157: Cali Williams Yost - Workplace Flexibility: Addressing Competitive & Talent Realities

Cali Williams Yost, CEO and Founder of Flex+Strategy Group, has pioneered workplace flexibility since 1995. Cali shares her journey from banking to becoming a flexibility strategist. She explains why flexible work is essential for business growth and attracting and retaining top talent. Cali explains the pitfalls of hybrid and flexible model policy-only approaches and the need for full operational system-wide integration. She urges leaders to rethink outdated work constructs and outlines practical steps for embedding flexibility into organizational culture for sustainable success.       TAKEAWAYS   Chapter 1: Origins of a Flexibility Strategist   [01:19] Cali studies English and Economics appealing to her two contrasting interests. [02:08] Cali's first job at a bank gives her training and allows her to go to New York City!   [02:43] Client relationships are key to success, but rigid systems cause Cali's colleagues to quit. [03:35] Cali sees flexible work as logical and proposes it, unsuccessfully to bank leadership. [04:30] A bank client CEO explains he offers flexible working to retain his employees long-term. [05:14] Urged by his business-driven reasoning, Cali leaves to become a flexibility strategist. [05:47] Cali gets an MBA to have credibility with business leaders about workplace innovation. [06:10] Cali joins Families and Work Institute, developing strategies to operationalize flexibility. [07:35] Workplace flexibility becomes an employee benefit part of policy, not operationalised. [08:45] Making policies operational, Cali develops 'work-life fit' and publishes her first book.   Chapter 2: Workplace Flexibility Before & During COVID   [10:13] Top down approaches are not effective so Cali dives deep into change management.   [11:15] Cali starts her own firm to take an operational, integrated approach to flexible working.   [12:26] Pre-2020, most companies had flexible work policies but they weren't operationalised. [13:50] Widespread flexibility was organic and inconsistent with more men working remotely.   [13:55] When COVID hit, companies with operationalised flexibility policies adapted easily. [14:19] Executives must reassess foundational work constructs and beliefs to adapt effectively. [17:00] The work challenges presented by leaders and younger employees "clash of contexts". [18:55] The upcoming demographic cliff makes flexible work necessary to attract and retain talent.   Chapter 3: Leading in the Modern Work Era   [19:26] Finding those ready to lead the change, challenge their context and hold space.   [19:48] Three change phases—assess, align, activate—are critical for embedding flexibility. [20:10] Leadership alignment is essential; one resistant leader can derail an entire initiative. [22:45] Employers investing in defining new working parameters unlock many benefits.   [23:59] Leaders need to be aware of what is and isn't working with employees.   [25:31] Critical willingness to hold space for change being messy and looking at work differently. [27:11] Mandating in-office days without data and strategic input erodes employee confidence. [27:52] Executives co-creating with employees to achieve aligned operational flexibility.   [29:55] Trust increases when employees participate in experimenting and defining the process.   Chapter 4: Intentional Future of Work Transformation   [32:11] Senior leaders must be intentional about work transformation.   [32:50] The sustainability of 5-day/week RTO policies especially for talent attraction/retention. [34:07] The significant, essential hurdle of stepping back and rethinking the old work model.   [35:12] Younger employees successfully create an intern integration program when empowered. [37:45] Talent shortages by 2032 make flexible models essential to business continuity. [38:33] AI will supplement, not replace, human workers—talent attraction remains vital. [39:42] Rigid workspace metrics must evolve to support dynamic, flexible workforce needs. [42:16] Organizational transformation requires change management and relationships with systems thinking.   IMMEDIATE ACTION TIP: Leaders need to assess their talent reality from now through 2030 – aligning the expectations of their workforce and the needs of the business.         RESOURCES   Cali Williams Yost on LinkedIn flex+strategy group website         QUOTES   Pre-pandemic "Flexibility was happening organically. It was happening inconsistently, and it was not optimized."   "The consistent recognition is - I need to do this differently. So what does that look like?"   "You have to be willing to hold the space because change is messy."   "This [flexibility] isn't a policy. This is a way of operating."   "We're getting ready to hit a historic labour cliff demographic cliff. There aren't gonna be people. The workers who are left? They are going to dictate how they're gonna work.  So you should be working right now on being employer of choice."  

Andrew Mawson, Founder and Managing Director of Advanced Workplace Associates, explores how organizations can enhance performance, especially by helping employees better manage their brain capacity. Andrew shares six evidence-based factors most impacting knowledge worker productivity. He discusses the neuroscience-researched factors affecting brain function and performance. Andrew offers actionable leadership guidance to reduce mental load, enhance employee well-being and resilience, and achieve sustainable results.       TAKEAWAYS   Chapter 1: Andrew's Early Career    [01:18] Andrew studies applied statistics finding it useful, later describing reality through numbers.   [01:59] Working in tech and defence, Andrew then joins Fujitsu and leads a program on intelligent buildings.   [02:47] Intelligent building initiatives aim to increase computing adoption and data integration.   [04:54] Advanced Workplace Associates is founded to bring a business- and people-focused lens to workplace strategy.   Chapter 2: Six Key Factors of Knowledge Worker Productivity   [07:31] Analysis of past research identifies top factors impacting knowledge worker productivity.   [09:28] Factor 1: Social cohesion emerges as the top factor boosting collaboration and innovation.   [10:43] Factor 2: perceived supervisory support with leaders tailoring their approach for each person.   [11:41] Factor 3: Information sharing enables a culture of openness, countering knowledge-hoarding.   [11:59] Factor 4: vision clarity helps employees connect their work to the team and corporate purpose.   [12:45] Factor 5: external communication makes teams challenge their ideas and be open to others' views.   [13:29] Factor 6: Trust underpins all factors, fostering belief that leaders and colleagues do the right thing.   [15:10] Leaders must create a level of certainty to reduce employee anxiety despite external turmoil.   [16:21] Social cohesion usefully creates a buffer during uncertain times, enhancing resilience.   Chapter 3: Research into Brain Performance   [17:16] Humans are individual brains – research identifies 14 key factors to optimise performance.   [18:42] Sleep (7.5 hours) is key for brain performance, with quality and preparation critical enablers.   [19:50] Hydration, exercise, and a good diet—with breakfast—are also essential for cognitive health.   [21:39] Leaders must recognize that lifestyle habits affect their team's productivity and wellbeing.   [23:00] AWA is running a cohort trial to educate leaders on brain health and track performance.   [23:57] After baselining, coaching how to integrate new habits and track performance.   Chapter 4: Cognitive Capacity & Managing Load   [24:56] Recognising finite brain capacity, environments can be designed to reduce mental loads.   [25:55] Everyone can better manage their well-being and outcomes using workspace that increases capacity.   [28:10] A story of making tea illustrates how cognitive load varies by individual and context.   [29:37] Brains are managing humans' entire systems unconsciously, consuming much energy.   [30:20] Personal stressors, such as family and finances, compound work demands and brain strain.   [31:24] Leaders need to monitor workload and not exceed employees' brains' capacity limits.   [32:34] When excessive load get to a point that it blocks capacity for planning and logic.   [33:26] Managers and employees can manage load together to restore cognitive function quickly.   [34:13] Organizations are communities of connected brains aiming to optimise knowledge flow.   [35:05] All six factors are linked and applied together can improve productivity and wellbeing.   Chapter 5: How Leaders can Improve Performance    [36:26] Leaders need to better understand how the brain works to enable high-performing teams.   [37:07] Most managers lack vital training; the six factors offer a useful playbook for leaders.   [38:17] How many managers believe social cohesion is their responsibility?   [38:58] Competitive pressures between teams create division and undermine collaboration.   [39:54] Leaders must promote and model trust and social cohesion to cultivate environments that enable success.       RESOURCES   Andrew Mawson on LinkedIn Advanced Workplace Associates (AWA) website       QUOTES   "The name of the game is to get everybody as socially cohesive as possible to allow fluidity of movement, of knowledge and, and collision of knowledge."   "[External communication is] the idea that you should expose your knowledge and your brain to other things…. going to other places and have other people challenge your understanding so that your understandings remain fresh."   "Humans have got a finite capacity and how that capacity is loaded and eaten into is also another important part of the jigsaw."   "Organizations really are communities of connected brains…I think the first thing the leaders need to do is understand more about the brain."   "Brains are the unit of production going forward in the world of knowledge work."   "We are all actually different…We should be trying to create an environment and giving people knowledge about the status of different spaces and things in the places in the building so they can go and choose."   "The duty of a leader is to try to create a level of certainty, create a vision, and create a direction of travel that is almost independent of the turmoil that's going on."

Corinne Murray, Director of Global Workplace Experience Strategy at American Express, and Sara Escobar, Founder of Wielding Workplace, are co-authors of newly-released 'WORK then PLACE'. Corinne and Sara draw on rich backgrounds from Gensler, WeWork, Hulu, and Netflix to share insights on culture, workplace experience, and productivity. They explain the need for intentional work design driven by employee experience—digital, physical, and experiential—and how human-centric, flexible approaches empower performance in the distributed modern work ecosystem.     TAKEAWAYS   [01:50] Sara starts out in TV production and then moves to Hulu.   [03:01] Joining Hulu as a startup, Sara chooses to develop their workplace experiences. [04:10] Corinne's time at CBRE, Amex, and Gensler, inform her strategic research at WeWork. [05:23] Strong cultures at Hulu and Netflix differ but are both developed with intentional design. [06:12] American Express builds its strong culture based on benefits resulting in long-tenure norms. [07:02] Organizations are not prepared for formal hybrid models before 2020.   [07:56] Employees pushed experience and flexibility into focus post-COVID. [09:20] Architects' and Real Estate's periodic interventions limit impact on ongoing work design.   [10:45] Flexibility jumped to a top employee after their pandemic experiences. [11:36] Empathy influenced leaders to formalize more balanced, hybrid work options.   [12:45] Executives reacted emotionally to shifting work models, resisting a major overhaul. [14:30] Mandates fail to justify office returns since workplace experience is not just physical. [15:44] Corinne and Sara connect in 2021 amid return-to-office debates. [17:08] Sara launches a consultancy to inform and facilitate new workplace strategies. [17:54] Sara reaches out to Corinne to co-author a book, sharing practical strategy frameworks.   [20:05] Corinne shifts focus from productivity to effectiveness. [22:56] To 'fix' productivity, it must be shared across teams, not owned by workplace. [24:56] Managers must hold accountability and measure output, not observe activity. [26:02] HR, IT, and workplace must partner to enable teams' effective outcomes. [27:21] Physical-first remits clash with flexible work goals. [28:36] Employees now better understand what makes work function well. [30:17] Team agreements are key to performance in modern work environments.   [30:48] Trust grows from enablement, not perks or parties. [33:27] Change must be incremental to facilitate adoption and avoid burnout. [37:10] Start with high-impact, low-effort changes for users. [39:40] Strategy must flex for global, regional, and role differences. [41:03] 'Standards' can allow interpretation, like principles, to enable adaptability. [41:50] The "Daisy" model supports incremental workplace changes. [42:59] Corinne highlights knowledge work – its growth, volatility and success factors. [47:01] Sara highlights external research, such as parenting models, that offer workplace insights. [48:30] WORK then PLACE encourages humans to focus on what technology cannot replace. [49:15] Start by auditing what works to incorporate rather than rebuilding from scratch. [51:25] IMMEDIATE ACTION TIP: To shift workplace experiences and outcomes, find an executive sponsor, then clarify why and how the change should happen, and how to measure progress.     RESOURCES Sara Escobar on LinkedIn Corinne Murray on LinkedIn WORK then PLACE     QUOTES   "The companies that I've worked with where the culture has been truly wonderful and truly driven forward the company's mission are where that culture is intentional." — Sara Escobar   "We are workplace people. We do believe in the value of the physical place. But it's not the catchall for everything." — Corinne Murray   "The workplace environment is truly physical, digital, and experiential." — Sara Escobar   "Productivity is the responsibility of everyone from the individual to the executives to workplace to HR to IT." — Sara Escobar   "We need to do this in a way that doesn't feel threatening and doesn't feel like an extra burden." — Corinne Murray   "If you think about, you know, old factory lines, you watched the widgets being produced. That is what we've still fallen into in knowledge work. But you can't watch knowledge work get done." — Sara Escobar   "We've identified things that are fundamentally harmful to the ability of knowledge work succeeding. And if knowledge work isn't succeeding, that means the humans doing the knowledge work aren't succeeding" — Corinne Murray  

Trond Aas is CEO and Co-Founder of Attensi, a leader in AI-powered gamified simulation training. Trond shares his background spanning quantum physics, consulting and gaming. He explains how gamification grounded in behavioral science drives engagement which enhances initial and long-term learning especially for younger employees. Trond describes motivation as a critical success factor for sustainable upskilling. He discusses metrics to demonstrate return on investment in skills development and how to improve skills gap issues starting with cultivating a trust-based culture of learning   KEY TAKEAWAYS   [01:17] Trond starts studying quantum physics to explore fundamental questions about nature.   [02:01] After doing research for his military service, Trond goes into industry seeking practical impact.   [02:38] Trond joins McKinsey as a business school type experience before pursuing entrepreneurship.   [03:10] Interest in games stems from early programming and creativity cultivated during university.   [04:08] In gaming, Trond reveals how behavioral science is used to drive engagement and learning.   [06:12] Tribal, team-based successes are key to stimulating successful collaboration online.   [06:25] Fascination with learning and awareness of superficial gamification drives Attensi's founding.   [07:44] Attensi applies science to drive motivation and behavior change with measurable results.   [09:40] Correlating simulated behavior with real-world outcomes to track learning impact.   [10:23] Measuring soft skills progress when observable behavior is hard to track.   [12:10] As technology evolves rapidly, upskilling must be ongoing across high-competence industries.   [12:50] Skill development tailored to specific job challenges is more effective than one-size-fits-all.   [13:45] Self-motivated learners thrive, while others need help to develop the motivation that anchors learning.   [14:47] Many Gen Zers lack key communication skills and may not recognize this development need.   [15:49] Most learning programs fail on motivation, which must be addressed first to succeed.   [16:22] Creating mastery experiences significantly increases learner motivation and outcomes.   [15:15] Game-based learning builds confidence that translates into better real-world performance.   [19:43] Companies underinvest in onboarding due to unclear ROI, hindering workforce readiness.   [20:08] Trond emphasizes data, ROI, and clear impact as critical for better training investment decisions.   [20:34] Attensi's research shows poor onboarding leads to lower confidence and performance.   [23:42] Skill masking arises when employees hide learning gaps, often from lack of psychological safety.   [24:18] Cultivating trust-based cultures is essential to reduce skill masking and promote learning.   [25:48] Focusing on core skills for each role facilitates the shift to becoming a skills-first organization.   [26:44] Skill-based organizations can start small and ensure programs drive skill improvements.   [28:33] Maintaining skill use needs continuous feedback, clear expectations, and learning structures.   [29:13] Organizations must define competencies to stand out and align training with competitive goals.   [30:37] Tailoring programs to learner motivation and challenges supports effective skills development.     IMMEDIATE ACTION TIP: Learning motivation and skills usage are cultivated through mastery. Help employees sense their achievement to encourage their enhanced performance and growth.   RESOURCES   Trond Aas on LinkedIn Attensi's website     QUOTES   "We can use these principles of games to drive engagement, drive interest, drive motivation—and then we should be able to impact real behaviors and measure that with data."   "Most people experience poor onboarding and most people are convinced that it affects their work afterwards."   "Skill masking is that people are actually hiding the challenges that they are having."   "Are your people motivated? And if not, address that—that's what you need to address to be able to develop your organization."   "When you are able to instill a feeling of mastery in people that has a huge effect on their motivation."   "A lot of people think that one [training] system or one approach will fit with all the different employees... and I think it needs to be a lot more nuanced than that."

Will Sentance, Founder at Codesmith and Visiting Fellow at Oxford University, explores why empathy is a foundational skill in engineering. He explains how empathetic interactions are core to building software, teams, and the trust necessary to scale tech-based companies. Will reflects on Codesmith's mission to empower people through thoughtful communication in a non-hierarchical learning environment. He describes how empathy, as a relational tool, expands technologists' critical communication capabilities driving clarity and collaboration, propelling their careers.     TAKEAWAYS     [00:26] Will is drawn to the intersection of analytical and intuitive disciplines from early education.   [01:45] Will feels a deep sense of possibility through his PPE studies and aims to pass that on.   [03:05] A mentor at Oxford influences Will's brief foray into international relations at the UN.   [04:30] Not suited to be an employee, Will seeks autonomy and creative power in software engineering.   [06:00] Will finds software to be materially satisfying and empowering as a pathway to opportunity.     [07:20] A surprising response to an early JavaScript workshop reveals his teaching clarity.   [08:15] Struggling to understand complex concepts helps Will become a better educator.   [09:30] Codesmith is founded to be an alternative path to power by mastering technology.   [10:20] Teaching coding is not just technical but an empowerment vehicle for long-term careers.   [11:40] Thoughtful communication at CodeSmith recognizes others' knowledge and emotional states.   [13:00] Empathy is about adapting communication to another person's experience.   [14:30] Coding success requires explaining systems clearly—communication is as vital as code.   [16:10] Leaders like Sam Altman show that technical communication drives modern tech leadership.   [17:45] CodeSmith uses pair programming to instill empathy through precise verbal technical articulation.   [19:00] Empathy begins with self-understanding and is trained through iterative collaboration.   [20:20] Breaking down code for others builds resilience and fosters a capacity to learn continuously.   [21:45] How different learning speeds and imposter syndrome are combatted by sharing struggles.   [23:00] Codesmith instructors are alumni because lived experience cultivates trust and relatability with students.   [24:20] Will's Oxford Fellowship explores how certain skills drive opportunity in an AI-transformed job market.   [25:50] The real skill is learning how to learn and explain complex ideas using unfamiliar tools.   [27:15] Codesmith interviews measure communication, problem-solving, and how applicants handle the unknown.   [28:30] The focus is on cultivating capacities, not just teaching frameworks or programming languages.   [29:40] Engineers and non-technical people alike must build clear, empathetic communication skills.   [30:55] Workshops for non-programmers empower leaders to engage confidently with technical concepts.   [32:00] Empathetic leadership respects team members' potential rather than relying on rules-bound oversimplification.   [34:20] Scaling AI must be matched with scaling human trust across teams and organizations.   [36:00] Will warns against systems that machines understand but humans cannot, which risks alienation.   [37:30] Open-source tools preserve accessibility and transparency in a fast-moving tech landscape.   [38:45] Many leaders are not engaging with AI tools, missing key learning and leadership opportunities.   [40:10] Building the engineering mindset—problem-solving and communication—without coding.   [41:30] Struggle is not a problem in learning; it is the engine of understanding and growth.   [42:40] Empathetic development depends on trusted relationships and cannot be scaled without sincere human investment.   [44:00] IMMEDIATE ACTION TIP: Deep learning happens through struggle which takes place in trust-based environments, so build trusting relationships to facilitate learning.     RESOURCES   Will Sentence on LinkedIn Codesmith's website     QUOTES   "The hardest part of coding isn't writing code—it's explaining code to others so that they can also either build it, understand it, or write it themselves." "Struggle is not a bug—it's the engine of growth." "We train empathy like nothing else in the program. We train it through pair programming." "You can't scale trust with AI. You need humans to scale trust." "We've even called it empathetic engineering at times. One of the principles of Codesmith is grow others even before yourselves." "It is not how vibey you are. It is not how chummy you are. It's pure and simply, can you precisely walk through based on the understanding of another person?" "Breaking something down means that I can have clarity about how I'm thinking about it, and therefore I can then build it up for you." "Struggle-based growth depends on someone else saying, 'You're important to me enough that I'm going to invest in you.'"  

Ginger Dhaliwal is Co-founder and Chief Product Officer of Upflex. A long-time tech entrepreneur and investor, she shares her human-first orientation which drives her passion for solving systemic challenges using technology and data—from micropayments to elder healthcare to flexible workspaces. Ginger discusses how intentional design, empathy, and sustainability are essential for building data-driven ecosystems that support a diverse, distributed workforce. She highlights behavioral indicators for shaping future-ready on-demand and long-term work environments, emphasizing collaboration and relationships.     KEY TAKEAWAYS   [00:29] Ginger studies social work and first focuses on understanding people and reskilling immigrants.   [01:40] Ginger's travel takes her to Malaysia where she joins a tech startup as the Internet takes off.     [02:35] At a government-supported R&D lab, Ginger builds a venture studio model.   [03:20] They attract international talent to spin off multiple startups solving real-world problems.   [04:05] One early product enables micropayments using mobile phone billing instead of credit cards.   [05:12] Learning to persuade large corporations to adopt emerging innovations and enter new markets.   [06:10] A healthcare venture connects remote patients in S.E. Asia to providers through internet cafés.   [06:48] Healthcare tech is adapted for the U.S. to support elders aging in place with sensor systems.   [07:50] Adoption fails to take off due to lack of interest from medical professionals in holistic data.   [08:40] Ginger gets disheartened, entrenched in the elder care community, and feels burned out.      [09:30] Considering identity, AI's impact, and future career direction.   [10:45] Personal remote work experience and coworking exposure lead to co-founding Upflex.   [11:50] Ginger sees coworking catalysing innovation with people from diverse industries co-located.   [13:10] Upflex becomes a platform to aggregate access to coworking spaces globally.   [14:40] Early clients like Nokia highlight retention, recruitment, and cost control needs.   [15:20] Real estate lacks actionable data, pushing Upflex to build a decision-support layer for companies.   [16:25] Ginger champions flexibility as a strategic asset for talent engagement, not a perk.   [17:35] COVID causes companies to confront data about remote work and location preferences.   [18:40] Upflex helps firms explore questions around hybrid work behavior using their data tools.   [19:25] Focus on location can mask deeper control and change adaptation issues in hybrid transitions.   [20:45] Data shows employees' behavior is consistent across corporate offices and on-demand coworking spaces.   [22:25] The global shift from individual desks to more collaborative meeting spaces.   [23:38] Most day passes are booked same day, while meeting rooms are booked days in advance.   [25:55] Coworking supports relationship-building and community connection as well as collaboration.   [27:30] Companies are repurposing coworking memberships for team days, pods, and local clusters.   [29:40] Upflex advises clients to view coworking as workplace strategy infrastructure.   [31:25] Businesses experiment with timeshare-type space arrangements to balance cost and access.   [33:10] Exploring partnerships with landlords to offer on-demand overflow capacity.   [34:50] AI is being integrated to optimize seat allocation and dynamic workplace management.   [36:15] Comparing Upflex's model to AWS—scalable space usage tailored to demand and cost savings.   [37:25] Ginger emphasizes redirecting real estate savings to reskilling as rapid tech changes cause workforce disruption.   [39:15] Identity loss from desk removals prompt incremental workspace changes. [41:00] IMMEDIATE ACTION TIP: To problem solve right now, there's no playbook, it's iterative. Come up with questions to test. Start small. Figure out a solution. Get buy in. Gather data for feedback to refine and grow.     RESOURCES   Ginger Dhaliwal on LinkedIn Upflex website       QUOTES   "I don't need to know the answers to things as long as I'm constantly thinking about solving these problems for people."   "Coworking as a model for innovation and ideation is a wonderful thing and it's in your backyard. It's a block away from your, where you live."   "How do we create a more sustainable lifestyle for people looking at the data. People losing 15 days of their lives commuting just didn't make any sense to us."   "We can create that data layer so that people can actually make decisions based on data and understanding those preferences and how people are using space."   "A lot of office space today is designed for productivity and it's shifting to collaboration. Coworking spaces are designed for that too, but also relationships. I think the evolution is we are all going to be craving relationships. It's not the collaboration that you're going for. You're going for the relationships."   "We're working with landlords to figure out how you can create those overflow spaces and, from a corporate standpoint, be able to not build for the peak, but build for the average and then have the resources, the unlocking of the network, to handle the overflow."  

Noel McNulty, Global Real Estate and Workplace Director at Twilio, brings learnings from hospitality to facilities and workplace experience in the tech and legal sectors. He explains how a "know your customer" mindset drives effective workplace design with personalized experiences. Noel discusses evolving from traditional facilities to values-driven workplace experience. After pandemic-based adaptions, he shares the emerging signals and realizations of the shift to flexible, remote-first work. Noel endorses curated events and environments to foster connection, engagement, and wellbeing to enhance productive, distributed work.   KEY TAKEAWAYS   [1:30] Noel moves from Ireland to the US, starting in hospitality before moving to facilities management. [3:09] Noel uses hospitality skills in facilities work, focusing customer service and operational efficiency. [4:28] Working on a large office restack, Noel is exposed to design, construction, and project management. [6:04] Getting to know each customer personally is essential to deliver effective workplace solutions. [10:41] Noel adopts Maya Angelou's insight that people remember how you made them feel. [13:14] Tech companies embrace high visibility events and high-touch workplace experiences. [16:23] Conservative sectors, such as law firms, foster very different workplaces to tech companies. [18:15] The pandemic halts a major growth period, forcing an immediate shift to remote working. [19:24] Downtime is used to catch back up, building playbooks and operational structure. [20:41] Phased office returns have strict safety measures, understanding psychological issues. [22:38] Leaders discover remote work productivity, adding asynchronous learning practices. [24:25] Pandemic-based work shifts lead to rethinking space use and global workplace strategy. [25:03] Twilio commits to remote-first for talent and customers, learning from new habits. [26:36] Using regular employee surveys to inform and guide culture and strategy. [27:51] Workplace experience is decisions are grounded by core values and principles. [29:22] "Open Work" is launched as a framework for distributed teams to thrive. [30:36] Effective workplace experience focuses on understanding customers and data, and cultivating curiosity. [31:24] Why empathy, self-awareness, and understanding needs are essential to inform workplace strategies. [31:45] Noel's coaching benefits his leadership, self-awareness, and support of everyone's well-being. [33:39] Noel recommends how reframing questions can unlock new perspectives. [35:11] IMMEDIATE ACTION TIP: To improve workplace experience, first, everyone gets to contribute as all their experiences matter. Secondly, get external inputs—there's a broad community all working on the same issues. Lastly, have fun with it.     RESOURCES   Noel McNulty on LinkedIn Twilio     QUOTES   "At the core of all of it, I think it's knowing your customer… that means actually getting to know them as a person, not just about the work they do."   "You can curate a more unified experience, but there's still personalization involved. It's about balancing both."   "Workplace experience is about how a company's values show up in the environment and how that reflects in how people are treated."   "Even as we've moved into this remote-first world, it's really about allowing people to be seen and heard."   "It wasn't just because they were a lawyer they got special attention—everybody got that attention, from secretaries to administrative staff."   "'Open Work' is our philosophy for how we allow our employees to thrive in a remote-first environment."  

Brian Robertson is Founder and CEO of GlassFrog and creator of the decentralized management and organizational governance system, Holacracy. Brian brings a software architect's lens to fixing organizational ambiguity. He outlines why clarity—not control—is the key to scalable leadership and self-managed teams. Brian explains the benefits of an organizational clarifying framework with dynamic role definitions and boundaries that enhance autonomy and results. He discusses how human-centric systems adaptations enable innovation, AI integration, and support business evolution.     KEY TAKEAWAYS     [01:34] Brian learns to read on software development books and leaves school early.     [02:00] Brian loves the structured thinking and clarity of software development.     [02:22] Seeing through a software architect's lens, Brain seeks to fix business's unclear operations.     [03:19] Brian starts a company as a lab to explore authority structure, work organization, management and more.     [03:54] Holacracy emerges: clarity-driven not consensus-based but everyone has a voice.     [06:03] Traditional job descriptions are outdated; clarity makes things easier as everything gets faster.     [07:06] Clarity evolves with tweaks for dynamic roles, adaptive processes, and efficient meetings.     [07:41] Optimizing decision-making to avoid the tyranny of consensus and top-down control.     [09:46] Biggest challenge in scaling is unlearning old habits and identity ties to status.     [11:03] Leaders should manage work, not people, and build systems others can lead within.     [12:10] Good leaders create clarity to prevent recurring crises and enable autonomy.     [13:08] Boundaries must be clear so people feel safe to act independently.     [14:15] Limits evolve over time; clarity comes from learning together.     [15:21] Roles are distinct functions with purpose, authority, and expectations.   [17:12] People hold multiple roles; work is modular and easier to shift or automate.   [19:05] Clear roles support influence, coordination, and decision-making.   [20:06] Governance allows anyone to adjust roles and expectations transparently.   [22:00] A new hire adds expectations to the founder's role in two minutes.   [23:12] Lack of clarity persists because defining work well is hard and often skipped.   [25:02] Everyone—not just leaders—needs to contribute to organizational clarity now.   [27:00] Clarity with adaptability helps tech-minded firms respond quickly to change.   [28:01] Zappos added market-based dynamics atop Holacracy to treat teams as micro-businesses.   [30:19] GlassFrog simplifies adoption by guiding organizations through incremental change.   [31:33] AI turns complaints into improvement proposals when structure is clear.   [33:30] Without clarity, AI struggles to support internal workflows.   [34:17] Holacracy empowers people to move from complaint to constructive action.   [35:10] Visionary leaders or incremental adoption paths enable systemic transformation.   [37:12] Teams often start with productivity or agile tools, then build structural clarity.   [39:00] Clarity must be continuously updated—not a static achievement.   [40:04] Empowerment needs limits; without knowing them, people can't lead.   [41:01] Self-leadership means owning your role and acting with confidence.   [42:00] IMMEDIATE ACTION TIP: Self-leadership—supporting people stepping up to be CEO of their role—requires clarifying limits to allow people freedom to lead within those limits.       RESOURCES   Brian Robertson on LinkedIn GlassFrog.com HolacracyOne's website     QUOTES   "Expertise is used to manage hard problems, to manage the work, not the people."   "If you need a boss who empowers you, you are in a fundamentally disempowering environment."   On leaders: "I've found that the leader's job is to create organizational clarity…They create the clarity that lets people step into their full power, their full freedom and lead… Their job is to obsolete themselves."   "They're defining boundaries. They're defining expectations. They're empowering by creating a system, a framework that is so clear that people don't need them to empower them. They can just simply step up into the power they have, because it's all obvious."   "Companies are complex adaptive systems in a massively complex environment in that kind of system."   "It's hard to use AI internally to companies if you don't have organizational clarity. If the way things work around here is in everyone's head, it's not clear and it's not consistent. It's hard for an AI to work with."   "It's training people to step out of just the victim mindset and into a co-creator mindset, into a 'I can actually drive change here'."   "We need the kind of environment and the kind of culture that supports people really stepping up and being a CEO of their role."   "How do we consistently generate clarity because clarity is subject to entropy? Whatever clarity we have as our business evolves will rapidly become out of date."   "Clarity itself is only as good as people can actually harness and use it by leading within it, by having that power."

Fréderic Tshidimba is the Co-founder and Chief Inspiration Officer at Empleyo, an Employer of Record (EOR) that helps businesses navigate international employment, remote staffing, and HR services. Fred shares his experiences growing teams in emerging economies. He discusses global talent flow and the need to make labor markets more liquid. Fred illustrates EORs' role in helping companies grow, accessing skilled workers and staying compliant. He describes how outsourcing international HR services opens up markets. Fred explains the value of fair employment contracts in supporting workers' financial security and mobility, while enabling employers to scale flexibly.        KEY TAKEAWAYS    [00:23] Fred studies business engineering with a focus on marketing and consumer psychology.    [01:40] Fred joins Coca-Cola in a digital marketing traineeship having no digital experience.    [02:25] Three key lessons at Coke: think big, prioritize execution, and focus on consumer insights.    [03:32] Transitioning to Nestlé, Fred focuses on the product portfolio and bottom-line.    [04:50] Fred declines a transfer to Italy and moves for his wife's new job in the Philippines.    [06:20] Discovering the Philippines' strengths in digital and outsourcing industries.    [07:16] Fred enjoys agency work in young, fast-paced, endorsement-driven S.E. Asian markets.    [08:50] A friend suggests co-founding a business to bridge digital expertise and outsourcing.    [09:45] Fred scales the business supporting global e-commerce and software clients.    [10:56] The venture grows by focusing on clients' needs as they scale.    [12:00] Riding two waves: the e-commerce boom and early globalization of talent.    [12:58] Fred gets bought out and launches Empleyo to enable global employment opportunities.    [14:10] Empleyo helps companies hire talent in countries where they don't have local presence.    [15:05] Startups often use Employer Of Record services after hiring remote workers independently.    [15:42] Pre-sales roles, software engineers, and mission-driven or tech specialists are key EOR hires.    [17:20] Startups use Employers of Record services for flexibility and growth.    [18:10] Fred sees labor becoming more liquid like capital, removing structural employment barriers.    [19:25] The workforce becomes a "work net" with collaboration transcending borders and time zones.    [20:40] Workers still want financial stability even as their multiple career paths become more fluid.    [21:35] Empleyo focuses on long-term contracts to give workers job security and legal protections.    [22:38] Companies need formal employment frameworks to scale responsibly and remain compliant.    [23:50] EORs take care of compliance needs, e.g. GDPR and NDAs, managing across client contexts.    [24:55] Empleyo focuses on emerging markets in S.E. Asia and Africa, also expanding in Europe, the US.    [26:05] HR becomes more strategic as companies seek talent aligned with purpose and growth goals.    [27:28] Fred emphasizes hiring local experts to navigate regional contexts and gain customer relevance.    [28:30] Internal mobility offers employees growth and engagement, especially in large organizations.    [29:35] Will future employment models continue to have fixed salaries and leave policies.    [30:50] Empleyo shares best practices learned from innovative clients.    [32:02] Personal cases, such as relocation during unrest or family planning, underscore Empleyo's human impact.    [33:15] Companies are prompted to think beyond borders—hiring a country CEO without a local office.    [34:20] Fred sees cross-border employment as a way to support families and keep communities intact.    [35:12] Fred is committed to keep expanding their horizons and connecting people through work.    IMMEDIATE ACTION TIP: Using an Employer of Record helps companies scale quickly and legally by hiring skilled remote workers globally.       RESOURCES    Frederic Tshidimba on LinkedIn  Empleyo.com        QUOTES    "Labor is pretty cranky… it's a factor that's not so liquid."    "We believe more and more in the concept of a "work net", not just a "workforce"."    "The workforce is getting more and more flexible, but people still need to be bankable."    "If you want talent with purpose, you often have to go further than your local market."    "Scaling with purpose means balancing speed with intentionality in your recruitment."    "Sometimes people just want to live in their community and work for a global employer—that's a beautiful thing."    "Our mission is to help labour become more liquid by making employment simpler, fairer, and more accessible."    "It's exciting because, in the end, it's about people, their lives, and helping them grow wherever they are."   

"JJ" Jessica Reeder, a workplace innovation and culture transformation leader, shares insights from her deep experience designing communications systems, scaling multicultural teams and aligning culture with strategy. Bringing pivotal learnings from early fully-remote companies such as Toptal and GitLab, JJ explains how self-management, thorough documentation, and systematized collaboration underpin successful remote work. She describes the cultural shifts required for hybrid and distributed workforces and advocates for systems thinking and clear communication to empower modern work managers.     TAKEAWAYS   [01:24] JJ didn't know what studying linguistics would entail when she chose it but she loved it.   [02:47] Linguistics gives JJ a framework to understand the history of humanity and migration. [03:10] Living in another culture opens up her global perspective and gives her a different lens. [04:24] JJ's appreciation for engineers stems from their clarity and direct information transfer style. [05:49] JJ transitions early to working remotely focused on content and communication projects. [06:35] Noticing the growth of formal distributed work, JJ joins one of the first all remote companies.   [07:14] JJ starts building a distributed community across cultures for a global virtual developer network. [08:15] Nurturing connections among talented remote professionals requires deliberate strategies. [08:56] Remote talent feels more connected when engaged with a peer community. [09:54] JJ moves to GitLab to explore systematized connectivity and is launched into remote work consulting by the pandemic. [13:01] GitLab was designed for remote work with full documentation, tools, and systems. [14:11] Realizations they need to understand other companies' different perspectives. [16:44] Conviction in remote work but recognition that unprepared managers are challenged. [18:30] JJ highlights self-management as a cornerstone of GitLab's decentralized operating model. [19:07] Clear documentation and SOPs reduce managerial load while teaching remote processes. [20:35] Others' embrace of remote work affirms JJ's long-held belief in the global distributed workforce. [22:34] JJ studies industrial organizational psychology and joins Upwork for an applied learning experience.   [23:24] JJ helps Upwork transition from an office-based to remote-first workforce. [24:12] Engagement is often relationship based, differing between employee and freelance contributors. [25:00] Emotional connection isn't always needed; the mission can generate engagement. [26:43] JJ finds that many workers thrive as project contributors without deep social integration. [28:08] More varied distributed operational models are needed, especially for larger companies. [30:36] Distributed work effectiveness requires more than dedicated time for human connection.   [31:25] Clearly documenting and consistently applying standard operating procedures and behaviors is crucial. [32:05] Standardizing—behaviors, tools, expectations—was a major Upwork project JJ worked on. [32:47] Accessible knowledge and intentional transparency are essential and must be intentional. [34:58] The Forest Ranger book gives JJ great insights about distributed operations.   [36:19] The 'manual' shows how philosophy, behavioral standards, transparency and documentation empower independent workers.   [37:24] To train distributed workers, companies must clarify expectations—behaviors, work, standards. [39:15] Hybrid work requires embracing a digital-first mindset even when working partially in-office. [40:54] IMMEDIATE ACTION TIP: To become digital first, one, understand time—such as core hours, two, communicate digitally—with documented processes, and three, systematize collaboration—designating how and where work is done. [41:57] Communication processes must be modeled by leadership and enforced by managers. [42:26] Systematized collaboration tools create visibility, drive cohesion, and replace physical context.     RESOURCES   "JJ" Jessica Reeder on Linkedin JJ's website The Forest Ranger book       QUOTES   "This decentralization of management. Instead of someone managing your work, there's somebody who is directing your output or directing your outcome. So understanding how to empower people to self-manage their work."   "Collaboration is really just about trading work back and forth and doing it in a very effective way."   "To be effective at our work, we need to have a source of motivation. We need to have proof that our work is doing something that we believe in. We do need to have some sort of a mission that we're contributing to, but we don't need to necessarily be deeply emotionally engaged."    "Having standard operating procedures and behavioral standards is clearly documented and consistently applied throughout the organization is crucial in remote work. It is absolutely a deal breaker if you don't have people understanding how they are supposed to work."   "One of those things where you have to decide - how transparent of an organization do we want to be. If we don't buy in on transparency, then we're going to have challenges with distributed work."   "Becoming a digital first organization doesn't block your ability to have a functioning hybrid organization. In fact, it enhances it. It really will make your hybrid organization more powerful. It will help people to get the most out of work, whether they're in the office or not."   "All of the things that you need to have a highly functioning team can be empowered by really embracing the digital first mentality."   "Collaboration needs to be systematized. It needs to happen on as few disparate tools as possible."