The Pirates of the Caribbean series has always been one of my favorites and one of the biggest reasons is of course: Captain Jack Sparrow.

He may not be the first example that comes to mind as far as effective leaders and even though he is often operating with incomplete information and questionable resources, people repeatedly choose to follow him.
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While I recognize that this is of course a fictional character and film, I wanted to share five leadership lessons that stood out to me from one of cinema's most unlikely captains.

The following phrase is one of my favorite mental models for how I approach discussions, decisions, and problem-solving:
“And then what happens?”
At first glance, it seems almost too basic to be powerful. In practice, however, it does something most teams struggle with: forces clarity.

My wife and I have a recurring problem. It goes like this:
I say, “I’m ready to go.” She says, “Okay, one second.”
Instead of waiting, I start another small task. Unload the dishwasher. Send an email. Tidy up the counter.
A minute later she says, “Ready!”, but now I’m mid-task.
So she starts something while waiting for me.
Then I finish and say, “Okay, now I’m ready.”, but she’s mid-task.
Suddenly the 10-minute departure has turned into 45 minutes.
No one was being lazy. In fact, we were both trying to be efficient.
And that’s exactly the problem.

It's easy to understand why it's still tempting to present a project's progress in phases like these:

• Requirements: 100%
• Development: 80%
• Testing: 30%
• Deployment: 0%

On paper, the project looks nearly finished. In reality, nothing usable has been delivered.
This is the trap of “% complete” reporting. It creates the illusion of progress without telling us the one thing that matters: when will value actually be available to customers?

"Every system is perfectly designed to get the result that it does." – W. Edwards Deming
​Why Systems Thinking MattersMost problems we face at work and in life aren’t isolated. They’re the result of many interconnected parts interacting over time. Yet we often try to solve them with quick fixes that treat symptoms instead of root causes.
Systems thinking is a way of seeing the whole instead of just the parts. It helps you understand how structure drives behavior and why well‑intentioned solutions sometimes make things worse.
This article discusses what systems thinking is and some examples of how to apply it in the real world.

Christopher Nolan’s Oppenheimer is, at its core, a story about building something unprecedented: the atomic bomb. While the ethical implications of the Manhattan Project are enormous (and should never be overlooked), the film also provides useful lessons in leadership, strategy, and execution that can still be applied today.
Here are some product management principles that stood out to me after reflecting on the movie:

In many teams I’ve worked with, when a challenge pops up there's often a rush to adopt specific tools, frameworks, or processes in hopes of improving productivity or alignment. This can be new apps for tracking work or communicating, new meetings or documentation practices. Sometimes this can help, but many times it feels like the issues that the team set out to solve haven't really gone away.
A big reason for this is that it is often easier to prioritize practices over principles.

I was a big fan of Rework and always felt the principles of that book were a great embodiment of the spirit of Agile (even though 37signals doesn't necessarily follow any of the frameworks that have been popularized alongside Agile). This made it particularly exciting when the book Shape Up was released which outlined their approach to product development.
When I started reading Shape Up, I knew there would be many great takeaways. I didn't, however, expect it to challenge so many assumptions I’ve internalized from years of working in Agile environments.
Below are a few of the ideas that really stood out to me:

Ever since I was in school, one thing I've always done first thing in the morning is make my bed. Since it seems like a relatively simple task I never really thought about the effect it had on the rest of of my day, over the years it’s become a popular example of how small actions can create flow and set the tone for the rest of the day. That single task delivers an early win, which gives a sense of order, accomplishment, and forward motion before you’ve even had your coffee.
That’s momentum in action.

n many organizations, there’s an unspoken belief that the most efficient system is one where everyone is operating at 100% capacity. On the surface, this seems logical (after all, idle time looks like waste) and if every person is busy all the time, surely the system is producing maximum output… right?
Unfortunately, reality doesn’t work that way. Optimizing for full utilization often creates hidden costs, slows the system as a whole, and erodes resilience.