Agile Conversations
Transform Your Conversations, Transform Your Culture

Agile Conversations is a practical, step-by-step guide to using the human power of conversation to achieve truly Agile results. Stop following meaningless rituals that don’t deliver results. Instead, unleash the unique human power of conversation to build effective, high-performing teams.


by Douglas Squirrel and Jeffrey Fredrick

“I think of this highly practical and immediately applicable book as the lost instruction manual to the most powerful and effective Agile tool we don’t even realize we have: Conversations. If you want to be successful with Agile, RTFM: Read This Fabulous Manual.”

— Alberto Savoia, Google's First Director of Engineering and Author of The Right It 
A Successful Digital Transformation Must Start with A Conversational Transformation
Today, software organizations are transforming the way work gets done through practices like Agile, Lean, and DevOps. But as commonly implemented as these methods are, many transformations still fail, largely because the organization misses a critical step: transforming their culture and the way people communicate.

Agile Conversations is a practical, step-by-step guide to using the human power of conversation to achieve truly Agile results. Douglas Squirrel and Jeffrey Fredrick, software leaders and executive consultants, show readers how to have the Five Conversations to help teams build trust, alleviate fear, build a compelling “why,” make commitments, and be accountable. These five conversations give teams everything they need to reach peak performance, and they are exactly what’s missing from too many teams today.

Stop following meaningless rituals that don’t deliver results. Instead, unleash the unique human power of conversation to build effective, high-performing teams.

"Agile Conversations provides much needed guidance on how to have the key discussions that form the foundation for strong and resilient working relationships, as well as a toolbox full of techniques for troubleshooting when conversations go awry. Full of practical, real-world examples, this book is a must read for anyone who has ever been frustrated or puzzled by  interactions at work.”

Elisabeth Hendrickson, Technology Executive and Author of Explore It!
About the Authors

Douglas Squirrel has been coding for 40 years and has led software teams for 20. He uses the power of conversations to create dramatic productivity gains in technology organizations of all sizes. Squirrel’s experience includes growing software teams as a CTO in startups from fintech to e-commerce; consulting on product improvement at over 60 organizations in the UK, US, and Europe; and coaching a wide variety of leaders in improving their conversations, aligning to business goals, and creating productive conflict. He lives in Frogholt, England, in a timber-framed cottage built in the year 1450.


Jeffrey Fredrick is an internationally recognized expert in software development with over 25 years’ experience covering both sides of the business/technology divide. His experience includes roles as Vice President of Product Management, Vice President of Engineering, and Chief Evangelist. He has also worked as an independent consultant on topics including corporate strategy, product management, marketing, and interaction design. Jeffrey is based in London and is currently Managing Director of TIM, an Acuris Company. He also runs the London Organisational Learning Meetup and is a CTO mentor through CTO Craft.


“The number of conversations at a party doesn’t make it a better party; the quality of the conversations does. Many books have been written about improving process and product in companies. I’m so glad this book finally addresses the people aspect: Learn to ask the hard questions, leave your bias at the door, and improve your own communication with this practical guide. If it’s hard, do it more often!”

— Patrick Debois, Founder of DevOpsDays
Downloads & Extra Materials

“This book provides an engineer’s approach to monitoring, troubleshooting and debugging conversations. Squirrel and Jeffrey always come across as incredibly mindful listeners and thoughtful discussion partners, and now I know why. Heuristics such as the Question Fraction are amazing—at the same time simple and memorable and incredibly insightful. Read this book to turn your communication skills into superpowers.”

— Gojko Adzic, Partner at Neuri Consulting
Squirrel & Jeffrey at DOES19 Las Vegas

Conversational Transformation

Have you bought all the books, held the trainings, followed all the practices—but you didn’t get the promised results? If so, there are almost certainly several difficult conversations you have been avoiding that could change your results dramatically. The good news is that there are proven, concrete steps you can take today to start a conversational transformation that will address these problems. 

“If you’re looking for a practical framework and techniques that will help fix broken team communication and dysfunctional culture, then you should read Agile ConversationsGoing beyond simple diagnosis, this handbook walks you through the Five Conversations you need to embrace in order to transform a broken culture into one that’s healthy and high-performing.”

—Paul Joyce, Founder and CEO of Geckoboard
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