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Home FUTURE OF WORK Podcast

Expert Future of Work Insights | Leadership of the Future with Dale Whelehan, Chris McAlister & Drew Jones

A powerful conversation with Dr. Dale Whelehan (4 Day Week Global), Chris McAlister (SightShift) and Drew Jones (author, The Open Culture Handbook) on leadership development, culture redesign and implementing a four‑day workweek for the future of work.

Frank CottlebyFrank Cottle
November 4, 2025
in FUTURE OF WORK Podcast, Workforce & HR
Reading Time: 15 mins read
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About this episode 

In this episode of The Future of Work® Podcast, we bring together three visionary leaders to explore how organizations can radically reimagine work: from reducing time to improving impact, from hierarchical management to leader‑creation, and from forced culture programs to conditions for authentic belonging.  

Dr. Dale Whelehan leads the global campaign for the four‑day workweek and helps companies redesign work systems to meet human psychological and physiological needs. Chris McAlister specializes in leadership development that creates self‑sustaining teams, not just managers. Drew Jones examines how workplace culture is shaped by environment, autonomy and experimentation. Together, they offer actionable insight into how forward‑thinking organizations can address burnout, evolve leadership, foster meaningful culture and make shorter workweeks a strategic advantage — not a cost. 

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About Dr. Dale Whelehan

Dr. Dale Whelehan, a Social Entrepreneur and leader at 4 Day Week Global—a not-for-profit organization shaping the future of work by championing the 4-day workweek. Recognized on TIME’s 100 Most Influential Companies of 2023 and Forbes’ 50 Future of Work Ideas, they’ve actively support international pilot studies and have garnered attention in leading publications like The Atlantic, INSIDER, The New York Times, Bloomberg, Fast Company, BBC, Sky News, and The Wall Street Journal.

About Chris McAlister

Since 2000, Chris McAlister has been obsessed with how leaders grow and develop. In addition to seeding the foundation of his career, this passion helped Chris navigate a very pivotal and unforeseen crisis. It was this opportunity to apply what he had learned over the previous decade that brought about a shift in Chris, from ‘knowing’ to truly ‘understanding’ what it meant to lead.

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This new awareness sparked a journey of discovery and experimentation that would lead Chris to author a process by which any motivated leader could operate at the edge of their abilities.

Over the last 12 years, Chris has delivered this process to small and mid-market company founders, physicians and Fortune 100 executives, venture fund managers and serial entrepreneurs as well as professional athletes and non-profit directors. Chris founded SightShift to help organizations operationalize the transformation of their leaders, producing sustainable revenue and profit growth beyond their expectations.

Today, Chris proudly serves and leads the movement from his offices in Columbus, Ohio.

About Drew Jones

Drew Jones, the man who has made it his mission to change how companies perceive and shape their culture. As a prominent anthropologist and author, his fresh viewpoints have drawn attention to the relationship between workplace culture, employee engagement, and innovation. With an approach inextricably linked to science, Drew’s understanding of human behavior and motivation transcends the traditional business mindset, reshaping our perceptions and offering tantalizing insights. With the knowledge accumulated from his research, he bestows a powerful tool in his latest book, The Open Culture Handbook.

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What you’ll learn 

  • Why the traditional work‑life balance model is outdated and what must replace it. 
  • How a four‑day workweek can act as a catalyst for redesigning work systems — not just reducing hours. 
  • The three fundamental psychological needs (competence, autonomy, connection) that drive health and happiness at work. 
  • Why true leadership development means creating other leaders and building intrinsic motivation rather than managing behavior. 
  • Which cultural levers are most potent for transformation. 
  • Practical steps leaders can take now to reduce inefficiencies, redesign work, and maintain productivity while working less. 
  • How workplace environment and culture intersect in remote, hybrid and in‑office settings to shape employee experience. 
  • The business case for work‑time reduction: retention, talent attraction, reduced burnout, stronger performance. 
  • How to lead with the end in mind — ensuring the team thrives when you’re not around. 
  • What shift HR and organizational leaders must make now to remain competitive in a global and AI‑enabled future of work. 

Transcript

Host AI

[ 00:00:00,630 ]Welcome to the Future of Work podcast, where we explore what’s next in work, workplace, and the human experience. You’re listening to a Future of Work Expert Insights, a special format where we bring together the most thought-provoking insights from our top guests around a single topic shaping the future of work.

Host AI

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[ 00:00:20,380 ] In this episode, we explore what modern leadership really looks like, from rethinking productivity and burnout to empowering teams and designing cultures that thrive on autonomy and meaning. Leadership today isn’t just about titles. It’s about trust, purpose, and the ability to adapt when everything around us is changing.

Host AI

[ 00:00:40,750 ] We’ve curated conversations with three of the sharpest minds in the industry. We’ve brought together three voices shaping that conversation. Dr. Dale Wellahan, Chris McAllister, and Drew Jones.

Host AI

[ 00:00:52,890 ] Each offering unique insights into leadership, culture, and the evolving mindsets reshaping how we lead. Grow and build resilient teams in the future of work. Let’s begin.

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Host AI

[ 00:01:05,920 ] As we rethink what it means to lead in a world that never stops moving, there’s one challenge every organization faces: how to sustain performance without burning people out.

Host AI

[ 00:01:18,180 ] Our first guest is Dr. Dale Wheelhan of 4 Day Week Global. He shares why shorter weeks aren’t just about time off. They’re about redesigning work around human energy, motivation, and connection.

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Host AI

[ 00:01:31,250 ] After years of hyper-connectivity and blurred boundaries between home and work, many people feel more burned out than ever. How can rethinking time, through models like the 4-Day Week, help leaders design organizations that actually protect well-being and performance?

Dale Whelehan

[ 00:01:47,070 ] What really emerged from the pandemic was a lot of positive things. People kind of, a collective wake up for many people that actually I’ve been living in sort of this change of the rhythm approach to work. And now I have a bit more autonomy and flexibility and I know how to look after myself a bit better. But also we saw a much more difficult ability to detach from work that didn’t exist pre-pandemic. So we now have people working from their sitting rooms, which is also their office and also their, you know, relaxing space. And so dedication and I suppose that engagement towards work. is why I think we now have an issue of burnout, not just within the caring professions, but also within, you know, the general workforce. And that is not going to go away, unfortunately, because we now live in a world where everything is hyper-connected. I think the idea of work-life balance is outdated. We need a new way of thinking about it because when does work start and when does it end?

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Dale Whelehan

[ 00:02:49,840 ] And that will differ from me as it does to you, and what you determine work to be. Um, And that also feeds into social media sites that we engage in, where we’re looking at a lot of, you know, global issues happening around the world, which is also feeding into global levels of stress and impacting on economies and all of those sort of things are contributing to reported levels of burnout within our workforce.

Dale Whelehan

[ 00:03:14,200 ] Your second question around why a four-day week as opposed to why would a four-day week do anything about that? It’s not so much I think the reduction in working hours alone that is going to be the silver bullet for solving some of these issues but it is the the catalyst to evoke change within organizations to redesign work in a way that’s much more congruent with human psychology and human physiology.

Dale Whelehan

[ 00:03:42,940 ] um and that’s where we look at things like what it is that motivate people within work in the first place and similar to how we have basic physiological needs like the need to eat to sleep to you know have shelter research has shown we have three fundamental psychological needs for happiness and health as well and they’re the need to feel competent in what we do the need to feel autonomous in what we do and the need to feel connected to people that matter to us most And what I find in four-day week trials is that you can actually redesign work through to accessing those three needs. So you’re getting both the employee, you’re gifting the employee something like additional time off, but you’re also guaranteeing to the employer. that productivity of the workforce is not going to diminish as a result of this as well. So you put that framework to play within organisations and ask people, well, what it is, what can we reduce?

Dale Whelehan

[ 00:04:44,030 ] What inefficiencies can we reduce within workplaces by 20%? in order to guarantee the same level of output, but also make sure we can work less time.

Host AI

[ 00:04:52,370 ] Dale shows how leadership begins with creating conditions for people to thrive, not just work harder.

Host AI

[ 00:04:59,310 ] If Dale challenges how we work, Chris McAllister challenges how we lead. Because leadership, he says, isn’t about control or motivation, it’s about meaning.

Host AI

[ 00:05:09,710 ] Our next guest, Chris McAllister, founder of SightShift, breaks down how true leaders grow other leaders, shifting from managing people to managing agreements.

Host AI

[ 00:05:21,150 ] Leadership today often feels like constant managing and motivating. But what if true leadership isn’t about control at all? How can leaders move from managing people to cultivating meaning and ownership within their teams?

Chris McAlister

[ 00:05:34,220 ] What a leader really is, you think about leadership, there’s so many definitions for it. At the core for us, we’re thinking about it in terms like this. A leader is defined by what they leave. How am I leaving this atmosphere, this space, this job, this role, this responsibility? The height of leadership is to think beyond yourself.

Chris McAlister

[ 00:05:53,950 ] And we have a specific definition in the way that we define that. A leader is someone who develops other leaders. And we have three characteristics underneath that to make it really tight, make it really clear for how to define it. But, you know, that’s the core and the essence of it. It’s too easy to think about leadership in terms of the energy you’re applying to the moment. And that’s a starting point, but it’s a terrible ending point. A leader has to think about how does this end? How do I finish this? Whether it’s a small moment, a big moment, a lifetime career, and everything in between. A leader learns how to make meaning for themselves and help others do the same. So we think about leadership in terms of, I’ve got to motivate you. I’ve got to provide extrinsic motivation. That’s again, a great starting point, but a terrible ending point because a leader thinks about what happens when I’m not around.

Chris McAlister

[ 00:06:46,540 ] What happens when I’m not there? So how does the team flourish? How does the culture go on to be all it can be? Few leaders have ever tasted an environment where the team is initiating on their own in better ways than that leader could.

Chris McAlister

[ 00:07:03,480 ] And we hear it all the time, you know, how rare that is. And so we’re looking for someone who knows how to learn, to make their own meaning, produce their own motivation, and teach others to do the same. That’s one characteristic. But this is the starting point, because if I’ve got to keep you motivated, well, then I’m not leading you. And here’s a great example. I end up managing you and nagging you.

Chris McAlister

[ 00:07:28,970 ] And when we think about the future of work, I like asking leaders this question. How many of you like managing people? And I’ll ask it to a large room of people. Raise your hands. Hands don’t go up.

Chris McAlister

[ 00:07:40,230 ] No, people don’t like to manage people because managing people is a lot like nagging your teenager to clean their bedroom. When are you going to clean your room? You can’t leave those dishes on the nightstand. This is a mess. What are you going to do? And what ends up happening in management is we have to try to provide this extrinsic motivation. We’re going to try to force something. We’re going to try to get them to behave. And at the end of the day, I understand at different levels of the organization, you have different ways you interact with people. We cannot be in the place where we’re exhausting ourselves that way. We have to, what we say is, lead people and manage agreements. All systems—everything—needs to be built with this intentionality of we are raising leaders. And yeah, they may stay in the organization and go up five levels, right? They may launch out and start their own company or go to that other company. There is a sense that we can’t be these controlling, insecure leaders—those I’ll love them if they stay and hate them if they leave.

Chris McAlister

[ 00:08:48,170 ] But we are doing what we’re doing with the end in mind. And the reality is, once you start getting these lower-level agreements in place, then you get to start putting these higher structures where it’s not carrot and stick. It is learning to find your own intrinsic motivation.

Host AI

[ 00:09:04,600 ] Chris reminds us that lasting leadership is about building independence, not dependence.

Host AI

[ 00:09:11,350 ] And if leadership starts with trust and meaning, it has to live somewhere real.

Host AI

[ 00:09:16,130 ] Our next guest, Drew Jones, anthropologist and author of the Open Culture Handbook, explains how culture isn’t engineered, it’s cultivated. Leaders can’t force it, but they can create the conditions where it grows naturally.

Host AI

[ 00:09:31,040 ] Many organizations still try to engineer culture from the top down, but authentic culture rarely works that way. How can modern leaders create the trust, freedom, and conditions for culture to grow naturally and drive innovation?

Drew Jones

[ 00:09:44,630 ] The onus falls on employees to change their behavior.

Drew Jones

[ 00:09:49,410 ] And statistics show that this rarely works. Those processes go on for four or five months.

Drew Jones

[ 00:09:56,740 ] People resist it. Management gets frustrated. They abandon it. And it’s like, well, what culture program? That was last quarter, right? And then on and on and on. And the futility just continues.

Drew Jones

[ 00:10:10,750 ] What companies can do is create material conditions where culture can develop and grow organically, because this is what humans do. You put people together in groups and they bind themselves through culture. So you can’t engineer it the way businesses seem to want to do, but you can create conditions for it to thrive. And so that’s the subtitle of the book is, you know, five questions. To drive engagement innovation, that’s really what I’m talking about. One is having a very clearly defined strategy that’s communicated, ideally in some form of storytelling manner, that has a compelling purpose, that gives people a sense of connection to the cause. One two is what people are working on. This is where I say that innovation is as much of an HR issue is as it is a business growth issue. Because when an employee comes in to work, if they’re cognitively stimulated and challenged to like create some new, either a process, a hack, or a concept for a business or a service, or whatever, that’s a fundamentally different kind of work than coming in to work and simply slashing costs all day

Drew Jones

[ 00:11:28,580 ] or scaling an existing business. So this is why companies like Gore, Electronics, Google, famously provide some amount of the work week to pursuing out-of-the-box innovative possibilities that stimulates people. What people are working on is critically important.

Drew Jones

[ 00:11:48,260 ] How they work on it, this is the classic case of how much management is enough. And this gets to the whole issue of trust and remote and hybrid work. But companies that are consistently innovative and have high levels of engagement also allow teams to largely self-organize schedules, internal team agreements, how they hold each other accountable. A company like Automatic, for example, the company behind WordPress. Employees basically hire and fire new staff. A new candidate comes in and does an audition for a couple of months, and then the team votes up or down. At Simcoe, people set each other’s salaries through this radical transparency.

Drew Jones

[ 00:12:29,830 ] team accountability so morningstar tomatoes the largest processor of tomatoes in in the in the world has no job titles organizations completely self-organizing so that how people work so that’s one The fourth is leadership, right? Does leadership trust its people and really cascade a growth mindset and tolerate risk? And so, right now, the turnaround at Microsoft can largely be attributed to Satya Nadella’s enthusiastic embrace of a growth mindset and tolerating risks. He says, ‘You know, the two things that drive us are continuous learning and the willingness to experiment.’ The cultural turnaround at Microsoft has led to this ginormous financial turnaround. Now it’s the third largest company in the world by market cap. And the fifth element is where people work. And this is where my model of culture really overlaps with the world of workplace because, rarely in standard corporate culture models, do you have any consideration of the physical environment where people are working?

Drew Jones

[ 00:13:35,340 ] But from a sort of materialist point of view, where you work is crucially important. It textures your everyday working, whether you’re at the office, with whom you’re working, the environment’s like, if you’re at home. So the workplace becomes a lever of shaping culture as well. So really, the five things are meant to be these tangible things, stories, experimentation, self-organization, and growth mindset, and workplace. But I do think, to your point about remote, I do think that the organic bonds of culture do develop more easily face-to-face. So while I am an advocate of remote and hybrid work, I do think that some amount of face time can be very healthy for building trust, not necessarily culture in the way necessarily the way a lot of CEOs talk about it. Because you’re right, if they cared about culture before, now they’re using remote as if it’s all of a sudden they found the culture religions.

Drew Jones

[ 00:14:36,630 ] Oh, we’re going to lose our culture. That’s a bit disingenuous.

Host AI

[ 00:14:42,590 ] It’s not about managing hours, people, or policies. From Dale’s push to redesign work around human needs, to Chris’s call for deeper purpose and autonomy, to Drew’s insights on cultural trust and experimentation. The real evolution in leadership isn’t structural, it’s relational. The question now isn’t, how do we lead better? It’s how do we build systems that lead with us?

Host AI

[ 00:15:09,700 ] Thanks for listening to this Expert Insights episode of the Future of Work podcast. If you found it insightful, share it with a colleague, leave us a review, or check out our show notes for links to each guest’s full interview. Until next time, keep asking not just where we work, but how we work better together.

Host AI

[ 00:15:28,350 ] If it’s impacting the future of work, it’s in the Future of Work podcast by allwork.space.

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Tags: Chris McAlisterDale WhelehanDrew JonesFUTURE OF WORK® PodcastLeadershipWorkforceWorkplace Wellness
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Frank Cottle

Frank Cottle

Frank Cottle is the founder and CEO of ALLIANCE Business Centers Network and a veteran in the serviced office space industry. Frank works with business centers all over the world and his thought leadership, drive for excellence and creativity are respected and admired throughout the industry.

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