Planning a Design Thinking Workshop with Constraints

We break down how we ran a design thinking workshop at the Venture Out Conference.

At Shopify, we’re passionate about infusing great design into everything we make and do. But what makes great design? More importantly, how can we extend great design practices to encompass not only the products we build, but the approach we take and behaviours we display?

These were the questions we faced at the Venture Out conference, this past March 15 and 16, 2018. Venture Out is a tech conference that connects LGBTQA+ folks interested in tech to career opportunities, role models, and each other. As a tech company that is committed to diversity, Shopify was thrilled to be the main sponsor for the conference.

One of the contributions we committed to for the conference, in addition to sponsoring it, (and alongside an incredible keynote by Andrea Ross!) was a Design Thinking workshop led by myself and Mina Smart. In the workshop, we challenged over 70 participants to learn and practice design thinking to create and test a prototype, all within 45 minutes!

Running this workshop with a group this size, in such a limited time frame was challenging. Usually, these workshops run anywhere from two hours to several days. In this piece, I’ll explore how we used the limitations and constraints we faced to our advantage to ‘design’ our workshop and make it a success.

Workshop leaders, Nathalie Crosbie (left) and Mina Smart (right)
Mina explaining Design Thinking

Constraint 1: Time

Design Thinking is an iterative process with several steps allocated to ideating, exploring, and building out ideas into products. In real life, such a process could take weeks, months or longer to execute. The task was to reconsider the concept of a shopping bag; however, we positioned it as a problem to solve. What kinds of problems do shopping bags solve, and why?

So we needed to execute this task with the same process, in just 45 minutes.We decided to view this time constraint as something that could benefit us. In light of our short time, we made several key decisions that allowed the workshop to run smoothly.

a) We did a workshop dry-run in advance. Practicing ensured we smoothed out any bumps in our execution, and allowed us to uncover inefficiencies in our original workshop design that we could course-correct for.

b) We made time for an ice-breaker even though time was short. Designing is vulnerable, so creating rapport between workshop collaborators was too important to sacrifice. Having so little time made longer ice-breakers impossible, so we opted for a 1 min icebreaker.

c) We clearly marked each stage of the design thinking process with a time limit visible to everyone, so participants were aware of how fast they had to work.

d) We pre-selected a problem for participants to solve. Pre-selecting the problem saved time that would traditionally be spent identifying potential problems to solve.

e) We encouraged participants to focus on the quantity of ideas they produced, rather than perfecting a single idea. It’s more important to have something to get feedback on early, than to polish a concept that may not meet the needs of the target audience.

f) We provided participants with worksheets that allowed them to keep track of the workshop stages, and monitor their ideas and progress as they moved through each stage.

Worksheets were provided during the workshop

The time constraint ultimately proved to be an asset to us. It forced us to stick to the essentials of the Design Thinking process, and the fast pace bonded people quickly and added a high level of energy and playfulness to the experience.

The workshop was fun way to meet people at the conference while learning about the fundamental principles of design thinking. Many laughs were laughed.

— Zach, workshop participant

Constraint 2: Space

We knew from the schedule that we would only have 10 minutes to set up for the workshop. What we didn’t realize until we arrived was that the space had been set-up auditorium style, with all chairs facing a stage, rather than with tables that allowed for an interactive workshop. Fortunately we had come a few hours early to see the space. This allowed us to:

a) Identify the need for tables.

b) Flag this for the organizers so they could find some tables for us in the hours leading up to the workshop.

c) Work together to quickly set-up 6 tables in that 10 min between the last talk and our workshop.

Space was tight but we made the most of it!
Participants were seated round-table style to encourage discussion

Similar to designing in the real-world, we addressed unexpected hiccups using collaboration, focusing on functional solutions (like quickly finding more tables) rather than perfection (having everything set-up perfectly in advance).

Constraint 3: Resources

At Shopify, prototyping often involves using digital tools like Sketch and InVision to build models. The tools weren’t available and it also wouldn’t be efficient to onboard people to them even if they were. Instead, we provided a variety of arts and crafts supplies and encouraged participants to build a new concept for a shopping bag using what was at their disposal.

Some of the materials we provided included pipe cleaners, tape, cardboard, twine, paper, rulers, and popsicle sticks!

Some participants build shopping bags shaped like boxes…

Other build tote bags, or backpacks…

Some even put together unique contraptions that we had never seen before!

We were reminded here that design thinking stems from a mindset, not a setup — the materials available don’t matter as much as being imaginative and communicating the rationale of your design.

Constraint 4: Skill Levels

The conference audience had diverse age ranges, experiences, and skill sets, so we designed our workshop to be fun and accessible for everyone.

A few decisions we made to ensure this:

a) Choosing a problem that was non-technical in nature. We didn’t ask participants to redesign a website or mobile interface, since some participants were newcomers to tech. We chose something simple that everyone could relate to: a shopping bag.

b) We asked participants to identify their discipline upon entering the room. Participants took stickers that identified them as developers, designers, or other. We then assigned participants to tables, such that there were diverse perspectives represented at each.

c) In a technical environment like Shopify, most people walk into design thinking sessions with baseline knowledge about what problem to solve. We chose to make our design thinking session as accessible as possible, so that no matter the education, skill level, or discipline, all could participate.


We were pleased that even with time, space, and resource constraints, and a large and diverse group of people, our participants learned and benefitted from the workshop.

Shopify’s Design Thinking workshop experience at Venture Out was a great catalyst to outside-the-box problem solving. I loved the overall structure of the workshop, with the focus on solving user problems and optimizing solutions.

— Tiffany, Workshop Participant

While our Design Thinking workshop was a learning experience for participants, it was also a learning experience for us. We were reminded of the importance of constraints, and designing around them. And we took away learnings that will inform how to we iterate on our Design Thinking ‘design’ the next time we run a workshop:

  • Scheduling dry-run earlier: We sent our invites to dry run out only a few days in advance, by which time fewer people were available.
  • Plan for highest number of attendees: We didn’t expect as much interest as we got, and had only enough tables and materials to accommodate ~70 participants when another 20 wanted to participate (some were so interested they sat nearby to listen even though they could not actively participate).
  • A check-in system for attendees: We would have loved to have the names and contact info of our workshop participants to be able to follow-up after the conference, stay in touch, and share design opportunities and resources.
  • More time: As much we loved the energy the fast pace provided due to the short workshop time, next time we would ask the conference for a bit more time for another round of prototyping and building for a fuller Design Thinking experience.

We were so honoured to be able to sponsor this conference, as well as have the opportunity to provide a keynote and host a workshop! Congratulations to the Venture Out team for a fantastically run conference — hope to see you all next year!

Interested in Design Thinking? Check out:

Planning a Design Thinking Workshop with Constraints was originally published in Shopify UX on Medium, where people are continuing the conversation by highlighting and responding to this story.

“Planning a Design Thinking Workshop with Constraints” Posted first on ” Design on Medium “
Author: Nathalie Crosbie

Author: Pawan Kumar

Leave a Reply

Close Menu
%d bloggers like this:
Skip to toolbar