Amanda Haworth

5 Best books on how to make conversation with anyone 2019

As any expert would tell you, making conversation is a learned skill, not a naturally inherited gift.

Fortunately for us, these experts have granted us the gift of putting their wisdom into writing so that we mortals can learn from their masterful ways.

The following five books are filled with tips, strategies, and advice for having nearly any type of conversation you can imagine.  From small talk to the inevitable tough conversations, these books will help you develop the skills you need to make conversation with any person in any situation.

1. “If I Understood You, Would I Have This Look on My Face?: My Adventures in the Art of Relating and Communicating”

This book, written by actor Alan Alda, is not only a helpful guide but also an enjoyable read.  Filled with humorous personal anecdotes and relatable examples, this New York Times Bestseller is first on my list.  Alda focuses on the importance of empathy in conversation, explaining how to really listen to the other person to better relate to them.  In an era when we communicate just as much (if not more) digitally than we do in person, this book takes us back to the reason why we communicate and how we can effectively use conversation to do so.

Find If I Understood You, Would I Have This Look on My Face? here.

2.  “The Fine Art of Small Talk”

This book by nationally recognized communication expert Debra Fine is second on the list. Small talk is the gateway to deeper conversation and can be used in virtually any situation.  Written specifically for people who are shy or nervous when it comes to making conversation, Fine offers tips for taking small talk beyond the weather and “them Yankees.” According to Amazon reviewer Edward Barton, the advice given in Fine’s book includes “immediately actionable confidence builders and lists of topics and questions.”

Find The Fine Art of Small Talk here.

3.  “Crucial Conversations: Tools for Talking When the Stakes are High”

This book boasts of being written by four New York Times Bestselling Authors: Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.  While the term “crucial conversations” can conjure images of frenzied whisperings about whether or not to push the red button, this category of conversation is defined by the authors as being the conversations you have on a day-to-day basis that affect your life.  Whether you’re up for a promotion at work, having an important conversation about the future of a personal relationship, or a college student trying to convince your parents to fund a spring break trip, this book addresses strategies that are applicable in any stage of life.

Find Crucial Conversations: Tools for Talking When the Stakes are High here.

4.  “Conversationally Speaking: Tested New Ways to Increase Your Personal and Social Effectiveness”

This book by Alan Garner takes a closer look at how to have conversations that accomplish what you need them to do. From teaching you to start a conversation to providing instructions for getting others to talk as well, Garner looks at the act of conversing from all sides to ensure that you are getting the most out of your conversations.  Garner also address the fear that many of us have when it comes to making conversation and being social in general: getting rejected.  Amazon reviewer JT commented, “This book provides a solid foundation for improving on anyone’s ability to converse. . . The book is solidly pragmatic and easy to follow.”

Find Conversationally Speaking here.

5.  “Difficult Conversations: How to Discuss What Matters Most”

Although last on the list, this book is one of the most important reads for anyone looking to be a skillful conversationalist.  Unfortunately, difficult conversations are an inescapable part of life, and the ability to handle them well can help determine their outcomes.  Written by Douglas Stone, Bruce Patton, and Sheila Heen, this book is a practical approach to having the conversations that you’d probably rather avoid.  Including important topics such as avoiding defensiveness, “reading between the lines”, and using problem-solving skills to make the conversation productive, this book is a necessary addition to any conversationalist’s library.

Find Difficult Conversations: How to Discuss What Matters Most here.

As the number one means of human communication, conversations are a necessary part of life– so you might as well be good at it, right? Developing your conversation skills will not only make socializing easier and more fun, but it will also increase your success in your personal and professional lives.

Found any other good reads on making conversation? Drop your favorite titles in the comments!

Amanda Haworth

Amanda is an introvert who's experienced too many awkward moments (of her own making) to count. Amanda has a cat, a coffee obsession, and more books than one person should reasonably own. She holds a Bachelor of Science degree in Human Development and Learning from the University of Memphis in Memphis, TN, where she did extensive study of lifespan psychology. Amanda wrote for's SpouseBuzz blog before joining Social Pro.

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