Work 20XX with Jeff Frick

Jeff Frick

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.

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

    6d ago

    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*

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

    Jun 4

    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

    26 min
  3. Jan 16

    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

    4 min
  4. 08/09/2025

    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

    15 min
  5. 08/07/2025

    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

    10 min
  6. 08/04/2025

    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

    13 min

About

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.