Series
Liberating Structures: Prioritization & Decisions
A fourteen-part series applying the Liberating Structures built for choosing under uncertainty — Ecocycle Planning, Panarchy, Critical Uncertainties, Agreement-Certainty Matrix, and Wise Crowds — to feature-development workshops across a CRM, an AI-native QA tool, an HR leave tool, a Shopify storefront theme, and a Shopify-embedded LMS.
14 parts · first published
- 01
Ecocycle Planning: A Lifecycle Review for a CRM's Feature Portfolio
A backlog only tells you what's next. Ecocycle Planning tells you what's dying, what's calcified, and what's ready to be born — by making a team physically place every feature on a lifecycle map and argue about where it really sits.
·7 min read - 02
Ecocycle Planning: Retiring Brittle Test Suites Without a Fight
Nobody wants to be the person who deletes the test suite someone spent three sprints writing, even when it's been red-and-ignored for months. Ecocycle Planning gives a room permission to say so out loud — and to fund what's actually working.
·7 min read - 03
Ecocycle Planning: Which Themes to Retire, Refresh, or Launch
Our theme catalog had forty-plus entries and nobody could say, in one sentence, which ones were dying, which were thriving, and which were still just an idea in a Figma file. Ecocycle Planning put every theme on one diagram and made the answer obvious.
·7 min read - 04
Ecocycle Planning: Auditing course guru's Feature Lifecycle
course guru's roadmap had a legacy export nobody dared touch and a certificate feature that had been 'almost done' for two quarters. Ecocycle Planning is the workshop that puts both on the same map and forces the room to say out loud which one is the actual problem.
·7 min read - 05
Panarchy: Roadmap Resilience Across Timeframes
Ecocycle Planning maps one cycle. Panarchy maps three nested ones at once — this sprint, this year, the market underneath both — and forces a team to name where a fast crisis could take down a slow bet, or where a slow bet is quietly strangling a fast fix.
·6 min read - 06
Panarchy: Roadmap Resilience for course guru
course guru doesn't have two cycles to worry about, it has three — and the slowest one belongs to Shopify, not to us. Here's how Panarchy surfaced that third scale, and what it changed about how we plan.
·6 min read - 07
Critical Uncertainties: Betting on AI Tutoring Without Pretending You Know the Future
course guru's leadership wanted a roadmap slot for AI tutoring. What they actually needed was a scenario map — because the two things that decide whether it works aren't things you can just go find out by asking someone.
·7 min read - 08
Critical Uncertainties: How Far Into AI-Generated Tests Should shortest Go?
shortest could let a plain-English prompt author the whole test, not just the steps. Whether that's the right bet depends on two things nobody in the room actually knows yet — which is exactly the shape Critical Uncertainties was built to handle.
·7 min read - 09
Agreement-Certainty Matrix: Sorting a CRM Backlog by How Well It's Actually Understood
Not every backlog item deserves the same process. The Agreement-Certainty Matrix sorts a quarter's worth of CRM work into simple, complicated, complex, and chaotic — and each zone gets a different kind of team, not just a different priority.
·7 min read - 10
Agreement-Certainty Matrix: Triaging Flaky Tests Before Choosing a Fix
"Flaky test detection" sounds like one engineering problem. It's usually three, tangled together, each demanding a different response. Here's how the Agreement-Certainty Matrix pulls them apart before a team burns a quarter on the wrong fix.
·6 min read - 11
Agreement-Certainty Matrix: Accrual Engine vs. UI for Leave Balance
Two items on the same leave-balance backlog can look equally hard and need completely different planning rituals. The Agreement-Certainty Matrix is how I stopped estimating a compliance change like a design experiment.
·7 min read - 12
Agreement-Certainty Matrix: Should Course Guru Build Certificates?
Certificates look like a checkbox feature — every LMS has one, so why debate it? Because for a Shopify-embedded app, the checkbox hides three real disagreements. Here's how the Agreement-Certainty Matrix stopped a team from copying a feature that didn't fit.
·7 min read - 13
Wise Crowds: The Merchant Advisory Panel That Actually Advises
Every theme storefront eventually gets a merchant advisory panel that turns into a status update nobody wanted. Wise Crowds — structured peer consultation, chair-turn and all — is the fix, and it works even better once real merchants sit in the consultant seats.
·6 min read - 14
Wise Crowds: A Manager Panel on the Leave-Approval Redesign
The managers approving leave requests every week have opinions they'll never put in a survey. Wise Crowds gets one of them into the client chair, turns their back to the room, and lets the honest version of the complaint come out.
·6 min read