Lead With Imagination: 21 Books That Changed How I Think About Leadership in 2025

I plan on reading as much as I can every year.

So honestly? Not quite 2 books a month feels like a bit of a letdown. But I’m always chasing questions—questions about what separates transformational leaders from transactional ones. What makes some people see possibilities where others see only problems? Why do certain leaders inspire movements while others barely maintain momentum?

These books aren’t listed in the order I read them—more like the order they’re connecting in my head right now.

And somewhere between my third read of Candice Millard’s The River of Doubt (Roosevelt nearly dying in the Amazon—still excellent!) and Henry Winkler explaining how he became the Fonz despite severe dyslexia in Being Henry, something crystallized:

The leaders who change things aren’t necessarily smarter—they just imagine differently.

Why Imagination Matters More Than Intelligence in Leadership

Let me show you what I mean through the lens of 21 very different books.

The Curiosity Principle: Seeing Stories Others Miss

Charles Kuralt drove backroads for a living.

I’ve been listening to his book America yearly for the better part of twenty-five years now. It’s hands down a favorite I return to for so many reasons. This year, I added Charles Kuralt’s Summer to the rotation.

Here’s what Kuralt keeps teaching me: he wasn’t just observing America—he was imagining it. He saw stories where others saw nothing. Small towns. Quiet people. Ordinary moments that contained extraordinary meaning.

That’s the thing about imaginative leaders: they’re insatiably curious about what everyone else drives past.

Candice Millard’s The River of Doubt reinforced this principle. Roosevelt’s imagination wasn’t wild dreaming—it was fueled by his willingness to venture into the unknown. To ask questions nobody else was asking. To see an unmapped river and think, “I wonder what’s there?”

The Timing Factor: When Matters As Much As What

Jesse Cole put a baseball team in yellow tuxedos and called it Fans First.

I heard him speak at a leadership event and bought his book the moment I got home. People said he was crazy. Now the Savannah Bananas sell out stadiums by reimagining what baseball could be.

But here’s what Daniel Pink’s The Scientific Secrets of Perfect Timing taught me: Cole’s genius wasn’t just what he imagined—it was when he executed it.

Timing isn’t luck. It’s a skill. And imaginative leaders understand that the right idea at the wrong time is still the wrong idea.

The Human Connection: Reimagining Relationships

Chris Voss taught hostage negotiators to say “that’s right” instead of “you’re right” in Never Split the Difference.

Two words. Completely different imagination of how humans connect.

Adam Grant’s Give and Take: A Revolutionary Approach to Success went even deeper: givers don’t just imagine win-win scenarios—they imagine an entirely different scoreboard. They see success as something that multiplies rather than divides.

This is where imagination becomes practical. It’s not about grand visions—it’s about seeing people differently than others see them.

The Structure Underneath: Building Frameworks for Imagination

Here’s an admission: Brian McDonald’s Invisible Ink: Building Stories from the Inside Out wasn’t that great of a book.

But buried in there was this one idea that stuck with me: every great story is built from the inside out. Structure matters. Framework matters.

You can’t lead imaginatively if you’re making it up as you go.

Joe Rigney’s Leadership and Emotional Sabotage and John Medina’s Brain Rules both reinforced this from different angles. Imaginative leaders understand the systems—emotional, neurological, organizational—that shape human behavior. They don’t just dream; they build frameworks others can inhabit.

The Sacred Dimension: Holding Space for Mystery

I wasn’t expecting a spiritual thread to emerge across my reading, but it did.
Tyler Staton reintroduced me to the Holy Spirit in The Familiar Stranger. Randy Alcorn painted Heaven in vivid detail in his book Heaven. Blaine Eldredge unpacked Jesus’s entire vision in The Paradise King. Andrew Peterson reminded me that imagination requires cultivation in The God of the Garden.

Here’s what they all said: Imagination isn’t just practical. It’s sacred.

The most transformative leaders hold space for mystery, not just metrics. They understand that some of the most important things can’t be measured, only experienced.

The Fear Factor: Naming What Holds Us Back

Napoleon Hill warned me about sabotage in Outwitting the Devil—how fear disguises itself as “being realistic.”

Joe Rigney said the same thing with different words in Leadership and Emotional Sabotage: anxiety will wreck your family, destroy your church, and ruin the world if you let it.

Imaginative leadership means seeing the obstacles others miss—or refusing to see the obstacles others invent.

The Humanity Check: Admitting What You Don’t Know

Alan Alda made me laugh-cry with Never Have Your Dog Stuffed—my second time through, and it hit even harder.

I’ve loved Alan Alda since absorbing MASH as a child. (Yes, I own the series on DVD. Yes, it’s also in my streaming library. Don’t judge me.)

Richard Paul Evans got vulnerable in Sharing Too Much: Musings from an Unlikely Life.

Both reminded me: imaginative leadership isn’t about having it all figured out. It’s about being human enough to admit when you don’t.

The Story That Changed Everything

Claire Keegan wrote Small Things Like These, which is only 128 pages but absolutely gutted me.

One man. One choice. One act of imagination that said, “What if I chose compassion over compliance?”

It changed everything.

This is what imagination looks like in real life. Not grand gestures. Not corporate vision statements. Just one
person deciding to see differently, and act accordingly.

Six Leadership Lessons on Imagination

Here’s what 2025’s reading taught me about leading with imagination:

1. You can’t imagine new possibilities if you’re not curious about what already exists. Kuralt taught me this through his decades of backroad journalism.

2. You can’t time your vision if you don’t understand rhythm. Pink and Cole showed me that when matters as much as what.

3. You can’t lead people you don’t truly see. Voss and Grant demonstrated that imagination transforms relationships.

4. You can’t build something lasting without structure. McDonald and Rigney proved that frameworks enable imagination, they don’t constrain it.

5. You can’t dream beyond your fears if you don’t name them. Hill and Rigney warned that anxiety disguises itself as realism.

6. You can’t create something meaningful if you’ve lost your sense of wonder. Peterson, Staton, Alcorn, and Eldredge reminded me that imagination has a sacred dimension.

I closed out the year with G.K. Chesterton’s Winter’s Fire: A Christmas—turning Christmas into philosophy, reminding me that the best imaginative leaders return to ancient wisdom, not just chase novel ideas.

Laurie Beth Jones’s Jesus, CEO said something similar: the deepest innovation often comes from the oldest truths.

What’s on your reading List?

I’m already building my 2026 list.

What are you reading that’s stretching how you see leadership? What’s teaching you to imagine differently?

Drop your recommendations in the comments below—I genuinely need them.

The Complete 2025 Leadership Reading List

1. America by Charles Kuralt
2. Winter’s Fire: A Christmas by G.K. Chesterton
3. The Scientific Secrets of Perfect Timing by Daniel Pink
4. Heaven by Randy Alcorn
5. Outwitting the Devil by Napoleon Hill
6. Invisible Ink: Building Stories from the Inside Out by Brian McDonald
7. Give and Take: A Revolutionary Approach to Success by Adam Grant
8. Fans First: Change the Game, Break the Rules & Create an Unforgettable Experience by Jesse Cole
9. Never Split the Difference: Negotiating as if Your Life Depended on It by Chris Voss and Tahl Raz
10. The Paradise King: The Tragic History and Spectacular Future of Everything According to Jesus of
Nazareth by Blaine Eldredge
11. Being Henry: The Fonz . . . and Beyond by Henry Winkler
12. Leadership and Emotional Sabotage: Resisting the Anxiety That Will Wreck Your Family, Destroy
Your Church, and Ruin the World by Joe Rigney
13. Sharing Too Much: Musings from an Unlikely Life by Richard Paul Evans
14. Jesus, CEO (25th Anniversary Edition): Using Ancient Wisdom for Visionary Leadership by Laurie
Beth Jones
15. The Familiar Stranger: (Re)Introducing the Holy Spirit to Those in Search of an Experiential
Spirituality by Tyler Staton
16. Never Have Your Dog Stuffed: And Other Things I’ve Learned by Alan Alda
17. Brain Rules (Updated and Expanded): 12 Principles for Surviving and Thriving at Work, Home,
and School by John Medina
18. The God of the Garden: Thoughts on Creation, Culture, and the Kingdom by Andrew Peterson
19. Small Things Like These by Claire Keegan
20. Charles Kuralt’s Summer by Charles Kuralt
21. The River of Doubt by Candice Millard