Five Lessons Learned From Teaching Design Remotely

The Instacart Design & Research Team
Instacart Design
Published in
7 min readJul 13, 2021

By Dan Shilov, Senior Product Designer

In January 2021, in addition to designing at Instacart, I took on a new responsibility — teaching a graduate level UX Portfolio course at University of Maryland. Having mentored designers previously and written a book about design interviewing, I was looking forward to expanding how I was contributing to the design community.

One of the things I enjoy about working at Instacart is our support and sponsorship of the design community. Many of our designers are active mentors outside of work. Recently Instacart sponsored HmntyCntrd, an organization run by Vivianne Castillo, an advocate for instilling diverse and inclusive practices in the design industry.

I couldn’t be more excited to teach. An opportunity to help shape the future class of designers in a tight knit setting? Sign me up! But as the date of the first class drew near the good old imposter syndrome started kicking in. Will I have enough material for a 2-hour class each week? How should I structure the lectures? What about homework? And most importantly how do I make sure that my students get the most value out of this class?

To make sense of it all, I approached teaching like a design problem, thinking through all its facets while brainstorming multiple approaches to help my users, or in this case students, engage with and learn the material.

I wanted to share some of the top lessons I learned while teaching:

  1. Start with a strong foundation
  2. Lean into the new teaching normal
  3. Show specific examples
  4. Adjust and iterate with feedback
  5. Consider the whole individual

1. Establish a strong foundation

Great design work starts with concretely defining the problem. Teaching a course is no exception. Before diving into the fun stuff, it helps to step back and ask:

  • What are the course prerequisites?
  • What concepts do I want my students to take away at the end of the course?
  • What is the most important thing to help them advance in their journey now?

As I was thinking through how to best address these questions, I also had to consider the class format of 7 lectures, 2.25 hours each every week. 15 hours of content seemed intimidating at first but as I started to outline the syllabus, the details started falling into place.

I slotted in 2 classes for student presentations — a mid-term review of sorts and a final presentation. I then chunked out the rest of the lessons based on the key concepts I wanted to communicate, primarily focusing on case study writing, design and portfolio execution.

My final outline for the portfolio course

Of course every plan looks perfect on paper, but how would I take this planning and integrate this into the reality of teaching remotely?

2. Lean into the new teaching normal

As working professionals in 2020, many of us have felt video conferencing fatigue. One of the early decisions I made for the class was to let students turn their cameras off if they chose to. To make sure students still paid attention, I sprinkled in impromptu questions and activities to help them engage with material more actively.

Activities helped students apply the material

Speaking of engagement, one of the best features of the virtual class was using break out rooms. For one design critique secession I facilitated 3 break out rooms of 3 students each. Every student got to present and receive an engaging critique from the other two students. They would then rotate every 15 minutes. Break out rooms encouraged all students to participate more actively compared to a larger group setting.

Aside from Zoom, we relied on tools such as Figma to collaborate and share work. Students were assigned homework to provide asynchronous critique to their classmates via Figma comments. And in turn things came full circle when I gave feedback to students on the quality of their critique.

3. Get specific, get hands-on

Initially my class started out slide-heavy. After all, isn’t that a common approach, lecturing with slides? After two courses and reviewing student’s work, I realized the message wasn’t always getting through. Questions would come up that were already addressed in a previous class, and although I encouraged students to be concise in their case studies, most of them ended up several pages long.

As creatives, we know that breakthrough learning comes from first hand experience. In my undergraduate days when I was taking courses like Sketching or Painting there was barely any mention of color theory or even history. Instead students were encouraged to draw or to paint and we learned how to evaluate our work through critiques.

Design is no different. Learning the language of design is one thing — but truly cementing that knowledge in one’s noggin takes an active, hands-on approach.

In practice, this meant doubling down on showing specific examples and letting students do the work. We did this by:

  • Learning about general UX Design portfolio structures and patterns
  • Looking at other designer’s examples and critiquing those
  • Writing case studies and critiquing the content
  • Designing and iterating multiple times on the case study

I saw a marked improvement in my student’s performance when we incorporated more critiques. The key takeaway? Active reinforcement of material through doing the work, presenting it, and iterating on it multiple times helped the learning stick.

4. Get feedback, iterate and improve

As designers we know that iteration is the name of the game. We come up with multiple options, we iterate, add, remove until we arrive at promising solutions. Teaching a course is no different.

In the beginning I was lucky enough to get support and critique from Carol Boston, who manages the HCI program at University of Maryland. She helped me refine my thinking, identify gaps in my curriculum, and provided tips on how I could engage my students more after observing our lectures and design critiques.

My colleagues at Instacart were also supportive and provided invaluable feedback. Justin Miller, a designer and a long-time design instructor himself (who introduced me to this opportunity in the first place), helped me refine the course material. My design manager, Tyler Monteferrante, provided feedback and suggested additional resources.

Lastly, in a true, user-focused session, I also solicited and encouraged feedback from my students. And they didn’t hold back! Based on their responses I cut down on the length of lectures and allotted more time for people to show and critique their portfolios.

5. Consider the whole individual

The objective of my course was to ensure students came out with a portfolio they could start using to apply for work right away. But as we know, the portfolio (albeit critical) is only one piece of the application.

Consider the whole individual

In my lessons I encouraged students to think about who they are as designers — their unique combination of interests, skills and superpowers. Landing a job is hard work and it begins by knowing who you are and assessing the right level of fit with the job. After all, every designer and everyone’s design journey is unique. As designers we should celebrate our differences and perspectives, because creativity thrives in diverse environments.

We spent time thinking about questions such as:

  • What does an ideal job look like? What are the characteristics of the company and teams I’d thrive in?
  • What are my unique skills and superpowers?
  • How can I succinctly summarize this in a statement?
  • How can my work amplify and reinforce my superpowers?

These types of questions helped students navigate their design portfolios, especially when they were deep in the middle of it, trying to make sense of all the complex information. Just like in any design project, it helps to step back and revisit the problem and the objectives that you’re trying to solve.

Paying it forward

Make no mistake, teaching was hard work. There were days when I was nervous about presenting, but after every class I walked away refreshed and inspired from our conversations. If you’ve ever mentored designers, I highly recommend looking into teaching. Working with students in a close knit setting and seeing them grow and improve each week is an incredibly rewarding experience.

I’ve been extremely lucky to have this opportunity to teach at University of Maryland, and am thankful for my team at Instacart for supporting my teaching efforts.

I couldn’t have done this without the support of my team:

  • Brett Rampata–for signing off on letting me pursue teaching
  • Justin Miller–for introducing me to the opportunity and connecting me with University of Maryland’s HCI program
  • Carol Boston–as the manager of the HCI Program at University of Maryland for spending the time to help me shape the curriculum and improve the coursework
  • Tyler Monteferrante for providing feedback, support and encouragement

With my first portfolio class wrapped up for Spring, I’m looking forward to coming back and also pursuing other avenues to teach design and make the learning accessible to current designers and future design leaders alike.

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