The Meg and Amy Show

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

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

HubSpot CEO Yamini Rangan shared a layoff memo for 660 employees.

- 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

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

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

Why do Sales, Customer Success, and Engineering keep hitting the same friction?

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

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

Enterprise AI isn't failing because agents aren't smart enough — it's failing at work design.

The future of work has AI agents in it — and payroll isn't ready. Eynat Guez, co-founder and CEO of Papaya Global, joins Meg and Amy to explain why the 2030 workforce is humans and agents side by side, and why your compliance infrastructure better be ready. Eynat bet the company on owning the payment rails instead of expanding into HCM — and she did it "regulated by choice," taking on seven financial regulators globally. She breaks down why payroll sits at the intersection of HR and finance, why "move fast and break things" actively destroys value in regulated categories, and how she rolled out AI inside her own company by limiting usage first to protect employees from costly mistakes.

⏱️ In this episode:

00:00 Introduction and Open Water Swimming

03:16 The Strategic Bet: Payments Over HCM

06:14 Why Payroll Companies Don't Actually Pay People

08:00 Global Payroll Complexity and the Compliance Gap

11:00 Agentic Compliance Knowledge Base and AI Tools

12:32 How Papaya Tackles Cross-Border Payment Transparency

15:00 Fintech Regulation, KYC, and Anti-Money Laundering

16:35 Building Direct Local Bank Networks Across 150 Countries

18:50 Compliance as a Competitive Differentiator with Fortune 500

20:23 The End Worker Experience and Pay Date Liability

23:06 CyberArk Case Study: Same-Day Expert Support

28:07 AI Transformation Inside Papaya

30:24 Building the AI Infrastructure and Measuring 3x Efficiency

33:18 Change Management: Change the People or Change the People

34:46 Managing AI Token Costs and Usage Limits

37:29 The AI Maturity Self-Assessment Tool

40:28 AI Agents as Workers: The 2030 Workforce Vision

43:49 Real-Time Pay, Fractional Work, and Individual HR Systems

49:23 Where the Name Papaya Came From

50:13 Leadership Corner: Getting Your Team to See What You See

59:46 When You Know Your Vision Has Landed

01:01:11 Takeaways: The Translator Role and Systems Thinking

🎯 Why payroll companies don't actually pay people — and where the real value lives

🏦 The "regulated by choice" strategy that turned compliance into a moat

🤖 How to roll out AI to your team without letting it fail them

📈 Why the 2030 workforce means ten employers per person

🔑 Leadership Corner: How to know when a new idea has actually landed inside your organization

Meg is a board member of Papaya Global.

📚 RESOURCES:

Papaya Global: https://www.papayaglobal.com/

🔗 CONNECT:

Eynat Guez: https://www.linkedin.com/in/eynatguez/

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 #AIStrategy #HRTech #globalpayroll