice * How founders build resilience and the muscle for rejection About Kelley: Kelley Steven-Waiss is Founder of Novaworks, an AI-native system for managing the total workforce. She served as CHRO for 13 years, founded Hitch, and writes on leadership and the future of work. About the show: The Meg and Amy Show with former tech executives Meg Bear and Amy Wilson — bold takes on AI, leadership, and the future of work. References: https://home.paworld365.com/events/26sfo https://www.ikonaanalytics.com/ https://www.themegandamyshow.com/ https://www.stratechi.com/six-sigma/ https://www.linkedin.com/in/davewright2?trk=public_post_feed-actor-name https://www.linkedin.com/in/briansolis https://www.linkedin.com/in/kelleystevenwaiss https://www.amazon.com/Infinite-Visionary-Transform-Businesses-AI-Forward-ebook/dp/B0GZLNRLMS #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #WomenInLeadership
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    1 hr and 3 mins
  • Why Enterprise AI Fails at Work Design, Not Agents | Siobhan Savage
    Aug 28 2026
    Enterprise AI isn't failing because agents aren't smart enough — it's failing at work design. Reejig CEO Siobhan Savage joins Meg Bear and Amy Wilson to reframe AI transformation for the enterprise. The constraint isn't agent capability — it's aligning AI with workflows, org structure, and business outcomes. Siobhan breaks down why the workflow is now the core unit of work, how to build internal AI Work Design capability instead of outsourcing to consultants, and why transparent, human-centric change management beats token-based theater. In this conversation: - Why "AI-first" measured by token spend makes employees hate AI - Where humans stay in the loop — nothing is running end-to-end yet - Upgrade vs. reimagine: why you don't "vibe code the bank" - How the best companies get surgical with use cases — and why the CIO + CHRO + CFO trifecta matters With hosts Meg Bear and Amy Wilson — former tech executives tackling AI transformation, leadership, and the future of work with bold takes and real expertise. Chapters: 00:00 The dumbest "AI-first" metric leaders celebrate 00:52 Meet Siobhan Savage, CEO of Rejig 03:34 Reejig's mission - building the way the world works 05:21 How Reejig built 25 models of real work 07:50 Where automation lands today - sub-tasks, not jobs 09:40 It's not an agent problem, it's a work design problem 11:07 From tasks to workflows & the ROI shift 13:23 Who's actually buying - CIO + CHRO + CFO trifecta 16:22 Inside the AI Work Design team 20:34 Work Architects vs AI Work Designers vs Agent Builders 27:05 Job Architecture vs Work Architecture 31:07 Why the workforce is dysregulated right now 34:26 Being bold & responsible with AI 37:53 Stealth change management explained 42:18 Leaders must set expectations, not theater 46:42 Energy, structure & what lights Siobhan up 49:08 Leadership Corner - Should you hire a Chief of Staff? 58:28 AI vs human Chief of Staff Watch the Shorts from this episode on the channel all week. #aileadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #AIStrategy
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    1 hr and 4 mins