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Leadership Reads to Curl Up With This Holiday Season
By 
November 18, 2025

As the year winds down, it’s the perfect time to reflect, recharge, and get inspired for what’s ahead. Whether you’re curling up by the fire or planning your 2026 goals, a great book can spark new insights and fresh motivation. From mastering strategic thinking to leading with empathy, these titles offer wisdom worth gifting (to yourself or someone on your team).

Keep scrolling for our holiday leadership book recommendations handpicked by the Awesome Journey team.

Eric's Picks

The Six Disciplines of Strategic Thinking

Michael D. Watkins

Why I Recommend This Book:

To become an effective executive leader one core skill is the ability to use data to spot patterns and themes that could lead to a possible trend or even a strategic initiative which is a key component of a quality strategic thinker!

Walking Through Anger

Christian Conte Ph.D.

Why I Recommend This Book:

In today’s world of Intense Polarization we need leaders who can de-escalate conflict/anger by applying a process that is outlined in the book so that you can generate action with others in difficult situations.

Tyson's Picks

Stolen Focus

Johann Hari

Why I Recommend This Book:

It digs into why it’s become so hard to pay attention and stay present in today’s world. The author does a great job of unpacking beyond our phones of the bigger picture of how our environment, work, and culture are pulling at our focus, and offers some insightful ideas on how to take it back.

The Culture Code

Daniel Coyle

Why I Recommend This Book:

It breaks down what makes some teams click while others struggle. The author shares real stories and simple habits that build trust, safety, and connection, making it a really thought provoking guide for anyone who wants to create a stronger, more connected culture at work or in life.

Pam's Picks

The Confidence Code: The Science and Art of Self-Assurance

Katty Kay and Claire Shipman

Why I Recommend This Book:

This book provides a science-based approach to understanding confidence, helping women overcome common barriers and build self-assurance for career success. It offers practical strategies for applying the science of self-assurance to real-world leadership scenarios.

It’s About Damn Time: How To Turn Being Underestimated Into Your Greatest Advantage

Arlan Hamilton

Why I Recommend This Book:

Arlan Hamilton shares her personal story of building a venture capital firm from the ground up while facing underestimation, offering a unique and empowering perspective for women who have experienced similar challenges. It provides a roadmap for building resilience, overcoming adversity, and strategically using the “underestimated” narrative as a catalyst for success.

Scott's Picks

Energetic Selling and Marketing

Lenka Lutonska

Why I Recommend This Book:

It focuses on a new way of Being to create sales in your business.

A Brief History of Everything

Ken Wilbur

Why I Recommend This Book:

It offers a more holistic approach to understanding and navigating our world.

Greg's Picks

Leaders Eat Last

Simon Sinek

Why I Recommend This Book:

Sinek reveals how great leaders create environments where teams feel safe and motivated to perform their best. It’s packed with insights on fostering trust and collaboration in the workplace.

StrengthsFinder 2.0

Tom Rath

Why I Recommend This Book:

Discover your unique strengths and learn how to leverage them for success. It focuses on maximising potential by building on strengths instead of fixing weaknesses.

Awesome Watch (2 min):

Simon Sinek on Why Accountability Partners Keep You Committed.

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