The 5 Best Books to Read with Your Executive Assistant

For many executives, reading (or if you’re like me, listening to) books related to the latest trends in leadership and time management is part of their developmental routine. However, many executives may be missing out on one of the best ways to build a better working relationship with their executive assistants.

I’m talking about reading some of the same books. It’s a practice my former executive assistant and I began somewhat accidentally a few years ago. One day, I had Kristie order a book for me that I’d heard a lot about, and Kristie decided to check out the same book at the library for herself. When I began talking about what I was learning from the book, Kristie surprised me by giving her perspective on the same content.

During that time, we learned one of the biggest benefits of going through the same book is that it gives us the ability to explore new ideas and concepts without having to take the time to explain them to each other. For example, if I tell Kristie I need to schedule some “deep work” time, she knows exactly what I mean because she’s read Cal Newport’s book by the same name. If Kristie tells me that she needs to share some “radical candor” with me, I know the feedback she’s going to give me is rooted in a desire to see me succeed in my position because we’ve both read Kim Scott’s book Radical Candor.

It truly puts us on the same page. 

If you’re an executive assistant reading this article, I strongly recommend asking your executive which books have had the biggest impact on their leadership style and picking up copies for yourself. Also, always be on the lookout for what they’re currently reading. The best way to “get inside the head of your executive” is to put the same thoughts and ideas in your head that your executive is putting into theirs. And there’s no better way to do this than by reading the same content. 

For the record, I’m not telling you to start a book club with your executive assistant. Kristie and I once tried to set up an intentional reading schedule where we’d meet to discuss specific chapters, but I think it only lasted a few weeks. Instead, if I find a particular book helpful or interesting, I’ll tell Kristie I think she should pick up a copy for herself (or, other times, Kristie has taken the initiative to find a copy for herself when I ask her to get a book for me). 

To help you on your journey (or if you don’t know where to start), here are a few books that we found helpful and believe would be beneficial for you and your executive assistant to read together.

1. Essentialism: The Disciplined Pursuit of Less – by Greg McKeown

There was a time in my life when I had a difficult time saying “no” to requests and, as a result, found myself constantly overworked, exhausted, and – strangely enough – not very productive. I like to divide self-help/leadership books into the following two categories: those that expose you to brand new ideas and those that reveal what you already know but haven’t figured out yet how to put into action. Essentialism is a prime example of the latter, and that may be why I love it so much.

When it comes to scheduling and calendar management, the themes explored in Essentialism are, well, essential. Author Greg McKeown does a terrific job of giving you a memorable three-part framework (Explore, Eliminate, and Execute) to help you focus your time and energy on the areas of your life that will produce the most value.

The benefits of reading Essentialism with your executive assistant should be obvious. As the gatekeepers of your schedule and calendar, your executive assistant should be your fiercest advocate when it comes to protecting and allocating your time in a way that creates value. Reading Essentialism together will hopefully lead to better processes that will result in better time and task management.  

2. Deep Work: Rules for Focused Success in a Distracted World – by Cal Newport

In a culture of near-constant distraction and availability, our inability to hone in on one task or project for an extended period has reaped undue consequences on our quality of life and work. And, according to Cal Newport’s Deep Work, we’re going to have to make a concentrated effort to restore our shattered attention spans and work ethic.

If you constantly find yourself checking your phone, jumping between tabs on your internet browser, or exhausted after a day of unproductive work, then Deep Work is a must-read. Much like Essentialism, Deep Work is all about figuring out how you want to spend your time, but with an added emphasis on diagnosing how modern workplace culture inhibits productivity. 

Of all the books on this list, Deep Work definitely led to the most conversations with my executive assistant and experimentation with my schedule. It’s an extremely relevant read, and the second half includes a lot of great recommendations on how to apply the principles explored in the book. 

3. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity – by Kim Scott

Kim Scott’s Radical Candor is a popular leadership book about building mutual trust with your direct reports and developing the ability to give and receive critical feedback. Scott divides personal feedback styles into the following four philosophies: Ruinous Empathy, Manipulative Insincerity, Obnoxious Aggression, and Radical Candor. She encourages her readers to move toward a healthy state where they can both care personally and challenge directly. 

Radical Candor was a great reminder for me of the importance of giving critical feedback. My natural tendency is to slip into the “ruinous empathy” quadrant of Scott’s graph. One of my key takeaways from Radical Candor was that if I cared about someone enough, I’d give them the hard feedback instead of keeping the feedback to myself to avoid hurting someone’s feelings. 

Depending on your leadership style (and where you fall on Scott’s feedback philosophy graph), your experience with reading Radical Candor may be completely different than mine. But if you struggle with giving critical (or positive) feedback to your direct reports, you should definitely pick up a copy of this book. And because you work closely with your executive assistant, you should get a copy for them as well. One of the most important takeaways for Kristie and me from Radical Candor was that it helped give us permission to give feedback to one another and provided a reminder that giving critical feedback is crucial to a great working relationship.

4. The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace – by Beatrice Chestnut

There are two types of people in the world - those who’ve heard about the Enneagram and those who are about to hear about the Enneagram. For first-timers, the Enneagram is a personality typology (like Myers-Briggs) constructed around nine “types” that encourage personal growth and development. The nine types are conveniently labeled as numbers (1-9), and each type has its own set of strengths, weaknesses, constraints, and healthy/unhealthy behaviors.

Beatrice Chestnut’s The 9 Types of Leadership takes the principles of the Enneagram and applies them to the workplace. Each chapter focuses on one of the nine types and how they interact with the other types. While some people may scoff at the idea of adopting another personality typology, the Enneagram is easy to understand, remember, and it’s relatable. I’m no expert on Enneagram, but I’m learning, and I think it’s an incredible tool for understanding you and your executive assistant’s strengths and weaknesses. 

Of the five books on this list, this is the one you don’t have to read in its entirety. After discovering your number, I recommend reading the chapter focused on your number and the chapter focused on your executive assistant’s number (and have your EA do the same). This book is a perfect example of giving you and your executive assistant a vocabulary to discuss the ways your distinct personalities may complement each other well and at times, present challenges in your working relationship. 

5. Boundaries for Leaders: Results, Relationships, and Being Ridiculously in Charge – by Dr. Henry Cloud

Clinical psychologist Henry Cloud has created a small publishing empire with his Boundaries series, but you shouldn’t overlook Boundaries for Leaders as more of the same. Of the books on this list, I’d probably rank Essentialism and Boundaries for Leaders as books I try to read at least once a year. No matter what type of leader you are, Boundaries for Leaders is sure to expose some blind spots that are impacting your workplace culture, team dynamics, and bottom line. 

Like The 9 Types of Leaders and Radical Candor, Boundaries for Leaders gave Kristie and me a shared platform from which to speak truth to one another. Once we were aware of the other’s professional boundaries and weak spots, it was easier for us to recognize when the other was becoming overworked, overwhelmed, and stretched too thin. This is the type of book that if I read on my own and came into the office with a bunch of different ideas on how we were going to change everything, it’d probably come across as mean or insensitive. But, since Kristie also read Boundaries for Leaders, it saved us a lot of time (and hurt feelings) because she already knew where I was coming from and was already on board.

As I said in the introduction, I’m not encouraging you to set up a book club with your executive assistant. You don’t even have to discuss the books together, but I truly believe that if you read the same books, you will find it extremely beneficial. Whether it is the five books I listed above or some other books you’re reading that have impacted you, buy a copy for your executive assistant. A helpful policy I enacted was that Kristie had a standing offer to purchase a copy of any book for herself that I was reading for work.  

I’m curious to know your thoughts. What leadership books helped you the most? Would you recommend any other books to read with your executive assistant? Let me know in the comments below. 

Kristie’s Thoughts

As Don and I discovered several years ago, reading the same books was revolutionary for our partnership as executive and executive assistant. As I began to read the books that were shaping Don’s leadership philosophy, I was able to better understand how he approached leadership, problem-solving, and decision-making. I was able to be a better sounding board for Don and provide helpful feedback. It gave us a foundation for communication and a mutual understanding as we worked together to better our effectiveness and productivity. I’ve even gone on to use some of what I learned in other roles supporting other executives.

All of the books Don mentioned above were impactful to our strategic partnership for different reasons, but here are a couple of specific takeaways that stood out for me…

1. Essentialism: The Disciplined Pursuit of Less (McKeown) - If I had to choose the most impactful book I read, it would be this one. Executives have extraordinary demands on their time, and Essentialism provided a good case for delegation and putting your limited resource of time and energy toward the things that matter most. As an executive assistant, this book provided a platform for me to have in-depth conversations with Don about what was essential to him. This allowed me to be proactive in managing his calendar and gave me a better filter for tasks that should (and shouldn't) come across his desk.

2. Deep Work: Rules for Focused Success in a Distracted World (Newport) - Reading Deep Work was greatly instrumental in my understanding of the challenges Don faced in accomplishing larger tasks that required concentrated time and thought like preparing for quarterly all-hands presentations or leadership team strategic meetings. Even though we would block off time on his calendar to focus on these tasks, those blocks always seemed to get overridden by the day's fires. Through our discussions, we realized that Don needed to get away from the office to dive into deep work fully. We began to brainstorm creative solutions and even booked an Airbnb for him to work from for multiple days. Being out of the office allowed him to get into the rhythm of deep work, which enabled us to be better prepared for large meetings and to have more intentional and effective communication.

3. The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace (Chestnut) - Reading this book helped me to learn more about my own (and Don’s) motivations and wiring. It gave us a language and structure to understand each other better and work towards optimum communication. For example, I'm a Type One. I live in the balance between welcoming honest feedback (because I place a high value on continuous improvement) and being sensitive to criticism (because I'm already my own harshest critic). This always made for an interesting conversation during annual reviews. Having Don recognize this tension within me enabled him to provide feedback in a way that showed he truly cared about me as a person and my development.

Now, as an executive assistant, I know your life is busy and the idea of adding “read business books” to the list may feel overwhelming. As I began to incorporate this as part of my self-development routine, I discovered a few tips that helped make it easier…

Utilize your local library - Business books can be expensive, but I found that my local library had many of the books that Don was reading and I could check them out for free. As Don and I began having meaningful conversations around what we were both reading, he offered that I could also get a copy for myself when I got a book for him. If this isn’t something your executive offers, maybe it would be a good opportunity to have a conversation about your personal development and how reading the same books can help get you on the same page. If that is not an option, I definitely encourage you to check your local library for resources!

Audio Books - My life is often on the go and I rarely have time to just sit and read a book. However, listening to books on my daily commute or when I am cleaning, meal prepping, or walking the dog helps me to carve out space for reading while still meeting the responsibilities in other areas of my life.

Alternative Tools - If you are a visual learner, tools like ReadinGraphics can help you visually connect what you've learned. These resources can also serve as great reminders or summaries of content that you’ve read. If you don't have the time to read an entire book, I encourage you to find a resource that summarizes the information for you, allowing you to still learn and gain insights.

Focus on small actionable items - Sometimes it’s easy to get inspired by what you learn reading a business book but then stall when it comes to implementation. You won’t be able to put into action every great idea you get when reading a book. However, I would recommend looking for what is actionable today (without overhauling everything) and starting there. You’ll be surprised at how making even small changes can add up to significant improvement in your partnership’s productivity, effectiveness, and communication.

Emmre is executive assistant software created by an executive and assistant for executives and assistants. Emmre's mission is to help supercharge productivity and maximize the strategic partnership between executives and executive assistants.