Deepening Connection through Discovery


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ChattyKathi is a Denver start-up that aims to spark engaging and insightful conversations with friends and family through SMS.

What I Did

  • Optimized their “Library Prompt” page where users customize their SMS prompts
  • Discovered an even bigger need for Onboarding redesign
  • Solutions helped increase value buy-in with users & set the product up for scalability success
Web-based application, SMS
Research, Strategy, Wireframing, Prototyping, Testing



Our stakeholders main area of concern at the start of this sprint was the state of their newly launched Library Prompts.

They wanted to remove their own biases and see if target new users could find value buy-in to the concept itself as well as find the process intuitive. With plans to grow from a D2C model to a B2B model within the next 6 months, they also wanted to make sure whatever solutions we came up with were scalable and in line with their business goals & target new users.
target user


C&C Analysis
With the libraries in mind as our stakeholders top priority, we wanted to dive into Comparative Analysis to see how content curation leaders in the field were conquering user customization.
While we looked at 10 competitors overall, we focused our research into companies who had experience with content curation, like Tumblr, Pinterest, Twitter & Behance. Since they had been able to master intuitive onboarding flows while also helping users customize their content experiences.
In particular, we found a lot of interest in how Tumblr did this, specifically on mobile, because of the visual way they were able to connect their parent and subcategories.

With new ideas on Library discovery, we then wanted to round off our C&C with a focus on our stakeholder identified competitors.
Both competitors occupy the social wellness space and both offer daily questions for users. Longwalks focusing their prompts on solo self care and Paired on couples. 

In our experience getting acquainted with ChattyKathi, it became clear the onboarding process was a big avenue to discovering the Library Prompts so we wanted to see how our competitors tackled that with a task analysis.
The most obvious key finding for us was that ChattyKathi’s onboarding flow was by far the lengthiest of the three. And with that realization, new questions for our team surfaced.
This was our first clue in our discovery phase that the onboarding flow may need to be part of our overall solution and influenced the user facing research we were taking on next.
Watching Users Lead the Way
What do existing and potential new users think & feel about the ChattyKathi onboarding process? After conducting 9 contextual inquiries with users across the globe, major trends and pain points started to emerge.
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Information Architecture
original chattykathi prompt library
Before diving into user flows to solve for our newly uncovered onboarding pain point, we wanted to first focus on our stakeholders primary concern; the prompt libraries. 

With over 100 internal libraries and 1,000 prompts and growing, we knew we first wanted to start with a card sort of a small sampling of ChattyKathi’s most popular categories to optimize for hierarchy & intuitive user navigation.
Next it was time to reimagine the onboarding flow to solve for our users biggest pain points that were discovered through contextual inquiry.
Top Pain Points
After consolidating and eliminating unnecessary screens in the original onboarding flow, we wanted to challenge ourselves to come up with a creative solution to “add phone numbers” which was the biggest challenge to new users across the board.

After sifting through obvious solutions like connecting to users' contacts, we decided we could leverage an existing bespoke ChattyKathi feature; their opt-in text buried in settings for users who did not automatically get a text to join their created chats. 
existing opt-in text
Our idea being, instead of having to manually add their contacts to the ChattyKathi chat, users would get to a screen with a similar message as the above and they could simply copy and paste it through a message on their own phones.
As excited as we were with our creative solution for our users biggest pain point, the messy constraints of the real world and business limitations forced us to go back to the drawing board. Because of the SMS API pricing ChattyKathi was currently using, they had a limited amount of numbers that would not make this solution viable for them at the moment. 

Luckily, our overall new and improved flow allowed us to switch out our innovative “Opt-in” feature screen for the traditional add numbers screen that we could still optimize.


With solutions in hand it was now time to make them tangible. We first started with a design studio method, this way we could generate lots of ideas in a short amount of time while also cherry picking the best solutions that we would eventually combine when we moved into wireframing.

While we did design for responsive web, we focused on a mobile first model because that is where most of ChattyKathi’s user traffic comes from.
Wireframes & Prototypes
Our target user, Newcomer Nina, would land on the existing ChattyKathi homepage and when she was ready to get started, enter into the new onboarding flow. She would then go through the existing/traditional sign-up process.
Next she would see our first new addition to the flow, a “How it Works” Screen so she could see the product in use and in context to help her understand what it is and what it will look like at the end of the sign up process.
Feeling more comfortable with what she is getting into, she would enter & verify her phone number and get started.
Nina then would be brought to the new “Libraries” screen where she now would get to name her chat, choose who she would be chatting with, what types of questions she wanted and what topics, all on one page.

We opted to consolidate all of this information on one page so that it would be easier for users to understand that the “Relationship Type” & “Types of Conversation” questions will customize the types of questions they will get. Something that was a disconnect to users in our contextual inquiries.
Next, Nina would then get to choose what topics and kinds of prompts she would like her group to discuss with our newly designed Library Prompt categories.
Then Nina would set the schedule of when and how often her and her group would hear from Kathi and get a prompt
And finally, her last step would be to add her friends' phone numbers to the chat.
Once done, she would get a confirmation & celebratory skeleton screen animation, and then be taken to the existing ChattyKathi dashboard where she would see the chat she just created if she ever needed to modify it.


Usability Testing
While the overall testing was successful with users noting this was a simple and intuitive experience (a massive improvement from our contextual inquiries) we did discover some insights for changes that would further improve the user experience.

Next Steps

While we accomplished our stakeholders goals and beyond during this 3-week sprint, there are still some next steps and recommendations we have in mind to ensure the success of our solutions.