Hamza Khan introduces himself in a way that catches people off guard. He was born in 1987, he loves hip hop, and he calls himself a horrible boss. Not because he mistreats people, but because he refuses to manage them in the traditional sense. His story is a sharp look at how leadership needs to change for Millennials and modern knowledge workers.
In one of his first office jobs, he learned this the hard way. Outside of his time in the Canadian Armed Forces, the Monday to Friday 9 to 5 grind never really fit him. One morning, he walked into his marketing agency job at 9:15 a.m., coffee in hand, only to find his boss standing by his desk, arms crossed, tapping his watch. The problem was not his work. It was the clock.
That day, Hamza had already checked his email, gone through his calendar, and stayed on top of things through Facebook, Twitter, WhatsApp, and internal messages. Nothing urgent had happened. The only big news on Twitter was Kanye West and Kim Kardashian attending a Jay-Z concert the night before. Still, his boss hit him with a line that would stick for years: “Hamza, you being late is bad for morale.”
It was not about results, it was about optics. It suggested he was not pulling his weight simply because he was not chained to his chair at 9:00 a.m. on the dot. For someone who sees himself as a committed teammate and a high producer, that hurt. It also became a breaking point.
For his last two weeks at that job, he played along with the system. He arrived early, at 8:55 a.m. every day. He sat at his desk for eight straight hours, watched movie marathons like The Godfather, Star Wars, and the extended Lord of the Rings, did zero real work, and left at 5:00 p.m. on the dot. Every day, as he walked past his boss, he heard, “Hamza, great job.” The message was clear: presence mattered more than performance.
That is the moment he quietly decided, “I will never be managed again.”
The Management Paradox for Millennials
Hamza’s story leads to a bigger tension many people feel at work. Growing organizations need some kind of management to coordinate people and resources. At the same time, most people, especially Millennials and younger workers, hate being “managed.”
That raises two tough questions: Can Millennials be managed? Or more importantly, should they be?
Hamza is firmly part of Generation Y. He was born in 1987, which puts him in the age group that now makes up more than half of the global workforce. People in his generation often hear the same labels:
- Entitled
- Lazy
- Disloyal
- Unmotivated
- Selfish
He jokes that quitting a job over the inability to show up 15 minutes late might feed those stereotypes. But his argument is that Millennials are actually built for tomorrow’s workplace, not yesterday’s.
They grew up in a connected world. They know how to find information fast, learn new tools, and create their own paths. They tend to be more resourceful and entrepreneurial. As Hamza puts it, he has buzzwords for days, but behind the humor is a real point: how they work and why they work does not match the expectations of traditional offices.
Here is how many people in his generation approach work:
- They do not have just one employer. They build a portfolio of work.
- They do not have just one specialization. They stack skills.
- They do not stay in one place for decades. They do “tours of duty.”
- They do not need a fixed office. Anywhere with Wi-Fi can be a workplace.
Compare that to the old model: one job, one title, one employer, one office, for as long as possible.
Treating these workers like factory staff under tight supervision is a mismatch. Their work is often creative, problem-solving, or information-based. Measuring them by start time and chair time instead of outcomes is not only frustrating, it is wasteful.
If you want a quick refresher on where these old attitudes came from, the history of management and motivation, including ideas like Theory X and Theory Y, is well summarized in resources such as the overview of Theory X and Theory Y by Douglas McGregor.
How We Got Here: The Factory Roots of Office Life
The modern workday did not appear out of nowhere. You can trace many of its rules back to factories during the Industrial Revolution.
At that time, companies were trying to scale up production. Large groups of people worked in the same place, at the same time, doing repetitive manual tasks. To keep things organized, someone had to control schedules, track output, and enforce discipline. That someone became the manager.
The 8-hour workday itself grew out of this context. Social reformer Robert Owen proposed the famous split: 8 hours for work, 8 hours for recreation, and 8 hours for rest. It was meant to correct an unhealthy, adversarial relationship between owners and workers, where people were often overworked and treated as expendable.
By the early 1900s, formal management had become normal. By the mid-20th century, companies had layered on countless theories and systems to “perfect” it.
One of the most important thinkers of that era, Peter Drucker, noticed that something was changing. We were moving away from simply making physical goods and toward handling information. He called this “knowledge work” and said, in essence, that the most valuable asset of any modern institution would be its knowledge workers and their productivity.
You can see how that clashes with the old mindset. In a knowledge economy, all the value in an organization walks out the door every evening. When that happens, command and control stops making sense, especially in places like:
- Creative agencies
- Startups
- Think tanks
- Media and publications
In these environments, people need freedom to think, experiment, and create. Tight control kills the very thing these organizations rely on.
If you want to go deeper into how managers have traditionally viewed workers, the Wikipedia entry on Theory X and Theory Y gives helpful context.
From Tradition to Trust: Theory X vs Theory Y
If you strip away jargon, a lot of bad management comes down to one word: tradition. We keep doing things because that is how they were always done. It feels safe. It is also a good way to shut down new ideas.
Two classic views of human behavior at work show up here: Theory X and Theory Y.
Theory X assumes things like:
- People are lazy.
- People avoid work when they can.
- People do not like responsibility.
It is like how kids react when they are told to mow the lawn or do the dishes. They will usually find something they would rather do.
Theory Y flips that on its head. It assumes that:
- People are ambitious.
- People are self-motivated.
- People can exercise self-control.
- People actually enjoy using their skills.
Under Theory Y, if you give people the right environment, they do not just work for a paycheck. They start to reach that top point of Maslow’s hierarchy of needs, the part often called self-actualization. They do their best work and feel deeply proud of it.
Hamza has built his leadership style on something close to Theory Y. He focuses on creating what he calls the “proper conditions” for great work.
Here is what those conditions look like for his teams:
- 100% trust from day one
People get clear areas of responsibility, clear goals, and clear deadlines. He assumes they are there for the right reasons and that they want to do good work. - Space, both physical and mental
There is an office, but no one is forced to sit in it. People can work from home or from another country, as long as their work is high quality and on time. He sees tracking hours as dehumanizing. - Co-creation instead of top-down orders
He does not just toss tasks over the wall. He pulls people into the process, so they feel emotionally invested in what they are building. - Real leadership, not just supervision
His teams told him they needed someone to guide them, protect them from some of the harsher parts of the organization and the industry, and help them prioritize. That is the role he tries to play. - A strong, human culture
He wants the workplace to feel like a community where people can be themselves, not a stiff office where everyone wears a mask. He credits a lot of this learning to his time at Ryerson University.
When all of this comes together, people do work they are proud of. They become more creative. They find meaning. They reach something closer to work life blend, instead of constant conflict between the two.
If you are interested in how leaders can shift their mindset from control to trust, resources such as the MindTools explanation of Theory X and Theory Y can add another layer of insight.
How a “Hands-Off” Leader Actually Leads
Hamza’s style did not come from an MBA program or a management textbook. It came from hip hop.
He is a lifelong fan of Shawn “Jay-Z” Carter. He has listened to the albums, studied interviews, and read about how Jay-Z built Roc Nation into one of the most successful labels of its time. What struck him was how Jay-Z manages other leaders, not just followers.
Think about the artists he works with: Kanye West, Rihanna, J. Cole, and others. These are strong personalities with their own creative visions. Jay-Z does not just see a roster. He sees unique people with their own ambitions. He creates an environment where they can each make “classic albums,” win awards, and still stay true to themselves.
Hamza tried to apply that idea very early. At 21, he led his first creative team, made up of student staff. If you have ever managed students, you know it is not easy to get their time and focus. They juggle classes, exams, part-time jobs, family, friends, and extracurriculars.
Without any formal training, Hamza defaulted to the best “blueprint” he knew: Jay-Z’s approach. One of his first team members was older, more skilled, and more experienced than him. That was intimidating. Instead of trying to control this person, Hamza did the opposite.
He told him, in essence: You are an adult, and you can manage yourself. I will not try to manage you. I will only manage priorities and workflow. If you are okay with that, we can do great things together.
That one decision gave him the confidence to lead larger and more complex teams.
At 24, at Ryerson University, he managed a much bigger student team. The group was so large that they were almost never all in the same room. Some joined meetings from their phones using FaceTime or Google Hangout, and he often had to run the same meeting multiple times.
This forced him to embrace technology not just for efficiency, but for connection. Online tools became ways to build community and keep everyone in sync, even when they were scattered across campus or the city.
By 28, he was managing full-time staff in the same “hands-off” way. He recognized that each person had different expectations and habits. Instead of forcing them into his mold, he adjusted his way of working to fit them.
His leadership principles can be summed up like this:
- Raise the bar on yourself first
If you want your team to do their best work, you have to bring your best self. He does not stand behind his team and say “Go.” He stands in front and says “Let’s go.” - Go to bat for your people
People want to know that their leader has their back. He will defend his team and support them, even when things get tough. - Invest in training and mentorship
If you are not learning, you are stuck. He pushes his team to grow personally, professionally, and academically. If they outgrow what he can teach them, he helps them find other mentors and opportunities. - Give time, space, and resources
He believes your best work happens when no one is breathing down your neck. So he gives people the room to experiment and own their projects. - Assign stretch projects
These are big, scary assignments that pull people out of their comfort zone. That is where real growth, and often real “magic,” happens. - Get out of the way
Once people are motivated and equipped, he steps back. He watches them take off.
J. Cole once said about Jay-Z, “Jay never compromised or interfered with my creative process… he let me figure it out, and it feels better to win like that.” Hamza tries to lead with that same spirit.
For more stories and talks that challenge traditional leadership, you can explore other independent events and speakers through the TEDx programs directory.
Outcomes, Not Outputs: Why This Approach Works
This all sounds ideal, but does it actually work?
Hamza is now on his fifth creative team. People who have worked with him have gone on to roles at large agencies, major media companies, and well-known publications. His teams have won regional and national awards. On the agency side, they have landed clients early that many firms do not even attempt to approach until years down the line.
It is not perfect. There are bumps, conflicts, and missteps like anywhere else. The difference is the focus. His approach centers on outcomes, not just outputs.
He likes to quote Antoine de Saint-Exupéry, who said something along these lines: If you want to build a ship, do not gather people to collect wood and assign them tasks. Teach them to long for the endless immensity of the sea.
In other words, do not just hand out checklists. Help people connect to the bigger purpose behind the work.
Here is a quick exercise. Think of a leader in your life. Maybe a manager, coach, teacher, or even a friend. If they called you tonight and asked you for help on a project, would you say yes? Would you give them your best effort, maybe even more than you have time for?
Most people would, if they feel seen, trusted, and supported. That feeling is the “proper condition” that makes excellence possible.
The End of Management and the Rise of Leadership
We are no longer in an era where organizations exist only to produce goods or even just to provide expert services. Today, they exist to create meaningful experiences for customers and for the people doing the work.
That changes the role of management. If people do not like to be managed, and if traditional management gets in the way of creativity and engagement, what should managers do?
Hamza’s answer is simple: stop managing.
He does not see himself as a boss in the classic sense. He sees himself as a friend, a mentor, a comrade, a resource, a cheerleader, and a coach. Coaches do not step on the field and play the game. They train, motivate, and prepare their team to win championships. Then they step back and let the players shine.
His challenge to anyone leading Millennials or the next generation is clear: do not manage, lead. You manage things. You lead people.
If you are in any kind of leadership role, formal or informal, the question is not “How do I control my team?” The question is “How do I create the conditions where their best work becomes possible?”
Conclusion
Hamza Khan’s journey from late employee to horrible boss is not about rebellion for its own sake. It is about refusing to confuse time at a desk with real value. His story shows that when you trust people, treat them like adults, and focus on outcomes instead of optics, teams grow and do better work.
The next era of work belongs to leaders who build community, set clear goals, and then get out of the way. It belongs to managers who are willing to drop the old factory mindset and adopt something closer to leadership at every level.
If you manage or hope to manage the next generation, take a moment to ask yourself: are you tightening control, or creating conditions for growth? The future of your team probably depends on the difference.
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