4 min read

From Frustration to Flexibility to Frequency

Advice from design thought leaders at IDEO, Frog Design, Coinbase, and PillPack

When design-thinking integrates seamlessly into a continuous delivery of user and customer value, awesome products and companies can emerge. At Underscore VC’s Core Summit, we heard from IDEO’s Matt Weiss about how design can help navigate the awkward “puberty stage” when discovering new products.

In addition to this product discovery phase, we reached out to design firms and design-oriented startups to better understand design-thinking in the context of product development. We dug in seeking to highlight successful characteristics of design-thinking in practice. Here are some highlights from our interviews with Harry West, the CEO of Frog Design — a global design and strategy firm, Matt Weiss, the Managing Director and Co-Founder of IDEO CoLab, Connie Yang, the Director of Design at Coinbase, and Jennifer Sarich-Harvey, VP of Design at PillPack.

One of the best indicators of product and design-oriented leaders is “an ability to be frustrated by problems”. Before you take a problem-solving mentality to the problems that you see, Harry West advises product and design leaders to first sit in the tension of that frustration to build empathy for the problem space. Over time, that frustration will breed focus as you become intimately aware of which problems are most important and why.

When asking Harry and Matt Weiss what common pitfalls to avoid in their experience with a multitude of companies, they both alluded to the rabbit hole of incremental product improvements. Especially in larger companies, there can often be a mentality of “keeping all doors open”. To combat this lack of specificity, Matt suggests a balance between flexibility and rigidity.

Referring to IDEO’s collaboration with PillPack as an example, the founders recognized that good design creates great experiences but also plays a role in shaping what’s next. Creating a fundamentally new kind of pharmacy meant that PillPack had to own the end-to-end experience and design from the ground up. Most importantly, it meant that they needed to do this with, rather than just for, their customers.

To do this, Jennifer Sarich-Harvey echoed the need to be flexible while maintaining a strong focus on your founding purpose. Drilling a level deeper, she shared the importance of designing flexibility into your organization and aligning it with the need to evolve based specifically on learnings from the customer.

For PillPack, the ability to build out the value proposition and experience with input from customers, early on, meant a continuous focus on design with customers at the core — It also meant giving teams the permission to be flexible in service of that focus. Jennifer pointed out that this doesn’t mean they’re flexible with everything, but that the precedent has “set the foundation for a culture of testing, learning, and iterating and is part of how PillPack has been able to change healthcare for the better.”

From a startup’s perspective, Connie from Coinbase shared that “sometimes the most valuable insights can come from a relatively small number of data points.” Especially in a fast-moving and incredibly early-stage industry like cryptocurrency, frequent learnings from a few can offer more timely insight than comprehensive campaigns. Unscientific tools (e.g., social media polls or surveying 5 friends) may give you interesting and different perspectives from a more rigorous and expensive process. The most important take away was that you should always be talking to your users, no matter what format.

Across global design firms and fast-growing startups, healthy design in practice is characterized by frustration (channeled into focus), flexibility (and rigidity), and frequency in learnings (even if unscientific). Let us know in the comments below how design is integrated with development in your world, or tweet at us here!

We’re always looking to chat with the next generation of design-oriented founders. If you’re working on something new, please reach out to us!