Crafting a 2-Day Design Workshop that People Actually Enjoyed

Katherine Lu
6 min readDec 10, 2023

In June 2023, I hosted a design workshop for 4 product squads. Not only was this an exciting challenge, I wanted to make this a rewarding experience for my participants, consisting of Product Managers, Product Designers, and Tech Leads. The official goal was to push the envelop on what a product homepage can do to retain users. My personal motivation was to align our product teams on a unified vision, and to convince the squads we need more cross-team collaboration.

Initially, I imagined the workshop as a 2-day event, and I got feedback from a hesitant workshop participant. “Two days is too long!” they lamented. “Can it just be one day?” I tried to pare it down to just 1 day, but after reviewing the entire schedule, it would be more than 4 hours; I knew this would be a hard sell, and wouldn’t garner the excitement I wanted.

I doodled quite a bit to think through the schedule, theory, and how to organise the groups. I considered various ideas that I soon scrapped, such as asking our UX researcher to function more as a consultant.

To set myself up for success, I sought feedback from researchers and designers. I asked myself…

“How might I create a workshop experience where every activity feels purposeful and the ideas generated are user-focused?”

Much of my decision making was rooted in what to prevent. I wanted to avoid:

  • ideas based on technical or product constraints
  • misalignment on our user persona

I thought the best way to achieve this was with a two day format, where the first day featured small talks and exercises (like the empathy map canvas), and the second day got to the core of the workshop with HMWs, wireframes, and voting.

I brainstormed the 2-day workshop as a user flow with milestones. This also helped me with timing.

Day 1— Inform

Day 1 Workshop Schedule

I wanted to “share the why” on Day 1, and did this with short talks, persona exercises, and creating an open environment to ask questions. (My days as a Resident Advisor in university helped me in creating a safe atmosphere where people could speak up and be transparent.)

I also coupled each activity with a desired outcome to keep myself on track, as seen in the Day 1 Workshop Schedule.

Completing the Circles Exercise, a creative kickstart to ideating.

After a shortened round of Ideo’s Circles Exercise, we jumped into talks from our UX Researcher and product manager to contextualise the topic.

Our UX Researcher Jiji giving a summary on our user research and traits on our target demographic.

The highlight of Day 1 was a little pocket guide I made so participants could refer to a proto-persona during the workshop for our empathy exercise and wireframing. This was inspired by Natalie Harney’s blogpost “What I’ve Learned Running Visual Thinking Workshops.” Spoiler alert: many of the participants did refer to it throughout the day!

I gave everyone a pocketbook, which included the proto-persona, his behaviour, needs & goals.

At the end of the day, I asked for people’s takeaways and gave a quick preview of day 2, so that information and exercises could “marinate” before we jumped into group-wireframing the next day.

Day 2 — Ideate

Day 2 Workshop Schedule

After a quick recap, I started the second day with another warmup: come up with a mascot for our product that would appeal to Joachim, our proto-persona. Again, I wanted to bring the focus on the proto-persona instead of relying on participants’ existing knowledge about our users because many have their own takes on who our target audience is. Our users vary in real estate portfolio size, financial mindset, and experience level as property owners. For the homepage concept, I wanted to de-emphasise power-users (they skew feature creation, in my humble opinion!). So, I asked participants to focus on a more “everyday” property owner.

The questions I posed to the participants on the 2nd day were:

How might we encourage users to subscribe to the premium membership?
How might we get users to explore or engage with the portal?
How might we get users to come back?

I formed teams so people would collaborate with others outside of their squads. I wanted to shake up the influence others had on their closest teammates in the hopes there may be different ideas shared and expanded on during the workshop Q&H (Question & Hypothesis as opposed to Q&A, as we don’t have Answers yet). Once the HMW exercise was complete, we moved into the sketching, and each team presented 1–2 wireframes for the group to vote on.

How We Voted

I have an unpopular opinion: I hate dot voting. The dots give no indication on the voter’s mindset. Are they coming with the perspective that we’re tight on deadline? Does their vote also speak to their respective team goals?

Instead, we voted along a quadrant to distinguish which concepts were voted Most Potential, Easiest to Solve, or Most Want to Work On.

By placing the concepts along a quadrant, we could see which ideas rested in the sweet spot of Easiest to Solve and Most Potential. Other great ideas, such as ones within Most Potential and Most Potential, could be tabled for later discussions.

The workshop concluded with a bit of a stalemate, as a discussion would have been needed to move forward with a final conclusion. I did not anticipate voting in such a way would be so open-ended as there is no “clear winner,” whih would have been the with traditional dot voting. As a result, it was difficult for me to bring workshop realities into a clear summary. However, new ideas and ways to configure the homepage were brought up, which later made their way into the next iteration of designs.

Lessons and Takeaways

People were enthusiastic, inspired even! One tech lead said: “Can we have a workshop for my team’s own initiatives?” Despite the accolades, I knew there were areas that can be improved for next time.

  1. A good workshop must be intentional and clear in goals. Even though this takes deliberate work and seeking feedback, the effort directly correlates with the quality of the workshop.
  2. Matrix dot voting was not a straightforward means towards a “winning concept.” The website is a tool that was designed in a modular way, where each tile in the product dashboard is dedicated to either a datapoint or specific piece of information. Therefore, there were overlapping concepts, so the winning concept would actually be an amalgamation of different ideas. This did not leave me with a clear direction unfortunately.
  3. Overplan, but save room for flexibility and creativity. I was not off schedule by more than 4 minutes, which means no one had to stay past lunch. (I also didn’t want to deal with any hangry participants!) I’m glad I allocated a strict time for each activity, but I also checked in on the teams during the work sessions.

All in all, the workshop was a great experience in terms of facilitation and gathering knowledge from the smart people I worked with. And judging from the survey I sent out afterwards, I believe participants would agree.

What have you learned from your own workshops, and how have you managed to bridge workshop results into reality? Please comment and share, or reach out via my website.



Katherine Lu

UX/UI Designer, terrible with plants (she/her) Learn more about me at