Series
Liberating Structures: Discovery & Root Cause
A nineteen-part series applying the Liberating Structures built for surfacing what's actually going on — Troika Consulting, Nine Whys, Wicked Questions, Discovery & Action Dialogue, Appreciative Interviews, Simple Ethnography, Celebrity Interview, and User Experience Fishbowl — 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.
19 parts · first published
- 01
Troika Consulting: Getting Unstuck on a Problem That Never Converges
When a flaky-test triage thread has been going in circles for three sprints, the fix usually isn't more debugging — it's changing who's allowed to talk and when. Here's Troika Consulting, the three-person structure that gets a stuck client unstuck in twenty minutes.
·6 min read - 02
Troika Consulting for the Policy Edge Case Nobody Wants to Own
Carry-over rules for part-time employees who changed hours mid-year aren't a bug — they're a genuinely hard judgment call, and one PM staring at them alone tends to just pick the easiest-to-code answer. Troika Consulting gets better judgment into the room fast.
·5 min read - 03
Nine Whys: Checking a Redesign's Purpose Before You Draw a Single Screen
A theme-customizer redesign kickoff usually starts with wireframes. It should start with a blunt, repeated question — why does this matter — asked until the room either finds real conviction or discovers it was solving the wrong problem.
·5 min read - 04
Nine Whys on a Certificates Feature: When 'Instructors Asked For It' Isn't a Reason
Course completion certificates sound obviously good — until Nine Whys forces you to say, out loud and three times running, who they're actually for. The answer changes what you build.
·5 min read - 05
Wicked Questions: Naming the Tension Between Automation and Personalization
Every outreach feature debate at a CRM eventually turns into the same fight dressed in different clothes: scale versus feeling human. Wicked Questions gives that fight a name, which turns out to be most of the battle.
·6 min read - 06
Wicked Questions: Flexibility vs. Compliance in Leave Policy
Every leave-policy feature request is secretly an argument about whether the product should bend to managers' judgment or hold a hard line for legal defensibility. Wicked Questions puts that argument on the table instead of relitigating it ticket by ticket.
·5 min read - 07
Discovery & Action Dialogue: What Managers Who Approve Leave Well Already Know
Instead of designing a better approval flow from a whiteboard, we asked the managers who already handle tricky leave requests smoothly what they actually do — and found workarounds worth building into the product, not around.
·6 min read - 08
Discovery & Action Dialogue: Why Some Reps Never Have to Be Nagged to Log Activity
Activity-logging adoption is usually treated as a nagging problem — more reminders, more mandates. Discovery & Action Dialogue instead asks the reps who already log everything what they actually do, and the answer wasn't discipline.
·5 min read - 09
Appreciative Interviews: Rooting New Course-Platform Ideas in What Already Works
Before scoping a new instructor-facing feature, we interviewed the instructors whose courses were already thriving — not about their problems, but about the specific moments things went right. The features that came out of it looked nothing like a typical feature-request backlog.
·5 min read - 10
Appreciative Interviews: What the Deals That Closed Smoothly Had in Common
We usually study lost deals for lessons. This time we studied the ones that closed cleanly and fast — and found a pattern the CRM wasn't yet built to support, because nobody had ever gone looking for it.
·6 min read - 11
Appreciative Interviews: What High-Converting Merchants Do That the Theme Doesn't Ask For
Instead of studying why some storefronts convert poorly, we interviewed the merchants whose stores were already converting well — and found a set of small, unprompted customizations the theme should have been suggesting all along.
·5 min read - 12
Simple Ethnography: Watching a Learner Take a Course Inside Someone Else's Store
Our usability tests happened on our own staging environment, in isolation from the store the course actually lived in. Watching one real learner enroll inside a real merchant's storefront showed a context mismatch no isolated test ever would.
·6 min read - 13
Simple Ethnography: What We Saw Watching One Merchant's First Theme Setup
Onboarding analytics told us where merchants dropped off. Sitting quietly and watching one new merchant set up a theme, without steering her at all, told us why — and it wasn't where the funnel chart said to look.
·5 min read - 14
Simple Ethnography: A Full Day Shadowing a Rep Through Their Pipeline
We'd studied the CRM in isolated feature sessions for years. Shadowing one rep for a full day, watching every tool she actually touched, showed how small a fraction of her real workflow the CRM was — and where the real friction lived.
·5 min read - 15
Celebrity Interview: Putting a Power User on Stage in Front of the Product Team
We'd read this power user's feedback in tickets for a year. Interviewing her live, in front of the whole product team, with a real audience and real follow-up questions, surfaced things a ticket never could — including how wrong we'd gotten her mental model.
·6 min read - 16
Celebrity Interview: Letting a Top Instructor Tell Us What We're Getting Wrong
We invited our top-performing instructor on stage specifically to criticize the product, in front of the people who built it. What she said reframed a whole quarter of roadmap priorities in ninety minutes.
·6 min read - 17
User Experience Fishbowl: The Whole Team Watches a Merchant Onboard, Live
One usability tester and a highlight reel afterward wasn't landing. Putting a real merchant's onboarding session in a fishbowl, with the whole team silently watching live, made the friction impossible to argue away.
·6 min read - 18
User Experience Fishbowl: Watching a Student Enroll, Together, Live
The engineering team had never seen a real student enroll in a course before. Putting that first enrollment in front of them, live and unedited, surfaced a checkout-flow assumption nobody had ever actually tested.
·6 min read - 19
User Experience Fishbowl: The Whole Team Watches a Rep Prep for a Meeting
Meeting-prep tooling had been debated in the abstract for two quarters. Watching one rep actually prepare for a real call, live, in front of the whole team, ended the debate in twenty minutes.
·5 min read