How to Design the Ideal UX Meeting

How to pose great questions, offer solutions, and present your designs in just the right level of fidelity.

Workday Design
Workday Design
8 min readAug 13, 2019

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By John Cheng, Sr. UX Designer at Workday

My first project as a UX designer was a complete failure. It also taught me much more about how to design a great product and how to lead the ideal UX meeting than school ever could.

Let me explain.

I was tasked by a client with creating an exciting new app that was going to define their industry. As it was my first project, and such an exciting one at that, I was eager to do well with my UX design process. However, things started to go south as soon as the project got underway. In our client meetings, I’d try my best as the “UX expert” to defend my work. But it seemed like as much as I tried to give reasons why my design was the right one, there was always something that the stakeholder — a blunt, technically-minded leader — didn’t like. “Have you thought about this??” he’d ask. And with each “no” that I gave, I could see him losing confidence in our whole direction.

I couldn’t win, and I felt frustrated and demoralized. So, like we’re all tempted to do, I started complaining to anyone and everyone who’d hear me. “It was his fault!” I’d say, feeling vindicated that he was keeping the project back because he didn’t understand good UX design.

Oddly, my design lead at the time never indulged my complaining. Instead, he encouraged me to shift from being stuck in frustration to observing where I could grow. With this new mindset, I started asking better and more introspective questions about my own effectiveness as a designer. Over time, I learned clear patterns of how I could lead teams to build better products.

Through this journey, I realized that it all starts with how we design meetings, and that realization has influenced the design process I use today at Workday.

A Meeting Is the Most Important Thing You Can Design

You might have had a situation like mine, where, during the course of a project, you meet with stakeholders to figure out some aspect of a design. Then, as the meeting unfolds, you realize that there are other factors you hadn’t considered, and you decide you need another meeting to talk again about the new problems. And so on.

The conversations stay shallow, project timelines starts dragging out, and confidence in the collaboration slowly fades.

Instead of just seeing how it goes, having clear agendas and discussion points helps you to create and manage a project’s momentum.

Structure Agendas Around Open-ended Questions You Want to Discuss

If you’re like me, you tend to want to present the one version of your best work, hope for as few questions or problem areas as possible, and just get approval.

However, a BIG problem quickly arises from this sort of yes/no conversation. If it turns out that someone doesn’t like something you’ve made, you’re back at square one, with no further clarity to move forward in the UX design process other than the fact that your last idea didn’t work.

Instead of structuring your design meetings this way, pose open questions about unknowns and assumptions in the design to solicit more collaborative feedback.

As an example, imagine you are designing a product that helps travelers plan their trip. After gathering user insights and some product constraints, you start to have some design questions that don’t necessarily have a black and white answer, but might make for a great discussion.

For this product, that may include questions like:

  • What kind of traveler do we want to target, and what might that mean for what we build?
  • What activities do we want to account for?
  • What do we hope someone might get out of the app once they’re done?
  • Or adding items, what is the general flow?
  • When do we imagine users coming back to the app?

Take five minutes to list out (or, of course, post-it!) all your possible questions about your product’s direction, group them thematically, and narrow in on the key questions you want to bring up during your next meeting.

Illustration by John Cheng of open design questions grouped into a few categories.

Using meetings to ask questions helps people on the team feel heard, breaks down big problems into more accessible chunks, and lowers the stakes of the conversation from approve/don’t approve to a more collaborative discussion. This leads to better, more thoughtful decisions, more often.

However, asking questions is only half the story. Think of all the meetings you’ve been a participant in. You’ll quickly realize that every time the meeting driver posed questions, the quality of discussion was much higher because you got to react to a variety of already-prepared options, rather than try to brainstorm on the spot.

Shape the Discussion by Visually Proposing Answers to Your Questions

This is where UX design comes in. Your superpower as a designer on a team is the ability to create deeper discussion about problems and questions by visualizing multiple, distinct solutions quickly for a team to react to.

The reason this is so powerful is because people are much better at generating unexpected, innovative ideas when they aren’t under pressure to also analyze and judge those same ideas. Often, they come up with ideas when they have quiet, personal space. In meeting contexts, where time-efficiency and decision-making are prioritized, people are better at reacting to, analyzing, and building off of existing ideas. Seeing a basic set of ideas in front of them keeps the team from being stuck on only one option, helps them consider ideas they might have prematurely dismissed, and collectively pick apart the relative strengths of each direction to make more informed decisions.

Let’s go back to our example of the travel planning app.

Perhaps one of the questions you want to ask stakeholders is “what kind of traveler do we want to focus on?”

Here, instead of simply posing this question in the meeting and hoping one of the participants has the answer, think of three or four possible answers the group might be able to choose from and discuss.

Perhaps we want to focus on adventure travelers that want to explore the outdoors, time-constrained travelers that want to get the most out of big cities they visit, or young parents that want to find a quick overview of things and find places to relax. Obviously, there may be more options than this, but this might be a good place to start the discussion.

From these options, quickly visualize each of these personas. This way, when you pose the question, “what kind of traveler should we focus on”, your audience has something quick and visual to digest (people are way better at digesting images than words).

Illustration by John Cheng of different travel types for a hypothetical travel app.

Try to go into your next meeting with several of these questions, along with visual solution options to choose from. You’ll find that you can confidently ask the question, give your audience a few options to choose from, and help them discuss the impact of each choice. Your audience might choose one option above the others, parts of different options, or it might spur even deeper conversation about something no one had expected!

Shape Your Interactions with Your Level of Design Fidelity

Once you have gathered reactions, it’s up to you as a designer to make decisions on what the next round of questions and options might be, perhaps involving more interface elements in varying levels of fidelity. Here’s an atypical, if rough, progression of visual detail as you iterate between each meeting:

1. Broad Design Direction (Sketches)

These are initial concept sketches that propose the most promising opportunities your team has to create or improve the user experience. Think of these as what you might otherwise whiteboard to quickly bounce around abstract ideas and flows.

Illustration by John Cheng of a broad design concept.

2. Interaction Ideas (Sketches)

These sketches propose possible solutions to the question, “What UI elements should we use to express the broad design directions?”

Illustration by John Cheng of interaction idea sketches.

3. Wireframes (Sketches and Digital)

These layout and flow-level sketches and digital prototypes help us answer the question, “What layouts, language, flows, and states makes our desired experience most usable?”

Illustration by John Cheng of sketched and digital wireframes.

4. Visual Flow (Mockups and Prototypes)

These high-touch assets answer the question, “What is the look and feel we want to best convey the experience and align with our brand?”

Pairing the right questions with each artifact in sequence helps you to make that highly thoughtful product by shepherding your stakeholders through the design process and affording them structured input at every step. Instead of input and discussion that goes off the rails, stakeholders are able to give thoughtful reactions comparing concrete ideas, and help you ask more specific questions that refine the design.

Break Bad Habits, Now!

I’d love to say I never repeated the mistakes of my first project again, but in reality, it took at least 10 projects to fully break bad habits. However, once I fully broke them, things started to change for the better. During one particularly memorable project, I remember my design lead at the time saying, “This may be your best work yet. The stakeholders’ confidence in us is as strong as ever, and every new iteration has so much intention and depth of options.”

Those mistakes and those wins are what helped me finally experience the power of these habits fully. Through more years of practicing and working with other designers to do the same, it’s clear that the ability to design an ideal UX meeting is the core skill that affects how we work together as a team. Shaping meetings to ask open ended-questions and propose solutions makes us better designers that not only fit into product organizations, but begin to lead them.

I’d love to hear from you. Where have you and your teams gotten stuck in meetings, and how have you designed your way past them?

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