Design work session

We solved a complex branching form using simple methods — and AI where it helped.

A real case, start to finish: how a 50+ question, four-path change-request workflow became a hybrid design that's clearer for users and easier to build. You'll tackle the same brief live — then see exactly how far more time and iteration can take it.
Saturday, June 27, 2026
Morning · ~75 min
Design team · hands-on
Hosted by Siva — bring a laptop, no prep needed
Part of an ongoing Saturday series
Why this session
One real problem, shown end to end

The change-request form we'll work on started as a branching requirements diagram with 50+ questions across four paths — the kind of brief that's easy to either over-simplify or over-engineer. We're going to run it as a live design exercise: I'll frame the problem, you explore it independently, then we compare notes before I show how far the same brief went with real iteration behind it.

This isn't a theory talk. You'll tackle the same brief live — independent exploration, then a quick share-out — before I open the actual JSON data model, the actual rule engine, and the actual console that shows risk and approvals updating live as you answer.

Agenda
~75 minutes — you build first, then we compare notes
Loose timing — the point is doing the exercise, not hitting the clock exactly.
0–10
Welcome & what we're doing today
Quick framing for the session — we're going to design something real, live, not talk about design in the abstract.
10–15
The problem, and the challenge
Walk through the real branching diagram exactly as it arrived — 50+ questions, four paths. The challenge: make it navigable without hiding the logic from the people who have to audit it.
15–17
Quick pulse check
Show of hands: sketch on paper, an AI tool, Google around for patterns — what's your first move? Sets the tone that any approach is fair game.
17–37
Independent exploration — 20 minutes, same brief
Everyone works solo on the same change-request challenge — sketch, Google, brainstorm with whatever AI tool you reach for, whatever you picked above. No syncing with each other yet. Ask questions as they come up — I'll be circulating, not lecturing.
37–57
Share results
~2 minutes each — everyone shows what they came up with and why. Rough is expected — that's the point of comparison, not polish.
57–72
The reveal — how far the same exercise can go
Before I show anything: guess how many hours I actually spent getting from a rough sketch to this. Then we open the real thing — the live hybrid, the JSON data model, the rule engine, the console with branching / risk / approvals updating in real time, and the one-pager that ties it together. Same brief you just had 20 minutes with — this is what more time and iteration buys you.
72–75
Q&A & wrap
Quick-fire from a prepared question set, plus whatever's still open — most questions get answered live while you're working, so this stays short.
How we'll work
The tool doesn't matter. How you use it does.
Claude, ChatGPT, Codex, Antigravity, Figma Make, pen and paper — use whatever's already on your laptop. We're not here to compare tools.

We're here to practice something more important: product development driven by a human who knows what they're solving for, using AI to move faster — not the other way around. Come as you are; nothing to install, nothing to prepare.
Outcomes
What you'll walk away with
How to turn a tangled branching brief into a data model — sections, questions, actions and rules — before designing a single screen.
How to run a fast, independent micro design session as a team, so you get real options to compare instead of one idea everyone slowly agrees with.
Where AI genuinely speeds up design work — and where it doesn't replace judgment about what's right for the user.
How to present multiple options systematically, so the feedback you get back is specific enough to actually act on.
How one shared data model can power very different UIs — so design exploration and engineering never drift apart.
A concrete feel for what iteration actually costs — comparing your own 20-minute take against how many hours of refinement separate a sketch from a demoable product.
Who it's for
Anyone on the design team — devs and BAs welcome too, since the case study spans all three. No prior context needed; we start from the original brief.
What to bring
Just a laptop, with whatever's already on it. No tool requirement, nothing to prepare beforehand — the brief is the one I introduce live, and you explore it with us in the room.
This is the first of an ongoing Saturday series — one real case, one sitting, hands-on. If this session lands, expect more of these picking up other live problems from the backlog.
Work Session · Designing With AI · Saturday, June 27, 2026 — Morning · See the full case study in index.html