Lead Like a Pirate: Change Management for New Leaders
Stepping into leadership, whether you're a brand‑new supervisor or joining a completely new organization, has a way of handing you change management responsibilities before you've even figured out how to log into all the systems. I’ve lived this cycle more than once: new leader in general, new leader in a new unit, new leader in a new department, new leader in a new organization. Each version came with its own challenges, lessons, and opportunities to grow.
And here’s the truth I learned every single time: change management doesn’t wait for you to “settle in.” It starts on day one.
Stepping into leadership also means stepping into a new identity, one that requires equal parts courage, curiosity, and humility. What no one tells you is that the early days of leadership feel a lot like boarding a ship mid‑voyage. The crew is already sailing, the winds are already shifting, and you're expected to steer with confidence even while you're still learning the map.
What helped me most in those moments wasn’t perfection. It was perspective. Change management isn’t a checklist; it’s a mindset. It’s the ability to read the room, understand the tides, and adjust your sails without losing sight of your destination. And like any good pirate, you learn to trust your instincts, your crew, and the tools you’ve collected along the way.
One of the biggest lessons I’ve learned is this: people don’t resist change, they resist uncertainty. They resist feeling unheard, unseen, or uninformed. When leaders communicate early, often, and with intention, the entire tone of a change initiative shifts. Transparency becomes a stabilizer. Empathy becomes a compass. And clarity becomes the anchor that keeps teams grounded when everything around them is moving.
Leadership can also be lonely, especially when you're new to a role or organization. That’s why building your own pirate council, a group of trusted peers, mentors, and thought partners, is essential. These are the people who remind you that you’re capable, that you’re growing, and that you don’t have to navigate uncharted waters alone. Every leader needs a crew.
And finally, give yourself permission to evolve. The leader you are on day one is not the leader you’ll be on day one hundred. Growth is the real treasure of leadership. Every challenge, every misstep, every success adds another pearl to your treasure chest (toolkit).
My Pirate Philosophy of Leadership
If you've ever worked with me, you've heard my favorite leadership mantra:
“Be a pirate. Take the pearls and leave the rest.”
Being a pirate isn’t about chaos or rebellion. It’s about discernment. It’s about scanning the sea of leadership advice, frameworks, and expectations, and choosing only what truly serves you, your team, and your organization. It’s about building a leadership toolkit filled with treasures: ideas, strategies, and resources that help you lead with clarity, confidence, and compassion.
And because not every leadership book is a sit‑down‑with‑a‑cup‑of‑tea kind of read, sometimes you need something stronger. So, pour yourself a pirate drink of choice, grab your compass, and let’s talk about the books that helped me navigate change when I was still learning the ropes.
1. Switch: How to Change Things When Change Is Hard — Chip & Dan Heath
🔗 https://heathbrothers.com/books/switch/
I read Switch with a colleague who, like me, had just been handed a massive change initiative early in his leadership role. We were both new, both overwhelmed, and both determined to lead well.
The book’s core framework includes the Rider, the Elephant, and the Path gave us a shared language for navigating organizational change. It’s simple, memorable, and incredibly effective across industries.
“For anything to change, someone has to start acting differently.” — Chip & Dan Heath
The Pearl I Took:
We enlarged the summary of the three elements, laminated it, and hung it in both of our offices. Every decision we made had to address at least two of the three:
Rider — the logic
Elephant — the emotion
Path — the environment
If we could confidently plan for two, we would move forward. We used this approach for nearly a year, and honestly, I still mentally dock myself into this framework whenever I’m struggling with a decision or anticipating the impact of change.
This book is a must‑have for any leader navigating complex change.
2. Effective Phrases for Performance Appraisals — James E. Neal Jr.
🔗 http://www.nealpublications.com/effectivephrases.html
This book entered my world when I first stepped into management. It’s not glamorous. It’s not philosophical. And it’s definitely not a sit‑down‑with‑a‑pirate‑drink‑and‑reflect kind of read.
But it is one of the most practical leadership tools I’ve ever owned.
A seasoned nurse leader handed it to me and said, “This will guide you through your career.” She was right.
Clear expectations are a form of respect.
The Pearl I Took:
This book taught me how to communicate performance expectations clearly and professionally. I’ve used it to:
Write performance evaluations
Build job descriptions
Set expectations
Coach staff
Clarify my own goals
Strengthen documentation
Improve performance conversations
I’ve purchased it for supervisors, managers, directors, and VPs. It’s timeless, industry‑agnostic, and always within reach on my shelf.
If you're building a leadership toolkit, this one belongs in it.
3. Start With Why — Simon Sinek
🔗 https://simonsinek.com/books/start-with-why
This book came into my leadership journey later, and I wish I had read it years earlier.
I realized that in my rush to implement change such as new workflows, new documents, or new processes I often skipped the most important part: the why. When you live and breathe a project, the why feels obvious. But to your team, it’s not.
“People don’t buy what you do; they buy why you do it.” — Simon Sinek
The Pearl I Took:
I now include a “Why” slide within the first three slides of any presentation. It doesn’t need to be long or dramatic, it just needs to anchor the work.
Rooting change in the why:
Builds trust
Reduces resistance
Strengthens organizational culture
Inspires teams
Creates alignment
It’s a simple shift that transforms how people receive change.
Final Thoughts: Whether You’re New or Seasoned, Be a Pirate
Leadership isn’t about having all the answers. It’s about collecting the right tools, frameworks, and philosophies, and knowing when to use them.
Whether you’re:
Stepping into leadership for the first time
Taking on a new role or scope
Navigating organizational change
Or refining your leadership style
These three books offer powerful guidance.
So go out there. Lead boldly. Navigate changes with intention.
And above all, be a pirate. Take the pearls and leave the rest.
Your Turn:
What leadership book has shaped your approach?
I’m always looking to add new pearls to my pirate map and I’d love to hear what’s on yours.