← Back to experiments

Design Buddies Community · Facilitation · Design Education · UX Practice

Stop designing.
Start questioning.

“Most designers know what good UX looks like. Very few have practiced the decisions that produce it, the prioritization under constraints, the moment you realize you designed for the wrong person, the discipline to question the brief before opening Figma.”

Role

Facilitator & Lead Designer

Participants

Emerging designers & PMs

Format

Full-day design sprint

Location

Vancouver, BC

Design sprint workshop cohort, Vancouver

Why I ran this

The gap isn't knowledge, it's practice under real constraints.

After years working across enterprise B2B, AI products, and complex platforms, one pattern became clear: designers who struggle aren't short on frameworks. They're short on reps. They haven't had enough chances to make a real design decision, with incomplete information, competing constraints, and something actually at stake.

I ran this workshop to give a cohort of designers exactly that. A structured day where the exercises aren't hypothetical, the feedback is direct, and the goal isn't a deliverable, it's a sharper instinct for how to approach the work.

Participants working through design exercises

Teams working through the assumption mapping exercise, no Figma, just thinking out loud on paper.

What I focused on

Three things I teach every designer who wants to work at a senior level.

These aren't workshop activities for their own sake. They're the thinking habits that separate designers who execute briefs from designers who shape them.

01

Question the brief before you answer it

The brief is a hypothesis, not a spec. Before any design work starts, I push teams to ask: what problem are we actually solving, for whom, and how would we know if we got it right? Most designers skip this step. Senior designers make it non-negotiable.

In practice

What this looks like in practice: mapping assumptions by confidence level before opening Figma.

02

Design the flow, not just the screen

A screen is the output. The journey is the work. I have designers sketch the full user experience (before, during, and after the product interaction), because that's where the real friction lives. You can't design a good screen inside a broken flow.

In practice

What this looks like in practice: journey maps on paper, not in Figma, to stay in problem-space longer.

03

Make a decision, then defend it

The most important design skill isn't ideation, it's prioritization. I have teams use a simple effort/impact frame to convert their insights into a ranked list of things worth doing. Not a backlog. Not "it depends". A decision, with a rationale they can stand behind.

In practice

What this looks like in practice: leaving the session with 3–5 specific next steps, not open questions.

Sprint prompts· Questions every designer should ask before opening Figma
01Before any research

"Who is the person under the most pressure in this flow, and what are they afraid of getting wrong?"

02During discovery

"If we remove every assumption we can't prove, what do we actually know about this user?"

03Before wireframing

"What would have to be true for this design to fail, even if it looks right?"

04During ideation

"Are we solving the problem the user has, or the problem that's easiest for us to solve?"

05During design

"What's the one thing a user needs to understand on this screen before they do anything else?"

06Before handoff

"If this shipped tomorrow and nothing changed, what would we regret not having questioned?"

Rapid sketching session
Workshop framing slide

Left: rapid sketching, constraints on purpose, screens off-limits. Right: the framing that opens the afternoon session.

What I've seen shift

Designers leave talking about problems, not features.

The clearest signal that a session has worked: by the afternoon, teams stop talking about what to build and start talking about what they don't know yet. That shift, from solution-first to question-first, is the whole point.

I've watched designers spend a full morning convinced they understood their users, then spend twenty minutes on a journey map and find three friction points they hadn't considered. That's not a failure of the morning, it's the workshop doing its job.

“The brief is a hypothesis. The journey map is your first research artifact. The prioritization matrix is your first product decision. Everything else is execution.”

How I open every session

Sketch artifacts from the session

Sketch artifacts from a sign-up strategy exercise, lo-fi on purpose. Fidelity is a distraction when you're still figuring out the problem.

Why this matters to me

Good design education is the same skill as good design.

Figuring out what someone actually needs, then building the clearest possible path to get them there, is what I do in product work every day. Facilitation is the same problem with a different output. The room is the product. The participants are the users. The session structure is the interaction model. I take it just as seriously.

← Back to experiments