Methods for defining complex problems into principled frameworks

Today's guest for the Story Series is Catherine Winfield, Design Director of Education for Chan Zuckerberg Initiative. Catherine is deeply fascinated by solving systems-level problems with multiple audiences or stakeholders. She believes that it is the ultimate application of design thinking.  

In this interview, Catherine shares her tactics on how she approaches defining complex challenges and turning them into principled frameworks providing clarity to the teams she works with. She also talks about the types of problems that provoke her the most, and how she thinks about the competencies her team needs to have to be able to solve the right problems.

Hi Catherine - Welcome! 

Can you talk a bit about your unconventional story and how you got to where you are? 

Thanks Julie, I actually got started in design through architecture. I had read an article about behavior change and space that cited data about student test scores increasing when classrooms had access to natural light and patient re-admittance rate dropping when rooms were painted with warmer neutral colors. I became fascinated with the idea that design decisions could impact human well-being in such implicit but important ways and went on to study architecture and spatial design for both my undergraduate and graduate degrees. 

After spending time practicing in the field and observing career opportunities in my graduate education I realized that the scale of impact I was hoping to achieve wouldn’t be possible in the architectural industry. 

During my graduate studies at MIT I began to look for ways to incorporate these types of behavior feedback loops into my design work and stumbled onto the field of product design and user experience. I finished my time at MIT studying in labs at the Media Lab and went onto to work for a few healthcare startups that used behavior change as a lever in their products and services to improve patient health and physician decision-making. 

I now lead a team at Chan Zuckerberg Initiative focused on improving student outcomes and teacher tools where many of these experiences have culminated. 

A small portion of the Education Design /UXR team at Chan Zuckerberg Initiative

What type of big problems are exciting for you to solve? What drives you to solve those problems?

I am deeply fascinated by solving systems-level problems with multiple audiences or stakeholders. I believe that it is the ultimate application of design thinking. 

In the digital product space systems-level problems are usually tackled by enterprise models and organizations because of the inherent complexity. However, these models often focus too heavily on the system (think of Electronic Medical Records, or Customer Relationship Managers) and not enough on the human experience within those systems. 

It’s really challenging to think from a system and end consumer perspective but I believe that is THE challenge our industry should seek to solve if we wish to have lasting meaningful impact within societal systems like education, healthcare or government.

It is certainly what drew me to my current role where we build tools to help teachers and students in K-12 education. The educational system in the U.S. is an incredibly complex thing, with policies being set at a district or even town level. Therefore, it's near impossible to scale great tactics when ones that equitably improve student outcomes are found. In our work it’s critical to think about the teacher, the student or the school leader's experiences but also how that school fits into a district, state, or region. 

In my prior work in healthcare working in the cardiology and oncology spaces I quickly realized that individual patient education, health literacy, and agency or autonomy had greater impacts on patient outcomes than any of our physician driven changes. It is why I sought out opportunities in the educational space. I believe the system we are seeking to impact is the meta system that will address so many of the challenges the US faces today including health, climate, and justice.

How do you approach defining complex challenges and turning them into principled frameworks providing clarity to your team?

When designing for and within complex systems it’s easy for teams to become overwhelmed or know how to link seemingly disparate concepts. Developing a framework to ease with potential confusion is now a huge part of my job. To be clear I think it is also a part of my work that is still being resolved. I believe priorities, relationships and tethering are three tools I try to use when building and guiding teams in complex spaces.

Ruthless prioritization

First, when there are many concepts team members need to juggle clear priorities cut through the noise and it is an important part of a leader’s role to make hard tradeoffs so that priorities can flow clearly. So when in doubt and faced with complexity force everything into a priority order. We do this with “even over statements” such as people’s work life balance even over speed or equitable outcomes even over scale.  

Understanding tensions or overlap in systems

This is where having a design background is helpful. If you can visualize even in the crudest of diagrams how things relate then you can help people understand tensions or overlap in systems. It may sound silly but try diagramming the power dynamics of adults in a student's life. There are teachers, mentors, school leaders, family members, peers, school counselors, coaches or maybe even tutors. Who is the most effective at supporting that student? Who is the most powerful lever at providing feedback? Is there a difference when it comes to life skills versus academics?

Tethering your team to something that won’t change

Third, is tethering, when you are guiding teams through complex spaces or ever-changing spaces it’s really important to tether folks to something that won’t change. That can be team identity, a single concept or mantra in your work, a framework that is not likely to shift. For example, while our organization worked to iron out many of our larger strategic questions our team focused on a maturity model. This helped us stay tethered to the "how" even if the "what" changed. We could discuss and plan how we wanted to evolve and mature as an organization and it provided some stability as the "what" of our work moved a little. Team charters, repetitive social rituals or a particular persona can all be things leaders can help teams stay tethered to while navigating complexity.

How do you think about the competencies your team needs to have to be able to solve the right problems, and how do you optimize for achieving those? 

Building effective teams can look and feel quite different depending upon what problems that team needs to solve. Bringing clarity to the space the team will operate in is a first step. For the team I lead we have a few unique aspects to our work:

  • First we work within an academic calendar so we ship things in annual cycles and try to minimize disruption to classrooms mid-year that is very different from shipping quarterly goals. 
  • Second, we built tools in partnership with other organizations that may or may not have familiarity with technology practices which means cross-organizational partnership requires relatively defined processes to ensure things can move forward. 
  • Lastly, we work in very content heavy spaces where academic, curricular, human development or training documents can become long and dense, therefore we need specialized content skills within design to deliver strong user experiences. 

Once I had a strong handle on how our team is different than other technology teams (recognizing we aren’t the only ones in the world operating in this way) I was able to think more directly about the types of people who would be happy working in that environment. For example, if we ship larger features for back-to-school annually then someone who is used to iterating really quickly and making big changes with little impact (such as in the consumer app space) may not be joyful working in this environment. That’s not to say that past experience always maps to what people are seeking in future opportunities but I try to very carefully think about who will be happiest working within our constraints and who will see opportunities where others see constraints. 

I believe this strategy to build a team coupled with tools for then helping that team navigate complexity are what helps our team thrive.


People who support Leadership Circle

Deepest thanks to the following people who graciously offered feedback
and support while beta testing Leadership Circle.

Leslie Yang

Director, Product Design

Jeff Smith

Senior Design Manager

Julie Zhuo


Aniruddha Kadam

Product Design Manager

Jen Kozenski-Devins

Head of Google
Accessibility UX

Jian Wei

Design Manager

Courtney Kaplan

Leadership Coach

Cammy Lin

Product Design Manager

Sun Dai

Senior Product Designer

Liana Dumitru

Design Manager

Mike Dick

Catherine Winfield
Design Director, Chan Zuckerberg Initiative
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