Olivia: A recent study found that 93% of knowledge workers want flexibility in when they work. But only 76% care about flexibility in where they work. Jackson: Ninety-three percent! That’s basically everyone. And it means for years we've been having this huge, dramatic debate about returning to the office, but we've been fighting the wrong battle entirely. It was never about the real estate. Olivia: It was never about the real estate. It was always about time and autonomy. And that fundamental misunderstanding is at the heart of the book we’re diving into today: How the Future Works: Leading Flexible Teams to Do the Best Work of Their Lives, written by Brian Elliott, Sheela Subramanian, and Helen Kupp. Jackson: And these authors aren't just academics observing from a distance, right? They have some serious skin in the game. Olivia: They absolutely do. They are the co-founders of Future Forum, which is a major think tank on this very topic, originally launched by Slack. So they have been swimming in the data and the real-world experiments from day one. They’ve seen what works, what fails, and why. Jackson: A think tank from Slack… that's fascinating, because the book itself tells a story about how even Slack, the company that literally built the tools for this revolution, was initially just as stuck in the old way of thinking as everyone else.

Olivia: Exactly. It's one of the most powerful opening points in the book. Before the pandemic, 79% of Slack's own engineering staff was based in the Bay Area. Their CEO, Stewart Butterfield, even moved to San Francisco specifically to be at the company's physical center. They believed, like most of us did, that innovation and culture happened through osmosis in a shared space. Jackson: That’s wild. The company that enables distributed work was itself deeply committed to co-located work. What does that tell you? Olivia: It tells you that the 9-to-5, office-centric model isn't just a habit; it's a deeply ingrained ideology. Butterfield himself is quoted in the book saying something incredible. He said, "I can't imagine how we ever would have come to believe this empirical fact that we could work so well with everyone working flexibly unless it actually happened." They had to be forced into it. Jackson: It was an accident of history. But why were we all so stuck? The 9-to-5 workday feels like a law of physics, but it's not. Where did it even come from? Olivia: The book traces it back beautifully. It’s an artifact of the Industrial Revolution. Before that, time was measured in seasons. But with factories, you needed to synchronize labor. Henry Ford was a huge innovator here. In the 1920s, he realized that his assembly line workers were more productive and made fewer mistakes with an eight-hour day and a five-day week. It was a brilliant move for manufacturing. Jackson: For manufacturing. That's the key. So we're still using a blueprint designed for building a Model T to run a company that builds digital products and services. No wonder the walls are crooked. Olivia: That’s a perfect analogy. The book argues that the nature of work has fundamentally changed. We're knowledge workers now. Our work isn't tied to a physical machine on a factory floor. It's in our heads, and it travels with us on our laptops. Yet our management practices are still based on "facetime" and physical presence. Jackson: It’s managing by walking around, but now it’s managing by checking who has a green dot on their status. It’s the same flawed logic. Olivia: Precisely. And the pandemic didn't break work; it just held up a giant mirror to what was already broken. It revealed that productivity didn't plummet. In fact, a Goldman Sachs analysis found that productivity actually rose 3.1% in the first year of the crisis. Jackson: Wow. So the great fear that everything would fall apart was completely unfounded. We were clinging to a system that wasn't even the most effective one to begin with. Olivia: We were. And that realization is the first step. The book makes it clear: you can't build the future of work on the ruins of the past. You have to start with a new blueprint.

Jackson: Okay, so the old blueprint is trash. We've thrown it out. But what does the new one look like? Because my fear, and I think a lot of leaders share this, is that if you just say "be flexible," you get chaos. Olivia: And that's the most common mistake. The book calls it "faux flexibility," and it's a recipe for disaster. The perfect case study they use is what happened at Apple and Google in 2021. Jackson: Oh, I remember this. The great return-to-office mandate. Olivia: Exactly. Apple's CEO Tim Cook sent out a memo mandating a return to the office on Mondays, Tuesdays, and Thursdays. He talked about how "video conference calling has narrowed the distance... but there are things it simply cannot replicate." It sounds reasonable on the surface. Jackson: But the employees weren't having it. Olivia: Not at all. A group of employees wrote a letter back saying the policy had already forced some of their colleagues to quit. They said they felt they had to choose between their families, their well-being, and being a part of Apple. It created this huge wave of resentment because it felt arbitrary and top-down. It communicated a lack of trust. Jackson: So if top-down rules are the wrong way, what's the right way? What's the alternative to chaos on one side and dictatorship on the other? Olivia: The book lays out a brilliant three-tiered framework. It's about building an operating system for flexibility, not just a set of rules. It starts with Principles, then you create Guardrails, and finally, you empower teams with Team-Level Agreements. Jackson: Okay, break that down for me. Principles, Guardrails, Agreements. Olivia: Principles are the 'why.' They are your organization's core beliefs about flexibility. For example, RBC, the Royal Bank of Canada, established a principle that "Proximity still matters," acknowledging the need for some in-person connection, but they balanced it with principles of choice and flexibility. Jackson: So it’s the North Star. It guides the general direction. What are guardrails? Olivia: Guardrails are the 'don't do this.' They are protective railings to prevent the company from sliding back into old, bad habits. A fantastic example comes from Dropbox. They worried about creating two different employee experiences—one for people in the office and one for people at home. Jackson: The classic hybrid meeting problem, where the remote people are just faces on a screen that everyone ignores. Olivia: Exactly. So Dropbox created a guardrail: "one dials in, all dial in." If even one person is joining a meeting remotely, everyone joins from their own device, even if they're in the same office building. This levels the playing field for participation. Another guardrail they set was establishing "core collaboration hours"—a four-hour window for synchronous meetings, leaving the rest of the day for focused, asynchronous work. Jackson: I love that. It’s not about where you are, but how you interact. Okay, so we have the 'why' (Principles) and the 'don't' (Guardrails). What's the last piece? Olivia: The last, and most important, piece is the Team-Level Agreement, or TLA. This is the 'how we'll do it.' The book argues that a one-size-fits-all policy for an entire company is foolish. The needs of an engineering team are different from a sales team. Jackson: Right, the sales team might need more client-facing time, the engineers might need more deep-focus time. Olivia: Precisely. So a TLA is a document co-created by each team that outlines their specific norms. When are our core hours? What's our policy on responding to messages? How will we build relationships? What days, if any, will we gather in person and for what purpose? Jackson: So it's not anarchy. It's guided autonomy. The company provides the principles and guardrails—the destination and the rules of the road—but each team gets to decide the specific route they'll take to get there. It’s like their own team constitution. Olivia: That's the perfect way to put it. It builds trust, it provides clarity, and it gives people the autonomy they crave, which is the real driver of satisfaction and performance.

Jackson: I can see how that framework works for tasks and schedules. The logic is solid. But what about the stuff that happens between the meetings? The culture, the connection, the feeling of being part of something. How do you build that through a screen? That's the fear every leader I know has. Olivia: It's the number one concern, and the book tackles it head-on with a really surprising insight. The data from Future Forum shows that flexible work, when done right, can actually increase an employee's sense of belonging. Jackson: Wait, how is that possible? That feels completely counterintuitive. Olivia: Because the traditional office wasn't a utopia of connection for everyone. For many people, especially those from historically underrepresented groups, the office can be a place of immense stress. They experience microaggressions, they feel pressure to code-switch, to conform to a dominant culture. Working flexibly can relieve that burden and allow them to bring their whole selves to work. Jackson: Huh. I never thought of it that way. The office happy hour isn't fun for everyone. For some, it’s just more work. Olivia: Exactly. The book argues that connection isn't a product of physical proximity; it's a product of intentionality. And to prove it, they tell this incredible story about a company called MURAL. Jackson: Okay, let's hear it. Olivia: In 2020, MURAL, a digital collaboration company, closed a huge round of funding. Normally, this would mean a massive party. But it was the middle of lockdown. So, with just two weeks' notice, their Head of Culture was tasked with creating a virtual celebration. Jackson: That sounds like a recipe for the world's most awkward Zoom call. Olivia: You'd think so! But instead, they created the "2020 MURAL World Tour." They sent physical props to every employee's home. They had themed Zoom backgrounds for different "destinations"—a snowy mountain, a tropical island, even outer space. They had breakout rooms where you could get your virtual passport stamped. It was incredibly creative and intentional. The result? People felt deeply connected, and new hires said they bonded more in that one event than they had in months. Jackson: Wow. That is way, way better than a stale pizza party in the breakroom. That's connection by design, not by default. Olivia: Connection by design. That's the core idea. And this new way of working puts immense pressure on the people who have to be the designers—the managers. Jackson: Right. This sounds like a nightmare for a traditional manager whose main skill is making sure everyone is at their desk by 9:05. That whole playbook is useless now. Olivia: It's worse than useless; it's destructive. The book points to research from Gallup showing that 75% of workers cite a bad manager as the number one reason for leaving a job. In this new world, the role of the manager has to fundamentally shift from being a controller of people to a catalyst of great performance. Jackson: A catalyst... I like that. What does that look like in practice? Olivia: It's about coaching. Google's famous "Project Oxygen" study set out to see if managers even mattered. They found that not only did they matter, but the very best ones were all great coaches. They create psychological safety, they give clear and direct feedback, they remove roadblocks, and they trust their people. They focus on outcomes, not activity. Jackson: So their job isn't to watch you work. It's to create the conditions for you to do your best work. Olivia: You've got it. It's a massive shift from "soft skills" being a nice-to-have to being the absolute core competency of modern leadership.

Olivia: It all comes together, doesn't it? You first have to dismantle the old ideology and realize the 9-to-5 office model is a historical artifact. Then you build a new system based on principles and guardrails, not just rigid rules. And finally, you power that entire system with intentional human connection and a new style of coaching-based leadership. Jackson: The big takeaway for me is that flexibility isn't a perk anymore. It's not a benefit you list next to dental insurance. It's the core operating system for a modern, high-performing company. And the book makes a powerful case that if you get this right, it's the single biggest competitive advantage you can have in the battle for talent. Olivia: It's a total paradigm shift. It’s about building work around life, not the other way around. The book is filled with these incredibly moving personal stories—a military spouse at Dell who was able to build a career despite moving five times, an executive at Atlassian who could work from her sister's house for a month to be with her nephew. This isn't just a business strategy; it's life-changing. Jackson: Absolutely. It makes you think. For everyone listening, the question the book leaves you with isn't if your workplace will change, but are you actively and intentionally designing that change, or are you just letting it happen to you? Olivia: A powerful question to end on. Jackson: This was fantastic. A lot to chew on. Olivia: This is Aibrary, signing off.