Jessica Swank, Chief People Officer at Box, joined us on The Modern People Leader. 

We talked about building an "org brain", preparing managers to lead teams of humans plus agents, avoiding agent sprawl and tech debt, and why every people leader needs to start experimenting with AI personally to stay ahead.

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Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode269

Sponsor Links:

🔗 Start a one-month trial with Viva for $950.

🔗 Talk to the team at Ethena.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

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(09:24) The GenAI Shift and What It Means To Become an AI-First Company

(11:07) Box’s Three Pillars for AI in People and Communities: Optimize, Elevate, Amplify

(13:25) Rethinking Roles, Skills, and Job Architecture in an AI-Driven World

(16:17) Who Leads the AI Transformation: HR, IT, or a Cross-Functional AI Council

(20:32) People Strategy in an AI-First World: Talent, Skills, and Leadership Expectations

(23:55) Hackathons, AI Certification, and Box’s Step-by-Step AI People Roadmap

(32:44) Leading Hybrid Human Plus Agent Teams and Rethinking Manager Responsibilities

(37:20) Coaching, Feedback, and Performance Expectations for AI Agents

(38:36) OKRs for Agents, Agent Sprawl, and Governance of Digital Employees

(42:29) Tech Debt, Agentic Debt, and How People Teams Decide What To Build, Buy, or Wait On

(47:47) The People Team Tech Stack: Build, Buy, Borrow, Bot in Practice at Box

(49:10) Practical Advice for HR Leaders Just Starting Their AI Journey

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

We dug into Foursquare’s North Stars of vibrancy and velocity, applying design thinking to the people function, and their team-based performance model.

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Downloadable PDF with top takeaways: https://modernpeopleleader.kit.com/episode268

Sponsor Links:

🔗 Learn more about TopicFlow.

🔗 Talk to the team at Ethena.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

Other Links Mentioned:

🔗 Kit’s blog on why culture starts with performance 

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(13:04) Kit’s story

(24:18) Why rebrand HR to People at Foursquare

(25:25) Naming, value proposition, and aligning the people team to business goals

(28:26) North Stars: “vibrancy + velocity,” big rocks vs prototypes, new engagement survey

(33:11) People function as a product: design thinking, journey mapping, cross-functional experience team

(39:09) First major bet: performance philosophy

(41:35) Team-based performance model and measurement alignment

(42:31) Transition to ONA focus

(43:50) ONA background

(47:30) Flattening org and team effectiveness coaching to support the model

(49:07) Tying behaviors to leadership principles, career matrix, and team-based recognition

(50:55) Research basis for high-performing teams vs teams of high performers

(54:23) Metrics: measuring velocity (+43%), tradeoffs on coaching/feedback, new interventions

(56:29) Theme of focus: advice for overwhelmed people leaders

---- 

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Shannon Hobbs, Chief People Officer at BNY, joined us to unpack how the bank is scaling its early-career pipeline, flattening org design, and running a culture-first transformation.

We discussed BNY’s in-house AI hub “Eliza” (99% employee certification, 15k+ agents, 100 digital employees), plus practical advice for CHROs on building AI capability safely and at scale.

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How BNY is betting big on early talent (PDF): https://modernpeopleleader.kit.com/episode267

Sponsor Links:

🔗 Talk to the team at Ethena.

🔗 Learn more about TopicFlow.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

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(07:31) Shannon’s career journey to CPO (Citigroup/Smith Barney → Morgan Stanley → JPMorgan → American Century → GEICO → BNY)

(10:36) Advice to aspiring CPOs: say yes to high-need roles; build varied skill sets

(12:59) BNY in 30 seconds: “the bank of banks,” custody/clearing and client solutions

(13:40) Why early careers matter now; meeting talent where they are(16:03) Scaling analysts: 500 → 1,000 → 2,000; investing despite headcount scrutiny

(19:12) Timeline & structure: cohorts, rotations, upcoming “franchise” track

(20:50) Manager enablement: teaching leaders how to leverage new-gen skills

(22:43) The manager role today and why flatter orgs help(25:03) What “flat” looks like: cross-functional pods, closer to clients, more accountability

(27:57) Finding hidden gems: visibility, time back via automation, rewarding talent work

(29:49) Transformation umbrella: why this is bigger than a reorg

(30:27) Platform operating model: phased rollout, end-to-end commitment

(32:26) Culture → clients: language, pillars, progress toward full adoption

(33:15) Robin Vince’s culture-first, level-agnostic leadership style

(34:27) Turning to AI: framing AI as an enabler, not the destination

(35:53) Eliza, BNY’s AI hub: built in-house for safety, control, and scale

(36:49) Onboarding & safety: 99% employee certification before use

(38:45) Hackathons, bootcamps, and recognition to drive real adoption

(40:07) What’s inside Eliza: chat, agent builder, governed access

(40:28) People Team Agent: launch story, 17k unique users in month one

(42:11) Host reaction to adoption stats; why this is notable

(43:33) Bottom-up tactics: sandboxing, storytelling, shared language

(44:12) Legal as early adopter; multi-touch education to reduce fear

(45:56) From “Excel fluency” to “AI fluency” as the new baseline

(46:48) Who builds agents? Personal vs. production; step-by-step path

(47:47) Idea intake → AI hub prioritization → production digital employees

(48:16) Host reflection: rethinking careers in financial services

(49:50) Final big question: how to build an AI hub in HR

(50:42) Shannon’s playbook: train, equip, dialog, and tie to culture & work redesign

---- 

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Luke O’Mahoney, Founder & Creator of Sapienˣ, joined The Modern People Leader.

We talked about the three emerging models of product-led HR, Agile theater, and how an enterprise company phased its shift to product-led HR.

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Sponsor Links:

🔗 Learn more about TopicFlow.

🔗 Talk to the team at Ethena.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

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(06:23) Luke’s early career in RPO and connecting talent acquisition to business strategy

(07:15) Transition into People Leadership and discovering Agile HR

(08:48) Applying product and marketing frameworks to people and culture

(09:54) Discovering a community around “PeopleOps as a Product” and founding SapientX

(10:46) Stephen reflects on HR’s evolution from Ulrich’s model to Agile

(12:37) Luke on why this iteration of Agile HR is sticking

(13:18) How being “unburdened by legacy HR” enabled innovation

(15:16) The shift from a procurement mindset to a product mindset in HR

(17:28) The gateway to product-led PX and why accessibility matters

(23:16) Luke explains the 3 models: HR as a Service, Programs as Products, and Work as the Product

(25:43) What “work as the product” means in practice

(26:50) How to determine which model fits your organization

(28:17) Context and readiness: tailoring PX as a product to company culture and maturity

(31:49) Luke defines “theater of Agile” and the danger of rituals without mindset

(34:04) Why HR needs to focus on real problems, not just initiatives

(35:25) Biggest blockers to real product-led transformation in HR

(36:44) HR’s perfectionism problem and the courage to experiment

(40:37) Why progress over perfection is key in PeopleOps innovation

(41:15) Stephen’s cohort experience with Jessica Zwaan’s Built for People

(44:15) Luke’s practical framework: solving employee problems and driving growth

(46:13) Iterative experimentation and measuring impact through baselines

(48:18) The need for playbooks and accessible frameworks

(49:13) Luke’s recommended resources and open-source toolkits

(51:00) Real-world examples: TomTom, Sastrify, and Build a Rocket Boy

(52:42) How TomTom built a People Product Team within a large enterprise

(55:10) Applying product-led HR even as a one-person team

(58:04) Launching HR products creatively—Gamified benefits and internal “fake employee” campaigns

(01:02:26) Why GTM mindset matters in HR launches

(01:03:11) The ROI of joy and excitement in PeopleOps work

(01:03:40) What HR leaders can expect on the other side of PX as a product

(01:04:40) Earning the seat at the table through measurable business impact

(01:06:52) Connecting people, process, and technology for business growth

---- 

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---- 

Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Darren Murph, a leading voice on distributed work and former leader at GitLab, Zillow, and Andela returned to the show.

We dug into the remote first maturity scale, the four-pillar operating model (knowledge, project, self, performance), and how to build an “org brain.”

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Sponsor Links:

🔗 Learn more about TopicFlow.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

---- 

(04:42) Darren’s new chapter: going independent and why the timing was right

(08:46) What’s changed since 2–3 years ago in remote/distributed work

(09:13) Identity crisis in companies and the RTO narrative

(11:09) The “operating system” of a company: where communication breaks

(12:45) What ELTs are really discussing now

(14:07) Under-the-radar topic: performance management as “fix the car, not just the driver”

(16:40) AI readiness requires distributed-friendly systems (recording, documentation)

(18:01) Remote-first maturity scale: where firms think they are vs. where they land

(19:44) Knowledge management as the first pillar and the “org brain” concept

(21:50) The four-pillar framework: knowledge → project → self → performance

(24:13) “Gold in, gold out”: documentation and meeting capture fuel AI

(26:00) Exemplars and ownership: Atlassian, GitLab, Doist; treating knowledge like a product

(28:18) Tools and handbooks: Notion, public handbooks, getting started fast

(30:13) MVP of an org brain and how functions build it out

(34:34) Project management done right vs. 47 one-on-ones; insurance/IT ticketing analogies

(37:47) Why this matters: time as compensation; segue to self-management

(39:59) Team agreements and operating with flexibility

(42:16) Measuring performance better: meetings, survey data, retention

(46:19) Legacy reviews vs. modern, continuous performance practices (Juro example)

(47:10) Organizational psychology: complexity theory and the pull back to “coherence”

(54:03) Rapid-fire questions

(58:43) Where to find Darren and work with him

---- 

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---- 

Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Brandon Weber, Co-founder & CEO of Nava Benefits, joined us on The Modern People Leader.
We talked about why benefits have become the second-largest company expense — and how HR can “moneyball” their healthcare spend, cut down on benefits-related admin work, and deliver better employee outcomes through the emerging “alt marketplace.”

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Nava Links:

🔗 Learn more about Nava.

MPL Links:

🔗 Buy your ticket for MPL Live Austin.

🔗 Go sign up for MPL Build.

---- 

(07:07) Brandon’s Founder Journey and 10-Month Sabbatical Spark

(14:06) The Broker as Market Maker: Distribution Problem in Employer Healthcare

(16:27) Why Benefits Are Strategic: From Cost Center to Business Lever

(18:28) Benefits Jumped to #2 Company Expense and a Talent Magnet

(20:53) HR Holds the Healthcare Purse Strings for Half of America

(21:15) Being Strategic with a Small People Team

(21:39) Explosion of Benefits Complexity (from ~6 to ~20 offerings)

(26:47) Status-Quo “Stockholm Syndrome” and Breaking the Cycle

(28:51) 2025 Renewal Pain Driving Change

(31:02) Automating Benefits Admin

(33:11) The “Alt Marketplace” of Health Plans, PBMs, and Point Solutions

(33:39) Examples of "Alt Marketplace": Garner Health Network Design; Sidecar Health Price Transparency

(40:58) Agentic Future: Auditing Carrier Bills and Auto-Remediation

(42:18) Renewal Season AI: From Spreadsheet Chaos to Real-Time Scenario Modeling

(43:16) Zapier Example: Benefits Help Desk and the Real Cost of Repeated Questions

(45:06) Nava’s AI Strategy for HR: Support, Admin Automation, Smarter Spend

(47:35) “Moneyball” Your Benefits Spend with Data Science

(48:06) Why Brokers’ 20-Year Spreadsheets Fail HR and CFOs

(51:05) Rapid Fire Questions

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---- 

Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Andrew Golden, Chief People Officer at RetailNext, joined us on The Modern People Leader.

We talked about how he’s driving transformation, why HR and IT must partner more closely, the power of building lightweight AI solutions in-house, and why he’s optimistic about the future of people teams.

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Sponsor Links:

🔗 Request a demo of ChartHop.

🔗 Talk to the team at Ethena.

MPL Links:

🔗 Go sign up for MPL Build.

---- 

(10:15) Burnout, Leaving RetailNext & Working in Family Accounting Firm

(11:49) Explaining RetailNext’s Business: Hardware + data insights for retail stores

(13:30) Why Andrew Returned to RetailNext & Rejoining After Private Equity Acquisition

(16:35) Restarting PeopleOps as a Product at RetailNext

(17:59) Partnering with PX Sapiens & Lean PX Design Principles

(20:16) Portugal Trip Lightbulb Moment: Rethinking HRBP model

(22:21) Moving Away from Traditional Org Charts → Workflow Alignment

(24:16) Practical Application: Embedding People Team into Business Workflows

(26:36) The Three Workflows: Pre-Customer, Post-Customer, and Transitions

(28:08) EOS (Entrepreneurial Operating System) & Core Processes in HR

(29:50) How EOS + PeopleOps as a Product Fit Together

(32:18) Redefining “Strategic HR” as Operationally Relevant HR

(35:20) Advice for Skeptics: Why Agile PX Matters

(36:57) Building HR Tools with AI: Andrew’s Employee Engagement Platform

(40:33) The SaaS vs. Build Trade-Off: Flexibility with AI Tools

(42:58) Why Now Is the Time: Optimism in HR’s Future

(59:36) How HR and IT Partner Together at RetailNext

---- 

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---- 

Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Gena Smith, CHRO at LVMH North America, joined us on The Modern People Leader. We talked about how she sparked an AI transformation across 75 LVMH brands, why HR should lead AI change management, and how to reframe AI adoption as a cultural and creative advantage.

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Sponsor Links:

🔗 Talk to the team at Ethena.

🔗 Request a demo of Workleap.

MPL Links:

🔗Go sign up for MPL Build.

---- 

(05:07) Gena’s Career Journey: From Texas to Global HR Leader

(10:34) Passion for People & Culture Sparked Abroad

(11:01) Serving on the Board of Parsons School of Design

(13:26) What’s in the LVMH Portfolio (and What People Don’t Know)

(16:55) The Culture at LVMH: Pride, Legacy, and Humility

(18:53) Managing People & Culture Across 75 Brands

(19:57) LVMH’s Decentralized Structure & Core Values

(22:48) How HR Anchors Culture Across the Group(24:11) The WSJ Conference that Sparked Her AI Learning Journey

(26:34) Building the HR AI Task Force & Their First Discoveries

(30:02) The “It Feels Like Cheating” Employee Mindset Around AI

(31:29) Why Marketing the AI Message Internally is Key

(32:33) Using AI in Creative Studios & Operational Areas

(36:28) Tackling Fear of AI & Job Security Concerns

(37:18) Why Upskilling is the Real Future-Proofing Strategy

(39:31) Normalizing AI Adoption & Creating Comfort

(42:21) Hot Take: HR Will Write the Blueprint for AI in Business

(43:49) Why HR Must Be on Every AI Governance Board

(45:14) Scaling Change Management Through Internal Campaigns

(46:29) Building LVMH’s AI Marketing Campaign from Scratch

(48:43) Advice for HR Leaders: Start Your Learning Journey Now

(50:54) Why Human Skills Will Become the Ultimate Currency

---- 

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---- 

Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

What happens when you put a mic in front of HR leaders and ask them for their unfiltered takes on AI?

In this episode, Daniel and Stephen recap their trip to HR Tech — where they recorded 12 quick-hit “AI Confessions” from folks they met on the conference room floor. From agentic workflows and custom GPT chaos to the real blockers slowing down AI adoption, this one’s packed with candid insights from the front lines.

You’ll hear what HR leaders from companies like Lumen, Articulate, and Airbnb.

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Sponsor Links:

🔗 Talk to the team at Ethena.

🔗 Request a demo of ChartHop.

MPL Links:

🔗 Go sign up for MPL Build.

---- 

(06:00) HR Tech debrief setup and the “non-Expo Expo” vision

(08:26) Vendor noise: everyone promises everything; how to curate for quality

(10:13) Trend: agentic workflows vs. true autonomous agents

(13:16) “One UI to rule them all” and platforms trying to do it all

(16:18) The HR “sandbox” idea and customization/vibe-coding future

(18:02) Governance should come first, not last

(19:24) New format intro: “AI Confessions” clip series

(20:10) Articulate: hype vs. reality, custom GPT maintenance tax

(24:36) Snapshot pain: stale docs and refresh gaps in tools

(25:04) Why an org brain/source of truth matters

(26:58) Biggest blockers called out: connectivity across the stack, tech limits

(30:57) Magic wand from Clip 1: payroll automation and smarter resume parsing

(34:43) Lumen: “AI diffusion,” empathy-first change and upskilling

(36:32) Creating safe spaces to experiment; role-by-role reskilling

(45:35) Myths and multi-agent maturity: where we really are

(48:20) Senior vs. junior agents; linking SMEs to AI via the org brain

(55:05) Airbnb: scouting the recruiting tech stack

(57:33) Is HR behind on tech adoption compared to other functions

(1:00:49) Biggest blocker: skills and resourcing gap in HR/TA teams

(1:03:32) Upskilling in practice: stipends, bootcamps, internal rhythms

(1:05:27) TA automation targets: scheduling, intake, JD drafts, calibration slates

(1:06:09) Change management is the hard part

---- 

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Past guests on MPL include Brené Brown, Annie Dean (VP of Team Anywhere, Atlassian), Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.

Angela Crossman, Hernan Chiosso, and Jean-Luc Charles joined us to debrief the “Yellow Pod” conversation from MPL Live NYC and what the group is actually doing with AI at work.

We covered opportunities vs blockers, “AI as coach” guardrails, why HR should own enablement, actionable next steps, and predictions for the AI-powered workplace.

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Sponsor Links:

🔗 Talk to the team at Ethena.

🔗 Book a quick walk through of Nava HQ.

🔗 Request a demo of ChartHop.

MPL Links:

🔗 Go sign up for MPL Build.

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(09:40) Why structured spaces help leaders make sense of AI noise

(11:40) Untangling AI talk: personal vs professional; HR practice vs company strategy

(12:47) State of adoption: ahead of the curve vs “head in the sand”

(14:00) Panel reflections: Dropbox digital twins, Duolingo’s AI mandate, leadership buy-in spectrum

(15:43) HR’s role with tech + legal: ethics, generational views, and people experience

(16:27) “Who owns AI?”—budget, skills, and priorities across functions

(19:36) Change management over pure tech: why HR is primed to lead adoption

(21:01) Community accelerates AI: the prompt for pods (biggest blocker and opportunity)

(23:31) Why the small-group format worked: quiet room, trust, generosity

(25:08) Opportunities first: practical use cases; AI for manager coaching (pros/cons)

(27:28) Blockers: ownership, resources, risk, and vendor noise

(28:05) Quick poll: Should AI be a “coach”? Alignment with values and judgment

(29:21) Using AI as a thinking partner—not a verdict

(31:43) People team enablement: prompt patterns, values-trained GPTs, internal guardrails

(32:20) Example from MPL: iterating a “super prompt” after guest feedback

(33:50) One action to take now: targeted demos to learn real use cases

(34:42) Don’t ban—enable: intentional adoption beats resistance

(35:30) Practical rollout ideas: leadership exercises with starter prompts

(37:07) Resource tip: OpenAI Academy prompts for HR (as a baseline to build on)

(38:13) Mind-blower: executive digital twins; event improvements for Austin (Dec 11)

(39:43) Feedback: design for introverts; keep a light warm-up

(40:26) Preserve the magic: curated room + structured but flexible prompts

(41:55) Rapid-fire predictions: the AI-powered workplace

(42:29) Prediction #1: AI is both disruption and solution (reskilling at scale)

(43:48) Prediction #2: A new kind of creativity—partnering with “semi-intelligent” tools

(44:31) Prediction #3: Hiring shifts toward problem framing and critical thinking

---- 

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Past guests on MPL include Brené Brown, Josh Bersin, Katie Burke (Chief People Officer, Harvey), Liz Fosslien, Helen Russell (Chief People Officer, HubSpot), Dave Scott (Chief People Officer, ADT), Melanie Rossenwasser (Chief People Officer, Dropbox), Crystal Boysen (Chief People Officer, Sprout Social), and many more.