The Product Management Book No One Talks About - Be More Pirate by Sam Conniff.

Big thanks to a good friend who first introduced me to while back (you know who you are). I’ve just finished reading it again (now sun faded!), and this time I think I understood it better (sometimes it takes me a while).

It’s not labelled as a product book, but I think every product person should read it. It’s a manifesto about rebellion, reinvention, and rethinking power structures told from history. The lives of 18th-century pirates. But, it is one of the most useful books I’ve read as a product leader.

Product management today often sits at the awkward intersection of innovation and complacency. We need to move fast, but follow the process. To be brave, but don’t rock the boat. To be visionary, but also realistic.

And that’s exactly where Be More Pirate resonates. It’s not about chaos for chaos’ sake. It’s about breaking the right rules, the ones that no longer serve the mission, your team, or your customers.

1. Stop following, start rewriting

The pirates didn’t just complain about the system. They wrote their own code. Democratic and fair, radical for its time and far more effective than the rigid structures they left behind.

Product teams often inherit ways of working or follow a methodology that no one really questions... sprint rituals, feature factories and roadmaps as project plans. Best practice that may not be best at all.

If something’s not contributing to you, your product or customer, change it.

2. Build with, not for

One thing I’d forgotten from the first time reading is how democratic pirate ships really were. Crews were diverse, they elected their captains, shares were distributed fairly and everyone had a voice.

Good product teams operate the same way. Great ideas should come from everywhere.

Sales people, designers, engineers, researchers and ops teams aren’t there to just execute the vision or live with the consequences. They are part of the vision. So involve them early, often, and honestly.

3. Make (smart) trouble

Pirates weren’t reckless. They were intentional troublemakers. They didn’t wait for permission. They saw injustice, inefficiency, unnecessary control and they challenged it.

Product managers should do the same.

If you’re prioritising roadmap items with no clear customer value, ask why. If the process slows down learning or delivery, fix it. If leadership is misaligned, don’t stay silent.

Push, respectfully and disrupt, thoughtfully.

4. Write your own charter

Pirates lived by charter. Not slogans or vague values, but shared agreements about how they worked, who got what, how they treated each other, and how they made decisions.

What’s your team’s charter?

Take the time to define what's important for your team. What you reward, what’s non-negotiable, how you treat failure. Then make decisions with this as a foundation.

5. Own the story

The Jolly Roger was more than a flag, it was a brand. Pirates were early masters of branding and narrative. And it worked... enemies surrendered without a fight because they believed in the myth.

Product needs the same understanding.

You’re not just managing a backlog, you are telling a story about what matters, where you’re going, and why people should care. Stakeholders, users, leaders and teams all need that understanding.

Don’t just present the numbers, make them mean something.

Being pirate isn’t about chaos, it’s about courage.

The pirate mindset is about knowing when the rules no longer serve the mission and having the courage to rewrite them.

Product leadership today isn’t about being safe. It’s about moving forward when there is no clear path. It's about building things that matter in ways that make sense.

So thanks again to the friend who introduced me to this book.

Order from Amazon: https://amzn.to/44H3v6e