The Five Best Books to Read with Your EA

As an Executive, I’m sure reading (or, if you’re like me, listening to) books related to the latest trends in leadership and time management. However, you may be missing out on one of the best ways to build a better working relationship with your Executive Assistant (EA).

I’m talking about reading some of the same books. It’s a practice my EA and I began somewhat accidentally a few years ago. One day, I had Kristie, my EA, order me a book I’d heard a lot about, and Kristie decided to order herself a copy. When I began talking about what I was learning from the book, Kristie surprised me by giving her take on the same content.

Since then, we’ve 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 explaining 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 also read Cal Newport’s book. Or 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.

It literally puts us on the same page. 

If you’re an EA 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 as 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 EA. Kristie and I tried once 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 herself up a copy (or, other times, Kristie has taken the initiative and ordered an additional 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 EA to read together.

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

There was a time in my life when I had a difficult time saying “no” to requests and, as a result, I found myself constantly overworked, exhausted, and – strangely enough – not very productive. I like to divide self-help/leadership books into two categories – those that expose you to new ideas and those that reveal what you already know but you haven’t yet figured out 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 EA should be obvious. As the gatekeepers of your schedule and calendar, your EA 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 – 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 of time 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 EA 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 – 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 four philosophies (Ruinous Empathy, Manipulative Insincerity, Obnoxious Aggression, and Radical Candor) and encourages her readers to move toward a healthy state where they can 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. Oftentimes, I’d keep 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 reading Radical Candor will 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 Radical Candor. And because you work closely with your EA, you should get a copy for them as well. One of the most important takeaways for us in 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 – 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 Meyers-Briggs) constructed around nine “Types” that encourages personal growth and development. The nine Types are conveniently labeled as a number (1-9), and each Type has its own set of strengths, weaknesses, constraints, and healthy and unhealthy behaviors.

Beatrice Chestnut’s The 9 Types of Leadership takes the principles of the Enneagram and applies it 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 EA’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 EA’s number (and have your EA do the same). This book is a perfect example of giving you and your EA a vocabulary to discuss the ways in which your distinct personalities may complement each other and clash together in your working relationship. 

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

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 I 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 off as too 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 EA.  You don’t even have to discuss the books together, but I guarantee that if you read the same books you will find it beneficial.  So whether it is the five I listed above, or some other books you’re reading or have impacted you, buy a copy for your EA. A helpful policy I’ve enacted is that Kristie has a standing offer to purchase a copy of any book I’m reading for work for herself.  

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


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