Most leaders are surrounded by content but starved for thinking.
Between podcasts, LinkedIn posts, and airport-bookstore leadership titles, it’s easy to consume ideas about leadership rather mindlessly without ever slowing down enough to wrestle with them. Many leadership books promise certainty, clarity, or a formula. Real leadership, as you know, is rarely that clean. It’s contextual. It’s paradoxical. It requires judgment.
Leadership is jazz.
As an executive coach, reading is part of my professional practice. In 2025, I read just under 70 books - not because volume makes someone wise, but because leadership demands exposure to multiple lenses, disciplines, and ways of thinking. One of my favorite things to do is to pick a specific topic and read 2-5 books on it from authors with different opinions to play with each different perspective.
That’s why I’m sharing an invitation in this article for leaders who want to dig into leadership more critically in their reading. This is for leaders who want to read less passively and practice more intentionally.
What This Invitation Is (and Isn’t)
This is not a race, a checklist, or a “read these 12 books and become a great leader” guarantee. Guarantees don’t exist and typically are promoted by people who are trying to sell you something you don’t need.
This is a simple structure designed to help leaders:
- Read consistently
- Engage ideas critically
- Explore nuance, context, and contradiction
- Develop their own point of view about leadership
You can do this alone or with others. You can adapt it to your season. The only real requirement is curiosity and honesty.
The Core Rules
1. Consistency
Daily Reading: Aim for 30-45 minutes a day from a leadership or adjacent book; annotate or journal as you go. I personally read with a pen and highlighter in hand and it’s not uncommon for me to have a bunch of earmarked pages for particularly thought-provoking books.
Monthly Essay: Read one thoughtful leadership essay each month - something that stretches or challenges your thinking. I like to look up guides around specific themes that are coming up more often through my coaching.
Diverse Voices: For every “traditional” leadership author, intentionally read one voice from a different background, geography, or lived experience. Leadership is more of an art than a science and you can learn so much from exploring other crafts.
2. Mindful Leadership Consumption
Genre Variety: Leadership books, memoirs, case studies, and even fiction that explores power, responsibility, and human systems.
Format Variety: Physical books, e-books, audiobooks, long-form essays, and newsletters all count.
Perspective Stretching: Seek leaders outside your industry and leaders who don’t lead the way you do.
3. Critical Engagement
Leadership Journal: Capture context, key ideas, reactions, questions, and experiments you want to try.
Personal Curriculum: Choose a quarterly focus (i.e. giving and receiving feedback, change management, team dynamics) and read books based on that focus.
Community: Talk about the books you are reading with a peer, a book club, or a thinking partner. Leadership thinking sharpens in conversation.
How to Anchor Your Thinking
As you read, return to a few simple questions:
- What assumptions is the author making?
- Where does this advice depend on context?
- What tension or paradox is being glossed over?
- What would this look like in my organization - not an ideal one?
- What insights am I taking away from this book?
- How will I turn my insights into action?
You don’t need perfect answers. You’re building discernment and taste.
Pause Triggers to Dig Deep
- If you are looking for specific ways to dissect what you are learning in a book, consider some of these pause triggers below. These pause triggers are signals to stop, re-read, review, and research.
- Read with a pen or highlighter to mark sections that stand out to you or leave notes in the margins.
- Earmark pages with information you want to go back to and reflect further on.
- Pause after every chapter and write down your key takeaways and questions in a journal. Re-visit these notes at the end of the book once you have the full picture.
- Stop when you encounter a strong claim - especially one you instinctively agree with or disagree with. Ask yourself why it feels compelling or problematic, and consider seeking out an alternative perspective before settling on your own initial view.
- Ask yourself, “What is actionable for my work context?” and find one small thing to experiment with in the month ahead rather than trying to implement everything at once.
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When I read a particularly thought-provoking book that ends up with many highlights and earmarked pages, I give the book a quick re-read reviewing what I marked up. Sometimes, I take this a step further and make my own Book Notes Google Doc so I have an easy to access guide on key topics of the book. This process is more time-intensive so I save it for books that I know I’ll want to circle back to often like The Effective Executive, The War of Art, The Leadership Challenge, and Nonviolent Communication.
A Simple Monthly Rhythm
Week 1: Read the opening chapters of your core book and annotate.
Week 2: Continue reading and note contradictions or tensions.
Week 3: Read one leadership essay and write a short reflection.
Week 4: Review your notes and discuss with someone you trust.
Repeat.
A Place to Start (If You Want One)
If you don’t know where to start, here are a selection of leadership books that I’ve read and highly recommend. I’ve included brief 1-sentence descriptions for each.
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The Effective Executive — Peter Drucker (Book Review here)
A foundational guide to effectiveness, decision-making, and disciplined leadership thinking. -
BE 2.0 — Jim Collins & Bill Lazier
A values-driven exploration of purpose, ambition, and personal leadership clarity. -
The Leadership Challenge — Kouzes & Posner
Research-based leadership behaviors translated into practical, observable actions. -
Everyday Leadership — Ross Blankenship
A reminder that leadership is practiced daily through small, intentional choices. -
Strong Ground — Brené Brown
A grounded look at courage, vulnerability, and integrity as leadership capacities. -
The Inner Game of Tennis — W. Timothy Gallwey
A timeless exploration of mindset, focus, and internal resistance applicable far beyond sports. -
Thinking in Systems — Donella Meadows
A primer on seeing organizations and leadership challenges as interconnected systems. -
Multipliers — Liz Wiseman
An examination of how leaders amplify (or diminish) the intelligence of their teams. -
Positive Intelligence — Shirzad Chamine
A framework for understanding mental habits and building leadership resilience. -
The Great CEO Within — Matt Mochary
A highly tactical guide to building teams, operating rhythms, and leadership systems. -
The 15 Commitments of Conscious Leadership (Book Review here)
An invitation to radical responsibility, self-awareness, and integrity in leadership. -
Nonviolent Communication — Marshall Rosenberg
A practical approach to communication that builds trust, empathy, and alignment. -
Transitions — William Bridges
A deeply human look at how people experience change and how leaders can guide it. -
The E-Myth — Michael Gerber
A lesson in designing organizations that work without relying on heroic leaders. -
How I Built This — Guy Raz
Founder stories told with an eye toward decisions, trade-offs, and real leadership moments. -
The Five Dysfunctions of a Team — Patrick Lencioni
A shared language for diagnosing trust, conflict, and accountability issues on teams. -
Measure What Matters — John Doerr
A practical framework for strategy, focus, and execution through Objectives & Key Results (OKRs). -
Leading Change — John Kotter
A clear model for navigating organizational change beyond slogans and urgency. -
The War of Art — Steven Pressfield
A sharp confrontation with resistance, discipline, and the inner work required to lead.
You don’t need to read them all (or any). You just need to read well.
The Invitation
If you’re a leader who wants to think more clearly, lead more deliberately, and resist the pull of shallow leadership content, consider this an open invitation.
Read slowly. Question deeply. Talk it out.
And if you find yourself reading one of these books and thinking, “I’d love to talk this through with someone,” reach out. I’m always happy to have a conversation about what you’re reading, what you’re wrestling with, and how it shows up in your leadership.