Review

This book provides a great theoretical grounding in what it means to be conversational. The principles of conversation resonated with me and I’ll definitely use them going forwards. I found the practical side of the book a little underwhelming, some useful exercises and frameworks but I’m not entirely confident that I could execute off the back of reading this.

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Key Takeaways

The 20% that gave me 80% of the value.

• Don’t start by designing the UI. Designing the container first makes even less sense when the containers are starting to disappear.
• Interfaces that seem conversational on the surface might not be conversational in practice
• Conversation is the oldest interface. Let’s get the machines to play by our rules.
• If you take a conversational approach to interaction design…
• follow the existing deep principles of how humans interact with one another
• create systems that succeed on human terms., no matter the mode of interaction
• Conversation is context-dependent and intimate
• Moving from publishing to engaging in conversation can be scary to companies
• Before literacy the only way to sustain an idea was to share it, and speak it to another person in a way that they’d remember it. Orality was the first interface!
• Writing was originally publishing, it was one way
• Oral culture is immediate and social, literate culture promoted authority and ownership. Technology is bringing us together again.
• Immediate → no delay between idea and reception
• Socially aware and group minded → billions can get the same message in unison
• Conversational → more interactive and less formal
• Collaborative → communication invites and enables a response
• Intertextual → products of our culture reflect and influence one another
• From documents to events. Literary writing isn’t interactive. Designing human-centred interactive systems should be conversational not literary.
• If we approach communication as an assembly of content rather than interaction, customers who expect a conversation will be disappointed, they’ll feel like they’ve been handed a manual instead.
• Software is on a path to participating in our culture as a peer. Software will be enough when we can interact in a way that has the qualities of conversation.
• Interactive systems should evoke the best qualities of human communities:
• Active, social, simple and present (Not passive, isolated, complex or closed off)
• Move past ‘computer literacy’ → it’s on us to ensure all systems speak human fluently

• Conversation is the fundamental interface between people.
• Being context aware is essential.
• Making a customer learn a new interface to get value from your product is bad business
• Interfaces need to be simple, intuitive and as similar as possible.
• It’s not the mode of interaction but the meaning of the interaction that creates the value. So don’t feel the need to be unique on the interface.
• Pragmatics (mutual understanding of implicit rules and agreements) make successful conversations possible
• Context contributes to meaning beyond what words themselves convey
• In conversation, there’s a principle of cooperation. Find the goal, and do your part.
• Four conversational maxims: Quantity, Quality, Relation and Manner (Paul Grice)
• Quantity: just enough information
• Quality: be truthful
• Relation: be relevant
• Manner: be brief, orderly and unambiguous
• Bonus 5th: be polite (don’t impose, give options, make the listener feel good)
• 1973 paper “The Logic of Politeness” by Lakoff
• A conversational facade often forces humans to focus more on the limits of the technology than on achieving their goals

Translating the maxims for the machine.

• Cooperative: If there is no cooperation there is no conversation
• Stay on the side of the customer, don’t let the technology dictate the range of interactions
• Be goal-orientated: the most basic principle of interaction design. Who benefits from using this?
• Context-aware: the better a system demonstrates knowledge of context, the more conversational it can be. The ability to respond to context is the difference between documents and conversation.
• Quick and clear: speed is important. Getting an interaction over with quickly makes it delightful. Ambiguity slows everything down. Precision is something machines should be able to provide (bad error messages are ambiguous)
• Turn-based: conversation is an exchange that happens in turns. Functional conversations require an understanding of who’s turn it is (conference calls are bad). You also need to request and verify any information you need at the right time
• Truthful: Setting the right expectations, give clear verifiable information, prevent confusion.
• Polite: Respecting time, anticipating needs, offering choices, understanding goals and context.
• Error-tolerant: A conversational interaction is tolerant of faults, anticipates errors and recovers seamlessly

• Paradox of conversational interfaces: they over promise the level of cooperation and in the end, provide a less human experience.

• Key Moments of Interaction
• Introduction
• Establish identity
• Command interest
• Communicate value
• Make an emotional connection
• Build trust
• Offer a clear next step
• Orientation: Where am I?
• Navigation helps with orientation. James Kalbach’s Designing Web Navigation
• Expectation setting: will i Find what I need here?
• Orientation: “Where am I in this site?”
• Topic switching: “I want to start over.”
• Reminding: “My session got interrupted. What was I doing?”
• Boundaries: “What is the scope of this site?”
• Navigation represents choices, choices are decisions and decisions are work. Offer the right choices at the right times
• Action: What can I do?
• What does your product or service allow customers to do?
• Actions must be goal-orientated, context-aware.
• Actions must provide feedback
• Implications of the action must be clear and apparent
• The sequence of actions should be predictable and cooperative
• Make actions reversible or provide clear warnings
• Help users recover quickly
• Guidance: They system wants you to succeed
• Opportunities for guidance:
• Sales: will this product solve your problem?
• Instructions: hints and onboarding
• Contingency messages: getting people back on track, error messages
• Notifications: interruptions that occur outside the context of interaction
• Documentation: reference materials
• Progressive disclosure: offering just what’s needed for the task at hand
• Characteristics of helpful notifications:
• Well timed
• Concise and clear
• Personalised and relevant
• Deliver value and enable action
• Generate interest and reward trust
• How much onboarding do you need?
• How different is your system from others you customer uses?
• How conceptually complex is your system?
• How much effort does the customer have to put in before getting something useful?
• Do Poka-yoke: Mistake proofing
• Avoid making assumptions about what users want in favour of understanding real world context

• The personality and design should be woven tightly together (e.g. playful colours, animation and voice)
• Before you can create meaningful interfaces you need to do research: Listen to real people talk about the services you provide
• The goal isn’t to sound like a customer, but to be meaningful to your customer and trigger the right associations
• Learn to like people → like and value your customers. Appreciate their perspective.
• Clarify your values → you need clear values to create a personality with integrity
• Template:
• We will be successful when {outcome}
• We care about {idea or thing} because {reason}
• We care about {idea or thing} because {reason}
• We care about {idea or thing} because {reason}
• If we were a person serving our customer our job would be {the primary role your product plays}
• And customers would describe us as the most {adjective}, {adjective} and {adjective} of any in that profession
• We never want to come off as {negative adjective}, {negative adjective} and {negative adjective}
• Know your role → be professional. What kind of object would your product be?
• Personalities adopt different tones depending on subject matter and context:
• Identity: Are customers interacting with the company, service or agent?
• Expertise: How much will the system know? and about what?
• Mood and attitude: most are neutral and slightly positive.
• Relationship: Advisor, teacher, assistant or tool?
• Begin with the mood and state of mind of your customer
• Expose yourself to excellence → listen to your customers, but also read great language.
• The Imagists → a group of poets → common speech and novel rhythms to create clear, precise images
• Ezra Pound Imagists manifesto
• Use no superfluous word, no adjective, which does not reveal something.
• Don’t use such an expression as “dim lands of peace.” It dulls the image. It mixes an abstraction with the concrete. It comes from the writer’s not realizing that the natural object is always the adequate symbol.
• Go in fear of abstractions. Don’t retell in mediocre verse what has already been done in good prose. Don’t think any intelligent person is going to be deceived when you try to shirk all the difficulties of the unspeakably difficult art of good prose by chopping your composition into line lengths.

• The degree to which a system feels human and goal-oriented in its interactions reflects how well its creators interacted with each other.
• Systems with visible seams are the results of handoffs and unresolved arguments
• Be conversational in your approach to design
• Cooperative, goal-orientated, context-aware, quick and clear, turn-based, truthful, polite, error-tolerant
• Give it your minimum → step away from feature design until you know the problem
• Minimum Viable Conversation Worksheet:

Deep Summary

Longer form notes, typically condensed, reworded and de-duplicated.

Introduction

• Many companies get nervous about copy. They have a single copywriter and approve all every word.
• Don’t conflate the value of the system it’s representation as a UI.
• Don’t start by designing the UI.
• Value doesn’t come from rectangles of features.
• Designing the container first makes even less sense when the containers are starting to disappear.
• A number of emerging technologies are changing how we interact with technology (cloud, IOT, smart phones, chat apps, machine learning)
• Conversation as an interface. Language as part of design.
• Interfaces that seem conversational on the surface might not be conversational in practice
• Conversation is the oldest interface. Let’s get the machines to play by our rules.
• Overly literal interpretations of the idea are leading to systems that are hard to use.
• VUI: Voice User Interfaces
• If you take a conversational approach to interaction design…
• follow the existing deep principles of how humans interact with one another
• create systems that succeed on human terms., no matter the mode of interaction
• A good conversation begins with an unspoken agreement and succeeds with cooperation towards a goal

Chapter 1: The Human Interface

• How we message is how we talk now.
• Why is messaging so popular? What attributes does it have?
• Feels like direct human contact
• Doesn’t require continuous attention
• Provides the give-and-take of conversation
• Unpredictable lag and irregular breaks (intermittent reward & dopamine)
• What can we learn from the draw of these bite-sized interactions?
• Always available human-connection is powerful
• Dopamine triggers
• Without exciting UI features messages can deliver personality, humour and narrative
• Imbuing interfaces with the attributes of conversation can be powerful
• Conversation is context-dependent and intimate
• Moving from publishing to engaging in conversation can be scary to companies
• The way humans use language (words) should anchor the foundation of all interactions with digital systems

• Prior to mechanical production, literacy was limited to the elite… by the time and cost of hand-copying manuscripts
• When our communication technology changes our culture changes too. But we’re still oral deep to our core.
• Before literacy the only way to sustain an idea was to share it, and speak it to another person in a way that they’d remember it. Orality was the first interface!
• Literacy decoupled shared knowledge from social interaction. Enabled us to transmit information through time.
• Writing was originally publishing, it was one way
• Oral culture is immediate and social:
• Spoken words are events that exist in time
• All knowledge is social, and live in memory
• Individuals need to be present to exchange in knowledge or communicate
• The community owns knowledge, not individuals (I wonder if LLMs will revert us back to this world).
• There are no dictionaries or authoritative sources
• Literate culture promotes authority and ownership:
• The printed text is an independent physical object, can be separated from writer
• Portable printed works enable individual consumption
• Print creates a sense of private ownership of words (plagiarism is possible)
• Print fosters a sense of closure
• Technology brought us together again (Secondary Orality)
• Immediate → no delay between idea and reception
• Socially aware and group minded → billions can get the same message in unison
• Conversational → more interactive and less formal
• Collaborative → communication invites and enables a response
• Intertextual → products of our culture reflect and influence one another
• From documents to events.
• Pages and documents are how information occupies space.
• Events are how information occupies time.
• Literary writing isn’t interactive. Designing human-centred interactive systems should be conversational not literary.
• If we approach communication as an assembly of content rather than interaction, customers who expect a conversation will be disappointed, they’ll feel like they’ve been handed a manual instead.
• Software is on a path to participating in our culture as a peer. Software will be enough when we can interact in a way that has the qualities of conversation.
• Interactive systems should evoke the best qualities of human communities:
• Active, social, simple and present (Not passive, isolated, complex or closed off)
• Thinking about human-computer interactions from a screen based perspective was never truly human-centred.
• The ideal interface isn’t noticeable at all → shrink the friction from thought to action
• Move past ‘computer literacy’ → it’s on us to ensure all systems speak human fluently

Chapter 2: Principles of Conversational Design

• You already know how to be human and sound human
• Making interactions with digital systems feel human is the hard part
• Unchecked, machine logic dominates
• Make it humane by designing it according to the principles of conversation and human interaction
• Definitions:
• Interface: the boundary over which two systems exchange information
• Interaction: the means by which systems influence each other
• People interact with one another because they get value from it. An interface is a way for a human to interact with another system and get value from it
• The interface is effective if it helps two parties in an interaction get what they need from each other
• Conversation is the fundamental interface between people.
• Being context aware is essential.
• Making a customer learn a new interface to get value from your product is bad business
• Interfaces need to be simple, intuitive and as similar as possible.
• Conversation is the interface most people know how to use
• It’s not the mode of interaction but the meaning of the interaction that creates the value. So don’t feel the need to be unique on the interface.
• We engage in conversation daily, but that doesn’t make us good at designing conversational interactions.
• Pragmatics (mutual understanding of implicit rules and agreements) make successful conversations possible
• Context contributes to meaning beyond what words themselves convey
• In conversation, there’s a principle of cooperation. Find the goal, and do your part.
• Four conversational maxims: Quantity, Quality, Relation and Manner (Paul Grice)
• Quantity: just enough information
• Quality: be truthful
• Relation: be relevant
• Manner: be brief, orderly and unambiguous
• Bonus 5th: be polite (don’t impose, give options, make the listener feel good)
• 1973 paper “The Logic of Politeness” by Lakoff
• A conversational facade often forces humans to focus more on the limits of the technology than on achieving their goals
• Translating the maxims for the machine.
• Cooperative: If there is no cooperation there is no conversation
• Stay on the side of the customer, don’t let the technology dictate the range of interactions
• Be goal-orientated: the most basic principle of interaction design. Who benefits from using this?
• Context-aware: the better a system demonstrates knowledge of context, the more conversational it can be. The ability to respond to context is the difference between documents and conversation.
• Quick and clear: speed is important. Getting an interaction over with quickly makes it delightful. Ambiguity slows everything down. Precision is something machines should be able to provide (bad error messages are ambiguous)
• Turn-based: conversation is an exchange that happens in turns. Functional conversations require an understanding of who’s turn it is (conference calls are bad). You also need to request and verify any information you need at the right time
• Truthful: Setting the right expectations, give clear verifiable information, prevent confusion.
• Polite: Respecting time, anticipating needs, offering choices, understanding goals and context.
• Error-tolerant: A conversational interaction is tolerant of faults, anticipates errors and recovers seamlessly.
• Paradox of conversational interfaces: they over promise the level of cooperation and in the end, provide a less human experience
• Don Norman wanted to leave machines to be machines, and celebrate that we’re different and good at different things

Chapter 3: The Principles in Practice

• Author highlights Google Search as doing the principles well:
• cooperative, goal-orientated, quick and clear, turn-based and error tolerant
• Many website put the burden of providing clean input data onto the user. Google fixes your mistakes, makes you feel like it’s on your side.
• Because it’s so easy to make a query, there’s little downside in running repeated searches.

• Context makes the conversation
• Drawbacks of using chat:
• Lack of context awareness
• Takes more time
• Unpredictable
• Not error-tolerant
• Avoid making assumptions about what users want in favour of understanding real world context
• Personality brings a conversation to life: personality is a set of stable characteristics that manifest in behaviour and responses. A distinctive and appropriate personality brings the principle of conversational design to life.

Chapter 4: The Power of Personality

• It takes effort and attention to create a personality
• Some brands create characters (people anthropomorphise). Google didn’t, you’re talking to all of Google. Who is Alexa?
• You may have to select a gender and offer a selection
• The personality and design should be woven tightly together (e.g. playful colours, animation and voice)
• Before you can create meaningful interfaces you need to do research: what are your users emotionally connected to?
• Listen to real people talk about the services you provide
• Understand what they value and how they talk about it
• Understand their full range of emotional states and context
• Anticipate the negative emotions (anxious, confused, overwhelmed, skeptical, bored, angry, frustrated)
• Listen for their tasks - what they expect the system to do
• As you develop personality and vocabulary of your interface - remember your goal isn’t to sound like a customer, but to be meaningful to your customer and trigger the right associations
• Learn to like people → like and value your customers. Appreciate their perspective.
• Clarify your values → you need clear values to create a personality with integrity
• Template:
• We will be successful when {outcome}
• We care about {idea or thing} because {reason}
• We care about {idea or thing} because {reason}
• We care about {idea or thing} because {reason}
• If we were a person serving our customer our job would be {the primary role your product plays}
• And customers would describe us as the most {adjective}, {adjective} and {adjective} of any in that profession
• We never want to come off as {negative adjective}, {negative adjective} and {negative adjective}
• Know your role → be professional. What kind of object would your product be?
• Personalities adopt different tones depending on subject matter and context:
• Identity: Are customers interacting with the company, service or agent?
• Expertise: How much will the system know? and about what?
• Mood and attitude: most are neutral and slightly positive.
• Relationship: Advisor, teacher, assistant or tool?
• Personality is difficult internationalisation. Transcreation not translation will be required. Transcreation is about creating a message that evokes the same emotions and has the same implications as the previous one.
• Humour is critical to human communication. Although it’s hard to codify. Humour depends on context and timing. Playfulness can backfire if the context isn’t right.
• Begin with the mood and state of mind of your customer!
• Expose yourself to excellence → start going where your customers go and look for examples of great language. How do people really talk?
• The Imagists → a group of poets → common speech and novel rhythms to create clear, precise images
• Ezra Pound Imagists manifesto
• Use no superfluous word, no adjective, which does not reveal something.
• Don’t use such an expression as “dim lands of peace.” It dulls the image. It mixes an abstraction with the concrete. It comes from the writer’s not realizing that the natural object is always the adequate symbol.
• Go in fear of abstractions. Don’t retell in mediocre verse what has already been done in good prose. Don’t think any intelligent person is going to be deceived when you try to shirk all the difficulties of the unspeakably difficult art of good prose by chopping your composition into line lengths.
• Avoidably ugly words:
• Avoid: compelling, helpful, quick, innovative, important, check out these hot topics, oops
• Avoid: submit (describe the specific action), my x (my account), click here
• Things that belong to the user should be yours, things that belong to the company should be ours… anything else that’s part of the experience doesn’t need a positive pronoun at all

Chapter 5: Getting it Done

• Any organization that designs a system (defined broadly) will produce a design whose structure is a copy of the organization's communication structure. Conway’s Law
• The degree to which a system feels human and goal-oriented in its interactions reflects how well its creators interacted with each other.
• A harmonious interface is the product of functional and inter-disciplinary communication and clear well-informed decision making.
• Systems with visible seams are the results of handoffs and unresolved arguments
• Be conversational in your approach to design
• Cooperative, goal-orientated, context-aware, quick and clear, turn-based, truthful, polite, error-tolerant
• Give it your minimum → step away from feature design until you know the problem
• How will the customer express their need? How will you understand their intention?
• What exchange happens at that point?
• What does the customer have to give you in order for you to solve their problem?
• What choices do you give them?
• How do you close the conversation by impressing the customer that you gave them something of value?
• How do you leave the door open to future interactions?
• Minimum Viable Conversation Worksheet:

• Working Tactics:
• Reiterate goals and principles
• Work in real time
• Encourage candid feedback
• Include decision-makers
• Talk about decisions over artefacts
• Never permit lorem ipsum → consistently iterate on language instead
• Read aloud every word