11 Books for Executive Assistants & Aspiring Chiefs of Staff 2022

2021 was the year of upskilling, resignations, promotions, starting new careers, starting businesses, and more. Suffice it to say that there was a lot of movement in and out of the workforce this year. I saw this first hand with countless Executive Assistants who moved, were moving, or wanted to move into Chief of Staff roles. If moving into a Chief of Staff role is one of your goals for 2022, check out this recommended reading list!

Books I recommend to help you get ready for leveling up your assistant career:

1. The Founder & The Force Multiplier: How Entrepreneurs & Executive Assistants Achieve More Together by Adam Hergenrother with Hallie Warner

This is the essential read (yes, yes, I’m biased) for Executive Assistants who want to strengthen their strategic partnership with their leader, and for those who are considering a move to a Chief of Staff role. You’ll hear some of my story, including how and why I decided to move down the Chief of Staff career path. And how, regardless of title, being a strong Force Multiplier is an incredible career opportunity.

2. Bet on Yourself: Recognize, Own, and Implement Breakthrough Opportunities by Ann Hiatt

Hear directly from Ann Hiatt, former right hand to the world’s top tech CEOs—Google’s Eric Schmidt, Amazon’s Jeff Bezos, and Yahoo!’s Marissa Mayer. Learn how she took charge of her career, leaned into learning opportunities, leveled up her leadership, and the habits and principles that can get you there too. She is a wealth of knowledge and I particularly appreciated hearing about her career journey from assistant to Executive Business Partner to Chief of Staff, and then Founder of her own leadership strategy and consulting company. Her advice will inspire you to bet on yourself and take action towards designing the career of your dreams.

3. Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time by Susan Scott

The one book I recommend to EVERYONE no matter what stage they are at in their career or whether they work in customer service, construction, or the c-suite. Who doesn’t need tactical tools and concrete examples to engage productively in tough conversations? That is what leadership is all about. Fierce Conversations gives you the right words to say what you mean, get the results that you want, and build stronger relationships along the way.

4. Powerful: Building a Culture of Freedom and Responsibility by Patty McCord

Patty McCord is the former Chief Talent Officer of Netflix and helped create the high-performance culture there. In this book, she shares her advice for creating a dynamic culture that will help propel your company into the future. Now more than ever, leaders need to consider why, where, and how their employees want to work, and some of the old tactics simply need to be thrown out. Companies today need to be adaptable, flexible, transparent, and able to create opportunities for growth. Chiefs of Staff have a direct effect on the creation of a company’s culture. This book will give you a fresh perspective on what is possible.

5. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz

The Hard Thing About Hard Things Book for Executive Assistants and Chiefs of Staff

Whether you work for a start-up or Fortune 50 company, Ben Horowitz’s book takes you behind the scenes and tells you the truth about how hard it is to build and run a business. For Chiefs of Staff and other Force Multipliers, understanding the ins and outs of business is important, but even more so, the mindset behind the leaders who must make the tough calls every day. Horowitz also dives into the wartime vs. peacetime CEO mindset which I think is critical for Executive Assistants and Chiefs of Staff to understand.

6. Chief Of Staff: The Strategic Partner Who Will Revolutionize Your Organization by Tyler Parris

This is a great book to understand the fundamentals of the Chief of Staff role, as well as the thought process CEOs go through when considering if a Chief of Staff is the right for them. Parris also discusses how to develop and grow the role over time.

7. The Personal MBA: Master the Art of Business by Josh Kaufman

Executive Assistants and Chiefs of Staff often contemplate whether or not a Master’s degree, specifically an MBA is necessary to progress in their career. There are a lot of different factors to consider if an MBA is the right move for you. However, The Personal MBA is a great place to start and offers all the essentials of business in a simple, well-organized book with real-world examples. It is important for Executive Assistants and Chiefs of Staff to have strong business acumen, and this book delivers.

8. Traction: Get a Grip on Your Business by Gino Wickman

You have probably heard of EOS, especially if you work at a start-up or in a small business. EOS (Entrepreneurial Operating System) is a proven method for business success. Wickman’s book dives into the six key components of a business and how to apply them to your work. Aspiring Chiefs of Staff need to understand the business from all angles in order to drive priorities and deliverables. EOS is a great system for achieving this.

9. Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

Bill Campbell was an executive leadership coach and business executive who mentored some of the most successful and visionary entrepreneurs and business leaders of our time. Trillion Dollar Coach outlines the key principles that helped these leaders grow and thrive. Whether you are helping to coach your Executive or other leadership team members, or simply want to improve your own leadership, this book is for you.

10. Thinking in Bets: Making Smarter Decisions When You Don’t Have all the Facts by Annie Duke

The average individual makes 35,000 decisions a day. And for leaders, decisions are their product. Over time, businesses succeed or fail based on the strength of their decisions. How can you make smarter decisions? How can you help your Principal make even better ones? Thinking in Bets offers the mental models and frameworks to help you do just that.

11. Give and Take: Why Helping Others Drives Our Success by Adam Grant

Give and Take By Adam Grant Book for Executive Assistants and Leaders

A large part of a Chief of Staff’s role is building consensus and working through others to achieve a desired result. Grant offers insights on how we can interact more effectively with others to increase productivity, work smarter, build stronger relationships, and ultimately achieve long-term success.

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