Work 20XX with 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.
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Tracy St.Dic: Rethink Hiring, Slope not Snapshot, AI Fluency, AI Interviews | Work 20XX Ep66
07/19/2026
Tracy St.Dic: Rethink Hiring, Slope not Snapshot, AI Fluency, AI Interviews | Work 20XX Ep66
Tracy St.Dic is Global Head of Talent at Zapier, where she's spent the last several years rebuilding hiring from the ground up for an AI-native world. "Slope, not snapshot" is her phrase — she's not interested in where a candidate stands today, she's interested in the angle of their learning curve. In this episode, Tracy makes the case that most of what companies call signal in hiring is actually noise. Resumes have flattened into interchangeable copy. Applications are increasingly fraudulent. And the traditional recruiter screen wasn't built for a world where the tools themselves change every few weeks, not every few years. We cover: Zapier's AI fluency rubric — one of the first of its kind, open-sourced to the community, and rebuilt from scratch as the bar for "capable" has kept moving Why raising the bar meant Zapier also had to raise the level of support, building resources for candidates to close the gap rather than just screening them out Ezra, the voice AI Zapier uses for first-round interviews — and the surprising discovery that candidates and recruiters both prefer it to a human screen Why an AI interviewer that doesn't interrupt, doesn't show impatience, and never runs out of time zone turns out to be the more humane first conversation, not the less Everything else is noise. Applications are noise. What's left, once you strip that away, is whether someone is actually climbing — and whether the people evaluating them can see it happen in real time. Better hiring isn't about finding people who already know everything. It's about finding people on the way up. Tracy makes the case. Recorded live at Running Remote 2026, Austin, Texas. Guest: Tracy St.Dic, Global Head of Talent, Zapier | zapier.com | linkedin.com/in/tracy-stdic Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick. Transcript and Show notes - Click Here YouTube - Click Here
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Sacha Connor v3: Not Technical, No Excuse, Leading AI Adoption | Work 20XX Ep 65
07/11/2026
Sacha Connor v3: Not Technical, No Excuse, Leading AI Adoption | Work 20XX Ep 65
Sacha Connor has been coming to Running Remote since 2019, when the conference was held in Bali, and this episode marks her third appearance on Work 20XX. Please join me in welcoming Sacha Connor back to the Work 20XX podcast. In Austin for the second year running with the team at Running Remote, we sat down with Sacha, founder and CEO of Virtual Work Insider, to trace how the conversation at this conference has evolved since that first trip to Bali, from synchronous versus asynchronous communication debates to what's dominating the room now: AI adoption inside distributed teams. Sacha admits she was scared of AI at first. She never worked at a tech company, never learned to code, and did not see herself as a technical person. That changed when she took a Lead with AI certification program and realized the skills translated more directly than she expected. Now she has built her own custom GPT trained on the five-piece meeting framework she teaches clients, purpose, product, process, pre-work, and people, and uses it to prep every agenda she runs. The conversation also digs into her sharpest observation of the day: AI adoption inside a company follows the same spectrum she has spent 15 years mapping for remote and hybrid work. Some organizations are virtual-first and moving fast, some are still figuring out basic policy on which LLMs employees are even allowed to use, and Sacha works both ends of that spectrum at once, from the executive suite down to the team actually trying to get the tools to stick. Her advice for anyone intimidated by the mandate from on high to "go use AI": experiment in your personal life first. She has used LLMs for her own family scheduling. Once it clicks personally, bringing it to your team gets a lot easier. We also cover her fifteen-year remote-iversary, the ERG she helped build at Clorox that grew faster than any other in the company, and her hot take on scheduled send.
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Lucy Stein: Clear is Kind, Assume Positive Intent | Work 20XX Ep 64
07/07/2026
Lucy Stein: Clear is Kind, Assume Positive Intent | Work 20XX Ep 64
Lucy Stein just watched Givebutter cross $10 billion in donations raised for nonprofits, ten years after she joined the company as employee number seven. Please join me in welcoming Lucy Stein to the Work 20XX podcast. In Austin for the second year collaborating with the team at Running Remote, we sat down with Lucy to learn how she built a People function from a completely blank slate, and what it takes to keep it intact as the company scales past 200 employees. Givebutter's culture runs on three codified values: radical transparency, no assholes, and wired for fun. Lucy breaks down what each one actually means in practice, from a weekly all hands where finance shares real revenue numbers, to an explicit team-wide push to assume positive intent before reacting to a Slack message. She also talks through the recent integration of We Are For Good, a nonprofit media and community company Givebutter acquired, and why culture fit was the very first thing she checked. The conversation closes on AI adoption inside a remote-first team, and Lucy draws a direct line between the skills that make distributed work succeed and the skills that make AI adoption succeed. Her advice for managers right now: PR for your team. When someone on your team is doing something sophisticated with a new tool, make sure it gets seen. Oh, and yes, we talk about Mr. Butter, the company mascot with a butter slice for a head. Lucy Stein: Clear is Kind, Assume Positive Intent | Work 20XX with Jeff Frick Ep 64 from Running Remote
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Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX Ep63
07/03/2026
Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX Ep63
Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX with Jeff Frick Ep63 from Running Remote Vini Coelho recently added Chief of Staff and VP Operations to his People and Culture role at Time Doctor, 140 people spread across 40 countries and 24 time zones. And Vini's met them all. Please join me in welcoming Vini Coelho to the Work 20XX podcast. In Austin for the second year collaborating with the team at Running Remote, we sat down with Vini to learn how he does creates and manages culture across such a wide georgraphical and cultural spread. Time Doctor uses its own workforce analytics tool built to track productivity and in the act of usage behaviour, converts it from what might be percived to be a survealance too, into a trust-building platform. Vini also makes the case that a company is a sports team, not a family, and explains why that distinction matters for how people actually commit to their work. We talk through what career growth looks like when the org chart is flat and vertical promotion is not a given, and Vini's answer is lateral growth: more responsibility, more influence, more relevance, even without a new title attached. The most surprising thread runs back to his time as a sommelier in a 2-Michelin-star restaurant. Hospitality taught him that the job was never the paperwork. It was the people. That is the whole philosophy, transplanted into HR at scale. Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX with Jeff Frick Ep63 from Running Remote
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Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX Ep62
06/22/2026
Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX Ep62
Let me re-read the transcript to nail the details and get Nick's language right.Here's the Libsyn description, built to match the Bobbi Wegner template: Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX Ep 62 Nick Francis co-founded Help Scout in 2011 and ran it as CEO for 15 years before stepping into the Chairman role in late 2025. Today he coaches founders, facilitates a CEO peer group, and speaks on leadership, remote culture, and building companies for the long haul. In this episode, Nick makes the case that the AI moment is not a cost-cutting exercise. It's a growth opportunity, and the companies that treat it like one will leave the others behind. The conversation starts with what it actually feels like at the top of the org chart, where there's no support built into the structure, and moves through the operational practices Nick built at Help Scout to keep a remote team calibrated, honest, and moving in the same direction. We cover: The loneliness of the CEO role and the two things that were transformational: a coach who could give hard criticism without organizational risk, and a peer group built on shared values The "War Council," a technique Nick picked up from Wade Foster at Zapier, using AI personas to pressure-test decisions from multiple angles when nobody around you wants to deliver bad news Calibration as an operating practice, not a document. Managers getting together every six months to stress-test rubrics, align on what great looks like, and minimize bias across the organization Why hard conversations don't happen in remote companies unless they're baked into the operating system Bifurcating engagement data to focus on high-performer feedback, and why that's not leaving anyone behind, it's investing where the ROI is highest High agency as the unlock for the AI era. Nick's belief that the capacity is in everyone, though in some folks it might just be dormant. You've got to wake it up. Why leaders thinking about AI only in terms of cutting costs and improving productivity are taking a short-sighted view. You can't save your way to growth. The job is still the job. The tasks are going to change radically. For an entrepreneur, this is heaven. Recorded live at Running Remote 2026, Austin, Texas. Guest: Nick Francis, Co-founder & Chairman, Help Scout | nickfranc.is | helpscout.com Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick. Transcript and Show Notes - Click Here YouTube - Click Here
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Bobbi Wegner: Culture Is Relationship at Scale | Work 20XX Ep61
06/18/2026
Bobbi Wegner: Culture Is Relationship at Scale | Work 20XX Ep61
Bobbi Wegner: Culture Is Relationship at Scale | Work 20XX Ep 61 Bobbi Wegner is a clinical psychologist, Harvard lecturer, and Founder and CEO of Groops — a psychology-based coaching platform built on a simple, solid premise: people are social beings, hardwired for connection. "Animals in suits" was her phrase. In this episode, Bobbi makes the case that culture is relationship at scale. Not the posters on the wall. Not the values deck. The actual strength of the connections between the people doing the work, accumulated one interaction at a time. We cover: Why AI adoption is fundamentally a behavior change problem — and why most companies are treating it like a software rollout The thoughts-feelings-behavior chain that drives every business outcome anyone actually cares about The impossible squeeze on middle managers right now, asked to hold teams together while navigating their own uncertainty The bifurcation Bobbi sees coming: companies that double down on people plus the tool, versus companies using AI as cover to cut When people are stressed and uncertain, their amygdalas are getting beat up all day long. A stressed, defensive amygdala is not a connecting brain. It's a surviving brain. And that shows up directly on the bottom line. Good psychology is good business. Bobbi makes the case. Recorded live at Running Remote 2026, Austin, Texas. Guest: Bobbi Wegner, Founder & CEO, Groops | drbobbiwegner.com | joingroops.com Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick. Transcript and Show notes - Click Here YouTube - Click Here
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Gianna Driver: How You Treat the Waiter, Humans First, Employees Second | Work 20XX Ep60
06/08/2026
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*
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Nadia Vatalidis: Extreme Async, Unguarded Feedback, Career by Initiative | Work 20XX Ep59
06/04/2026
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
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Liam Martin v2: Distributed Intelligence, AI-Native Organizations | Work 20XX Ep58
05/29/2026
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
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The Big Game: Worst to First – Culture, Talent, Champions | Work 20XX Ep57
02/10/2026
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 Transcript, show notes, links and references.
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Work 2026: AI Adoption, Curiosity, Continuous Learning | Work 20XX Ep 56
01/16/2026
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
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Liam Martin: Community Retreat, Remote, AI | Work 20XX Ep55
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 - Transcript and Show Notes -
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Michael Melen: Talent Pool, Growth Opportunity | Work 20XX Ep54
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 - Transcript and Show Notes -
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Melinda Stallings: Positivity, PechaKucha, Gifts, Reset | Work 20XX Ep53
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
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Robert Phelps: Cybersecurity, People, Responsibility, Test | Work 20XX Ep52
08/03/2025
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 - Transcript and Show Notes -
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Karrie Sullivan: Results, Resilient, Reluctant, Readiness | Work 20XX Ep51
07/18/2025
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 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 - Transcript and Show Notes -
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Henrik Jarleskog: AI Squad, BarCeptionist, Full Stack Hospitality | Work 20XX Ep50
06/30/2025
Henrik Jarleskog: AI Squad, BarCeptionist, Full Stack Hospitality | Work 20XX Ep50
Henrik Järleskog, has been on my radar for some time. He’s an active member of the ‘future of work’ community on LinkedIn, frequently contributing articles, keynotes, posts, panel discussions, podcasts appearances and more. I knew I’d have him on eventually…. And then he dropped the post … ‘Not one hand went up’ And went on to describe his team of AI agents, working for him. His dirty dozen, cabinet, team of rivals, assistants, advisors, and worker bees, helping Henrik 3x to 4x himself as he described. From to , the list is long and detailed. So the time is now. Please join me in welcoming Henrik Jarleskog to Work 20XX We delve deep into the concept of ‘Full Stack Hospitality’ and it’s relevance in the future of work, workplaces, offices, and places where people gather. Sodexo is the 420,000+ employee behemoth you may not be familiar with, serving over 80 million consumers daily in over 45 countries, so Henrik has data, especially after being tasked to focus on the post pandemic workplace. And then there is his AI adoption story. While many struggle to find GenAI applications in daily life, Henrik has jumped in with both feet, taking courses, joining communities, and actively upping his game, not only in the name of future of work, but helping to define how organizations move forward with everyone brings a team of 30 assistants to work. How much faster can we go? How much more can we accomplish when 80% solutions are delivered in hours, not days? I think you’re going to enjoy this episode. Henrik Jarleskog: AI Squad, BarCeptionist, Full Stack Hospitality | Work 20XX podcast with Jeff Frick Ep50 YouTube - Transcript and Show Notes - © Copyright 2025 Menlo Creek Media, LLC, All Rights Reserved
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Brian Robertson: Authority, Clarity, Limits, System | Work 20XX Ep49
06/06/2025
Brian Robertson: Authority, Clarity, Limits, System | Work 20XX Ep49
Brian Robertson’ leadership philosophies are based on empowering the system, not the people. With clear limits, an ‘act don’t ask’ permissive mindset, the culture seeks to foster more entrepreneurial leadership, when people can exercise authority and autonomy, rather then sitting around, waiting to be told what to do. As the founder of Holacracy and a veteran entrepreneur, Brian brings a new model for leadership and decision-making, rooted in clarity, authority, and giving people the ability to act. Recorded at Running Remote in Austin, Brian shares how companies can unlock speed and autonomy by creating transparent systems where roles are dynamic, authority is clearly defined, and people are trusted to lead without waiting for permission. He explains why most “empowerment” efforts fall flat, how limits actually expand freedom, and what it looks like when even the newest hire can shape the CEO’s responsibilities. From roundabouts to role maps, this conversation is packed with practical takeaways for leaders looking to future-proof their teams and ditch outdated command-and-control models. Empower the system. Please join me in welcoming Brian Robertson 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. Brian Robertson: Authority, Clarity, Limits, System | Work 20XX podcast with Jeff Frick Ep49 from Running Remote YouTube - Transcript and Show Note - © Copyright 2025 Menlo Creek Media, LLC, All Rights Reserved
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Mindy Honcoop: Fractional, Upskill, Micro dose Change | Work 20XX Ep48
06/02/2025
Mindy Honcoop: Fractional, Upskill, Micro dose Change | Work 20XX Ep48
Mindy Honcoop helps people grow, one micro dose at a time. As the founder of Agile in HR and a seasoned people leader, Mindy brings a unique lens as her path started in the juvenile justice system, working with kids, and figuring out how happiness, and being one’s best self at work, contributed to a child’s well being. At Running Remote, Mindy emcee’d the outside stage for two days, absorbing insights, and sharing her own perspective on the evolving nature of leadership, work, and upskilling. In this episode, she shares how fractional roles work, her approach to growth and creating a people and skills roadmap, and then training her way out of the engagement, upskilling the internal team to take the business up a notch. Mindy has a laser focus on a market segment where she identified a gap she could fill. Micro dose change is just one secret she shared. Please join me in welcoming Mindy Honcoop 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. Mindy Honcoop: Fractional, Upskill, Micro dose Change | Work 20XX podcast with Jeff Frick Ep48 from Running Remote #MindyHoncoop #AgileHR #MicrodoseChange #Fractional #Upskill #Microdose #Change #FractionalLeadership #Upskilling #FutureOfWork #RemoteWork #PeopleOps #Digital #Distributed #Remote #Hybrid #Workplace #RunningRemote #LeadershipDevelopment #HumanCentered #WorkplaceTransformation #ContinuousImprovement #TeamCulture #Interview #Podcast #Work20XX YouTube - Transcript and Show Notes -
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Justin Harlan: Move for $10K, Stay for Community | Work20XX Ep47
06/01/2025
Justin Harlan: Move for $10K, Stay for Community | Work20XX Ep47
Justin Harlan wants you to move to Tulsa. But not just for the $10,000 check. He wants you to consider building your life in Tulsa. As Managing Director of Tulsa Remote, Justin leads a groundbreaking initiative to attract talented, remote workers to diversity Tulsa’s economic base beyond oil and gas with more knowledge workers. To grow greater Tulsa, as well as the newly transplanted community. Tulsa is also investing in ‘placemaking’ to increase the probability that these newest residents will stay for the long team. And it’s working. With over 3,500 people relocated and an 85% retention rate, Justin and team are hitting the right levers. People are coming for the incentives, they’re staying for the quality of life. Please join me in welcoming Justin Harlan to the Work 20XX podcast. And thanks Justin and Austin Remote for being active sponsors of Running Remote, hosting the welcome reception. Recorded 2025-April-29 at the Running Remote conference in Austin, Texas. Special thanks to the Tulsa Remote team and our friends at Running Remote. Justin Harlan: $10K to Move, Stay for Community | Work 20XX podcast with Jeff Frick Ep47 from Running Remote #TulsaRemote #Talent #Distributed #Digital #Remote #Hybrid #RemoteWork #TalentAttraction #RelocationIncentives #CommunityBuilding #EconomicDevelopment #QualityOfLife #JustinHarlan #FutureOfWork #DistributedTeams #RunningRemote #PlaceBasedInnovation #HybridWork #DigitalNomads #Interview #Podcast #Work20XX YouTube - Transcript and Show Notes -
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Zach Boyette: Remote, Design, Freedom, Games | Work 20XX Ep46
05/30/2025
Zach Boyette: Remote, Design, Freedom, Games | Work 20XX Ep46
Zach Boyette got a business class view of the world and decided to build a life, and company around the freedom to design one’s own life, not only for Zach the traveler, but all the employees, regardless of the design they choose, living anywhere in the world. As co-founder and CEO of Galactic Fed, Zach leads a 100% remote, 150-person global marketing agency. They designed the company from the bottom up around the principle of giving agency to employees to design they life they want to lead. At work, at home, and in their communities. Built on a foundation of documentation, writing things down, no single point of failure. They’ve developed blueprints to describe in detail how to do various projects, from kicking off a client engagement, to interviewing new candidates. And time together, the focus is on fun. Show and Tell, Games, and more. Since the work is digital, together time is used to strengthen the human connections. Please join me in welcoming Zach Boyette to the Work 20XX podcast. Where we’re reminded yet again, that it’s better to be one in a million, than one of a million. Thanks again Zach. Recorded 2025-April-29 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and Team Running Remote. Zach Boyette: Remote, Design, Freedom, Games | Work 20XX podcast with Jeff Frick Ep46 from Running Remote YouTube - Transcript and Show Notes -
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Phil Kirschner v2: Vibe, Pulse, Transparency, Nudge | Work 20XX Ep45
05/24/2025
Phil Kirschner v2: Vibe, Pulse, Transparency, Nudge | Work 20XX Ep45
Phil Kirschner returns to Work 20XX with a fresh perspective on how we actually get work done, and exploring a concept he calls “vibe officing.” And yes, it’s a verb. As Phil puts it, “technology should help us be more human,” navigating between spaces, people, and pulse moments with greater flow and fewer barriers. Sitting face to face from Running Remote in Austin, Phil shares practical insights for leaders navigating change for their teams and organizations, culture shifts, and compliance challenges, with an update on New York City’s Local Law 97. Please join me in welcoming Phil Kirschner back to the Work 20XX podcast from Running Remote. As founder of PK Consulting, former McKinsey expert, and veteran of WeWork’s meteoric ride, Phil has seen firsthand how organizations build, adapt, and sometimes stall. His new newsletter, The Workline, has quickly become essential reading for workplace strategists, changemakers, and executives trying to align culture, operations, and experience. We dug a little deeper into a few choice editions. Thanks again Phil. Recorded April 24, Running Remote, Austin Special thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote Phil Kirschner v2: Vibe, Pulse, Transparency, Nudge | Work 20XX podcast with Jeff Frick Ep45 from Running Remote YouTube - Transcript and Show Notes -
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Sophie Wade v2: Digitalized, Multi-Gen, What Is | Work 20XX Ep44
05/20/2025
Sophie Wade v2: Digitalized, Multi-Gen, What Is | Work 20XX Ep44
Sophie Wade returns to Work 20XX with a powerful reminder, the future of work is digitalized, multi-gen, and human-first. And that’s not a typo, it is a process of work being broken down, and digitalized, and to quote Sophie, ‘the tech driven world and operations is changing how we work, not the other way around.” In person, from Running Remote in Austin, Sophie shares deep insights on how empathy, adaptability, and trust are reshaping workforce dynamics. Please join me in welcoming Sophie Wade back to the Work 20XX podcast from Running Remote. As founder of Flexcel Network, author of Empathy Works, host of the Transforming Work podcast, and creator of the Work in Progress Report newsletter, Sophie has been a relentless advocate for designing work experiences that prioritize empathy, people and performance. Literally hundreds of thousands have attended her LinkedIn Learning classes in pursuit of a more responsive, flexible, and inclusive workplace. And breaking news, she’s launching a new series of classes on Sophie Wade dot com this month. The first one, Selling with Empathy. Lots more in the show notes. Recorded April 30, Fair Market, Austin Special thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote Sophie Wade v2: Digitalized Multi-Gen, What Is | Work 20XX podcast with Jeff Frick Ep44 from Running Remote YouTube - Transcript and Show Notes -
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Brian Elliott v3: Invest, J-Curve, Goals, Team | Work 20XX Ep43
05/16/2025
Brian Elliott v3: Invest, J-Curve, Goals, Team | Work 20XX Ep43
Brian Elliott returns to Work 20XX with a fresh lens on scaling distributed work, investing in people, and navigating the J-curve of technology adoption inside teams. Because what works for supporting distributed teams, works for increasing team AI adoption. Align on real goals, only three to five, and check in with tweet sized updates, once a week, on those three goals. Please join me in welcoming Brian Elliott back to the Work 20XX podcast from Running Remote. As co-founder of Future Forum, co-author of How the Future Works, and now with his new Newsletter, Work Forward, Brian is a data-filled champion of distributed teams years and years, long before Covid, before it was in fashion. He continues in that tradition with his latest, the Work Forward newsletter, chock-full-o case studies, research, and exercises to help you get more out of your team. He pulls from the best, including a heavy dose of Atlassian, PagerDuty, and Neiman Marcus. Recorded April 30, Fair Market, Austin Special thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote Brian Elliott v2: Invest, J-Curve, Goals, Team | Work 20XX podcast with Jeff Frick Ep43 from Running Remote YouTube - Click Here Transcript and Show Notes - Click Here
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Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX Ep42
05/14/2025
Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX Ep42
Sacha Connor returns to Work 20XX and asks, how do you self advocate, make sure the right people see and are familiar with your accompaniments, skills, and potential, when the most important factor when being considered for that next promotion or fresh opportunity is an AI agent preparing a list of candidates for consideration. Are you on the agent’s radar? What digital persona is assembled by the AI after consuming the knowledge management system data, presentations, actions plans, meeting notes, agendas, project summaries, IMs, emails, meeting transcripts, and more digital exhaust? How does it compare to others? Please join me in welcoming Sacha Connor back to the Work 20XX podcast at Running Remote, As Founder and CEO of Virtual Work Insider, Sacha has long been a leading voice and resource for building distributed team success for years. In this episode, we explore how in today’s AI world, people must signal their value to not just their managers and people who make decisions, but the AI agents that create the nominations based on a wide swath of internal systems communications data. Recorded April 29, Fair Market, Austin Special Thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote Sacha Connor v2: Self-Advocacy in the Age of AI | Work 20XX podcast with Jeff Frick Ep42 at Running Remote YouTube - Transcript and Show Notes - Episode Page -
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Ryan Anderson v2: Support Rich Interpersonal Interactions | Work 20XX Ep41
05/10/2025
Ryan Anderson v2: Support Rich Interpersonal Interactions | Work 20XX Ep41
Ryan Anderson and his global research team are spread across more than 20 countries, allowing them to study a wide variety of built environments, workplaces, homes, schools, and healthcare, not just remotely, but in person. That in-person presence is critical. It gives them the ability to feel what’s happening in different types of spaces, each designed around distinct objectives. Ryan also hosts one of the leading podcasts in the space, About Place—a true masterclass in all things design, workplace, and beyond. In fact, his podcast was one of my earliest and most valued resources as I dove into this community and topic. So it was a real pleasure to sit down in person at Running Remote 2025 in Austin. Ryan shares how experience-based design isn't just about furniture or aesthetics, it's about creating environments that support engagement, autonomy, and wellbeing. We explore the purpose behind workspace design, the data behind engaged teams, and the human factors that too often get overlooked. Ryan also talks about the role of choice and trust in workplace effectiveness, and why spaces that reflect organizational values are more important than ever. Please join me in welcoming Ryan Anderson back to the Work 20XX podcast. Recorded April 29, 2025 | Fair Market, Austin Thanks to Liam Martin, Egor Borushko, Ana Maria Bennett & Team Running Remote Ryan Anderson v2: Support Rich Interpersonal Interactions | Work 20XX podcast with Jeff Frick Ep41 from Running Remote YouTube - Transcript and Show Notes -
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“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX Ep40
05/09/2025
“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX Ep40
Jessica “JJ” Reeder was there, with Darren Murph, at GitLab, early pandemic, when suddenly the entire world was interested in their masterpiece, the GitLab Remote Work handbook. When the world was thrown into remote and distributed work over a weekend in Spring 2020, and answers to many of the questions were contained in the tens of thousands of words, and thousands of pages in the GitLab remote work playbook. As JJ recently reminded, that work started a decade ago. She and Darren are no longer at GitLab, and the Pandemic is 5 years removed and fading in the new rear view mirror. Good news, eyes on the future. The future is AI-powered. Good news, the same behaviors, attributes, and best practices that powered success in distributed teams, are the same required to increase team AI adoption. The long held dream of a high functioning organizational knowledge platform, is finally, almost here? Please join me in welcoming “JJ” Jessica Reeder to the Work 20XX podcast. JJ and team are implementing said knowledge platform in her new role at Upwork. As we discuss in this interview, it’s about the hard work, and everyone doing their part, that builds the buy in, and the data base, to dramatically improve the chances of success, wide spread adoption, and a significant reduction in the time spent searching for information. Thanks again, JJ. Editor’s Note: Recorded 2025-April-29 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team for collaborating with Work 20XX to capture these in-person interviews with the top minds shaping the future of work. “JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work podcast with Jeff Frick 20XX Ep40 from Running Remote YouTube - Transcript and Show Notes -
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Mark Cruth: Agreements, Alignment, Explicit, Foundations | Work 20XX Ep39
05/06/2025
Mark Cruth: Agreements, Alignment, Explicit, Foundations | Work 20XX Ep39
Mark Cruth, Principal Modern Work Coach and Advocate at Atlassian, has been knee deep in the Atlassian system of work for years. A driving force behind Atlassian’s Team playbook,and a big fan of starting from templates, Mark has been helping organizations implement better ways of working. Such a treat to sit down with Mark at the Atlassian Team ‘25 event in Anaheim, California. He walked me though some of this foundational team effectiveness philosophies, starting with alignment around goal, clear working agreements, clear roles and responsibilities, and an emphasis on getting closer with the teams one step removed, upstream, and downstream, to stay aligned. Please join me in welcoming Mark Cruth to the Work 20XX podcast Let’s make things more explicit. More communication, fewer assumptions. Thanks again Mark. Editor's Note: Recorded 2025-Apr-10, Anaheim Convention Center. My first solo onsite recording with some new gear. Missing my rock star production team. Special shout out to Rob Castaneda and Team ServiceRocket for sharing their booth to enable this recording. YouTube - Transcript and Show Notes -
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Dominic Price v2: Curiosity, Impact, Listen, Value | Work 20XX Ep38
05/03/2025
Dominic Price v2: Curiosity, Impact, Listen, Value | Work 20XX Ep38
Dominic Price returns to Work 20XX, this time from the floor of Atlassian’s Team ’25 conference in Anaheim. Dom shared his candor, introspection, experiences, and hopes on the back end of a busy week, in person, across a small high boy table, on far more than the future of work. Simultaneously tired out and fired up, it promises to take some fun and unexpected turns. Dominic has multiple frameworks, available to all, which can help all teams perform better. From the User Manual, to Working Agreements, the Personal Moral Inventory to the Modern Work Manifesto, think of them as intentional guide rails to prevent unnecessary friction and turbulence down the road when unfounded assumptions collide into behavior and attitude differences around specific actions. Sometimes resulting in intentional internal sabotage. Dom is more than playbooks. He leans into the learning attitude, and looking in for opportunities to have existing beliefs challenged and updated with new information, so we can evolve and progress, not get stuck. Beyond active listening, ask questions, be a catalyst, be curious, be explicit in your acceptance and actively seek out alternative views, approaches, and opinions. How would you approach this problem? What would you do differently? Be the catalyst to move the knowledge forward. Please join me in welcoming Dominic Price back to the Work 20XX podcast This time, live and in person, from Atlassian Team ‘25. Thank you Dom Editors Note: Recorded 2025-Apr-10, Anaheim Convention Center. My first solo onsite recording with some new gear. Missing my rock star production team. Special shout out to Rob Castaneda and Team ServiceRocket for sharing their booth to enable this recording. YouTube - Transcript and Show notes -
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Peter Marquez: Evolution, Ecosystem, Responsive, Rovo | Work 20XX Ep37
04/26/2025
Peter Marquez: Evolution, Ecosystem, Responsive, Rovo | Work 20XX Ep37
Peter Marquez, Chief Customer Officer at ServiceRocket, joins us from the floor of Atlassian Team '25 in Anaheim to share his frontline perspective on the vibe and announcements, including Rovo, Atlassian’s AI assist, now included with purchase. With over a decade of experience, we cover the ecosystem, evolution of the market, and company. Customer expectations are shifting, Atlassian's footprint more strategic. Rovo promises to significantly reduce the TTI … Time-To-Information (I just made that up) sitting on top of a unified data structure, including the transcripts from looms and meetings. If we're reliable, we don't always have to be right. But we always want to be present. We always want to be available. - Peter Marquez: Please join me in welcoming Peter Marquez to the Work 20XX podcast Thank you Peter. Editor's Note: Recorded 2025-Apr-09, Anaheim Convention Center. My first solo onsite recording with some new gear. Missing my rock star production team. Special shout out to Rob Castaneda and Team ServiceRocket for sharing their booth to enable this recording. YouTube - Transcript and Show Notes -
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