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Work 20XX with Jeff Frick

Work 20XX with Jeff Frick

Hosted by Jeff Frick

BusinessTechnologyInterviews guests

Episodes

60

Latest episode

Jun 2026

Language

EN

About the show

Welcome to Work 20XX A show focused on the future of work as we navigate transformational times. I'm your host Jeff Frick. We'll talk to the practitioners, with 100,000s of newly empowered employees, looking for a different relationship with their employer. We'll talk to the technology providers, who are responding to these changing demands with new tools leveraging the latest in AI and ML. We'll explore the impacts of the rising tide of gig workers, solopreneurs, consultants, and 1099 services that enable them to cater to a global market. We'll talk to the academics, authors, and thought leaders who are helping us all get a better handle on what's really going on, and what it means to each of us. Our goal is to bring you the human story behind the issues, the context, and the relevance in the spirit of sharing best practices and experiences so we can all contribute to making the future of work better for people, organizations, and our world.

Listen to episodes

60 recent
June 8, 2026Episode 6016 min

Gianna Driver: How You Treat the Waiter, Humans First, Employees Second | Work 20XX Ep60

Gianna Driver didn't come to Running Remote 2026 as a remote work evangelist. She came as a Chief People Officer who believes, deeply, that how you design the spaces where people gather, physically, culturally, organizationally, determines everything about the kind of company you actually become. Not the kind you say you are. The kind you are. And that conviction didn't come from a business school case study. It came from growing up on the other side of privilege. Her mother emigrated to the US as a mail-order bride. Gianna knows what it feels like to be on the outside looking in. That experience shaped everything, how she hires, how she leads, how she thinks about who gets a seat at the table and whether the table itself is worth sitting at. Being humans first and employees second isn't a tagline for her. It's a worldview forged long before she had a title. So we got into the good stuff. Starting with the waiter test. For critical hires, Gianna takes candidates to dinner and watches how they treat the wait staff. Not as a trick. As a window. One CRO finalist interviewed brilliantly right up until the server got his order wrong. That was the end of the process. It's a small moment. It tells you everything. We talked about mistake-making as a leadership competency, normalizing failure fast, cost-effectively, and without fear, and why organizations that run on cultures of fear are leaving performance on the table every single day. We talked about the machine-to-machine hiring pipeline and what gets lost when the humans step out of the loop. And we went to the hard places: DEI, the political headwinds, the companies pulling back. Gianna's answer was clear and unequivocal. Call it whatever you want. If the words are triggering, find new words. But the spirit, building inclusive, diverse teams because the science says they produce better outcomes and because it's the right thing to do, that doesn't get to go away because it became inconvenient. And she made a prediction, on the record: companies using AI as cover for layoffs are going to see a boomerang. They've over-cut. They'll need to rehire. And the talent they let go won't be waiting. Good leadership is good leadership. These aren't lessons for remote teams or hybrid teams or any particular org chart configuration. They're for anyone who takes people seriously enough to be intentional about the conditions they create. Please join me in welcoming Gianna Driver to the Work 20XX Podcast. --- *Editor's Note: Recorded May 2026 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team.* *Gianna Driver: How'd You Treat the Waiter, Humans First Employees Second | Work 20XX Ep60 with Jeff Frick from Running Remote 2026* *YouTube – Click Here* *Transcript and Show Notes – Click Here*

June 4, 2026Episode 5926 min

Nadia Vatalidis: Extreme Async, Unguarded Feedback, Career by Initiative | Work 20XX Ep59

Nadia Vatalidis flew 10,000 miles, almost halfway around the world, to share her insights at Running Remote 2026 in Austin. And the distance is more than geographic. She doesn't live in the US, Europe or Asia. Her vantage is from South Africa, which povides a unique look 'back' if you will at the rest of the tech scene, with a differernt 'reality' check than I have here in Palo Alto, CA, in the eye of the storm, or even Asia or Europe or Austraila for that matter. Sometimes it's harder to tell what's happening when you're standing in the middle of it. Nadia was there at the beginning. Over a decade ago, working alongside Darren Murph at GitLab in those early days, helping define what would become the blueprint, reference, dictionary, thesaurus and operations manual, the anchor document, for distributed work around the world, the  'GitLab Remote Work handbook, ' published open source, for the benefit of all. That kind of longitudinal perspective is rare, and she's added to it since, moving from GitLab through other fully remote companies to her current role as Head of People at Doist, 100% remote, 100+ people, 40+ countries. So we got into the good stuff. Extreme async, functioning radical candor against 40+ cultures, and self managed careers. What does it take to create the conditions where honesty lands as a gift instead of a grenade, across so many different baseline cultural norms? Nadia explained their shadow program, giving people a chance to try before they buy in different types of roles, departments, and functions. And showing her care for the people, Nadia reinforced that even if that if helping someone grow means they eventually outgrow the company, that's not a failure. She celebrates the growth and development. That's the whole point. It gets celebrated. A great illustration and example of the mature, adult, professional, working demeanor required to operate in a world that prioritizes growth and improvement, at the risk of ruffling a few feathers (unintentionally). And of course we got into how Nadia specifically and Doist generally are leveraging AI to deliver more with their existing team. Good management is good management. These practices aren't just for remote or hybrid teams. They're for any leader who takes people seriously. And if Nadia was willing to fly half way around the word to share, I can assure you it well worth your 25 minutes. Please join me in welcoming Nadia Vatalidis to the Work 20XX Podcast. Editor's Note: Recorded May 2026 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team. Nadia Vatalidis: Extreme Async, Unguarded Feedback, Career by Initiative | Work 20XX Ep59 with Jeff Frick from Running Remote 2026 YouTube - Click Here  Transcript and Show Notes - Click Here

May 29, 2026Episode 5828 min

Liam Martin v2: Distributed Intelligence, AI-Native Organizations | Work 20XX Ep58

Liam Martin joined me fresh off the stage at Running Remote's 10th event, a milestone that puts into sharp relief just how much the landscape has shifted since that scrappy little secret called remote work became the world's crash course in 2020. What started as documentation, async, and trust has evolved into something far bigger: the realization that the skills and culture remote-first organizations built out of necessity are now the precise prerequisites for becoming AI-native. The conversation moved fast, from the absurdity of AI writing reports that humans then feed back into AI to decode, to a genuinely new management KPI (watch your team's token usage, not just their hours), to Liam's central thesis for this year's keynote: we are no longer simply managing distributed people, we are managing distributed intelligence. And the remote community, almost by accident, got there first. Please join me in welcoming Liam Martin back to the Work 20XX Podcast. Editor's Note: Recorded May 2026 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and Team Running Remote. Liam Martin: Distributed Intelligence, AI-Native Organizations, Remote-to-AI Pipeline | Work 20XX podcast with Jeff Frick from Running Remote 2026 Austin YouTube - Click Here  Transcript and Show Notes - Click Here

February 10, 2026Episode 575 min

The Big Game: Worst to First – Culture, Talent, Champions | Work 20XX Ep57

Indiana went 16-0 and won the national championship with 7 blue-chip recruits. Their opponents had 110+. What does Curt Cignetti's talent evaluation strategy teach us about the future of work? It's not about return to office. It's not about hybrid schedules. It's about creating an environment that enables people to do the best work of their lives—finding the best talent, empowering them with AI and modern tools, and building a culture where everybody plays every play. This is the future of work: strategic evaluation over pedigree, development over credentials, empowerment over control. YouTube  https://youtu.be/7H-lLnr_3x8 Transcript, show notes, links and references.  https://www.work20xx.com/episode/the-big-game-worst-to-first-culture-talent-champions-work-20xx-ep57

January 16, 2026Episode 563 min

Work 2026: AI Adoption, Curiosity, Continuous Learning | Work 20XX Ep 56

Welcome to 2026! After four years and 50+ episodes of Work 20XX, it's time to evolve the conversation. The return-to-office debates? We've covered them exhaustively. The real action now is in AI adoption, continuous learning, and building the skills that matter for distributed work. In this episode, Jeff shares his vision for Work 20XX in 2026, including why he's shifting focus away from return-to-office topics, the AI training with Kyle Moschetto that transformed his workflow, and his commitment to increase episode frequency this year. Key Topics: The evolution of workplace conversations since 2021 Why return-to-office debates are no longer the priority AI adoption and practical training insights coming in 2026 Evergreen topics that never age: distributed teams, communication, leadership, team effectiveness The importance of curiosity and continuous learning What's next for Work 20XX The workplace has changed dramatically since the show started. Our conversations need to change too. This episode sets the stage for a year focused on practical AI adoption, team effectiveness, and the skills that create meaningful work in a distributed world. What's Next: More episodes, more frequently. AI adoption stories and practical insights. Deeper dives on distributed leadership and team effectiveness. Shorter, more focused conversations. What We're Moving Beyond: Return-to-office mandates and hybrid work debates have been thoroughly covered. Time to focus on what actually helps people do better work. Let Jeff know what you want to hear in 2026. What topics are you curious about? What challenges are you facing? What skills are you trying to build?     EPISODE DETAILS: Episode Type: Show Update / Vision Statement Host: Jeff Frick Recording Location: Palo Alto, California Date: January 2026 Topics: Future of Work, AI Adoption, Distributed Teams, Remote Work, Leadership, Team Effectiveness, Continuous Learning, Workplace Technology, Professional Development

August 9, 2025Episode 5515 min

Liam Martin: Community Retreat, Remote, AI | Work 20XX Ep55

Liam Martin shared his full circle moment with me at Running Remote, almost 5 years to the day he was forced to cancel Running Remote's last visit to Austin, April 2020. With prior stops in Lisbon and Montreal, Running Remote's return to Austin was a community fest.  Remote first organizations focus more on in-house retreats than anyone outside of the actual travel industry. Industry leaders needed their own retreat. And Running Remote was born in 2018. After the reflection, the conversation turned to the future, and the intersection of remote management practices, AI adoption, and the impact of hiring the 'best for the job' AI proficient talent, regardless of location.   Please join me in welcoming Liam Martin to the Work 20XX Podcast. Editor's Note: Recorded 2025-April-30 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and Team Running Remote. Liam Martin: Community Retreat, Remote, AI | Work 20XX podcast with Jeff Frick Ep55 from Running Remote 2025 Austin #RemoteWork #RunningRemote #AI #Leadership #CommunityBuilding #FutureOfWork #RemoteTeams #GlobalTalent #WorkplaceInnovation #ScalingBusiness #HybridWork #SaaS #DigitalNomads #Entrepreneurship #RiskTaking #EventManagement #BusinessGrowth #Digital #Distributed #Remote #Hybrid #Office #FoW #Workplace #TechnologyAdoption #RemoteFirst #EmployeeEngagement #WorkplaceCulture #Interview #Podcast #Work20XX YouTube - Click Here  https://www.youtube.com/watch?v=LOKJ7j_yqNM&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt&ab_channel=TurntheLenswithJeffFrick   Transcript and Show Notes - Click Here  https://www.work20xx.com/episode/liam-martin-community-retreat-remote-ai-work-20xx-ep55

August 7, 2025Episode 549 min

Michael Melen: Talent Pool, Growth Opportunity | Work 20XX Ep54

Mike Melen took a college side hustle, and built it into a growing global digital marketing agency. After starting full remote, Mike opened an office in Bergen County, New Jersey. Covid closed the office, and SmartSites is back to being fully remote to stay. Remote hiring opened up the available talent pool beyond his Bergen County, New Jersey. Suddenly, Mike could hire people with the special skills needed, regardless of where they plugged in their laptop.  Mike learned early on that the best people want opportunities to grow, so he set an annual goal of 30% growth. He hired younger, less experienced people and invested in them to grow and advance along with the companies. Fourteen years later, SmartSites has grown to 400 people. Please join me in welcoming Mike Melen to the Work 20XX podcast. Editor's Note: Recorded 2025-April-30 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and Team Running Remote. Michael Melen: Talent Pool, Growth Opportunity | Work 20XX podcast with Jeff Frick Ep54 from Running Remote 2025 Austin  #Remote #Digital #Distributed #Async #Work #FoW #Workplace #Talent #Career #BergenCounty #DigitalMarketing #DistributedTeams #Global #HiringStrategy #Leadership #Scaling #RemoteTeams #SmartSites #StartupJourney #TalentPool #TeamGrowth #WorkFromAnywhere #SmartSites #RunningRemote #Interview #Podcast #Work20XX   YouTube - Click Here  https://www.youtube.com/watch?v=MosbOY0uFUI&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt  Transcript and Show Notes - Click Here  https://www.work20xx.com/episode/michael-melen-talent-pool-growth-opportunity-work-20xx-ep54

August 4, 2025Episode 5313 min

Melinda Stallings: Positivity, PechaKucha, Gifts, Reset | Work 20XX Ep53

Melinda Stallings brings the power of positivity to the workplace and stage. Founder of The Positive Consultant and curator of DisruptHR Austin, Melinda promotes the "infinite power of positivity," consulting with individual organizations and extending her reach as the force behind DisruptHR Austin, where she builds programs such as the 2025 theme, Envision, Empower, Elevate, helping people thrive in the workplace. I also learned about PechaKucha, a Japanese storytelling format built around the idea of "talk less, show more." At DisruptHR, this translates into speakers having just 5 minutes, with 20 slides that auto-advance every 15 seconds. No stress there. With her focus on pausing, reflecting, reframing, and resetting, Melinda reminded me that there is usually a gift in the negative. You might not see it right away, but look no further than the Odyssean journey at the center of our best stories. There has to be some pain along the way. Please join me in welcoming Melinda Stallings to the Work 20XX Podcast. Editor's Note: Recorded 2025-April-30 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and Team Running Remote. Melinda Stallings: Positivity, PechaKucha, Gifts, Reset | Work 20XX podcast with Jeff Frick Ep53 from Running Remote #Positivity #Gifts #Reset #EmployeeExperience #FutureOfWork #Culture #HR #HumanCenteredLeadership #KindnessMatters #AustinTX #DisruptHR #Leadership #Digital #Distributed #Remote #Hybrid #FoW #MelindaStallings #PechaKucha #Podcast #RemoteWork  #RunningRemote #Storytelling #TeamCulture #ThePositiveConsultant #Interview #Podcast #Work20XX   YouTube - Click Here  Transcript and Show Notes - Click Here

August 3, 2025Episode 5210 min

Robert Phelps: Cybersecurity, People, Responsibility, Test | Work 20XX Ep52

Robert Phelps helps keep remote teams secure, often before they even know they're at risk. As President of Creative IT, Robert and team provide IT services for companies that are too small to build an in-house department, or those that need a little assist.  Robert and I spoke at Running Remote 2025 Austin, before his keynote, 'The Hidden Bottleneck: Why Remote Teams Struggle to Scale (and How to Fix It Today),' on the cybersecurity challenges of remote and distributed teams, and the responsibility for user and companies, even if most of their apps and IT are hosted at a large public cloud provider like AWS, Google Cloud, or Microsoft Azure. With the world trying to convince us to click, it comes back to people, educating, training, and as Robert stresses, testing to make sure they understand, and don't take tempting bait.  Compliance and Security, never go out of style. But the challenges and degree of difficulty only increase over time.  Please join me in welcoming Robert Phelps to the Work 20XX Podcast  Editors Note: Recorded 2025-April-30  at the Running Remote conference in Austin, Texas.  Special thanks to Liam, Egor, Ana, and Team Running Remote. Robert Phelps: Cybersecurity, People, Responsibility, Test | Work 20XX podcast with Jeff Frick Ep52 from Running Remote  #Bottlenecks #CARA #Cloud #CMMC #Compliance #Culture #CyberSecurity #Distributed #Enablement #Experience #FoW #IT #Monitoring #Onboarding #People #Platforms #Remote #Responsibility #Risk #Scale #SOC2 #Teams #Test #Threats #Training #Trust #Workplace #RunningRemote #MenloCreekMedia  #Interview #Podcast #Work20XX  YouTube - Click Here  https://www.youtube.com/watch?v=aDE6yTpz1No&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt Transcript and Show Notes - Click Here  https://www.work20xx.com/episode/robert-phelps-cybersecurity-people-responsibility-test-work-20xx-ep52

July 18, 2025Episode 5152 min

Karrie Sullivan: Results, Resilient, Reluctant, Readiness | Work 20XX Ep51

Karrie Sullivan has been on the edge of digital transformation since the earliest days of digital media, with a stint at Cars.com during the late '90 internet boom. She knows about getting people to change behavior, to adopt the new, to do things differently.  As she said, people won't change behavior just because you ask them. People will change behavior to fit in. Especially if you hand them proven peer produced playbooks. Today, Karrie leads Culminate Strategy Group, where she and her team specialize in accelerating new technology adoption by identifying and working with key change agents. That influential 15% sits between the early adopters (the "bleeding edge" 5–7%) and the risk-averse majority (the "we've always done it this way" 80%). The Resilient middle 15% hold the key to broader adoption of the new, in this case, more people in the organization putting the power of AI to work for them in their daily tasks.  Please join me in welcoming Karrie Sullivan to the Work 20XX podcast. In this wide ranging conversation, we cover the interaction of workplace, AI, transformation, psychology, behavioral science, change, adaptability, and a whole lot more. Karrie brings clarity to the chaos of transformation. The through line: how to increase AI adoption, and more broadly, how to assimilate change faster, so your people can do more, with less, faster, by putting the right tools to work. Karrie Sullivan: Results, Resilient, Reluctant, Readiness | Work 20XX podcast with Jeff Frick Ep51 YouTube - Click Here  https://www.youtube.com/watch?v=jt66YYGRCMs&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt   Transcript and Show Notes - Click Here  https://www.work20xx.com/episode/karrie-sullivan-results-resilient-reluctant-readiness-work-20xx-podcast-with-jeff-frick-ep51

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