2016: The Year of Adventure

Lessons working with Stanford’s d.school, IDEO, & school districts

Before I begin, here’s some context:
2015: Awakening > 2016: Adventure > 2017: Alignment

2015The Year Of Awakening: I fell extremely ill with Grave’s Disease, an autoimmune disorder that left me within a month 20 pounds lighter, less hair, heart palpitations, and too fatigued to even open a water bottle. Though the illness proved treatable, the sheer human terror of contemplating my mortality gripped me. I fell into a deep depression for I still had yet to accomplish my dreams, or figure out my purpose in life.

Through hundreds of hours reading, meditating, and soul-searching, I saw clearly my own victimization by, and participation in the specter of mindlessness haunting our time. As a victim, I suffered from prescribed definitions of success (i.e. I wore my participation in the Cult of Busy as an honor), As a perpetrator, I harbored apathy, us-vs-them mentality, and selfishness. As a former skeptic of spirituality and emotions, I suddenly discovered a depth in my self that I have never experienced — a wholeness, an awakening. I emerged from these reflections that:

As a Silicon Valley designer, the real bugs aren’t in the software, but in our hearts.

I needed to share this work with the world, and it shouldn’t take an autoimmune disorder for a person to discover their place in the world. I decided the best place to share this work with others was through education.

I left my previous startup in August 2015 and began building the foundations for 2016, attending education conferences, and reflecting on the key ingredients necessary for holistic education.

2016 The Year Of Adventure: I took a leap and decided to try my hand living the consultant life. I got to work with some really thoughtful organizations like IDEO’s Teachers Guild, Stanford d.school, and San Francisco Unified School District. I’d like to share with you some of my highlights below:

After a serendipitous Twitter exchange with Experience Institute’s Director of Programs, Aaron Wilston-Ahlstrom, I was introduced to one of their badass Fellows, Jonathan Lazatin. He and I chatted about our similar trajectories of going more from a maker role to a teacher role, and later he introduced me to one of the high schools he interned at — Design Tech High (d.tech), a public charter high school in Burlingame CA founded to teach both staff and students design thinking. I volunteered at d.tech in October by training their staff in how to craft design portfolios from working in industry.

After d.tech received a grant from the Chan Zuckerberg Initiative (Mark Zuckerberg’s foundation focused on, among many things, personalizing learning for all kids), they created a position for me in January called “Designer in Residence” to (1) improve d.tech’s design programming for students; and (2) create various resources to help staff adopt design thinking as a change management process. The Stanford d.school’s K12 Lab was also hired through the grant so for eight months, so I had the exciting opportunity to work at the intersection of design thinking and education. Here are some of the most proudest contributions from my time there (the detailed case study can be found in my portfolio):

A Rubric for Assessing Design Thinking: PROCESS | SKILLS | MINDSETS
Personalization Levers: A Tool for Training New Teachers to Personalize Learning Experiences For Students
Design Thinking Playbook: Using Design Thinking as a Change Management Process in K12 Schools

Some Lessons Learned Along The Way

  1. Teaching high schoolers is incredibly hard. I learned despite my best intentions for wanting to help my students and explore my interest in education, coming into a high school assuming design thinking was the panacea for all problems was ignorant, selfish, and akin to colonialism. I learned how incentive-sensitive students are and how intrinsic rewards (curiosity) conflicts with extrinsic rewards (grades). I learned there’s a powerful tension between teacher needs (classroom management, ability to connect with as many students as possible) vs. student needs (relevance between material and undisclosed needs [i.e. significance, connection, challenge, authenticity]). I learned students have a low tolerance for artificial projects that aren’t solving real needs for others (i.e. design a wallet for another student), and instead would prefer to work with external stakeholders like a local business in solving their problems. I experienced firsthand how little bandwidth and time there is to actually teach a class, reflect, prepare for upcoming lessons, grade, and give feedback. This gave me so much more empathy and appreciation for teachers, and helped me understand why educators are often dismissive and even contemptuous of outsiders trying to “innovate” in education. Without ever stepping into a classroom yourself, you do not deserve to tell a professionally-trained teacher how to be better. I am most grateful for this humbling lesson.
  2. Innovation in schools requires a great degree of foresight, planning, stakeholder buy-in. After working at d.tech, I (naively) imagined how awesome it would be to work in other public schools, facilitating design sprints, incorporating design thinking into the curriculum, and creating a culture of constant iteration. But then I realized how many conditions need to be in place in order for a school to adopt design thinking: (1) the entire school’s staff needs to be bought in; (2) competency & training is a constant need and high quality train-the-trainer programs are rare; (3) the amount of time staff have to practice design thinking must be made built into their schedule, otherwise it will never be prioritized. Most public schools do not have the luxury of starting from scratch, so d.tech is a rare case, and I wonder how feasible it would be to actually assist other schools in their innovation.
  3. Sharing the best practices in other industries in education can both be powerful and dangerous. I asked myself often while at Design Tech High, “What frameworks and practices from other disciplines might be (1) relevant and helpful in a high school, and (2) which ones aren’t?” (1) Areas that were useful: User Job Stories applied to rubric design to contextualize who, what, why vs. just talking about the what; and Blue Ocean Strategy’s Four Actions Framework questions (Do More Of, Do Less Of, Start Doing, Stop Doing) applied to semesterly Post-Mortems for feedback & reflection. (2) What wasn’t useful: rapid prototyping cannot be applied to student learning because unlike software development where a failed app prototype has no material consequence on users, public schools cannot afford to perform randomized control trials to prototype different learning experiences for students.

In 2014 I attended Tradecraft, a bootcamp for professionals transitioning into UX, Growth, or Sales careers. As part of the professional development, we had the opportunity to take a two-week version of Stanford Graduate School of Business’ renowned MBA elective, Touchy Feely, which teaches young leaders over ten weeks the skills for emotional intelligence, including:

  • Understanding one’s “operating system” of beliefs & habits, and how to update them to foster more productive relationships
  • Learning to give and receive constructive feedback to strengthen performance and relationships.
  • Practicing new ways of expressing emotion that improve communication and influence
  • Turning conflicts into problem-solving conversations.

While taking the class, I learned that how we connect, influence, and communicate is in fact a skill that can be learned. I took multiple versions of the class (2-weeks at Tradecraft, 1 week through Stanford Continuing Studies, and the official 10-week version during my training as a facilitator). Below are some visuals illustrating more precisely what happens in the class and why it has been so powerful for me and others.

Some Kind Words From My Students:

“I think you have an incredible talent for delivering feedback that is highly impactful and creates connection.” — Stanford MBA Student
“I think you’re very perceptive and very aware. That’s something I really admire. You can sense and pull out more from someone. You just sense if there’s something someone hasn’t fully captured or discussed. I don’t know how you do it, but it’s amazing” — Stanford MBA Student
“From day one I have looked to you as a model. How to understand my emotions and how to express them. You not only understand your own emotions but also ask thoughtful questions that get to another layer of emotions. You know so much about your own emotions that you’re able to help us get more in touch with ours.” — Stanford MBA Student

Lessons Learned

  • Behaviors in others that appear illogical to us are in fact perfectly logical for them, we just don’t understand their logic. I learned that phrase from one of my mentors, Ling Lam, who is a brilliant facilitator. He taught me that when a person exhibits a behavior that appears illogical to us (i.e. an adult throwing a tantrum, extreme levels of self-censorship), it is likely a behavior that was learned earlier in the person’s life to get a key human need met (survival, connection, significance, certainty) but is now “outdated” and no longer serves them as well. For example, there was a woman in one Touchy Feely session who rarely spoke up, and when she finally did, would apologize for speaking, retreating back into silence. Ling Lam said, “It is like you are asking ‘Do I matter?’”. She erupted into tears, as did many others in the room who were touched by the poignancy of the observation. In a debrief, Ling Lam explained that the woman was exhibiting a cluster of behaviors that were symptomatic of the dilemma of “If I speak up, I’ll be punished” and “If I don’t speak, do I really matter?” This psychological insight taught me how to lean into curiosity whenever I found others exhibiting behaviors that were confusing or even bothersome, creating more “space between stimulus and response” as described by Viktor Frankl.
  • As humans, technological progress has outpaced human evolution, so to adapt, we must unlearn our impulses that no longer fit our environment. Humans evolved under conditions that threatened our survivability (i.e. hidden animal predators) and thus are wired to notice the negative vs. embrace the positive (negativity bias). Though we no longer face life-or-death situations on a constant basis, we are habituated to avoid threats. Our operating system of habits and perception is outdated, yet we are rarely taught how to notice and update our system. For example, vengeance is an intuitive response to deceit, yet causes mutual harm — especially in professional settings, and our culture’s glorification of the pursuit of happiness stigmatizes negative emotions and pain, which stunts our growth.
  • Feedback is usually avoided by both deliverer and receiver because it is executed poorly, but it is a learnable skill. A profound learning for me in my training and facilitation is that there is a sharp distinction between WHAT I OBSERVE and WHAT I ASSUME. Ineffective feedback conflates the two (i.e. “You were late and so you don’t care about the project” conflates the OBSERVATION “you were late” and the ASSUMPTION “you don’t care about the project.”) Effective feedback, on the other hand, separates the two and creates an opportunity for joint problem solving (i.e. “You arrived 10 minutes after the agreed upon 10:00 AM for our meeting. I’m worried that this project may not be a priority for you. Can you help me understand what’s going on?”) The concept also applies for the receiver in how he/she responds, so continuing the above example, a defensive response might look like “I don’t care about the project? You clearly don’t value my contributions.” A effective response may look like “Yes I am 10 minutes late, and accept full responsibility. I also hear that you worry about my commitment to the project. Is this concern just related to my tardiness, or is it a larger concern we should discuss?”

IDEO’s Teachers Guild

The Guild is run by by IDEO’s Design for Learning Studio and Riverdale Country School’s Delta Group. Teachers Guild brings together teachers to collaborate and solve 30 education challenges in three years. As a Creative Catalyst, I coached teachers nationwide through an online design thinking sprint to develop solutions for student character-learning, resulting in a playbook released to over 26,000 educators on Character Day (September 22, 2016).

Big Takeaway: Design thinking is much harder to facilitate online because when you combine a profusion of ideas with little in-person touchpoints, there’s less facilitation that can be used to help participants adopt mindsets like deferring judgment or embracing ambiguity — both of which are critical to the success of a design sprint.

Harvard University Graduate School of Education

I started my year-long online masters certificate in education leadership (to be completed in 2017). In 2016 I took two modules: Leading Learning and Managing Evidence. The first one focused on frameworks for understanding “learning,” noticing the intersection of race and learning, and creating processes for more efficient collaboration between school staff. The second one focused on understanding various impact evaluation methods, such as randomized control trials, difference in differences, regression discontinuity, etc.

Big Takeaway: In Instructional Rounds For Education, Richard F. Elmore defines the improvement of learning more systematically in the form of a triad between Student, Teacher, and Content, with Tasks as the connecting tissue. Investing in any one singular part of the triad (i.e. teacher professional development) without investing in the others results in no improvement in learning.

San Francisco Unified School District’s Innovation Lab (iLab)

iLab aims to improve SFUSD’s education through design challenges and innovation awards. I was brought on board as an Innovation Coach to help one of the innovation award participants, E.R. Taylor Elementary School, with their design challenge. They noticed at family events there tended to be higher participation among Asian families than that of Latino families or African American families. I guided E.R. Taylor staff through a two-month design sprint, resulting in $12,500 in funding to bridge the engagement gap.

Big Takeaway: Design thinking is a potent process when addressing well-scoped challenges (i.e. at d.tech, we ran a design sprint on “how might we help teachers understand students beyond academics to better serve their needs?” led to creating an activity that teachers introduced to their students during intersession, leading to observable differences in relationship between teachers and students). However, when it comes to a challenge as systemic as equity, political strife, and change management, the process can only break those problems into smaller more manageable pieces, sometimes the sum of which still cannot solve the total problem.

Nasdaq Entrepreneurial Center

Nasdaq Entrepreneurial Center is a non-profit in San Francisco dedicated to providing entrepreneurs with quality resources and access to mentors, training, and networking — all at no charge. Though the Nasdaq Entrepreneurial Center had an abundant supply of resources and mentors focused on the business-side of entrepreneurship, I was brought in to help their inaugural class of Milestone Makers — 12 startup CEOs / founders — develop competency in the emotional-side of leadership. I also had the opportunity to coach an awesome founder in the healthy food space.

Big Takeaway: Those at the helm of companies often feel alone because they walk the fine line of self-disclosure vs. self-censorship. When disappointments arise — a funding round didn’t close, not hitting a product milestone, losing a key team member — the impulse to retreat away and hold all the fear / anger / confusion alone ultimately leads to burnout and a dangerous norm of concealing problems. Instead, founders could benefit from working with a coach, therapist, or peer circles to exercise the muscle of mindful self-disclosure (just enough vulnerability to jolt the team towards problem-solving, but not too much to incite fear and diminished trust in the leadership).

Oxford Day Academy (ODA)

ODA is a public charter high school for East Palo Alto, CA slated to open in fall 2017, and combines design thinking, social emotional learning, and civic engagement to nurture its students to be ready to navigate the colleges and careers typically reserved for alumni of our nation’s most elite private preparatory schools. I conducted research on available design thinking and social emotional learning programs that would be relevant for high schoolers, and was a thought partner for the executive director in defining how the two would be integrated into the student experience. I helped create all the key visuals in our application to Lauren Powell’s XQ Superschools Challenge grant, where we made it to the finalist round, but unfortunately did not win.

Big Takeaway: Charter hearings can be incredibly educational in understanding what is important at the district vs. county levels when approving a new public charter high school. I learned the district level is fiercely meticulous about a new school’s instructional model, expecting every detail about the student learning experience from teacher qualifications (since we have an unorthodox “Social Emotional Learning Coach” position) to procurement of 3rd party sources of learning (i.e. Boys & Girls Club, Design for Change). The county level, on the other hand, was more interested in the experimentation of new school models. It was easy to get angry when we were denied our petition at the district level, but that only necessitated an increased level of rigor in designing ODA’s instructional model, so I sincerely appreciated their critiques.

2017The Year Of Alignment: 2016 was such an incredible learning experience and now I’m excited to bring my intersection of design, education, and social emotional learning to a Learning and Development role in an organization that helps others learn or collaborate more efficiently (i.e. Coursera, Udemy, Slack).