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Content Design
for the 

Conversational UI
Design & Content Conference 2019
Melanie Seibert
Sr. Content Strategist, WillowTree
@melanie_seibert
2
3
Hey Google, 

make it warmer.
4
September 2018:
24% of U.S. households

own a smart speaker
Source: Nielsen
4
5
December 2018:
2.5 billion digital voice 

assistants in use
Source: Juniper Research
5
Voice Platform Marketing
If you haven’t encountered a
conversational interface yet, 

you will.
6
7
Content Design for the Conversational UI
1. The Conversational UI
2. The Design Process
3. Easy Ways to Explore
Content Design for the Conversational UI
8
A type of user interface consisting
primarily of content.
The Conversational UI
Content Design for the Conversational UI
9
Content is the design.
You’re the designer.
The Conversational UI
Content Design for the Conversational UI
10
1. Text
2. Voice
3. Multimodal
3 Formats
Content Design for the Conversational UI
• Facebook Messenger
• Slack
11
Text
Content Design for the Conversational UI
12
Voice
• Amazon Alexa
• Google Home
• Apple Siri
• Microsoft Cortana
13
Voice + Text
Multimodal
Done. Your
alarm has been
set for 6 a.m.
14Typing speed: Brown, CM (1998). Human-Computer Interface Design Guidelines.
Speaking speed: Yaun, Liberman, Cieri (2006). “Towards an Integrated Understanding of Speaking Rate in Conversation.”
Typing
Speaking 130 wpm
40 wpm
Read300 wpm
“Speed Reading," The University of Chicago Student Health and Counseling Services, 2017. 15
Listen130 wpm
Intents Entities
What’s the best place to eat 

in Vancouver that’s not too pricy?
best place to eat
Vancouver not too pricy?
Find food best
Vancouver
not too pricyAdditional Context
Location
Previous reviews
Allergies
1 2 3
Analysis4Contextual
Action Fulfillment
56
Feedback 

Confirmation or request
for Additional Information
Action
Call to any relevant APIs
API
Anatomy of a Conversation
Recording Conversion to TextUser Input
System Output
“What’s the best 

place to eat in 

Vancouver 

that’s not 

too pricy?”
16
Intents Entities
Find food best
Vancouver
not too pricyAdditional Context
Location
Previous reviews
Allergies
1 2 3
Analysis4Contextual
Action Fulfillment
56
Feedback 

Confirmation or request
for Additional Information
Action
Call to any relevant APIs
API
Anatomy of a Conversation
Recording Conversion to TextUser Input
System Output
“What’s the best 

place to eat in 

Vancouver 

that’s not 

too pricy?”
17
What’s the best place to eat 

in Vancouver that’s not too pricy?
best place to eat
Vancouver not too pricy?
18
Content Design for the Conversational UI
1. The Conversational UI
2. The Design Process
3. Easy Ways to Explore
“If you approach a new piece of web
content with ‘how shall I write this?’, that’s
writing or editorial. 

If you approach it from ‘how am I going to
get this across to the audience in the best
way possible?’, that’s content design.”
19
Sarah Richards 

Author of Content Design
What is Content
Design?
Where Content
Strategy and 

Product Design
overlap.
20
Content Design for the Conversational UI
The Design Process
Content Design for the Conversational UI
Start with data
21
“Can I
replace the handle
User Input
on my ?”product
Customer
Service Logs
Interviews
Content Audit
22
Content Design for the Conversational UI
23
Content Design for the Conversational UI
The Design Process
Content Design for the Conversational UI
Write a user story
for each intent
24
What’s a User Story?
“A user story is a way of pinning down what
the team needs to do… without telling them
how to do it.”
Sarah Richards | Content Design
25
User Story:
“As a _________________,

I want to _________________,
So that I can _________________.”
26
User Story:
“As a product user,

I want to know whether I can replace the handle,
So that I can avoid having to buy a new product
when the handle breaks.”
27
The Design Process
Content Design for the Conversational UI
Prototype the
conversation
28
“Wizard of Oz” role-play 

(on Slack).
The Design Process
Content Design for the Conversational UI
Design the Flow
30
Content Design for the Conversational UI
Flows to design
Golden Path
The designed intents.


Entry Point
How is your bot invoked?


Error Paths
Can the bot recover when it doesn’t
understand or receive input?
Escalate to a Human
When should a person take over?


Linking to Accounts & Other Platforms
How do you need to integrate with other
services? Examples include purchase, add to
shopping list, message someone, call someone.
31
Content Design for the Conversational UI
Flow chart.
32
Content Design for the Conversational UI
33
Content Design for the Conversational UI
34
Content Design for the Conversational UI
35
The Design Process
Content Design for the Conversational UI
Train the Bot
36
User interviews.
Training data generation 

(on Slack).
38
The Design Process
Content Design for the Conversational UI
Design the
Personality
39
Example:
Westminster Catechism
40
WHO WE ARE WHO WE’RE NOT
Bloomstein’s 

“messaging architecture” 

method
✖️✔️
42
1. Supportive
2. Optimistic
3. Formal
4. Humorous
5. Motivated
Personality Framework
43
How…
…is it?
Supportive
I root for you. I will try to help you
achieve your goals rather than
pursuing my own agenda.
Opposite: adversarial
How…
…is it?
44
Personality Framework
Personality Framework
Optimistic
I speak in positive terms. I try to
see the upside of everything.
Neutral: realistic
Opposite: pessimistic
How…
…is it?
45
Personality Framework
Humorous
I like to entertain and amuse you—
and myself.
Opposite: serious
How…
…is it?
46
Motivated
I’m enthusiastic and excited about
our conversation.
Opposite: reserved
Personality Framework
How…
…is it?
47
Personality Framework
Formal
I carefully observe rules of
etiquette and present myself in a
“highbrow” manner.
Opposite: casual
How…
…is it?
48
Supportive
I root for you. I will try to help you
achieve your goals rather than
pursuing my own agenda.
• Opposite: adversarial
Optimistic
I speak in positive terms. I try to
see the upside of everything.
• Neutral: realistic
• Opposite: pessimistic
Humorous
I like to entertain and amuse you—
and myself.
Opposite: serious
Motivated
I’m enthusiastic and excited
about our conversation.
• Opposite: reserved
Formal
I carefully observe rules of
etiquette and present myself
in a “highbrow” manner.
• Opposite: casual
Personality Framework
How…
…is it?
49
0
0.5
1
1.5
2
2.5
3
3.5
4
4.5
5
Supportive
Humorous
FormalMotivated
Optimistic
Golden	path Error Entry	&	exit
Optimistic
Supportive
Humorous
FormalMotivated
Bot

Personality
——— Golden path
——— Error
——— Entry & Exit
51
Content Design for the Conversational UI
Example: Designed Intents
User
First Draft: WillowTree Bot
“Currently I am configured to discuss
myself, and answer whatever questions
you might have about how I work, 

what I am, what I can do, how to
configure me, and so on.”
Formal: longer, uses passive voice.
Realistic: focuses on what it can do right now.
Reserved: sticks to the facts.
“What types of things
do you know about?”
52
Content Design for the Conversational UI
Example: Designed Intents
User
Revision: WillowTree Bot
“Right now, I know about myself.
But I can extend my database to
learn about any topic. Do you
have any suggestions?”
Shorter, less formal.
Optimistic: focuses on what it can do in the future.
Motivated: interested to learn about your domain.
“What types of things
do you know about?”
The Design Process
Content Design for the Conversational UI
Create and
Refine Scripts
53
54
Content Design for the Conversational UI
Designing for Modality
5 5
Content Design for the Conversational UI
Voice Tip
Manage content density
with “landmarking.”
Amazon Alexa Skills Kit Glossary 56
Content Design for the Conversational UI
• Establishes trust
• Supports a natural dialogue
Voice Tip
Manage content density
with “landmarking.”
Horoscope for what sign?
Do:
57Amazon Alexa Skills Kit Glossary
Ask Astrology Daily 

for my horoscope.
Content Design for the Conversational UI
How to Simplify Your Responses - Amazon Alexa Voice Design Guide
Manage content density
with “landmarking.”
58
Do:
At 10 a.m., you have the

weekly status meeting 

with Rachel and Natasha.
Don’t:
You have the weekly status

meeting with Rachel 

and Natasha at 9 a.m.
What’s happening 

at 10 a.m.?
Voice Tip
Content Design for the Conversational UI
Example: Cortana
59
Manage content density
with “landmarking.”
Voice Tip
How long does it take to 

get to the Richmond airport?
Content Design for the Conversational UI
The cheeses you may like are cheddar,
gouda, Jarlsberg, porter cheddar, St. Agur
blue cheese, gorgonzola, brie, gruyere,
sharp cheddar, and reggiano parmesan.
Amazon Alexa Voice Design Guide 60
Don’t:
Do:
Here are the cheeses you may 

like: cheddar and gouda, as well 

as gorgonzola, parmesan, 

and brie.
Use “chunking” 

to aid comprehension.
Voice Tip
Content Design for the Conversational UI
Use shorter responses. Example: Cortana
61
Voice Tip
Are there any restaurants

open right now?
Content Design for the Conversational UI
Provide clear choices.
Amazon Alexa Voice Design Guide 62
Voice Tip
Would you like
brie or gouda?
Don’t:
Do:
We have brie or gouda.
Which would you like?
Content Design for the Conversational UI
Screen Tip
Use timing to break up
longer utterances.
63
Content Design for the Conversational UI
64
Content Design for the Conversational UI
65
Content Design for the Conversational UI
66
Content Design for the Conversational UI
Use Quick Replies
(aka “chips”).
Facebook Messenger
Google Assistant
Screen Tip
67
Content Design for the Conversational UI
Take advantage of web links.
Zulily on Facebook Messenger
Screen Tip
68
Content Design for the Conversational UI
Multimodal Tip
“Design prompts for both the ear and the eye. It’s easiest
to start with the spoken prompt, imagining what you
might say in a human-to-human conversation. Then,
condense it to create the display prompt.
Google Design Guidelines
69
Content Design for the Conversational UI
Google Assistant 70
1. The Conversational UI
2. The Design Process
3. Easy Ways to Explore
71
Content Design for the Conversational UI
Actions on Google
https://developers.google.com/actions/templates/first-app 72
73
https://blueprints.amazon.com 74
Alexa Skill Blueprints
Thanks!
75
Content Design for the Conversational UI
Melanie Seibert
Sr. Content Strategist, WillowTree
@melanie_seibert
Content Design for the Conversational UI
Keep Learning
• Sarah Richards, Content Design
• Margot Bloomstein, Content Strategy at Work
• Cathy Pearl, Designing Voice User Interfaces
• Google Design Guidelines
• Amazon Alexa Voice Design Guide
• Sophie Kleber, Designing Emotionally Intelligent Machines (SXSW 2017)
• Whitney French, “Shortcuts to Chatbot Emotional Intelligence”
• WillowTree, "The Executive’s Guide to Driving ROI with Voice Experiences"
76
Content Design for the Conversational UI
Thanks to:
• Daniel Atwood
• Shadiah Garwell
• Ayesha Zafar
77

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Content Design for the Conversational UI - Design + Content Conference 2019

  • 1. Content Design for the 
 Conversational UI Design & Content Conference 2019 Melanie Seibert Sr. Content Strategist, WillowTree @melanie_seibert
  • 2. 2
  • 4. 4 September 2018: 24% of U.S. households
 own a smart speaker Source: Nielsen 4
  • 5. 5 December 2018: 2.5 billion digital voice 
 assistants in use Source: Juniper Research 5
  • 6. Voice Platform Marketing If you haven’t encountered a conversational interface yet, 
 you will. 6
  • 7. 7 Content Design for the Conversational UI 1. The Conversational UI 2. The Design Process 3. Easy Ways to Explore
  • 8. Content Design for the Conversational UI 8 A type of user interface consisting primarily of content. The Conversational UI
  • 9. Content Design for the Conversational UI 9 Content is the design. You’re the designer. The Conversational UI
  • 10. Content Design for the Conversational UI 10 1. Text 2. Voice 3. Multimodal 3 Formats
  • 11. Content Design for the Conversational UI • Facebook Messenger • Slack 11 Text
  • 12. Content Design for the Conversational UI 12 Voice • Amazon Alexa • Google Home • Apple Siri • Microsoft Cortana
  • 13. 13 Voice + Text Multimodal Done. Your alarm has been set for 6 a.m.
  • 14. 14Typing speed: Brown, CM (1998). Human-Computer Interface Design Guidelines. Speaking speed: Yaun, Liberman, Cieri (2006). “Towards an Integrated Understanding of Speaking Rate in Conversation.” Typing Speaking 130 wpm 40 wpm
  • 15. Read300 wpm “Speed Reading," The University of Chicago Student Health and Counseling Services, 2017. 15 Listen130 wpm
  • 16. Intents Entities What’s the best place to eat 
 in Vancouver that’s not too pricy? best place to eat Vancouver not too pricy? Find food best Vancouver not too pricyAdditional Context Location Previous reviews Allergies 1 2 3 Analysis4Contextual Action Fulfillment 56 Feedback 
 Confirmation or request for Additional Information Action Call to any relevant APIs API Anatomy of a Conversation Recording Conversion to TextUser Input System Output “What’s the best 
 place to eat in 
 Vancouver 
 that’s not 
 too pricy?” 16
  • 17. Intents Entities Find food best Vancouver not too pricyAdditional Context Location Previous reviews Allergies 1 2 3 Analysis4Contextual Action Fulfillment 56 Feedback 
 Confirmation or request for Additional Information Action Call to any relevant APIs API Anatomy of a Conversation Recording Conversion to TextUser Input System Output “What’s the best 
 place to eat in 
 Vancouver 
 that’s not 
 too pricy?” 17 What’s the best place to eat 
 in Vancouver that’s not too pricy? best place to eat Vancouver not too pricy?
  • 18. 18 Content Design for the Conversational UI 1. The Conversational UI 2. The Design Process 3. Easy Ways to Explore
  • 19. “If you approach a new piece of web content with ‘how shall I write this?’, that’s writing or editorial. 
 If you approach it from ‘how am I going to get this across to the audience in the best way possible?’, that’s content design.” 19 Sarah Richards 
 Author of Content Design
  • 20. What is Content Design? Where Content Strategy and 
 Product Design overlap. 20 Content Design for the Conversational UI
  • 21. The Design Process Content Design for the Conversational UI Start with data 21
  • 22. “Can I replace the handle User Input on my ?”product Customer Service Logs Interviews Content Audit 22 Content Design for the Conversational UI
  • 23. 23 Content Design for the Conversational UI
  • 24. The Design Process Content Design for the Conversational UI Write a user story for each intent 24
  • 25. What’s a User Story? “A user story is a way of pinning down what the team needs to do… without telling them how to do it.” Sarah Richards | Content Design 25
  • 26. User Story: “As a _________________,
 I want to _________________, So that I can _________________.” 26
  • 27. User Story: “As a product user,
 I want to know whether I can replace the handle, So that I can avoid having to buy a new product when the handle breaks.” 27
  • 28. The Design Process Content Design for the Conversational UI Prototype the conversation 28
  • 29. “Wizard of Oz” role-play 
 (on Slack).
  • 30. The Design Process Content Design for the Conversational UI Design the Flow 30
  • 31. Content Design for the Conversational UI Flows to design Golden Path The designed intents. 
 Entry Point How is your bot invoked? 
 Error Paths Can the bot recover when it doesn’t understand or receive input? Escalate to a Human When should a person take over? 
 Linking to Accounts & Other Platforms How do you need to integrate with other services? Examples include purchase, add to shopping list, message someone, call someone. 31
  • 32. Content Design for the Conversational UI Flow chart. 32
  • 33. Content Design for the Conversational UI 33
  • 34. Content Design for the Conversational UI 34
  • 35. Content Design for the Conversational UI 35
  • 36. The Design Process Content Design for the Conversational UI Train the Bot 36
  • 38. Training data generation 
 (on Slack). 38
  • 39. The Design Process Content Design for the Conversational UI Design the Personality 39
  • 41. WHO WE ARE WHO WE’RE NOT Bloomstein’s 
 “messaging architecture” 
 method ✖️✔️
  • 42. 42
  • 43. 1. Supportive 2. Optimistic 3. Formal 4. Humorous 5. Motivated Personality Framework 43 How… …is it?
  • 44. Supportive I root for you. I will try to help you achieve your goals rather than pursuing my own agenda. Opposite: adversarial How… …is it? 44 Personality Framework
  • 45. Personality Framework Optimistic I speak in positive terms. I try to see the upside of everything. Neutral: realistic Opposite: pessimistic How… …is it? 45
  • 46. Personality Framework Humorous I like to entertain and amuse you— and myself. Opposite: serious How… …is it? 46
  • 47. Motivated I’m enthusiastic and excited about our conversation. Opposite: reserved Personality Framework How… …is it? 47
  • 48. Personality Framework Formal I carefully observe rules of etiquette and present myself in a “highbrow” manner. Opposite: casual How… …is it? 48
  • 49. Supportive I root for you. I will try to help you achieve your goals rather than pursuing my own agenda. • Opposite: adversarial Optimistic I speak in positive terms. I try to see the upside of everything. • Neutral: realistic • Opposite: pessimistic Humorous I like to entertain and amuse you— and myself. Opposite: serious Motivated I’m enthusiastic and excited about our conversation. • Opposite: reserved Formal I carefully observe rules of etiquette and present myself in a “highbrow” manner. • Opposite: casual Personality Framework How… …is it? 49
  • 51. 51 Content Design for the Conversational UI Example: Designed Intents User First Draft: WillowTree Bot “Currently I am configured to discuss myself, and answer whatever questions you might have about how I work, 
 what I am, what I can do, how to configure me, and so on.” Formal: longer, uses passive voice. Realistic: focuses on what it can do right now. Reserved: sticks to the facts. “What types of things do you know about?”
  • 52. 52 Content Design for the Conversational UI Example: Designed Intents User Revision: WillowTree Bot “Right now, I know about myself. But I can extend my database to learn about any topic. Do you have any suggestions?” Shorter, less formal. Optimistic: focuses on what it can do in the future. Motivated: interested to learn about your domain. “What types of things do you know about?”
  • 53. The Design Process Content Design for the Conversational UI Create and Refine Scripts 53
  • 54. 54 Content Design for the Conversational UI
  • 56. Content Design for the Conversational UI Voice Tip Manage content density with “landmarking.” Amazon Alexa Skills Kit Glossary 56
  • 57. Content Design for the Conversational UI • Establishes trust • Supports a natural dialogue Voice Tip Manage content density with “landmarking.” Horoscope for what sign? Do: 57Amazon Alexa Skills Kit Glossary Ask Astrology Daily 
 for my horoscope.
  • 58. Content Design for the Conversational UI How to Simplify Your Responses - Amazon Alexa Voice Design Guide Manage content density with “landmarking.” 58 Do: At 10 a.m., you have the
 weekly status meeting 
 with Rachel and Natasha. Don’t: You have the weekly status
 meeting with Rachel 
 and Natasha at 9 a.m. What’s happening 
 at 10 a.m.? Voice Tip
  • 59. Content Design for the Conversational UI Example: Cortana 59 Manage content density with “landmarking.” Voice Tip How long does it take to 
 get to the Richmond airport?
  • 60. Content Design for the Conversational UI The cheeses you may like are cheddar, gouda, Jarlsberg, porter cheddar, St. Agur blue cheese, gorgonzola, brie, gruyere, sharp cheddar, and reggiano parmesan. Amazon Alexa Voice Design Guide 60 Don’t: Do: Here are the cheeses you may 
 like: cheddar and gouda, as well 
 as gorgonzola, parmesan, 
 and brie. Use “chunking” 
 to aid comprehension. Voice Tip
  • 61. Content Design for the Conversational UI Use shorter responses. Example: Cortana 61 Voice Tip Are there any restaurants
 open right now?
  • 62. Content Design for the Conversational UI Provide clear choices. Amazon Alexa Voice Design Guide 62 Voice Tip Would you like brie or gouda? Don’t: Do: We have brie or gouda. Which would you like?
  • 63. Content Design for the Conversational UI Screen Tip Use timing to break up longer utterances. 63
  • 64. Content Design for the Conversational UI 64
  • 65. Content Design for the Conversational UI 65
  • 66. Content Design for the Conversational UI 66
  • 67. Content Design for the Conversational UI Use Quick Replies (aka “chips”). Facebook Messenger Google Assistant Screen Tip 67
  • 68. Content Design for the Conversational UI Take advantage of web links. Zulily on Facebook Messenger Screen Tip 68
  • 69. Content Design for the Conversational UI Multimodal Tip “Design prompts for both the ear and the eye. It’s easiest to start with the spoken prompt, imagining what you might say in a human-to-human conversation. Then, condense it to create the display prompt. Google Design Guidelines 69
  • 70. Content Design for the Conversational UI Google Assistant 70
  • 71. 1. The Conversational UI 2. The Design Process 3. Easy Ways to Explore 71 Content Design for the Conversational UI
  • 73. 73
  • 75. Thanks! 75 Content Design for the Conversational UI Melanie Seibert Sr. Content Strategist, WillowTree @melanie_seibert
  • 76. Content Design for the Conversational UI Keep Learning • Sarah Richards, Content Design • Margot Bloomstein, Content Strategy at Work • Cathy Pearl, Designing Voice User Interfaces • Google Design Guidelines • Amazon Alexa Voice Design Guide • Sophie Kleber, Designing Emotionally Intelligent Machines (SXSW 2017) • Whitney French, “Shortcuts to Chatbot Emotional Intelligence” • WillowTree, "The Executive’s Guide to Driving ROI with Voice Experiences" 76
  • 77. Content Design for the Conversational UI Thanks to: • Daniel Atwood • Shadiah Garwell • Ayesha Zafar 77