Design Leadership



Before design school, I never considered myself a “creative” person. What I realized at school, however, was that the term Creativity was ill-defined and in fact could be adapted to almost every aspect of life, work, and relationships. Bearing in mind this new way of seeing the world around me, I began my journey into the discovery and fostering of creative culture and design.

What I have since honed in on is the fact that part of our job as designers is to figure out what is not working (at a company, in a relationship, etc), find out why, and take steps to resolve it. I like to ask “why” to get to the root of problems and will not shy away from digging into challenging problem areas.


Always focused on solving user needs to make the world a more organized and efficient place, my design strives to empower the user by reducing distractions, using consistent design standards, and organizing information with distinct hierarchical sections.

I really love our hangouts. I used to get stressed during Design Critiques but with you I don’t feel that at all and it’s really nice.
— Anthony (Designer @ Oscar)

Fostering Design Culture

Many of the companies I join do not have established and respected design teams. It is usually one of my first goals as a design leader to educate the broader team about the value of design and the role design can play in many parts of the organization.

Befriend allies

  • Find and get to know design counterparts across the organization (product, engineering, operations, customer success).

  • Offer help (design or otherwise) on things others are working on or struggling with.

  • Become a sort of design consultant within the company offering to help think through workflows and advise on design direction.

  • Listen to and empathize with colleagues’ struggles to figure out how you can help them.

  • Be a connector and facilitate conversations between teams that can help each other.

  • When new employees start, make an effort to get to know them to share more about what you do and how you can help them right from the start.

Teach design thinking & strategy

  • Give others on the team a book about design (one of my favorites is The Design of Everyday Things, especially for those with very little design awareness) or encourage others to read an article and discuss.

  • Host a lunch and learn where you discuss the different aspects of design, how you approach design specifically at the company, and walk through some fun group exercises.

  • Organize a design week where the entire company is encouraged to participate in design exercises, brainstorming sessions, or mini design sprints.

  • Write and send short design blog posts or snippets about things the design team is working on.

Get people excited about design

  • Go for walks or grab coffee with others throughout the company and get to know them. Forming personal relationships with people keeps you and design top of mind.

  • If you find someone in the company excited about design, offer to pair with them or have them shadow you to get more familiar with the design process and how you approach problems.

  • Grab any opportunity to speak at internal events about the power and value of design.

  • At RedOwl we moved into a new office and had the opportunity to brand the space. One of the designers on my team created an abstract owl-centered image that we got the entire office involved with. We turned it into a sort of paint-by-numbers event where we ordered pizza and beer and had fun painting together as a team.

Our paint-by-number branded owl behind our Halloween photo!

Our paint-by-number branded owl behind our Halloween photo!

Design Critiques

Constructive, regular design critiques are a staple of any design team, but how they are executed can result in vastly different experiences both for designers and end users.

When I joined Oscar, the team was relatively junior and there were no design leaders and the weekly critiques consisted of unstructured, volunteer-based presentations of work. What this meant was no one felt the need or felt comfortable sharing their work and the sessions were unproductive. I revamped our critiques using some of the following tactics:

  • Communicated the value of design critiques, constant feedback gathering, and the general design process to the design team.

  • Each person would share something they are working on, however small, and tell the team what kind of feedback they are looking for. Ideally this would happen with some thought provoking questions.

  • No negative, unstructured, emotional feedback! It’s easy to get sucked into a habit of saying “I don’t like that.” without elaborating. Instead we discussed tactical feedback after clarifying questions about the user goals or workflows were answered.

  • Brought in guests to the critiques. Some designers at Oscar did a good job of gathering feedback from people outside of the design circle, but others could use some improvement. We started bringing in 1-2 guests to each critique, usually an engineer, product manager, product marketing manager, or end user to broaden the circle of critiques and get a fresh pair of eyes on the work.

Over the next few months, we continued to evolve our design critiques.

  • Gave each designer 30 minutes two times per week to present a piece of work (required each week).

  • Split the critiques into smaller groups. As our design team grew from 6 to 10, it was difficult to find enough time for everyone to get the feedback they needed. Splitting into smaller critique sessions divided by team (ex - internal tools was one team and digital member facing was another team) helped everyone maintain more context into what each other person was working on, given that they were in similar domains and were guaranteed to see the work progress each week.

  • Split each domain-specific critique into two weekly sessions. We found it difficult to focus on critique for more than 1.5-2 hours at a time so we held twice weekly critiques.

  • Feedback given in the form of “how might we” proposals and questions.

  • Experimented with each person giving one positive piece of feedback and one constructive piece of feedback after each of us digested the work after a few minutes of silence.

  • Experimented using sticky notes to give that feedback in a print-heavy critique.

  • Experimented with having one senior designer participate in the critique of the opposite domain (ex - a senior designer on internal tools would join the critique of the digital member facing team).

No matter how well you structure design critiques, it’s possible that some team members will still feel more comfortable giving and getting feedback in a smaller setting. Ensure that you notice who is speaking up and who is keeping quiet during critiques and make sure to follow up with them 1:1 after the session.

Design Critique

Speaking Engagements

Throughout my career I’ve been able to speak to various audiences about anything from overall design, specific feature design, career growth, and organizing your life. Public speaking is something I’m passionate about and a great way to build design awareness inside or outside of any organization. I’ve even been able to present at remote events either with a pre-recorded video or joining remote via Google Meet.

Speaker at:

  • Cornell Tech: Designing Healthcare

  • Parsons the New School for Design: Career Growth in Tech and Design

  • Oscar Health: Designing for Provider Services

  • Oscar Health: Designing Paperless Communications

  • Oscar Health: Women in Tech Career Night

My favorite topics to speak about are:

  • Design thinking and how it can add value to any department

  • Building teams (design and otherwise)

  • Fostering culture within an organization

  • Career growth / mentorship

  • Organizing your life

Oscar Speaking Engagement

Design Counterparts

The engineering, product, and design “trinity” is one of the most important relationships within an organization. Building strong relationships with design’s counterparts helps facilitate product development and ensure the team is bought in to new features and key decision making. Once a solid group dynamic is established, any single part of the “trinity” can speak to the needs and points of view of the other parts.

Have Fun!

At the end of the day, if you’re not having fun with friends at work, it’s going to be hard to stick around regardless of the pay or the work.

  • Hang out outside of work. I planned game nights where the team would leave the office and go to a nearby board game bar where we’d play a couple of games with some food and drinks.

  • Eat lunch together. The design team sat spread out so that we could be closer to our product and engineering counterparts, but we still made an effort to eat lunch with each other almost every day to keep our design culture alive.

  • I started a Friday Recap session where all of the designers would share something fun they were doing outside of their normal work in lightning-round style updates. This sparked creativity, collaboration, and helped to build the strong design culture. These evolved into Friday Bagels & Brainstorms where in addition to sharing fun updates we could ask for feedback from design team members we didn’t normally get to work closely with, usually due to the different domain focuses.

  • We brought a little (actually a lot!) of fun to our annual Halloween costume contests one year by the design team dressing up as fonts (Sarah’s (on the left) amazing idea!).

Part of the design team’s Halloween costume contest: fonts! Left to right: Roboto, Franklin Gothic, Helvetica

Part of the design team’s Halloween costume contest: fonts! Left to right: Roboto, Franklin Gothic, Helvetica