Facilitating a Design Sprint

Olivia Cheng
11 min readJul 13, 2021


A while back I came across a facilitation guidebook in my inbox from AJ&Smarts’ newsletter. My initial thoughts were: “free? Count me in”. Then, “what the hell is facilitation”?

Of course, I knew what facilitate meant, as in the dictionary definition of the word. But words tend to mean different things in different contexts. (Just like bread refers to carbs in Walmart, but means money in cool kid lingo). And in the context of the UX world, facilitation spoke to an entirely different practice in the design process.

In short, facilitation is a hands-off design consultation. It usually takes the form of a workshop of some sorts where the facilitator teaches and walks a group through a problem-solving process. The important takeaway is that as a facilitator, you are a neutral party who supports others to solve the problem. This means you don’t overstep your boundaries in providing answers; you’re simply there to provide a path and perspectives.

After binging AJ&Smarts’ guide and Youtube videos, I was eager to put into practice my new nuggets of knowledge. But where would I even start?

“Sometimes the stars just align and you don’t question it.”

I had been goofing around with my friend, Val, and geeking out about this new thing I learned when she brought up her worries about her passion project that she started a couple months ago. It was a routine conversation; I would often hear her out about the doubts she was having or lend a third party’s perspective on her troubles about moving forward on the project. Somewhere along the way, it clicked. A way we could both fulfill our goals and help one another. A way for her to get the boost she needed with her project and for me to get some judgement-free, hands-on experience with a cool, new practice.

Call it subliminal messaging, a coincidence, or just me being an opportunist. Sometimes, the stars just align and you don’t question it. What follows are my takeaways from this adventure.



The very first thing I had in mind as an ad-hoc facilitator was to work out what kind of workshop would help them the most at their stage in the project. Study Beans is a personal passion project started by Val and Carolina to alleviate pain points around the current student learning process. A deeper conversation with Val uncovered that they had garnered a lot of user research in the form of interviews thus far and were struggling on next steps. I decided a design sprint was the best outlet for them to channel their research data into a concrete problem and testable solution.

Screenshot of Basecamp homepage, where everything related to the project from calendar to materials are centralized.
Screenshot of the here.fm setup before the big brain activities.

Next came project coordination, setting up workspaces, and scheduling dates. I used this opportunity to try out a bunch of new remote working tools. For centralization, I used Basecamp, a workspace centralization tool recommended by one of AJ&Smarts’ articles. For meeting and working, I set up a room in here.fm (highly recommended by Val), a software mainly marketed as a hangout spot. I chose this over other tools like Miro in order to cater to my audience and create a relaxed and fun space they could feel comfortable being honest in. Here.fm comes with a built-in Youtube player, gifs, and stickers that I thought would come in handy with getting people to open up and be creative.

Digital posters created to help guide learning and application of new concepts.

Prior to the sprint, I also created a couple learning materials to guide those unfamiliar with the design process tools. We then cleared our calendars and coordinated 4 hours a day across 3 days to commit to the design sprint. All that was left to do was dive in.


DAY1__Defining the Challenge, Producing Solutions

An email sent the day before our first session.

Setting Expectations

Before the first day started, I was extremely mindful of wanting to set the right tone. As an empath, I’m very aware of how emotions and expectations can impact one’s performance. Keeping in mind who my audience was (young college grads, first serious passion project, friendly faces), I set out to create a casual, inviting, and colorful workspace.

We began on here.fm with a quick walkthrough of all the tools we would be working with. I went over ground rules (Monica from Friends was right when she said, “Rules help control the fun!”), the agenda for the sprint in general, and then the agenda for the day. I also took some time to gather expectations from both Val and Carolina so I could get a clearer idea of how to concretely help them get what they wanted out of the sprint. I really appreciated how open-minded the both of them were in terms of deliverables; this expectation to explore really gave them room to think without restrictions.

Carolina expressed that she wanted recordings of the sessions to look back on, which is something I should have prepared for prior to the sprint. Some time went into figuring out how to record and what software we could use for better audio. (Since I was typing and taking notes throughout, it was better for someone else to record).

Lesson: Get expectations before the sprint. Leave cushion time during each session for technical difficulties.

Reaching their North Star. It feels good to align!

Consistency and Convergence

“It felt like seeing an old couple renew their vows.”

Our first task of the day was to review their user research, synthesis, and any other artifacts they had accumulated thus far. Something I had not predicted was both parties having entirely different methods of communicating their findings. While Val brought in quotes and examples, Carolina had contributed bigger ideas and themes. Though their different perspectives come in handy later on, it was difficult to organize at this stage.

Lesson: Make it clear what artifacts are expected to be delivered before the sprint. Get people organized on what they should prepare and provide formats.

Next was my favorite part: figuring out what their partnership’s North Star was. Personally, I love seeing people and missions align. I don’t think there can ever be too much of getting on the same page. In this case, Val and Carolina thought they were already aligned on their mission, but this exercise had helped them realize some discrepancies within their motivations. Reaching a deeper understanding of one another lent to a shared drive that sparked newfound inspiration. It felt like seeing an old couple renew their vows.

Writing and choosing problem statements to turn into How Might We’s.

A New Mindset

There were a lot of personal challenges that came with reorienting my position from a creative to an objective third party. One of the most difficult aspects of the process was learning to partake without critiquing. As a designer, I’m used to critique naturally being part of the conversation. However, partway through workshopping one of Carolina’s problem statements, I realized I was being influenced by my own opinion on the unpolished gem I saw in her ideas.

Lesson: Double check before speaking: is it a critique or a guiding statement? Will it impact their decision or make them think for themselves?

I’ve had my fair share in tutoring in the past, but teaching strategic design is very different from straightforward subjects like math or basketball. Design is always toeing the line between following frameworks and creating space for freedom in the process. As someone who still feels ambiguous about where I stand in relation to this line, it was difficult to guide others to find their spot. Great teaching strikes the balance in showing them how to do something rather than telling them exactly what to do.

Amidst all the newfound struggling, the first day came to a close in a flash. With four hours of work behind us and a new, shiny star to run towards, Day 1 ended in high spirits.


DAY2__Sketch, Sketch, Sketch

The Process

Flying off the high from Day 1, we started out Day 2 strong by resetting the upbeat atmosphere with some music and reviewing all the progress we had made up to now. As we reiterated our HMW’s and ran through completing a simple journey map, I caught onto some feelings of anxiety around doing the process “right”. Because both of them were new to this process and learning on the go, there was an unconscious fear that effectiveness derived from perfection which I had to address.

Lesson: Remind yourself and sprinters to not focus on the perfection of each step, but the process and their thoughts!

Val presenting her sources of inspiration in our Lightening Demos while Carolina takes notes.

Structured Creativity

The rest of the day was followed by rounds of structured ideation which included sparking inspiration through Lightening Demos and then getting ideas down with 4-Step Sketching. Since this was a passion project without many constraints, I wanted them to spend as much energy on exploration as possible (versus getting clouded by constraints at this point). The 4-Step Sketch exercise was a great way to ease Carolina (who doesn’t have as much experience working in the creative mindset) into drawing out her imagination.

I had both of them take notes while the other was presenting their ideas, but to ensure they were both on the same page I took on summarizing after each big point as well. Design is a constant conversation and while we get to solutions fast, it seems easy to get lost and derail just as quickly.

Lesson: Summarize as the facilitator to make sure everyone is taking away big points and a shared understanding of what just happened.

They talked through their concepts and brainstormed around different ideas, big and small. It was here that I was challenged once again to refrain from opinionating. It was really difficult for me to not react and bounce off all the ideas that were flying around, but I had to remember that my views shouldn’t impact their project. Whenever I had overwhelming thoughts, I would write them down as notes to try to get it out of my system. (They could revisit those once the sprint was finished if they wanted). We finished the day by choosing a concept both of them liked and each diverging once again to storyboard their version of it.

Lesson: Find ways to disassociate yourself from the creative process like muting yourself and writing down comments you would usually make.

Val presenting details of her ideas and sketches.

Time and Energy Management

Working a new part of your brain for long hours can take a toll on working and we felt the clouds set in halfway through Day 2. We tried to keep the energy up by setting different music, taking breaks, and even hosting mini dance parties in between. Sketching and ideating on paper helped them break away from the screen and change up their setting.


Day3__Prototype and Plan

What’s the most obvious indicator of a great workout? Feeling sore the next day. On Day 3, our brains were really feeling the repercussions of the sprint. For the runners, this had been the most creative work they had done for their project thus far. I took time in the beginning to warm-up as always, but instead of going straight to review afterwards, I asked for their expectations for the sprint again. Their answers were much more concrete and deliverable-focused compared to their answers on the first day and I felt that was a great indicator that we would be able to finish strong. I reminded them of all their work they had done in such a short amount of time already and encouraged them to push through the final lap.

Lesson: Empower ownership and remind sprinters to look back at their work as motivation. Give them credit for everything they’ve done up to this point and let them envision the finale!

Val and Carolina working off their storyboard to prototype screens in Figma.

Hands-Off Advice

“It’s important to keep participants on track, but not make them feel constricted in what they can say.”

Compared to the other days, prototype day is when sprinters put their heads down and work. This was the easiest day for me as a facilitator, since most of my work was done. I took the spare time in between breaks to pick out playlists, plan next steps, and prep some reflection statements for Val and Carolina to take home.

We started the day by finishing the storyboard where we left off. As they discussed what steps to include, I could tell the topics of their conversation were getting too narrow in scope. I reminded them that their goal was to journey out an MVP and to worry about smaller details (themes, buttons, smaller features, ect.) later. Inspiration can sometimes hit hard at moments like these and you’ll feel like you have so many ideas you want to include. It’s important to keep participants on track, but not make them feel constricted in what they can say. These ideas are great to have and a good way to make them feel heard is to note them down and save it for later.

Lesson: Keep an ear on what’s happening and pop in for gentle reminders to focus on the big picture.

It was also important for me to realize that people are more than capable of self-regulating. After I reminded them to focus on the big picture once, they began to remind each other when they felt like they were getting too caught up on a detail. We wrapped things up by writing out a user research plan and outreach for their participants. I saved some time at the end for a conclusion and promised to follow up the week after for a reflection session.



Whew, what a week! It was the best feeling in the world to be able to take some time and sit on what just happened. The following Monday, I scheduled an hour with Val and Carolina to go over their initial goals and expectations and how the sprint had fulfilled them. One of Val’s goals was to figure out how to collaborate better with Carolina to which I had gathered some observations around their personalities and working styles. I shared some advice on how they could mesh Val’s out-loud and creative thinker persona with Carolina’s quiet and structured thinker persona.

The most difficult challenge for me was taking away that perspective of a designer and turning it into one of a facilitator. I needed to keep reminding myself that the pressure of a good output and great design solution wasn’t on me; that wasn’t my goal. My goal was to facilitate a good working space, help them work better together, and create a process. The outcome was theirs to own.

A big thanks to the amazing friends I’ve been blessed to meet over quarantine and amazing resources the design community offers! It was awesome to see them push themselves through this process (Val expressing it was the most creative she had seen Carolina work) and I’m really thankful they gave their all to commit to the end. I can’t wait to explore more ways we can have fun designing together for the future!

Chatting about Ghibli movies after a tiring final day.

How did I do for my first workshop? What would you do differently? Is there anything new you want to try out but haven’t got the chance to yet? Let me know by commenting or emailing me, I’d love to hear you out!

Resources I Used:

AJ&SMART FACILITATION GUIDEBOOK | Design Sprint | Design Sprint Videos

Some Playlists:

Bossa Nova | Funky Jazz | Ghibli | TrapSoul Beats | Mario

Reach out to Val and Carolina to learn more about their project!



Olivia Cheng

Self-taught UX designer who has recently come to enjoy the growing pains of learning. A deep love for ethics and future tech. 🌚🌝