Episode 42 | Your AI transformation has a shelf life — and it's getting shorter

Episode 47| The AI Rush of 2025 Set the Skills Agenda Back. Here's What Comes Next | David Blake

🚀 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

Episode 46 | Are You Making Me Money or Saving Me Money? | Maria Colacurcio

🚀 Maria Colacurcio asked her own AI agent to pull a code repository. Three times. It refused — and directed her to men on her team. That moment is the throughline of an episode about what's actually breaking in compensation, what AI buyers will spend on now, and the org-design conversation every founder is dodging. Maria is the CEO of Syndio — the company that defined the market for pay-equity software and is now pioneering Decision Intelligence for Pay. Customers include Walmart, Microsoft, and Salesforce. ⏰ TIMESTAMPS: 00:00 Cold open 00:41 Welcome 01:38 The Starbucks origin story — Rob Porcarelli and the 150-page crosstab report 04:32 The Pay Fairy: governing the pay decision at the moment of decision 10:55 "Be a little reckless" + you cannot cram AI learning in 15-minute gaps 14:42 The ClickUp read — wide bands, $1M packages, and systemic underleveling 21:20 The leapfrog: skills-based pay → outcome-based pay → outcome-based pricing 22:51 Anthropic's pricing change and Maria's 4-bucket hard-ROI framework 27:38 Glass box, not black box — the pay-decision audit trail 30:28 Market data is one input — not the anchor 33:33 Cindy the agent + "fluid, not full-time" domain expertise 40:21 The $40M → $100M reset: "Am I still the right person for this job?" 47:19 The LinkedIn moment — what Maria's own AI agent told her, three times 51:34 Leadership Corner — laid off, networking, and the market that moved past you 59:05 Wrap 🔑 KEY INSIGHTS: - AI vendors face a new bar: "Are you making me money, or saving me money?" The era of AI-for-AI's-sake is ending. - Pay decisions belong in a glass box, not a black box — every input, model version, override, and human-in-the-loop adjustment logged. - Wide pay bands don't break pay equity by themselves. They raise the stakes — every $1M package needs a defensible "why." - "You cannot cram AI learning in 15 minutes between meetings." Leaders modeling AI fluency need real headspace, on weekends and evenings. - The org reset from $40M to $100M needs specialists, not all-around athletes. And the founder question every sitting CEO is dodging is "am I still the right person for this job?" - Domain expertise has to be fluid, not full-time — hire your AI vendor SMEs forward, not in-house. 📚 RESOURCES: Syndio: https://synd.ioZev Eigen (Syndio co-founder): https://synd.io/authors/zev-eigen/ Steve Magness (Man in the Arena): https://www.stevemagness.com/ Trung Phan (referenced in the LinkedIn story): https://www.readtrung.com/ 🔗 CONNECT: Maria Colacurcio: https://www.linkedin.com/in/mariacolacurcio/ Instagram: @megandamyshow LinkedIn: https://www.linkedin.com/company/megandamyshow #PayEquity #PayGovernance #AIBias #AIROI #ResponsibleAI #LeadershipInTheAIEra #FoundersJourney #MegAndAmyShow

Episode 45 | Your Experience Just Became a Tax. Here's What Still Pays

🚀 Amy and Meg dig into Jaya Gupta's "experience is now a tax" frame — and what actually survives when AI makes credentials look like overhead. Learn why the most golden job for the next decade is the translator role, how to stop optimizing AI for speed and start using it as an anxiety reducer, and why "manager wars" is the wrong fight to be picking right now, in this conversation on business transformation and leadership in the AI era. ⏰ TIMESTAMPS: 00:28 Welcome & Mother's Day at the Valkyries 02:21 A listener note + show goals 04:04 The three arcs: what survives, how do we survive, what's next? 05:27 Arc 1 — Experience is now a tax (Jaya Gupta) 12:17 The calendar unlock: AI as anxiety reducer (not productivity) 17:02 The most golden job: judgment, taste, and the translator role 21:30 If your org won't give you a pathway (and Couch-to-5K for AI) 23:48 Arc 2 — Curiosity survives credentials (Ethan Mollick on AI slop) 29:42 Authenticity is the new black — 17 years later 33:43 From trends to convergences 34:52 Arc 3 — The Next Great Moat: the shape of your company is the moat 38:25 Manager wars, two-prong leadership, and heart-centered ops 41:25 Strategy in the AI fog: optionality, zero budget, clean sheet 51:10 Leadership Corner: positioning for an opening (without circling) 58:04 Outro 🔑 KEY INSIGHTS: - Experience is only a tax if you treat the old playbook as the asset. The real moat is your perspective on patterns plus your willingness to be a translator between how work used to get done and how it gets done now. - The bigger AI use case for senior leaders isn't productivity — it's anxiety reduction. Meg's calendar unlock: "should I do this thing?" before "how do I fit this in?" - The Claude-language tic is making good thinkers harder to read. If you're writing with AI, own your voice and accept the typos — polished-and-fake costs you trust. (Meg: "I've given up. I'm back to my grammar mistakes and typos.") - "Manager wars" — the loud "we don't need middle managers" narrative ignores what managers actually do: help people feel seen, not just feel chosen. Meg's two-prong move (know them + sales-pitch the growth) is the playbook. - Strategy under AI fog: assume a zero budget, take the smallest commitment that buys you information, and build on a clean sheet of paper instead of an existing model that's already serving you. 📚 RESOURCES: Jaya Gupta — "Experience Is Now a Tax": https://www.linkedin.com/pulse/experience-now-tax-jaya-gupta-kxb7c/ Jaya Gupta — "The Next Great Moat": https://www.linkedin.com/pulse/next-great-moat-jaya-gupta-6onwc/ Hillary Gridley — "Your Couch to 5K for AI" (Lenny's Newsletter): https://www.lennysnewsletter.com/p/your-couch-to-5k-for-ai Ethan Mollick — One Useful Thing (the Claude-language piece): https://www.oneusefulthing.org/p/claude-code-and-what-comes-next Marketoonist — "AI Written, AI Read": https://marketoonist.com/2023/03/ai-written-ai-read.html Meg Bear — "Authenticity is the new black" (2008): https://www.megbear.com/post/authenticity-is-the-new-nbsp-black Meg Bear — "The future is interdisciplinary": https://www.megbear.com/post/the-future-is-interdisciplinary Patty Azzarella: https://www.linkedin.com/in/pattyazzarello/ Adam Grant — Think Again (book) Toby Stewart — "The Future Is Shrouded in AI Fog" (Harvard Business Review): [add link] Dara Curran (Intercom) — on tripling dev productivity by assuming a zero budget: [add link] 🔗 CONNECT: Submit Leadership Questions: megandamyshow@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #FutureOfWork #AITransformation #Leadership #ManagerWars #AILeadership #CareerGrowth #MegAndAmyShow

Episode 44 | Running Pilots Is Not a Strategy. It Never Was. | Charlene Li

🚀 Running Pilots Is Not a Strategy: Charlene Li — three-decade authority on disruptive leadership and co-author of Winning with AI: The 90-Day Blueprint for Success — breaks down the consistent failure mode she's watched leaders repeat across the internet, social media, and now AI. Learn why "adapting" beats "adopting," why reinvention is the real AI opportunity (not efficiency), and the structural risk no one is naming: agents going to individual contributors who've never been trained as managers. ⏰ TIMESTAMPS: 00:00 Cold open — "running pilots and calling that a strategy" 00:21 Episode intro 01:14 The Altimeter years with Brian Solis: studying disruption 04:09 Three decades, one failure mode — and what's different this time 06:11 Experimentation vs. pilot purgatory 08:08 Don't run readiness assessments — name the gaps instead 11:20 Reinvention beats efficiency: the Concentrix case (130k people, +5% workforce) 16:22 Leading through vulnerability: honesty over having the answers 19:56 Who owns AI inside the org — and why it's not IT 26:26 Handing AI agents to ICs who've never been trained as managers 29:53 The 90-day blueprint: strategy in stone, plan in pencil 40:42 FOMO and FOGI: the cost of staying frozen on AI 47:46 Leadership Corner: rethinking "self-promotion" 🔑 KEY INSIGHTS: - Running pilots is not an AI strategy. You have a business strategy — think about how AI supports it. - The gap that matters in 2026 isn't between adopting AI and not. It's between adapting your organization and just adopting tools. - Readiness assessments are designed to tell you you're not ready. Instead: name the gaps you need to fill to hit your strategic objectives. - Reinvention beats efficiency. Don't 10x one person and eliminate nine — 10x everyone and 100x the business. - You're handing AI agents to people you've never trained to manage. The IC-as-agent-manager gap is the structural risk almost no one is naming. 📚 RESOURCES: Winning with AI: The 90-Day Blueprint for Success (Charlene Li & Dr. Katya Walsh): https://www.amazon.com/Winning-AI-90-Day-Blueprint-Success-ebook/dp/B0GQM9PD3P [https://www.amazon.com/Winning-AI-90-Day-Blueprint-Success-ebook/dp/B0GQM9PD3P]  Charlene Li's website: https://charleneli.com Brian Solis on The Meg & Amy Show (referenced): https://youtu.be/ZrNWHzmWpJU?si=rIeBVrq1NcUmwZyk [https://youtu.be/ZrNWHzmWpJU?si=rIeBVrq1NcUmwZyk]  🔗 CONNECT: Charlene Li: https://www.linkedin.com/in/charleneli/ Submit Leadership Corner questions: megandamyshow@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #AIStrategy #BusinessTransformation #AILeadership #DigitalDisruption #WinningWithAI #CharleneLi #FutureOfWork #ExecutiveLeadership #MegAndAmyShow

Episode 43 | You Don't Have an AI Problem — You Have a Constraint Problem | Han Yuan

Han-Shen Yuan — who led mobile engineering at eBay and Netflix and took Upwork to IPO as SVP of Engineering — explains why AI transformation is a constraint problem before it's a software problem. Learn why the real bottleneck is rarely the technology, what a "loose grip on your identity" means for senior leaders right now, and why cutting headcount on the back of AI productivity gains is eating your own future, in this conversation on business transformation and leadership. ⏰ TIMESTAMPS: 00:00 Cold open & welcome 03:02 Why Han went back to school: the "checksum of knowing" 06:16 When AI blurs every role, who are you? 08:32 Inside Han's consulting practice 13:23 Holding a loose grip on your identity 17:08 Are the "AI layoffs" really AI layoffs? 20:58 What's real vs. hype in enterprise AI 25:02 AI transformation is a constraint problem, not a software problem 29:38 Anti-patterns: "token maxing" and cutting headcount 33:38 Why making your job obsolete protects it 42:31 Leadership Corner: finding clarity when the ground shifts 51:11 Outro: Meg & Amy debrief 🔑 KEY INSIGHTS: - AI transformation is a business process optimization problem — find the system's true constraint before applying AI, or you'll optimize the wrong thing and see no benefit. - The human reviewer is often the real bottleneck. Generate 100x more code and you've 100x'd the review queue, not the throughput. - The professionals who thrive hold a "loose grip" on their identity — willing to do different things to get the job done instead of clinging to one role. - Cutting headcount on AI productivity gains is short-sighted: no one has ever had "too little work and too many people." Redeploy the new capacity to grow. - The way to protect your job is to make it obsolete in service of something bigger — the minute you're defending your role, you've already lost. 📚 RESOURCES: Han-Shen Yuan on LinkedIn: https://www.linkedin.com/in/hanshenyuan/ Han's article on "authentic chameleon leadership": https://h6y3.substack.com/p/the-authentic-chameleon-leadership UC Berkeley Master of Information and Data Science (MIDS): https://info.ischoolonline.berkeley.edu/requestinfo/mids 🔗 CONNECT: Han-Shen Yuan: https://www.linkedin.com/in/hanshenyuan/ Submit Leadership Questions: megandamyshow@gmail.com Instagram: https://www.instagram.com/megandamyshow/ LinkedIn: https://www.linkedin.com/company/the-meg-amy-show #AITransformation #FutureOfWork #Leadership #AILeadership #CareerGrowth #DigitalTransformation #MegAndAmyShow