Prev @ the LEGO Group
Using Storytelling to Bridge Families with a NYT Crossword
2024
Project summary ✦
We joined a 4-day competition with the prompt: How might we bring young adults (18–24) and their parents closer together? Our winning solution was a personalized NYT crossword that turned parents' stories into custom clues. We built two versions: a fully AI-generated crossword and an MVP that delivered the same emotional impact with lighter AI requirements.
OVERVIEW
Navigating a pivotal time of change
As young adults move from high school to college and then into work, they experience a lot of change — and so do parents.
Parents and young adults approach connection very differently
Parents and young adults approach connection differently
Young adults:
Parents:
Young adults prefer low-effort interactions and are comfortable using technology. Parents are more willing to invest time but struggle with tech. Parents also find it harder to initiate deeper conversations.
With time, connection grows harder
connection is harder with time
By high school graduation, young adults have spent 93% of the time they'll have with their parents.
By high school graduation, young adults have spent 93% of the time they'll have with their parents.
Based on The Tail End essay by Wait But Why
Based on the tail end essay from "wait but why"
a key insight
a key insight
Stories are a powerful way to move beyond surface level conversations
stories are a powerful way to move beyond surface level conversations
Young adults grow up seeing fragments of who their parents are. Listening to their stories helps complete the picture and strengthen the connection between them.
Young adults grow up seeing fragments of who their parents are. Listening to their stories helps complete the picture and strengthen the connection.
stories help us bond
Stories help us bond
however, sharing these stories is not easy
these stories require the right build up and prompting is hard.
How can we provide an entry point to be able to overcome these barriers and share these stories?
concept
concept
Crosswords as a Starting Point for Connection
Crosswords as a Starting Point for connecting these groups
We used the NYT Mini Crossword as a familiar, cross-generational ritual to cut through the buildup and awkward prompting. By grounding stories in a daily game, we made sharing feel natural instead of forced.
We used the NYT Mini Crossword as a familiar, cross-generational ritual to cut through the buildup and awkward prompting. By grounding stories in a daily game, we made sharing feel natural instead of forced.
The Mini isn’t just a game—it’s a catalyst for connection
The Mini is a catalyst for connection
Why we chose the new york times
Why we landed on the nyt
Few brands are as trusted for storytelling as The New York Times. Beyond the Mini, its cultural staples show how stories bring people closer:
Few brands are as trusted for storytelling as The New York Times. Beyond the Mini, it has other cultural staples that focus on storytelling.
The Perfect Moment: Mother’s and Father’s Day
we chose Mother’s and Father’s Day for this mini experience
People are more likely to show up for special one-time moments than commit to ongoing habits. That’s why we anchored this experience to Mother’s and Father's Day.
Key insight: people are more likely to show up for one-time moments than commit to habits. That’s why we anchored this experience to one special day.
our setup broken down
SOLUTION
A CUSTOM MINI CROSSWORD FOR MOTHER'S AND FATHER'S DAY: MADE WITH YOUR PARENTS' STORIES
*All mockups were created in the context of Mother's Day.
AWARENESS AND INVITING PARENTS
PARENT CROSSWORD CREATION
YOUNG ADULT CONSUMPTION
solution
Custom mini crosswords about your parents' stories on Mother's and Father's day
01 event discovery on nyt
Social media requires active input
The event had to be discoverable on the homepage with limited real estate
The timeline gave users just enough space to prepare, while still creating urgency to act
02 parent creates crossword
Social media requires active input
We crafted intentional prompts for parents, which later turned into crossword clues
We had parents speak their stories aloud to make it easy and more personal
02 YOUNG ADULT SOLVES CROSSWORD
Social media requires active input
Swapping the daily crossword for a low-lift entry point to kick off meaningful conversations
Designing for continuity—so the exchange extends beyond the starting point crossword
technical deep dive
HOW DO WE GENERATE THESE custom CROSSWORDS? artificial intelligence can't do it (YET)
HOW DO WE GENERATE THESE custom CROSSWORDS? ai can't do it (YET)
We tested multiple AI models to generate custom crosswords. After many tries, we realized the tech wasn’t there yet. Here’s an example of ChatGPT’s best attempt— we prompted it to create a 5x5 grid it created a 5x4 grid that only worked horizontally.
We tested multiple AI models to generate custom crosswords. After many tries, we realized the tech wasn’t there yet. Here’s an example of ChatGPT’s best attempt— we prompted it to create a 5x5 grid it created a 5x4 grid that only worked horizontally.
We tested multiple AI models to generate custom crosswords. After many tries, we realized the tech wasn’t there yet. Here’s an example of ChatGPT’s best attempt— we prompted it to create a 5x5 grid it created a 5x4 grid that only worked horizontally.
Even after careful prompting, AI couldn’t make it work
Even after careful prompting, AI didn't work
We designed an mvp that reduces AI load
an mvp that reduces AI load
Matching NYT's standards is important. This is why we shifted to a flipped approach: instead of generating entire crosswords, we used prompts to guide meaningful stories that connected back to a pre-made puzzle.
Matching NYT's standards is important. This is why we shifted to a flipped approach: instead of generating entire crosswords, we used prompts to guide meaningful stories that connected back to a pre-made puzzle.
prompts help parents recall stories that align with crossword answers
prompts help parents recall stories that align with crossword answers
However, we still mapped out our ideal flow for when ai is ready
However, we still mapped out our ideal flow for when ai is ready
Instead of relying on AI to get everything right in a single prompt, this method works step by step. Once a few words are locked in, the app switches to targeted prompts—using existing crossword entries (like ‘develop’) to guide the next ones. The goal is to balance personalization with puzzle feasibility.
Instead of relying on AI to get everything right in a single prompt, this method works step by step. Once a few words are locked in, the app switches to targeted prompts—using existing crossword entries (like ‘develop’) to guide the next ones. The goal is to balance personalization with puzzle feasibility.
reflection
We took our prototype to NYC — and came home with first place in a competition
We took our prototype to NYC — and came home with first place
PRESENTING To top designers from apple, Google, Meta
PRESENTING To top designers from Google, Meta, LinkedIn, notion, and other companies
The feedback was to center the experience around storytelling, focus on a specific moment rather than the entire flow, and explore how this could help the NYT generate more revenue.
Although winning was great, the real gift was the feedback we received. Here are three takeaways I'll carry forward:
reach out to view my full project
This project came with plenty of other design decisions, like why we chose to build the Mini or design for mobile over desktop. I’d be more than happy to walk you through the rest over a coffee chat or interview! In the meantime, check out my other projects:
