The Question Every Leader Should Be Asking Their Team

2:30 · The dream deficit: Why engagement hasn't moved in 20 years

20 years. Billions of dollars same exact result. And we keep asking the same question how do we make employees more engaged? Wrong question. The right question the one that changes everything is so simple, it's almost embarrassing. Most people aren't disengaged from work, they're disconnected from their own dreams. Think about that. Not disconnected from the company mission not disconnected from their manager disconnected from themselves from what they actually want their life to be because nobody ever asked. Your manager never asked, your HR department never asked, and your performance review didn't have a section for it. Fairly certain your onboarding didn't include it. Your exit interview might have hinted at it, but by then it's way too late. I've been in organizations for years as an integrator. I've sat in hundreds of meetings.

Strategic planning, quarterly reviews, annual planning, people discussions, and in all those meetings, all those hours of diagnosing what's wrong, why performance is lagging, why turnover is high, I can count on one hand the number of times someone asked, "Do we even know what these people want?" Not what they want from this job, what they want from their lives. We'll measure everything else. We'll track their KPIs, their customer satisfaction scores, their output per hour, 360 feedback. We'll build scorecards and dashboards and responsibility map, and none of it none of it includes the most basic question a human being can be asked. And here's the thing that breaks my heart. Most people have stopped dreaming.

Not because they don't have dreams, but because nobody has ever treated them like a whole human being with a life worth designing. The architects of the next economy, every single one started the same way. Someone sat across from them and asked the question that nobody had ever asked before. Let's go back to the man, the blank page. Because his story is about to get interesting. The man staring at the blank page is a custodian. He works third shift at a manufacturing company. Mops floors, empties trash, cleans bathrooms. He's good at it. Reliable, thorough, but invisible. The kind of employee companies love because they never have to think about them.

Then, the company does something unusual. They hire a Dream Manager. Not a consultant or a coach, a Dream Manager. A person whose entire job, their whole reason for being in the building, is to sit across from employees and ask about their dreams and help them make progress. The Dream Manager walks the custodian through 12 categories. Physical dreams, emotional dreams, intellectual, spiritual, psychological, material, professional, financial, creative, adventure, legacy, and character. 12 rooms of a complete human life. And the instruction is simple. Write down as many dreams as you can, up to 100. He laughs. 100? Can't think of five. And that's not because he's imaginative. It's because 27 years of being treated like a function, clock in, clean, clock out, taught him that his dreams don't matter.

7:00 · The janitor's list: 47 dreams nobody knew about

Not here, not to anyone. The Dream Manager doesn't push, doesn't motivate, just keeps showing up every 2 weeks, sitting across from him, asking the question. Three months later, he has 47 items. 47, spanning all 12 categories. In the physical, he wants to run a 5K. Emotionally, he wants to tell his daughter he's proud of her more often. Financially, he wants to open a savings account. And on the creative side, he wants to learn how to play a guitar. Now, here's the surprising one. For an adventure, he wants to see the ocean. And one dream, buried in the professional category, that nobody he wanted to start a cleaning supply company.

Think about that. The man mops floors for a living. And hidden inside that work, invisible to every manager, every performance review, every HR system, was an entrepreneurial dream. He knew cleaning, he knew products, he knew what worked and what didn't. He'd been unknowingly building expertise for 27 years. He just never had permission to dream about what to do with it. His employer doesn't just encourage the dream. They become his first client. Let me say that again. His employer became his first client. Now, I want you to think about what just happened, because it's easy to hear that as a feel-good anecdote and miss the structural significance.

A company invested in a person's dream, not their job performance, not their quality metrics, their dream. A dream that had nothing to do with the company's strategic plan. A custodian wanted to start a cleaning supply company. That is not on any organizational chart, and that is certainly not in any business case. Best thing, the company's response wasn't "That's nice, but focus on your role." The response was "How can we help you build that?" That is not generosity. That is architecture by design. Because here's what happened next. And this is the part that matters for everyone listening. Not just custodians, not just people in manufacturing, everyone. Turnover at that company dropped 60% in the year after launching the Dream Manager program. Not because of his story alone, but because everyone in that building saw something they'd never seen before.

Company that actually cared about the answer. And that changes everything. When people see that dreams are taken seriously, genuinely, structurally, and systematically, they stop looking for the exit. Because for the first time, someone treated them like a person worth investing in. Think about what that means for recruit. For retention. For culture. You don't need a ping-pong table. You don't need beer on Fridays. You don't need another all-hands meeting where the CEO talks about mission and values. You need one person. One trained Dream Manager who sits across from your people and asks a question nobody else is asking. And then you need the system to actually follow through.

And that's where the integrator comes in. But we'll get to that. So, remember the executive who went blank? Her story is connected to this one in a way I haven't I yet. But first, I need to talk about why the question itself is so powerful. Because it's not just a nice thing to ask. It's the most important diagnostic tool in organizational transformation. The Dream Manager methodology starts with the principle so simple sounds naive. A company can only become the best version of itself to the extent that its people are becoming better versions of themselves. That's not a poster for the break room. That's design principle. Maybe the most important one for the next economy.

Because most organizations do the opposite. They optimize function and ignore the human. They build the role and forget the person sitting in it. They design performance systems that measure output and never once ask, "What is this person building toward? What does their life look like? What rooms of their life are empty?" And then they're surprised when the person leaves or disengages or does just enough to not get fired. Here's where my EOS integrator brain kicks in. In the entrepreneurial operating system, we have a concept, right people, right seats. It's foundational. You need the right humans in the right roles for the business to thrive, right?

13:00 · The Dream Manager methodology + EOS integration

But here's what I've learned after years of integrating these systems. You can't know what right means if you don't know what the person is building toward. You can put someone in the perfect seat and if every room of their life outside of work is condemned, they're a flight risk. Not because the seat is wrong, because the whole house is falling apart. The Dream Manager conversation is the missing in It's the diagnostic that makes the responsibility map honest. It makes the people assessment three-dimensional. And it takes the right person, right seat from a slogan to a practice. Let me make this concrete. I've sat in quarterly planning sessions, weekly leadership meetings, annual planning, you name it.

Where we're looking at the responsibility map trying to figure out why someone is in the right seat and keeps underperforming. The data says they should be thriving. The skills match, the role fits. Everything on paper is perfect. Every time, every single time, when someone finally has a real conversation with that person, the answer is the same. Something outside of work is falling apart. Whether it be their marriage, a health scare, or a parent who needs care, or a dream that died and took their energy with it. EOS is brilliant at building systems, meeting rhythms, scorecards, rocks, quarterly pulses. I believe in every one of them. But those systems measure organizational health.

They don't measure human. And the organization is made of humans. The Dream Manager methodology is the leading indicator. The 12 rooms are the human scorecard. When someone is growing across multiple rooms, they bring that energy into every meeting, every project, every decision. When every room, except the professional one, is condemned, you got a person who shows up as a function, not as a force. Dreams without systems are wishes. Systems without dreams are simply prisons. The Dream Manager provides the dream. The integrator builds the system that protects it. Which brings us back to the woman in the corner office. Because she's about to learn this the hard way.

She did everything right. MBA, corner office, 3,000 employees, the board respects her, the numbers are good, compensation is in seven figures. She's the one who approved the Dream Manager program for her company. She saw the data, the retention numbers, the engagement scores, the ROI. Smart investment, good leadership. Then, during the facilitator training, the session where in leaders learn the methodology before it rolls out to employees, the facilitator turns to her and asks the question, "What are your dreams?" 47 years old, and she goes blank. Not uncomfortable blank, not modest blank, completely and terrifyingly blank. She cannot name a single dream outside of work. Her professional room has a mansion.

Her financial room has fairness. And every other room, she hasn't walked into it any of them in years. Some of them decades. And in that moment, she realizes something that changes the entire trajectory of the program. The executive who can't dream can't lead people towards theirs. It's not a nice to have. It's a structural problem. If the leader hasn't done the work, hasn't walked into her own four rooms, hasn't been honest, hasn't modeled vulnerability, and the program is a benefit, not a belief. People can smell the difference. Remember the honest failure we'll explore later this season. The company who Dream Manager program collapsed. Postmortem revealed same thing. The CEO never did his own 12 room. The program was something he offered to employees, not something he lived. But this executive, she doesn't make that mistake. She goes home that night and sits down with the 12 categories alone. Pen and paper, no facilitator, no audience.

17:30 · The CEO who went blank

And she did something terrifying. Her legacy room says, she wants to be remembered as a great mom. But her adventure room is blank, spiritual room is empty, and her creative room just has flat-out cobwebs. She's 47 years old, and the rooms that would make her a whole person, the rooms that would make her a better leader, are condemned. She starts the program differently after that. She doesn't roll it out as a perk. She shares her own 12 rooms, including the empty ones, with her leadership team first. Then asks them to do the same. And this is where it gets interesting. Because what happens next is not what you'd expect from corner office executive built her career on competence and control. She tells her direct reports that her creative room is empty, that she hasn't made anything her hands, her imagination, in over a decade. She tells them that her adventure room is a list of trips she's planned for clients that she's never taken herself. And she tells them her character her remedy has a dream she's embarrassed to say out loud. She wants to be the kind of person who just shows up and for her friends.

But, she hasn't been that person in years. The best thing is that the room doesn't judge her. The room exhales. Because every person at that table has the same empty rooms and they've been hiding. And when the leader goes first, when the leader says, "I have dreams I've neglected and dreams I've abandoned." It gives everyone else permission to be human. That vulnerability, that willingness to be a whole person in front of the people she leads is what makes the program real. Not the budget, not the facilitator, but the leader's honesty. Now, I told you earlier there was a software engineer who quit and traveled the world. She came home empty. Her story connects to both of these.

And it's the one that ties this episode together. She was brilliant. Everyone said so. Top performer. Three promotions in 5 years. Awards and bonuses, all the metrics that say you're winning. But, she was miserable. Not the dramatic kind of miserable, quiet. The Sunday night dread going. Kind you're not the kind where you're not unhappy enough to quit and not happy enough to care. So, she does what a million burned out professionals dream about. She quits, sells her stuff, and books a one-way ticket. Bali, Portugal, Costa Rica 18 months. The reality, 18 months of running from something she couldn't name towards something that she couldn't find because leaving was never the answer. Leaving was just the loudest response to the question that she'd never been asked.

Then, she comes home broke and directionless and sitting in a coffee shop with a friend who just so happens to be a certified dream architect. The friend doesn't give advice doesn't suggest another trip doesn't recommend therapy or career coaching. She pulls out a piece of paper and I'm not making this up. It's literally a sheet of paper and walks her through 12 dream categories. And for the first time in her life the engineer has a framework for what she actually wants. Not what she's running from what she's building towards. Her adventure room was overflowing. 18 months of traveling will do that. But her professional room was gutted.

Financial room was certainly in trouble and her intellectual room was starving. Her spiritual room, she'd never even acknowledged. And here's something nobody tells you about quitting. When you leave without a framework, you just rearrange the imbalance. She went from a life where the professional room is a mansion everything else was condemned, to a life where the adventure room was a mansion and everything else was a den. Same problem different address. The 12 rooms didn't give her answers they gave her a map. And when you can see the whole map, you stop making decisions based on one room. So she starts small in the intellectual. She enrolls in an online course not for her career but for her curiosity. For her spiritual room, she starts a meditation practice.

23:00 · The engineer who quit, traveled, and came home empty

Her financial room, she rebuilds her savings with a plan attached to a time. And her character room, and this one surprised her, she writes down the kind of person she wants to become. Not the kind of engineer, the kind of person. But here's the beautiful part, when she could see the whole house, all 12 rooms, she stopped running. Because she could finally see that problem wasn't with the job, the problem was that she'd been living in two rooms of a 12-room house and wondering why she felt cramped. She goes back to her old industry, same field, different company, but a completely different relationship to the work. Because now she knows that the work is for.

It's not about passion, it's not about purpose, not yet, that comes later. It's about which rooms of your life the work is supposed to furnish. Which rooms need different heat. Three people, three blank pages, a custodian who'd never been asked, an executive who'd never been honest, an engineer who'd never had a framework. Same problem, same Someone sat across from them and asked a question. The question isn't revolutionary, it's not clever, and it's not proprietary. It's four words, four. What do you want? But the act of asking it with intention, structure, with 12 categories to give the answer architecture is the most powerful intervention in organizational transformation, maybe in human transformation. Because when you ask someone what they want, you're saying something else underneath the question.

You're saying, I see you. Not your role, not your output, you. The whole person, all 12 rooms. And that might sound soft. I know it might sound soft to some of you. You're running a business after all. You've got payroll to make, customers to serve, and systems to build. You don't have time for 12 rooms. I get it. But here's what I know after years as an integrator. The companies that treat people like whole human beings don't just feel better, they perform better with 60% less turnover, higher engagement, more innovation, and better retention. Not because they're nicer, because they're smarter. They understand that the human is the system. Invest in the human and the human will invest in the work. Last season, I told you stories about people leaving the dream economy. It was full of people who walked away from systems that didn't see them.

Those stories were true and they mattered. But, what if they didn't need to leave? What if someone one person in their entire organization had just asked the question? The executive didn't leave. She stayed and became the leader her people needed by becoming a whole person first. The engineer left, came back, and finally understood why she needed the framework to know what staying meant. This season, I'm walking you through the construction site. Every episode is a blueprint. We're going to explore the 12 rooms. We're going to watch companies build the Dream Manager programs that transform retention, engagement, and innovation. Not through perks, through genuinely caring about the humans doing the work.

We're going to stress test the architecture. We're going to inspect its blind spots, and in the finale, I'm going to turn the question because here's what season 2 predicted. The revolution has happened. People are redesigning work. Income, community, education, but season 3 asks, it's a harder question, who's designing what comes next? And the answer is not Silicon Valley, it's not venture capital, and believe it or not, it's not AI. It's the person who sits across from another human being and asks, "What are your dreams?" Then build system that makes the answer possible. That's a Dream Manager. That's an integrator. And by the end of this season, find you my job, that's you. And it starts the same way every time. A blank sheet of paper, a pen, and a question nobody asks. So, if this episode made you think of someone, a leader who needs to ask the question, an employee who needs to be asked, or someone staring at their own blank page, please send it to them. Sometimes the most important thing you can do for someone is show them the question exists.

27:30 · Convergence: The question that changes everything

Subscribe if you haven't. This season has 11 more blueprints, and they build on each other. If you're a business leader wondering how to build the system around the dream, how to make this sustainable, not just inspirational, that's what I do. I'm a certified Dream Manager and an EOS integrator. I help organizations build both, the dream and the system that protects it. You can find me at trinitywall.com. Next episode, we walk into the 12 rooms, all of them, even the ones you've been avoiding, especially those. >> If this episode made you uncomfortable, good. That means you were paying attention. The future belongs to leaders who stop managing people like assets and start investing in them like humans. See you next time and remember, dreams aren't frivolous. Ignoring them is.