We all find ourselves in situations where a question needs to be asked, but we hesitate. Whether it’s addressing a difficult topic at work, seeking clarity from someone who’s being evasive, or simply wanting an honest answer to a personal issue, knowing how to ask is often more important than the question itself.

How to Ask Awkward Questions explores the art of phrasing, timing, and tone — helping you approach uncomfortable conversations with confidence rather than fear. Drawing on years of real-world observation and insight, Matthew J Toomer shows how good communication is less about confrontation and more about understanding human behaviour.

The book examines how body language, choice of words, and emotional cues can completely alter how a question is received. You’ll learn practical techniques to frame questions in a way that gets people talking rather than shutting down, turning awkward moments into productive dialogue.

Each chapter focuses on a common real-life situation — from workplace honesty and customer service to personal relationships and public accountability. Whether you’re interviewing, negotiating, or simply trying to get a straight answer, this book provides a calm, structured approach that gets results without creating conflict.

Grounded, intelligent, and often surprisingly humorous, How to Ask Awkward Questions is both a practical handbook and a reflection on how communication shapes trust. It’s written for anyone who believes that asking the right questions is the first step toward genuine understanding.

Available soon to download.
Compatible with Kindle, Apple Books, and all standard e-readers.