Kenny’s Thinking Garden

Hi — I’m Kenny. I work in product.

About this site

This is my public thinking garden — a space where ideas grow, get challenged, and update over time. Notes here are living documents, not finished answers.

Most portfolios show outcomes. This shows the reasoning behind them — including how assumptions change, where constraints matter, and when the original framing turns out to be wrong.

If you’re evaluating me for a product role, you’ll find case studies and thinking frameworks here too. But first and foremost, this is where I think.

How to read this site

Not all notes are meant to be read the same way.

There are three types of nodes:

Case Studies
Real product work — end-to-end thinking on problems I’ve worked on.

Mental Models
The frameworks I use — problem framing, decision making, belief updating.

Explorations
Early-stage ideas and experiments — intentionally rough and evolving.

Start here (3-5 minutes)

If you only read a few things, read these:

Problem Framing — how I define the right problem
Helper Match SG - Case Study — a full product thinking walkthrough
Product Management as a System — how PM actually works beyond the textbook

Case Studies

Insights - Case Study — Remote operations platform for smart access and facilities
API Product Arc - Case Study — Productising an enterprise API in a connected infrastructure environment
Analytics Architecture Correction - Case Study — Correcting analytics ownership boundaries in an event-driven platform
Helper Match SG - Case Study — Marketplace for maid transfers in Singapore

Articles

Product Management as a System — A 4-part exploration of how PM actually works

Mental Models

Problem Framing — Defining the right problem before solving it
Decision Making — Making structured decisions under uncertainty
Belief Updating — Updating beliefs when new information appears
GenAI Development - From Vibe Coding to APM — How I think about AI-assisted development
GenAI Development - From APM to OpenSpec — Evolved from APM; OpenSpec as the leaner approach

Plans

PO to PM Transition - Positioning Strategy — How I’m positioning for PM roles

New here?

→ Start Here