Book details

  • Genre:business & economics
  • Sub-genre:Management
  • Language:English
  • Pages:184
  • eBook ISBN:9798317843809
  • Paperback ISBN:9798317833916

How to be an Awesome Boss

Intentional Strategies that Produce Results—and Respect

By Larry Olmstead

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Overview


A practical leadership guide for managers navigating today's fast-changing workplace. Drawing on decades of executive leadership, consulting, and organizational development experience, Larry Olmstead argues that great leadership is intentional—and that strong people management is one of the most important drivers of organizational success. Written in a direct, accessible style and grounded in real-world examples, "How to be an Awesome Boss" provides actionable guidance, practical tools, and facilitation guides for first-time supervisors, experienced managers, executives, nonprofit leaders, entrepreneurs, and HR professionals alike.

What they are saying about "How to be an Awesome Boss"

How to Be an Awesome Boss is a must-read for anyone who leads people or hopes to someday. Through engaging stories, real-world examples, and practical advice, Olmstead shares powerful leadership lessons that inspire readers to become more effective, compassionate, and successful managers. The book goes beyond management theory, offering actionable insights that can be applied immediately to build stronger teams, earn trust, and bring out the best in others. Whether you're a first-time supervisor or a seasoned executive, this book will challenge the way you think about leadership and leave you with valuable tools to become the kind of boss everyone wants to work for.

- Rachel Small, Chief Operating and Financial Officer, German Marshall Fund

How to be an Awesome Boss is filled with inspiration and practical examples for anyone leading a team. The content is readable, actionable, and written with humor and compassion. Larry Olmstead's own character and experience shine through in sharing stories from his career in communications and community development. The world would be a better place if we had more awesome bosses!
- Katy Castagna, President & CEO, United Way Monterey County, Salinas, CA

Larry's writing style is crisp and clear and fun. And the message is fantastic. The anecdotes are completely relatable and great illustrations of the challenges. I hope this gets used in college classrooms because it's the clearest and most accessible such text I've ever read. I've already recommended it to two friends, one who is already in a leadership role and one who is about to assume one.
- Carole Leigh Hutton, retired CEO, editor & marketing executive

I consider myself blessed and a better version of myself because of the leadership of Larry, former CEO & President of United Way of Northern CA. While working at UWNC, I witnessed transformational work within our community because of Larry's humble yet strong leadership. If you are looking for deep insight and actionable outcomes of transformational change, unlocking your potential, and leading with boldness, empathy and integrity, I encourage you to take the time to soak in years of experience and knowledge from Larry.  Cheers to you, in becoming a better version of yourself!
- Cherish Vasquez, MA, LMFT

How to be an Awesome Boss is a very readable, practical, and quick guide on how to become an intentional leader in any setting. Larry Olmstead, a journalist at heart, offers an entertaining and useful perspective on the main issues that managers and leaders face in the workplace, with helpful facilitation guides to lead discussions with leaders at different levels within any organization. This is a very useful tool for building people-skills in your company, with the goal of producing greater results and more job satisfaction at every level.
- Donnell Ewert, Board Member, The California Endowment and retired Director of Health and Human Services for Shasta County, CA.

How to be an Awesome Boss is full of advice from a man who’s had the experience to back up his suggestions. Having worked alongside Larry for many years, I can attest to his following the principles he details. A good reference to keep close at hand.
- Susan Lewis, executive assistant to the CEO, Knight Ridder (retired)

I’ve had occasion to read more than my fair share of books on leadership over the course of my career. How to be an Awesome Boss felt like a fresh approach to the topic. As is true of similar books, it includes insights grounded in the experience of a seasoned leader; in this case, the leader is one who has served in and supported a wide variety of organizations. The case studies or vignettes are detailed and provide rich context to what the author shares.  What stood out to me, however, was the emphasis placed on self and group reflection and on intentional, what I might call values-driven, action. In ending many chapters with questions for discussion, the author acknowledges the importance of connection, collaboration, and of working to craft specific responses to challenges operating in a specific context.  The exercises provided in the appendix are useful tools that can be adapted for use in any organization. Whether you are a C-suite executive, manager, someone who exerts leadership in your organization without a title that suggests such a role, or a business/leadership coach, you will find wisdom and support in these pages.  And you just might want a second copy to share with a colleague. I did.

Sharon Brisolara, PhD, Director, Inquiry That Matters

How to be an Awesome Boss provides a real-world perspective of the challenges, opportunities and successes of leadership, while highlighting specific scenarios dealing with employees in a myriad of workplace settings. The book is well-written and a must-read for anyone in a leadership role. Every "boss" should have a copy in their library for easy referral.

- Greg Balkovek, Redding (CA) Planning Commission; retired business and non-profit leader

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Description


What makes someone an awesome boss? According to leadership consultant and longtime executive Larry Olmstead, it takes more than charisma, personality, or authority. Managing people well requires intentionality.

Drawing on decades of management, consulting, journalism, and organizational development experience, Olmstead presents leadership as a set of learnable skills and daily disciplines that directly shape organizational culture, employee performance, morale, retention, and trust.

Written in an accessible, conversational style and reinforced with real-world examples and stories, Olmstead demonstrates how strong leaders combine accountability with empathy, ambition with realism, and high standards with genuine respect for people. Readers are provided with actionable guidance on communication, performance management, coaching, conflict resolution, employee development, workplace culture, trust-building, and leading teams through uncertainty and change. 

Designed for anyone who leads people -- or anyone who aspires to management roles -- How To Be an Awesome Boss includes Facilitation Guides to help HR leaders and managers drive leadership discussions deep into their organizations. Practical rather than academic, the book equips readers with immediately usable leadership tools while making a broader argument: organizations perform better when people are led with intentionality, consistency, accountability, and respect.

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About The Author


Larry Olmstead is a management consultant bringing decades of experience in executive leadership, operations, and HR and organizational development roles. Olmstead retired as President & CEO of United Way of Northern California in 2025 after nine years at the helm and 15 years as an executive in the United Way network. Olmstead's career began with more than 25 years in the media industry as a journalist and executive for news and human resources. A Pulitzer-Prize finalist for reporting from Africa, Olmstead helped lead newsrooms to two Pulitzer Prizes and shared in the Pulitzer won by The New York Times for its coverage of the 1993 World Trade Center bombing. As a consultant, Olmstead has helped clients including Associated Press, Ebony Magazine, Newegg.com, Cisco Systems, United Way, and others. Due to his expertise in media, leadership, management, and diversity and inclusion, Larry has taught in executive development programs at Harvard and Northwestern universities. He holds a bachelor's degree in business administration from Simpson University and studied journalism and political science at George Washington University. For more on Olmstead and his work, visit www.leadwithlarry.com.

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