All In a Week’s Work — How We Tackled the Five Day Sprint Process

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All In a Week’s Work — How We Tackled the Five Day Sprint Process

Kelci Shipley/The New York Times

It may have been the second week in October, but it felt like summer camp. For five consecutive days, eight members of the New York Times Games team hid away in a conference room armed with pads of sticky notes, a blank whiteboard wall and a bit of nervous energy: we were actually going to give this thing a shot.

“This thing” being an entire work week dedicated to product development and design thinking, inspired by the book “Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days” by Jake Knapp, John Zeratsky and Braden Kowitz at Google Ventures.

Our team is known for the New York Times Crossword, but we’re always thinking about ways to improve our existing product and new playing experiences we could create. Compressing these ambitions into the five day sprint process meant that each day had a specific focus, which allowed the week to go from talking about big problems on Monday to testing a solution with a working prototype on real users on Friday.

But we didn’t just show up Monday to see what happened — we did a lot of prep work. We assembled our sprint team and assigned roles. I took on the role of Facilitator, which meant reading the book cover to cover and knowing how to guide the team through the process while keeping everyone on track.

By the time the first morning came, we were ready.


The first day also happened to be the boldest. The morning started by revisiting our long-term goal to create an experience that gives our users a sense of accomplishment every day. We turned our assumptions into thoughtful questions and asked ourselves things like, “What does it mean for a user to feel accomplished?” and “What motivates them?”.

Kelci Shipley/The New York Times

The afternoon was spent talking to our Marketing, Design, Editorial and Technology teammates who are experts on our product. Those conversations helped us define the challenges we wanted to focus on for the week: to create a sense of fulfillment and meet users in their individual moments.

Our product’s complex nature means that we have an array of users with different levels of knowledge and skill. But whether our users can solve a Monday puzzle in 15 minutes, or whether they consider doing half of a Sunday puzzle a victory, we want them to feel good in each instance of their experience.

At the end of the day, we synthesized this information and mapped it to a user journey, which helped us focus on the solution we wanted to design for.


With day one behind us, we started sketching solutions to the problems we defined in our discovery. We started by discussing elements of comparable experiences that we could look to for inspiration, such as developing reading skills or feeling accomplished in a fitness app. The solution sketching segments were highly structured and timed, meant to emphasize critical thinking over artistry. Each person left with one solution sketch to be reviewed the next day.


One of the keys for the week was to keep moving through it, even when we found ourselves in moments of doubt. The uncertainty of our success was my greatest challenge because I had to balance the execution of a particular day’s segment with the hope that I was guiding everyone on the correct path. This made Wednesday a critical day in the sprint, and a convenient one to get breakfast catered.

Energized and caffeinated, we reviewed each person’s sketches using methods of evaluation such as silent voting, written comments and verbal discussion. The methodical approach felt a bit awkward at times, but it minimized irrelevant tangents and accelerated decision-making. And it led us to one of the most exciting moments of the week: illuminating the thing we would create.

At this point, we threw some of “Sprint’s” rules out the window. The book suggests creating a prototype with elements from each sketch, but we decided to focus on one idea we really liked and evolve it.

Kelci Shipley/The New York Times


On Wednesday, we put together a storyboard of how our prototype would function, so Thursday was devoted to bringing that prototype to life. To make our prototype, we used a sequence of pieces of paper to mimic the look and feel of interacting with a digital screen. The afternoon was spent designing game elements, crafting editorial and shuffling through a lot of Spotify songs. I did my best to keep the momentum going with help from of Michael Jackson, Whitney Houston and other ’80s pop icons.

And then like that, it was on to day five.


Getting to Friday is an accomplishment in and of itself. By design, the week was packed with moments of anticipation, doubt and exhilaration. Though we felt all of these emotions leading up to Friday, when we gathered to watch real people interact with our prototype a sense of calm settled over the room.

Armed once again with pads of sticky notes and sharpies we noted interesting behaviors, insights and emotions as the five user testing sessions were conducted by The Times’ Audience Insights team. Through the user testing, we were able to confirm that what we created was something people were delighted to play. But even if our prototype was something people didn’t enjoy, it wouldn’t have meant the sprint was unsuccessful.

The point of going through a five day sprint is to learn and gather insights, so the pressure wasn’t on whether or not the prototype performed well (although it was a nice bonus). In addition to seeing what worked well in the prototype, we learned what things people craved and how we could provide our users with an even better experience.

The goal of the sprint was to learn and we achieved it.

So what happens now? After that week, we left with many questions we still wanted to answer. We’ve been actively iterating on the prototype and figuring out more variables we want to test with users.

The sprint asked for a big commitment, however our return on the five day investment was immense. We gained new tools and frameworks for executing brainstorms and we continue to incorporate pieces from this process into our discovery strategy.

Kelci Shipley is a Program Manager for The New York Times Games team. She works closely with the Crossword product and the people that build it.

All In a Week’s Work — How We Tackled the Five Day Sprint Process was originally published in Times Open on Medium, where people are continuing the conversation by highlighting and responding to this story.

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