The Meg and Amy Show

🚀 Laurie Ruettimann has been saying the things HR won't say for twenty years — and she's starting to wonder if any of it worked. In this conversation, she argues that most advice is projection, financial freedom is the foundation of authenticity rather than a brand strategy, and AI isn't what's making work unbearable. She also gets emotional on mic. And tells us about the thank-you notes she wrote after putting her cat down.

⏰ TIMESTAMPS:

00:00 Introduction — Laurie Ruettimann

04:33 Inventing a life you can actually control

11:19 Financial freedom, overwork, and detachment at work

16:54 Reading outside your industry and the empathy gap

25:41 Personal brand, haters, and authenticity as a class issue

36:57 The honest question: has this work been worth it?

44:28 AI anxiety vs. what's really making work hard

49:59 The Roxy letters — why people keep showing up

52:01 Leadership Corner: restructuring, lesser roles, and severance

🔑 KEY INSIGHTS:

- Most advice is projection. When Laurie sits with clients now, she rarely gives advice — she witnesses. And she tells them what they actually need to hear: "It's not you. You're not broken. The system is broken."

- Financial freedom isn't a brand strategy — it's a precondition. You can't be authentic when you're still paying student loans. "Be yourself" only lands once you can afford to leave.

- Career advice was built for whoever got into power first. Most of it doesn't work the same for women or people of color — because it reflects the tactics of a cohort that was mostly male.

- The number one thing working parents worry about isn't AI. It's the cost of childcare. Blaming AI for workplace anxiety misses the structural problems that were already there.

- The secret to being a more empathetic leader isn't a leadership course. It's reading outside your industry — geopolitics, historical fiction, stories from contexts nothing like your own.

📚 RESOURCES:

Betting on You by Laurie Ruettimann: https://laurieruettimann.com/books/betting-on-you/

Incorruptible by Eric Ries: https://www.incorruptible.co/

🔗 CONNECT:

Laurie Ruettimann: https://www.linkedin.com/in/laurieruettimann/

Meg Bear: https://www.linkedin.com/in/megbear/ | https://megbear.com

Amy Wilson: https://www.linkedin.com/in/amy-wilson-insight/

Instagram: https://www.instagram.com/megandamyshow/

LinkedIn: https://www.linkedin.com/company/the-meg-amy-show

YouTube: https://www.youtube.com/@TheMegandAmyShow

#CareerAdvice #FinancialFreedom #WorkplaceTruths #Leadership #HRLeadership #CareerDevelopment #WomenInWork #AuthenticLeadership #MegAndAmyShow

🚀 Jess Von Bank has spent 20+ years on every side of the HR tech problem — vendor, buyer, analyst, practitioner. She co-founded Now to Next to close the distance between an AI strategy and human outcomes, and she's writing her way through it publicly with the Human Thesis, a seven-part Substack series, and her forthcoming book Work Like a Mother. In this conversation, Jess makes the case that most organizations are running AI adoption programs when what they need is embodiment — and those are not the same thing. Handing out licenses, counting logins, and calling it transformation is a procurement decision. Embodiment is when someone in a call center starts imagining the insurance products she could build from the data AI just unlocked. The gap between those two conversations is the gap between cutting costs and finding new markets.

⏰ Timestamps:

00:25 Guest Introduction: Jess Von Bank

01:24 Racing, Ragnar and Finding Your Amy

05:14 Founding Now to Next: No Old Answers

08:52 Why AI Transformation Keeps Failing

14:50 What Is Different About This Transformation Cycle

16:04 Automation vs Reinvention: The Hands, Heads and Hearts Framework

17:43 Where AI Goes Wrong in Talent Acquisition

21:36 Hiring Without Job Descriptions: A First Principles Experiment

24:23 Adoption Is a Procurement Decision: Defining Embodiment

27:18 From 5% to 30% Improvement: The Telecom Case Study

30:35 Too Much Choice and the Danger of Scattershot AI Rollouts

31:54 Paving the Path: Change Leadership and Cognitive Dissonance

34:14 Change Is the Strategy: Reframing Change Fatigue

37:21 Workforce Representation in AI Decisions

39:18 Human Gaps Are Transformation Gaps: Diagnosing the Wounds of Change

43:00 Skeptics, Pragmatists and Power Users: No Winners and Losers

44:25 Retaining Work Experts Over Tool Experts

47:12 Workshop Story: Innovation vs Substitution in a Call Centre

49:03 Writing, Storytelling and The Human Thesis Substack

51:58 Dear Daughters: Ten Years of Private Journals

54:34 Training Claude on Her Voice: The One Rule She Never Breaks

55:46 Work Like a Mother: The Book

59:56 Leadership Corner: Should I Take the Stretch Role?

⭐ In this episode:

- The adoption vs. embodiment distinction — why your ROI is missing and what actually closes the gap.

- The hands, heads, hearts framework for sorting work: what AI should own entirely, what it should augment, and where you need to create more human capacity, not less.

- Why "failure fatigue" is the real diagnosis behind what most leaders are calling change resistance — and what changefulness (adaptability as a default state, not a crisis response) looks like inside an organization that has actually built for it.

- The five wounds of change your AI rollout is landing on whether you're tracking them or not: fear of replacement, loss of mastery, decision fatigue, trust erosion, and identity disruption.

- Amy's take on the highest-stakes paradox of this moment — outsourcing your imagination to the very tool you're trying to imagine with.

- And the one rule Jess gave Claude when she trained it on her voice, and what happened the day she asked it to break it.

Jess Von Bank joins hosts Meg Bear and Amy Wilson for Episode 50. If you're leading an AI transformation and measuring success by adoption rates, this episode names what's actually in the way — and what it looks like when an organization builds for changefulness instead.

#AITransformation #ChangeManagement #HRTech #WorkforceTransformation #Leadership #MegAndAmyShow

🚀 AI didn't add a new chapter to the software story — it restarted the book at page one. In this solo episode, Meg and Amy explain why that makes sensemaking the scarce skill right now, who earns the role that survives every era of disruption, and what it actually looks like to stop waiting and build.

🔑 IN THIS EPISODE:

- The agentic HR moment: NovaWorks and SOL just came out of stealth — two agentic HCM platforms, both founded by women Meg and Amy know and have worked with. Meg (a NovaWorks board member) and Amy (whose former Workday colleagues founded SOL) make the case for why this moment is architecturally necessary, not just exciting: current HR systems were built on the assumption that work structure is static. That assumption is now wrong, and no amount of configuration fixes it.

- Meg's EDS theory: how Ross Perot predicted today's AI moment, and why we're back where it all started

- The leadership gap: "ready-fire aim" rollouts, mass dysregulation, and why sensemaking is the missing piece

- The Golden Job: the translator who bridges what work used to look like and what's now possible — and why sensemaking is the missing ingredient

- Personal vs. enterprise token strategy: Amy's two-gear system (Pro vs. Max 5x, CoWork vs. Code, Ethan Mollick's "spikiness") + Meg's enterprise framework — 3 buckets, 80% margins going to 50-60% or upside down

- Leadership Corner: a PM who thought he needed a new job — turns out he needed to start building

⏰ TIMESTAMPS:

00:36 Welcome + agentic HR: NovaWorks and SOL out of stealth

04:17 Meg's EDS theory: AI restarted the software lifecycle

15:23 Sensemaking: the leadership gap hiding in plain sight

22:33 The Golden Job — the translator IS the sensemaker

26:40 Amy's personal token strategy

36:48 Meg's enterprise token strategy (embedded hot take)

47:04 Leadership Corner: "He thought he had a job problem"

58:35 Closing Thoughts

📚 LINKS FROM THIS EPISODE:

▸ Meg's newsletter Issue 21, "Coming of Age" — https://www.linkedin.com/pulse/meg-amy-show-newsletter-issue-21-the-meg-amy-show-dgghc/?trackingId=nPX2o4GahAvkl5vguIYJtg%3D%3D

▸ Amy's article: "A Love Letter to Product Managers: This Is Your Moment Don't Blow It" — https://www.linkedin.com/pulse/love-letter-product-managers-your-moment-dont-blow-amy-wilson-f2mqc/

▸ NovaWorks (Kelley Steven-Waiss, CEO) — https://novaworks.ai

▸ Sol (Erin Yang, CPO/COO + founding team) — https://www.meetsol.com/

▸ Ep 47 — David Blake (naps and nervous system regulation) — https://youtu.be/GGO-Ggr4yOQ



🔗 CONNECT WITH US:

📸 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/

🚀 You're Not Unmoored. You're Unchained. | Nick Mehta on identity, reinvention, and the AI reckoning hitting every SaaS company. After stepping down as Gainsight CEO, Nick joins Meg & Amy to reframe what comes after the title ends — and breaks down forward deployed engineers, "token maxing," and why AI-native startups generate 10x the revenue per employee.

⏰ TIMESTAMPS:

00:00 Cold open: unmoored vs. unchained

01:25 Nick's mom, arm wrestling, and the immigrant-parent comparison trap

04:57 Why he stepped down as Gainsight CEO after 13 years

08:43 Handing off well: the "Project Washington" succession plan

11:27 Feeling unmoored by AI vs. feeling unchained

17:24 Why the SaaS CEO has the hardest job in tech right now

23:37 The New Work Foundation and Gen Z's future of work

27:09 Amy's contrarian take: why it's good for kids to reject AI

31:52 Forward deployed engineers and the new customer success

39:00 "Token maxing," the CFO reckoning, and AI's real economics

44:13 Leadership Corner: stay, jump to an AI startup, or downshift?

🔑 KEY INSIGHTS:

- Every leader has a shelf life — treat succession as a structural inevitability, not a personal failure.

- "Unmoored vs. unchained": the same upheaval can be two opposite stories. The work is getting to the unchained side.

- Low valuations create transformation freedom — when there's less to lose, it's easier to reinvent.

- Forward deployed engineers are customer success rebuilt for AI — and consumption pricing finally aligns the vendor's incentives with yours.

- "Token maxing" was the hot-dog-eating contest; the CFO reckoning is the hangover. AI in the enterprise has to be a business case, not a tech demo.

📚 RESOURCES:

The Trevor Project (our Pride Month dedication — please consider donating): https://give.thetrevorproject.org/campaign/797408/donate

New Work Foundation (Nick + Clara Shih): https://www.newworkfoundation.com/

Larridin: https://larridin.com/

Ben Horowitz, "Nobody Cares" (a16z): https://a16z.com/nobody-cares/

"Chop Wood, Carry Water" by Joshua Medcalf (h/t Doug Merritt): https://www.amazon.com/Chop-Wood-Carry-Water-Becoming/dp/153698440X

🔗 CONNECT:Nick Mehta: https://www.linkedin.com/in/nickmehtaInstagram: https://www.instagram.com/megandamyshow/LinkedIn: https://www.linkedin.com/company/the-meg-amy-show

#AILeadership #AITransformation #CustomerSuccess #SaaS #FutureOfWork #ForwardDeployedEngineers #Leadership #MegAndAmyShow

🚀 The AI rush of 2025 didn't move the skills agenda forward — it stalled it. That's the contrarian read from the founder of Degreed, the company built to make skills the currency of the workforce.

David Blake walks us through why he thinks 2026 is the most important year of your career, what leader-led learning looks like when agents can actually run it for managers who were never trained to teach, and why he survives the SaaSpocalypse by remembering Degreed has always been an education company — not a software company. Plus the disarming answer to how he's run this thing for 14 years: naps.

David is the co-founder and CEO of Degreed, the learning and skills platform he started in 2012 with a mission to "jailbreak the degree" — recognize the skill, not the credential. He's the co-author of The Expertise Economy and the co-creator of the Skills Quotient framework. He recently opened the Top of the Hill All Girls Secondary School in Kenya with Mary Murimi.

⏰ TIMESTAMPS:

00:00 Cold open — "Showing your soft underbelly"

00:31 Welcome and intro

01:39 The Kenya school — Mary Murimi and Top of the Hill GSS

06:01 The 12th Amendment, the VP election, and VICE.RUN

07:18 "Learners will inherit the earth" — Eric Hoffer and the original bet

10:11 The contrarian read — AI set the skills agenda back in 2025

13:13 Amy: AI has skills too — the human + AI hybrid

13:42 Meg: AI fluency to do what? + the simple-simple-simple skills trap

20:14 Sending agents through your corporate training — the corpus as guardrails

21:42 The most important corporate training is "who are we as a company?"

25:40 Edge cases: Singapore, Waymo, and the Disney complexity frontier

27:54 Three quick thoughts — full employment, "2026 is the most important year of your career," dynamic teams

32:29 The Degreed team call — showing your soft underbelly to your whole company

34:54 Parenting kids in the AI tidal wave — set a goal, work backwards

37:26 Meg: "Our experiences are not helpful for our children"

44:17 Maestro, Degree.ai, and the competing narratives on AI wrappers

48:00 Leader-led learning — agents for managers who were never trained to teach

50:30 The Murdoch sale, Vox Media, and where the economic rents actually go

52:00 Why Degreed is an education company, not a software company

56:15 The disarming answer to running this for 14 years: naps

58:01 Wrap

🔑 KEY INSIGHTS:

- AI didn't move skills forward in 2025. It sucked the oxygen out of the room — IT had to roll out AI, attention moved on, and the skills agenda paused across most enterprises.

- The most important "corporate training" content most companies are missing is their own mission. L&D's next role is custodian of organizational context — the corpus your agents actually need.

- Leader-led learning is the agentic system's biggest unlock. Line managers (who were never trained to teach) can now run training-on-demand for their teams.

- Economic rents in SaaS migrate back to the LLMs. The wrappers are exposed. Survival means knowing what kind of company you actually are.

- For kids navigating this: maintain a love of learning AND the meta-skill of knowing how to learn. Your maps don't apply to their territory.

📚 RESOURCES:

Degreed: https://degreed.com

David Blake's LinkedIn post on Learning Rewired: https://www.linkedin.com/in/davidblake/

The Expertise Economy (book): https://www.amazon.com/Expertise-Economy-Smartest-Companies-Succeed/dp/1473677009

Top of the Hill All Girls Secondary School: https://topofthehillgss.org/

Mary Murimi (Top of the Hill founder): https://www.linkedin.com/in/mary-murimi-9402b82a/

Patti Constantakis (Walmart.org, on the skills cold-start): https://www.linkedin.com/in/patti-constantakis/

VICE.RUN — bipartisan VP election reform: https://vice.run/

Eric Hoffer — "Learners inherit the earth": https://en.wikipedia.org/wiki/Eric_Hoffer

Sangeet Paul Choudary's Reshuffle (referenced by David — see our Ep 18 conversation with Sangeet): https://www.youtube.com/@TheMegandAmyShow

NYT on the Vox Media / James Murdoch sale: https://www.nytimes.com/2026/05/20/business/media/vox-media-james-murdoch-sale.html

🔗 CONNECT:

David Blake: https://www.linkedin.com/in/davidblake/

Submit Leadership Questions: megandamyshow@gmail.com

Instagram: @megandamyshow

LinkedIn: https://www.linkedin.com/company/the-meg-amy-show

YouTube: https://www.youtube.com/@TheMegandAmyShow

#SkillsAgenda #AIStrategy #LeaderLedLearning #SaaSpocalypse #Degreed #EdTech #FutureOfWork #LeadershipInTheAIEra #MegAndAmyShow