The author, Carolyn Jeskey, in action at a design thinking workshop. Photo by Daniel Lombardi

 I’ve been learning about design thinking slowly and steadily since 2006. I’m sure I am not the only one whose optimism about what a team could achieve together grew exponentially after viewing the Nightline video The Deep Dive – aka, How IDEO Redesigned the Shopping Cart, for the first time. Seven years later, one might say I am a design thinking convert, not to mention a complete sponge.  

Last year, I formally incorporated design thinking into the work of my organization, the Community Transportation Association of America. Peer Insight has been important to this transition, training my colleagues and I on design thinking activities and skills, and co-designing a facilitation process used by seven community teams to improve job access transportation connections for low-wage residents.

As I venture into training transportation change agents in design thinking, I am indebted to the design thinking tools, visual aids and experiences available to me from design thinking experts and practitioners. I feel I can confidently relay both the value and application of this process. There is a great support network out there for learning about design thinking and it’s growing rapidly.

Resources on Design Thinking

Here are a few of my go-to resources on design thinking: 

ONE. At the beginning of any introduction to design thinking I love to show the Venn diagram, below, from’s Human-Centered DesignToolkit.

 Image from:

Image from:

The diagram hones in on three essential aspects of a successful solution: technical and operational feasibility, financial viability, and customer desirability. This is a picture that is truly worth a thousand words.

TWO. When explaining the overall process of design thinking, I use Peer Insight’s 4-phase graphic, called the 4Qs. Below is a version that Peer Insight adapted for our work with the job access communities.

 The Four Questions of Design Thinking from  Designing for Growth: a design thinking tool kit for managers (Columbia Business School Press, 2011). 

The Four Questions of Design Thinking from Designing for Growth: a design thinking tool kit for managers (Columbia Business School Press, 2011).

During workshops, I like use a large-size poster of this graphic to show what happens during times of divergence and convergence during the process. The entire graphic is useful for marking milestones and showing how the work of each phase links with the one before and after. I have a particular appreciation for how the transitions between each phase join at the narrow points. It’s these points of convergence— synthesizing data and making decisions— that give me great energy and show me that progress is being made. Especially when working with communities, it’s important to note the points in the process at which a group can take stock of its work-to-date; making thoughtful decisions, and plan for next actions.

THREE. While I could go on, I’ll just end with one great resource for design thinking tools —Stanford’s Use Our Methods site.

 Screenshot from:

Screenshot from:

These descriptions of key design thinking activities are brief —1 page each— and convey practical instructions as well as heart and soul and reminds me of the larger principles I want to embody as a design thinker: listening,wondering, keeping an eye on the end user, and transformation through iteration.

What are your go-to resources on design thinking?

At Peer Insight, we’ve mastered the art of design thinking and use these skills to understand our users, create an effective strategy, and spark innovation across the entire company.

See how we use design thinking as part of our toolkit. 

Message me: @CarolynJeskey

Carolyn Jeskey is the director of Community Engagement at the Community Transportation Association ofAmerica. One of her most rewarding roles is working with state and local coalitions to bring customer-centric mobility solutions to their communities.