Creative Leadership Lessons From Chris Hassan | Brafton

Picture yourself in a boat on a river, or on a train in a station — or wherever you’re setting up for work today. Chris, your manager, has assigned you a priority project. 

You jump on a quick call while he explains the project specs in detail and asks if it makes sense. Don’t get me wrong — you’re a professional. But this isn’t like the other empires you’ve taken down before. Reluctantly, you tell Chris you’re unsure if you can complete it by the end of the day.

How does Chris respond? 

1. Asks you 37 questions. 
2. Throws metaphorical penguins at you.
3. Launches an unofficial campaign to rename the Editorial chat room “The Situation Room.”
4. Compliments your shoes. 

If you’ve ever worked with Chris, you’ll know the correct answer:

5. All of the above, depending on the situation.

Unconventional as it may appear at surface level, there’s a deeper strategy, mounds of experience and a fully intertwined relationship with creativity backing his approach. So, let’s unpack each of these responses and explore what Chris Hassan, recovering comic strip creator and Senior Vice President of Editorial, brings to Brafton’s leadership lineup at the cusp of 15 years.

(Along the way, see if you can spot the references to guess what his three favorite bands were in high school.) 

Fixing a Hole: Questions and Creativity

Through a managerial lens, Chris will tell you that the most frustrating word in the English language is can’t. In editorial environments, writers’ sharpest tools are their raw materials: imagination and an ability to ask questions, communicate and think. Yet, coaching a team of writers inevitably means navigating the blocks that slow momentum and cloud judgment.

“When you’re working with the written word, you have a blank canvas — anything is possible,” he shares. “So, when someone says ‘I can’t,’ the first step is to find out why. Then, it’s a matter of figuring out what’s next. If we’re missing information, let’s find it. If we’re not sure where to start, let’s talk it over.”

Chris’s approach to creative leadership is rooted in empathy, reciprocal learning and problem-solving. As a writer himself, he’s no stranger to procrastination and overthinking. That firsthand experience sharpens his ability to support others.

Creativity is like a utility belt with the tools you need to survive. “The writers I work with have all these tricks and hacks to get results. I draw from my team’s experience and add their tools to my utility belt,” he explains.

“But the same works in reverse. If a writer is stuck, I’ll talk about when I was in that spot or share some hacks I’ve tried. The goal is to go back to the flow chart, back to the can’t: There is no can’t, nothing is impossible.” 

And sometimes, the most valuable question can’t leads to is: “What can I do?”

What Penguins Can Teach Us About the Blank Page and Beyond

Chris is comfortably acquainted with blank pages and fresh starts. Shifting from hands-on editorial production to a leadership role meant channelling creativity through a different lens. So, to reengage with his creative process, he recently dusted off an old habit — drawing comic strips. 

This came as a nod to his childhood comics featuring original characters like Penguiy*, conceived as a kid, where every page began with nothing but a penguin and the kind of inspiration that comes only in dreams.

“I missed that feeling of needing to create, and part of me wondered if I still had it in me. So I sat down with a blank page and made it up as I went — the comic equivalent to freewriting.” Chris found that the story’s direction became clear once he started. “Before I knew it, I’d written and illustrated about four pages.”

Here, we can see how a childhood comic morphed from a Penguiy origin story into a life lesson: get started, explore the space between and trust that the jigsaw will fall into place once you do. Now, leading a team of writers and creatives, Chris still carries the same philosophy.

“It’s about the ‘I don’t know how to do this’ thing. You can start with a blank page and see where things go. You’ll find your direction, but you don’t necessarily have everything plotted out at first.”

Turns out, the penguins know what they’re doing.

You and Whose Army? Lessons About Genuine Leadership

When Chris talks about leadership, he frames it less like a title and more like a responsibility that lives and dies by the people you work for. 

“I pull from politics when it comes to how I manage,” Chris admits. “I view my team as constituents. If they’re frustrated or problems aren’t getting solved, I’m not doing my job.”

He shows up every day with an awareness that leaders can lose sight of those they’re there to support. “You’re always reading or hearing about people unhappy with their leadership out in the world, and I don’t want that for my team. I want to be a better leader.”

Chris’s team and fellow managers have also been among the most powerful collaborators in solving challenges. “If things aren’t getting done through the established system, then we need to rethink the system. If people disagree with my decision, I’m happy to leave my door open to talk about it,” he adds. “I’ve learned a lot from people who have disagreed with me, and that’s helped me grow. I’m not interested in yes people.”

Resilience and a willingness to lead from the middle of the pack are central to how he manages: with a good joke, perseverance and a firm handle on collaboration.

Getting By With a Little Help From Friends

If you ask Chris what he values most about his role, he’ll tell you it’s the people. “The moments I enjoy most,” he says, “are when I can let my guard down and actually talk to the people I work with.”

Much like Penguiy’s comic adventures, those conversations make up the pages of a bigger story, where characters grow, dynamics shift and the team’s narrative evolves. “You’re turning pages, and we’re building a story together.”

For Chris, leadership is about being part of the plot, learning from others and showing up for the people around him. That relationship-first mindset shapes a team culture where trust, humor and shared experience make the work more enjoyable for everyone. And if you learn a member of the team has pet shrimp or collects vintage gumball machines, even better.

*If you haven’t met Penguiy, you can learn more about him here.