NYC Design Competition — Oct 2024
Bringing parents and children closer together using storytelling through the NYT Mini Crossword

TIMELINE
1-Week Sprint for NYC Design Competition
ROLE
Technical Product Thinking, User Flows, Visual Design
TEAM
Sonya Surapaneni (Designer)
Hong Yu Wong (Designer)
Michael Zaslavskiy (Designer)
TOOLS
Figma
Protopie
PROBLEM
A week to take a stab at a big problem
THE BRIEF
How can we help parents and young adults (16-26) get closer to one another?
FIG. 1
ME AND MOM :)
UNDERSTANDING
Navigating a pivotal time for both parents and children
Young adults are experiencing a lot of change.
FIG. 2
The relationship between parent and child is also undergoing a major shift.
Children are:
Creating a new life of their own
They are looking for guidance around new experiences and relationships.
Learning to appreciate their parents more
They are maturing through new challenges and starting to understand parents' good intentions.
Parents are:
Redefining their role as a parent
They are seeing their child grow into a fellow adult while grappling with them leaving home.
Rekindling personal goals and relationships
They are finding more time to dedicate to themselves or to other members of their family.
Children and parents have different pain points and needs.
Children are:
Willing to put in less time and effort
Unless there is a special occasion, something with too much friction may feel inaccessible.
More technologically savvy
This generation grew up with technology and is familiar with more complex interface patterns.
Parents are:
Willing to put in more time and effort
Parents are willing to go the extra mile to help or support their child, especially during this time.
Less technologically savvy
Parents of today's young adults are technology-familiar, but might struggle with complex tasks.
CORE INSIGHT
A parent’s story is a powerful artifact to bond over
To really know someone, you have to understand their journey
We have an extremely limited view of our parents' lives.
There are rich experiences and relationships that we may never know unless we ask.
FIG. 3
This is my grandfather, Thomas Baker — from LINDY MAIO ON UNSPLASH
However, telling stories about yourself isn't easy
There's a right time and place
Some stories only feel right to tell in certain situations — whether lighthearted or serious.
A good prompt goes a long way
Prompts are essential for remembering specific stories and uncovering details within them.
And as we age, there is less and less time to share
A DIFFICULT TRUTH
FIG. 4
graphic inspired by STATISTIC IN "The Tail End" from Wait but why
SOLUTION HIGHLIGHT
The Solution: Custom Mini Crosswords about your parents on Mother’s and Father’s Day
*All mockups were created in the context of Mother's Day only.
Discovery: Helping people learn about the event on the main NYT Games screen
How do we balance giving people ample time for discovery but also limit the time window to create urgency?
Onboarding: Introducing the feature and building up to the event
How can we explain the event quickly and make it easy to share with a parent?
Parent Flow: Creating the Crossword by telling stories
How can we make it easy for possible for parents to interact with and stay engaged throughout the process?
This is the "ideal world" solution. AI is not currently at the point where it can generate high quality custom crosswords.
More about this below!
Child Flow: Children solve the Mini Crossword and hear about the stories behind it
How can we maintain the regular crossword solving flow while incorporating stories in a meaningful and compelling way?
How can we continue the conversation beyond the experience?
MY ROLE
PRODUCT THINKING
Aligning with the NYT brand ethos
The NYT believes in sharing authentic stories
Fostering parent-child connections through storytelling aligns perfectly with a company centered on sharing authentic stories.
The NYT already dabbles in this space around very personal stories — the column Modern Love, which shares personal experiences around love of all forms, just celebrated its 20th year anniversary.
FIG. 5
A PEEK AT THE NYT MODERN LOVE COLUMN
NYT Games as a medium for connection
Games like Wordle and the Mini are familiar and fun across generations
NYT Games are recurring, shared experience that people of all ages enjoy.
It fits into the routines of young and old people alike.
FIG. 6
Snippets of friendly (family) competition around nyt games
TECHNICAL FEASIBILITY
Using my knowledge of LLMs to ground the Crossword creation process in reality
TESTING USING LLMS
I asked ChatGPT and Claude to create a 5x5 Crossword using a few generated parent stories. TLDR: They did terribly.
FIG. 7
ChatGpt and CLaude's Attempts at a one shot crossword
AI isn't good enough right now to create a good crossword reliably.
Each word in a puzzle must interconnect to form real words both vertically and horizontally.
This is a difficult constraint to meet, and takes trial and error + a deep knowledge of existing words and phrases.
Crosswords should be built one word at a time rather than all at once.
Each additional word is dependent on the previous ones, so each process will vary based on the existing letters on the board.
THE IDEAL SOLUTION
Imagining what the Mini Crossword creation process would look like if AI was good enough
Flexible First Words
When the crossword is more empty, we can use more customized or niche words related to the parent’s stories.
FIG. 8
Giving parents broader prompts and generating words custom to story
2.
Directed Word Prompts
Once there are a few words in the puzzle, there are limitations to what the others can be. Find possible words and provide prompts related to those words.
FIG. 9
Detecting possible words and creating prompts related to those words
3.
Filling in the Blanks
If there are only a few words left, we can use generic Mother’s / Father’s day words to complete the puzzle.
FIG. 10
Fill in the remaining gaps with words related to the holiday
THE REALISTIC SOLUTION
Being realistic with what we can do today
The NYT Crossword has an extremely high bar for quality that they are unwilling to lower.
If any errors occur, which we know AI is heavily prone to, it would be a bad look on the company and the brand of the NYT Crossword.
This "ideal world" solution will probably not be feasible OR viable for a while.
FIG. 11
The history of the nYtimes crossword, spearheaded by margaret farrar 80+ years ago
Instead, the puzzle editors can create a special "themed" crossword for everyone
This would take out the need to create a custom crossword in terms of the words and entries.
Using the words in the final puzzle, we would then collect parent stories via prompts related to each word:
1.
Mother's / Father's Day Themed Mini Crossword
The NYT puzzle editors would create a Mini Crossword as normal with a Parents' theme.
2.
Collect stories related to each of the Puzzle words
We would give parents storytelling prompts related to words that are in the puzzle.
3.
A Mini experience with integrated parent stories
The solving and post-solving experience would showcase the stories we collect.
RESULT
We got valuable feedback on our project from leading industry designers
FIG. 12
us presenting together in nyc!
A few key points and takeaways from this project
Explore unconventional, unexpected solutions
Dream big — you never know what you could end up with!
You don't always have to design end-to-end
Make sure the strongest areas of user and business value are developed — the other parts can be less fleshed out.
Multiplayer UX needs crystal clear visuals
When there are multiple people involved in a flow, break down how each interaction affects each person.
THE FULL DESIGN PROCESS
There's a lot more to see behind the scenes
Please reach out to me if you'd like to learn more!
I typically walk people through more detailed research and design explorations in an interview environment or coffee chat.
Mini vs. Full Crossword
Why we chose the Mini
Storytelling Input Methods
Text vs. Voice vs. Video
The Post-Mini Experience
The ultimate goal