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The Meg and Amy Show

The Meg and Amy Show

By: WRKdefined Podcast Network
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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 Career Success Economics
Episodes
  • The One Question That Reveals Your Real Capability Gap with CEO Tom Monahan

    The One Question That Reveals Your Real Capability Gap with CEO Tom Monahan
    23 Oct 2026
    Why hasn't AI showed up in the P&L yet? Heidrick & Struggles CEO Tom Monahan joins Meg and Amy. His one question that reveals your real capability gap: If you just told your team to go do that, what wouldn't happen? Tom unpacks why the CEO job is now a two-way ambassador role, and why moving AI from the CEO story to the CFO numbers is the real test. He also makes the case for managers in an age of flat org charts, and why AI should mean better work sooner — especially for junior talent. Featuring Tom Monahan, CEO of Heidrick & Struggles, in conversation with Meg Bear and Amy Wilson. TIMESTAMPS 00:15 - Meet Tom Monahan, CEO of Heidrick & Struggles 01:19 - Lessons from a family carnival business 02:42 - Most businesses are all about the people 04:20 - Why the CEO job is getting more complex 05:49 - The CEO as two-way ambassador 12:18 - The one question that reveals capability gaps 17:51 - Move AI from the CEO script to the CFO numbers 19:02 - Using AI for immersive candidate scenarios 25:39 - Why demanagerizing has not worked 31:06 - When build costs go to zero, advisory value rises 35:52 - Better work sooner for junior talent 39:19 - 4 qualities of leaders who win now Subscribe to The Meg and Amy Show for bold takes on AI leadership, CEO leadership, and the future of work. 📚 RESOURCES: Show Up to Win by Jeff Sanders and Kelly O. Kay (Heidrick & Struggles): https://www.heidrick.com/en/pages/show-up-to-win-book "Finding the Human Core of Competitive Advantage in the AI Era: Avoiding the Pygmalion Trap" by Tom Monahan and Les Csorba: https://www.heidrick.com/en/insights/frontier-tech/finding-the-human-core-in-ai-era Route to the Top 2025 (Heidrick & Struggles research): https://www.heidrick.com/en/insights/chief-executive-officer/route-to-the-top-2025-the-ascent-redefined "From Hierarchy to Intelligence" by Jack Dorsey and Roelof Botha (Block): https://block.xyz/inside/from-hierarchy-to-intelligence Level 5 Leadership (Jim Collins): https://www.jimcollins.com/concepts/level-five-leadership.html Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox Generally Accepted Accounting Principles (GAAP): https://en.wikipedia.org/wiki/Generally_Accepted_Accounting_Principles_(United_States) Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias "The Future Is Interdisciplinary" by Meg Bear: https://www.megbear.com/post/the-future-is-interdisciplinary Heidrick & Struggles: https://www.heidrick.com/ 🔗 CONNECT: Tom Monahan: https://www.linkedin.com/in/tlmonahan/ Jeff Sanders: https://www.linkedin.com/in/jeffsanders2/ Kelly O. Kay: https://www.linkedin.com/in/kokay/ Tobi Lütke: https://x.com/tobi 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/ #AILeadership #FutureOfWork #ExecutiveLeadership #MegAndAmyShow #EnterpriseAI #AIStrategy
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    51 min
  • What Every Executive Woman Should Know About Perimenopause

    What Every Executive Woman Should Know About Perimenopause
    16 Oct 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 2 min
  • HubSpot Layoff Memo: What She Got Right and Wrong

    HubSpot Layoff Memo: What She Got Right and Wrong
    13 Oct 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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    13 min
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