Talk Like You Mean It: A Designer’s Guide to Conversational Interfaces

Note: This book is being published chapter by chapter as a living draft. Sections marked TBD are placeholders for material that is still in development, and the structure may change as the ideas evolve. What you’re reading here is part of an ongoing writing and design process. The final compiled version will be refined, expanded, and polished based on these early drafts.

Chapter 1: Why We Talk to Machines

Status: Published

  • The Rise of the Conversational Interface
  • More Than a Chat Bubble
  • The Dance of Voice and Interface

Chapter 2: Intentional Interfaces

Status: Published

  • What Do Users Actually Want?
  • The Who / What / How Framework
  • The Messiness Between Goals and Intents
  • Designing for Clarity Without Killing Personality

Chapter 3: Thinking in Conversations

Status: Published

  • Conversations as UX, Not Just Dialogue
  • Mechanical Speech Chains vs. Human Chatter
  • Trust, Repair, and Emotional Nuance
  • Where Conversations Break (and How to Fix Them)

Chapter 4: Personality by Design

Status: Being Written

  • The Persona / Personality Divide
  • Writing Like a Character, Not a Robot
  • The Power of Consistency
  • Tone, Power, and Micro-Behaviors
  • When “Memorable” Becomes a Problem
  • Branding Through Conversation
  • Interaction Goals as Personality Anchors
  • Design Traps and Trade-Offs
  • Stories in Practice

Chapter 5: Designing Prompts: Small Words, Big Impact

Status: Not Started

  • What a Prompt Really Is
  • Prompt Types (and When to Use Them)
  • Cue Design: Pointing the Way Forward
  • The Weight of Words
  • Tone and Personality in Prompts
  • Breaking the Rules on Purpose
  • When Prompts Misfire
  • Write Like You Mean It

Chapter 6: Conversations That Grow Over Time

Status: Not Started

  • Why Conversations Need Memory
  • Memory Models: Short-Term vs. Long-Term
  • Multisession Interactions
  • Personalization Without the Creepy
  • When Forgetting Is a Feature
  • Growth With Boundaries

Chapter 7: Designing Across Ecosystems

Status: Not Started

  • Why Ecosystems Matter
  • Multimodal Interfaces: Voice, Touch, Text, Visuals
  • Multichannel Journeys: One Bot, Many Places
  • Shared Devices and Multiuser Interactions
  • Designing Across Time, Devices, and Contexts
  • Accessibility and Inclusion in Complex Systems
  • When Ecosystems Collide
  • Design Principle in a Sentence

Chapter 8: Prototyping Conversations

Status: Not Started

  • Why Prototype a Conversation?
  • Sketching Dialogue: Not Just Screens
  • Visualizing Dialogue Flows
  • Roleplaying, Scripting, and Playtesting
  • Failure Loops, Edge Cases, and the Unexpected
  • From Prototype to Vertical Slice

Chapter 9: Prototyping to Production

Status: Not Started

  • Why Prototyping Matters
  • Usability Testing for Interfaces That Talk
  • Metrics Beyond Clicks: What Success Sounds Like
  • Collaboration Across Roles
  • Accessibility, Bias, and Ethical Guardrails
  • Iterating Toward Launch

Chapter 10: From Launch to Lifelong Learning

Status: Not Started

  • The Myth of “Done”
  • Iteration Isn’t Optional
  • Signals in the Noise
  • Adding Without Breaking
  • Maintenance as Design Discipline
  • Growth with Guardrails

Chapter 11: Designing by Principles, Avoiding Pitfalls

Status: Not Started

  • Principles in Practice
  • From Idea to Implementation
  • Where Things Break (and What to Do About It)
  • Funny Failures, Serious Lessons
  • Design Exercises You Can Steal
  • The Workshop Method

Chapter 12: The Future Has a Voice

Status: Not Started

  • The Age of Ambient Tech
  • Agents vs. Products
  • Where Chatbots End and Interfaces Begin
  • Designing With AI, Not Just For It
  • Ethics in an Always-On World
  • A Speculative Look Ahead

Author

I'm Tony, an Experience Designer and storyteller who believes the best digital experiences feel invisible yet transformative. I run IDE Interactive, teach at Columbia College Chicago, and love sharing what I've learned along the way.