The Modern People Leader: Forward-Thinking HR

Alexis Fink joined us on The Modern People Leader. We talked about how AI is changing work, why org design needs to move beyond boxes and lines, and how curiosity, influence, courage, and better systems thinking can help people leaders design for the future.
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(14:10) The One-Way Door of AI and Work
(17:15) Why AI Transformation Will Take Longer Than 18 Months
(19:05) What Org Design Means in the AI Era
(20:30) Work Organization, Decision Rights and the Role of Machines
(22:15) Why the Org Chart Is the Wrong Question
(23:05) Inverted Pyramids, Hourglass Models and Different Assumptions About Talent
(25:00) The IKEA Example: Turning Automation Into New Human Work
(28:05) Why AI Should Free Capacity, Not Just Eliminate Jobs
(31:40) How to Reframe the Headcount Reduction Conversation
(33:25) Breaking Through Constraints, Vendor Issues and Learned Helplessness
(36:45) Budget Constraints and the Problem With Legacy Decision Rights
(40:20) Lessons From Past Transformations at Microsoft
(43:00) Creating a Hard Gate for Vice President Promotions
(44:10) Creating a Real Individual Contributor Career Path
(47:30) What Has Changed About Change Management
(49:05) Multiple Layers of Change and the Need for a Clear North Star
(50:25) Avoiding Shiny Object Syndrome and Finishing the Last Mile
(53:10) The Difference Between Influence and Convincing
(55:45) Creating Gravitational Pull Instead of Pushing
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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.

Dean Carter (Best-Selling Author, 4x CHRO, & CEO of Instill)  joined us on The Modern People Leader. 
We talked about the career pivots that shaped his life, what Patagonia taught him about purpose and play, and why trusting your gut, taking big swings, and doing the right thing can lead you somewhere better than the plan you originally had.
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Sponsor Links:
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
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(12:30) Dean’s Career Story Through Life Pivots
(23:20) The Moment Dean Decided to Work in HR
(28:45) Choosing His Daughter Over Career and Leaving Fossil
(33:40) Choosing Patagonia Over Bigger Career Moves
(37:50) Work as Play
(39:00) Humility, Simplicity and Living the Patagonia Way
(41:40) Dean’s Advice for People Considering a Major Career Pivot
(43:20) Showing Up Fully After You Make the Choice
(46:30) Making the Best of Any Choice You Make
(48:40) Why Big Misses Mean You Are Swinging Hard Enough
(50:00) Career Emergence and How the Path Reveals Itself
(56:10) Building AI That Saves Jobs Instead of Taking Them
(58:25) Career Advice: Think Two Jobs Up, Not One Job Up
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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.

D.V. Williams, Chief People Officer from Match Group joined us on The Modern People Leader.
We talked about why Match is betting on Gen Z talent, how skills are replacing titles as the new currency of work, and how Match is thinking about flexible mentorship and early-career programs.
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Sponsor Links:
🔗 Learn more about Beqom at beqom.com/mpl
🔗 Learn more about Tilt at hellotilt.com/mpl
MPL Links:
🔗 Go sign up for MPL Build.
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(10:45) Why Match Is Betting on Gen Z Talent
(12:00) Why Product and People Strategy Need to Align
(15:20) How Gen Z Thinks About Work Differently
(17:00) How Tinder Improved Engagement and Shifted the Internal Culture
(18:20) Becoming Product-Led and Consumer-Focused
(19:00) Flattening the Org and Getting Doers Closer to Decisions
(23:45) Why Tenure and Title Are Outdated Proxies for Value
(24:20) Skills as the New Currency of Work
(24:45) Rebuilding Mentorship Around Skill Acquisition
(25:20) Flexible Mentorship and the “Tinder for Skill Acquisition” Idea
(30:15) How Match Is Approaching AI Internally
(31:00) Equipping Employees With AI Without Framing It as Headcount Reduction
(31:20) Match’s AI Day and Employee-Led Experimentation
(34:00) How Dating Apps Are Evolving With AI and IRL Experiences
(35:00) Using AI to Help People Show Up More Authentically on Dating Apps
(40:15) Match’s Cross-Functional Rotational Program
(41:30) Match’s Internship Program: 20,000 Applicants for 26 Roles
(43:35) How the 2026 Rotational Program Is Different From Traditional Programs
(45:35) Why Curiosity Beyond the Job Description Matters
(48:05) Focusing Development on Skill Acquisition, Not the Next Title
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💡 Follow The Modern People Leader on LinkedIn
😊 Follow Daniel Huerta on LinkedIn
😊 Follow Stephen Huerta on LinkedIn
---- 
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.

Christy Lake, Chief Administrative Officer at Twilio, joined us on The Modern People Leader. We talked about how AI is changing work, why skills, governance, and human judgment matter more than ever, and how Twilio is thinking about remote-first work, employee experience, and curiosity in the AI era.
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Sponsor Links:
🔗 Learn more about SixFifty
🔗 Explore the 2026 ​Deloitte Human Capital Trends Report
MPL Links:
🔗 Go sign up for MPL Build.
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(11:20) The Hardest Thing on Christy’s Plate as CAO
(12:00) Why AI Is the Biggest Transformation Christy Has Seen
(13:00) Upskilling, Security, Data and Governance in the AI Era
(14:30) Why AI Does Not Have a Clear Playbook Yet
(15:25) Why This AI Cycle Comes With So Much Fear
(17:30) Building a Skills Infrastructure for the Future of Work
(18:15) Tasks, Roles and Where Human Judgment Still Matters
(19:15) Twilio’s Three-Horizon View of AI Change
(25:00) The Task Construct of Work and AI-Able Work
(26:00) Why Existing Companies Still Need Org Design and Change Management
(29:00) The Future of Employee Experience and the One Prompt Box
(31:15) Why UX Will Matter More in the Future of Work
(32:00) Why Companies Should Not Move Too Fast Without Human-in-the-Loop Design
(33:40) Why People Still Need to Be Seen, Recognized and Thanked
(36:00) Why Twilio Stayed Remote First
(38:10) Hiring From Anywhere and Becoming a Net Talent Winner
(40:45) Remote-First Companies and AI-First Readiness
(42:00) AI Burnout, Remote Work and the Pressure to Do More
(44:10) Why AI Upskilling Is Becoming Nights-and-Weekends Work
(48:05) Why Constant Change Leaves People Without a Sense of Mastery
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💡 Follow The Modern People Leader on LinkedIn
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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.

Becks Port, Chief People Officer at Okta, joined us on The Modern People Leader. We talked about why AI agents should be treated like digital coworkers, how Okta is thinking about agents on the org chart, and what the future of HR, career development, security, and team design could look like as humans work alongside machines.
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Sponsor Links:
🔗 Learn more about Beqom at beqom.com/mpl
🔗 Learn more about SixFifty
MPL Links:
🔗 Go sign up for MPL Build.
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(07:45) AI Agents as Coworkers and Digital Workers
(08:20) Why Agents Need Managers, Accountability and Clear Handoffs
(09:00) Which AI Agents Belong on the Org Chart
(11:10) Deconstructing and Reconstructing Roles Around AI
(13:15) How AI Is Creating New Roles at Okta
(15:45) Why Okta Is Adding an Agentic Coach to the Org Chart
(18:20) Decision-Making With Human and Agentic Coworkers
(19:10) Why Task-Level Granularity Matters for AI Delegation
(20:45) Okta’s Head of AI Transformation Role
(21:15) Building Agentic Coaches and Onboarding Agents
(22:00) Upskilling Employees to Become AI Proficient
(23:15) The Future Structure of the People Team
(25:00) Coaches, Advisors, Workforce Architects and Embedded Tech Talent
(27:10) Why AI Proficiency Is the Safest Career Bet
(29:10) Why Graduate Programs and Rotational Programs May Make a Comeback
(32:35) Why Getting an Agent on the Org Chart Is a 12-Month Process
(34:35) Securing AI Agents, Access and Kill Switches
(37:30) Digital Colleagues That Never Sleep
(40:05) Why Future Teams May Be Organized Around Processes Instead of Functions
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📬 Subscribe to our weekly newsletter to get episode recaps
💡 Follow The Modern People Leader on LinkedIn
😊 Follow Daniel Huerta on LinkedIn
😊 Follow Stephen Huerta on LinkedIn
---- 
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.