Asked to lead a new team on a design discovery initiative, I had to quickly learn to facilitate collaboration, generate momentum, build cohesion and light a path through uncertainty. Here's what happens when you leave a pack of wild creatives on their own for 3 full months.
Hint: EVERYONE DIES.
Using design thinking methodologies and processes, explore the digital commerce space and identify opportunities for innovation, expansion, and experimentation.
I would lead the project and present progress at scheduled checkpoints with UX leadership. At the end of the quarter, we would present to Senior Leadership in Product, Engineering, Strategy, and Design.
We would be running something like agile, with 12 separate, week-long sprints. Our design process would be similar to the Double Diamond framework, with iterative loops of divergence and convergence.
Each sprint would be given a different theme, with defined activities and target outcomes.
We needed a shared knowledge base to start from, so we invited friends, colleagues, coworkers, and strangers to our office for open, exploratory interviews and sketching sessions. We were trying to uncover common themes in the way people relate to the items they buy.
At the same time, we put together a Google survey of general questions around how people conceptualize the things they own. After a week and 188 responses, we synthesized the results.
We quickly began to see overlapping themes of what's most important to our participants:
• Identity, aspiration, self-image
• Seasonality, special events
• Quality, value, emotional connection
To make our research more accessible, we built a blog and created a new post for each of the topics we researched. These were things like alternative business models, fashion trends, new or novel value propositions, success and failure in brand perception, market differentiators. Really anything interesting that appeared on the path.
From a process perspective, the idea is that this wide research would collide with our qualitative insights at some point.
Every Friday started with a convergence exercise, writing things we’ve each individually learned and observed the past week on post-its, then grouping insights into themes. By going deep individually, then sharing with the team, we each became experts in certain aspects of the industry while creating a hive mind of collective understanding. Over time, these learnings became detailed insights, and team expertise rose quickly.
Our "How Might We" statements were informed by our research and shared principles. We worked on these until they really resonated with us, and we hung them up on the wall of our shared work space.
These statements were incredibly important for us and stuck with us throughout the entire process. They were a litmus test for new ideas, and served as guiding principles when we needed direction.
Startups were experimenting with direct to consumer subscription boxes, bundles, and add-ons, and customers loved them each for different reasons. Walmart has the second largest inventory of items in the world but they had not yet explored these models in any serious way. We were interested in testing it, but we needed a compelling category.
We were inspired by a Finnish government program that started over 75 years ago. They would give new parents a box full of essentials for their newborn, and the box itself would be the baby's first crib, reducing the infant mortality rate significantly. It was such a great program, and a really efficient and effective use of materials to solve real world problems.
Forming a brand relationship with a customer during important life events can potentially build lifetime brand loyalty. Baby is a popular category for Walmart, but average order size within the category was relatively low.
We wondered, could we donate baby boxes to hospitals, doing something great for the world while improving brand perception and forming a channel to connect with prospective customers?
We believe that offering curated bundles to new and expecting parents will make the journey to parenthood easier, increase brand loyalty, average order size, and offer an opportunity for add-ons and subscriptions for essential items.
To test the viability of the offering, we went to Walmart and bought all the items that would go into a baby bundle. Everything, including the box it comes in, is available at the store.
We wanted to test the concept but didn’t want the Walmart brand to impact the integrity of our results. We decided to build a live prototype website as if it were a new company. We would test it with a wide audience of both expecting and new parents.
Myself and our visual designer worked in Figma, iterating on the basic structure of the prototype pages.
I bought the domain “bundledwith.love” and a plan on Wix. We got to work building out the test site, simple branding, concept pages, and product offerings, then published it to the web.
When the results came in, we got a high NPS and trust signals. Most interesting to us were the reasons why our participants did not want to buy the essentials bundle:
It was clear to us that bundles are very helpful, but to make the offering compelling, to instill confidence and provide real value, we needed to create content that educates and informs, and then seamlessly integrate shopping items in.
What if we offered bundles, starter packs, kits, and comprehensive guides for anything? What if they weren’t just for life events or categories, but for personal growth?
I put this pitch deck together in Keynote and played it for our VP in our next project review. (video)
The concept came across perfectly.
The VP loved it, so we pushed ahead.
There were many weeks of design exercises, exploration, and iterations to follow.
We mused on a "Get Outdoors" pack that has everything you need to go camping for a weekend, and comes in a plastic tote. Printed on the lid of that tote are instructions on how to start a fire, pitch a tent, safety tips, survival tips. Just like the Finnish baby box - everything serves a purpose. Reduce waste, provide value, make it easy.
We mused on bringing in a social aspect. What if you could create an account and join a community of people looking to "Get Fit?" You could share your story, find and create accountability. You could even help others Get Started.
The idea was
We could go anywhere with it.
I built a prototype in Principle to show some of the animation and interaction design elements. (video above)
The end of the quarter was quickly approaching and we needed to pitch this idea to leadership. We designed a Get Started home page and a handful of child pages. (below)
At the end of the quarter, the team flew to our headquarters in San Francisco to make the executive pitch. I put a deck together that told the story of the whole design process, and had the team help create assets for our prototype so we could present something that felt realistic. The executive team loved the concept.
Our next directive was to partner with the UX team at Jet.com, meeting them at their office in New York to figure out how to turn the concept into a broader content and design strategy. In Portland, we would continue building concept pages and user testing, reporting back to the executive team at the end of another quarter.
When you work on a project with big expectations, there is a sense of uncertainty constantly looming over your shoulder. You have no idea where you're going, so how do you know how to get there? Through many years of songwriting I learned to be comfortable in uncertainty, even revel in it, because the process will leave you with something beautiful, or worst case scenario you'd have something less than perfect that gets you closer to the next great thing.
Before this project, I never had to lead a team through these feelings. To a team of diverse personalities through the uncertainty so inherent in the design process, it takes a blind trust in the process, continuous infusions of optimism, creative exercises, a conscious ebb and flow of pushing hard and relaxing, and the ability to visualize new perspectives and inspire others to see them with you.