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maps, this conversation is packed with practical takeaways for leaders looking to future-proof their teams and ditch outdated command-and-control models.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

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https://www.youtube.com/watch?v=Vv7awiTqQQY&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

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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

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https://www.youtube.com/watch?v=Zc-JKzPVZMw&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

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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

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https://www.youtube.com/watch?v=mQCMEJBGsgg&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

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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

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https://www.youtube.com/watch?v=75Q077l_SRc&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

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https://www.work20xx.com/episode/zach-boyette-remote-design-freedom-games-work-20xx-ep46

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

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https://www.youtube.com/watch?v=vNfo6fLWjSM&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt

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https://www.work20xx.com/episode/phil-kirschner-v2-vibe-pulse-transparency-nudge-work-20xx-ep45

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

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https://www.youtube.com/watch?v=uWXG1mNidpg&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt&index=1

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https://www.work20xx.com/episode/sophie-wade-v2-digitalized-multi-gen-what-is-work-20xx-ep44

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

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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

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Transcript and Show Notes - Episode Page - Click Here