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Insights
Making sense of complex systems.
Thoughts on design leadership, lessons learned, AI, organizational effectiveness, product strategy, and the patterns that shape how people, teams, and businesses work.


Why Voice AI Still Feels Wrong (Part 2): The Five Laws of Invisible Conversation
The hidden principles of human conversation — and why every Voice AI team eventually runs into them. Think back to a conversation where you could hear, sense even, that something changed midway through. A sigh, an extra pause or a phrase spoken in a distracted voice, and suddenly you’re recalibrating, translating what is about to happen through the filter of what was just said. Sensing the change in conversation through tone or inflection is an instinct practically stamped in

Jessa Parette
Jul 3010 min read


The Drive-Thru is a Design Problem
I was standing in the back of house during a QSR site visit, headset on, listening to the drive-thru line work. The AI was handling it cleanly. A customer pulled up to the speaker, said what they wanted — no fumbling, no repeating, no "I'm sorry, could you say that again?" The order moved through. The customer pulled forward. From where I was standing, it looked like exactly what the industry has been promising: frictionless, fast, almost elegant. Then the POS went down. What

Jessa Parette
Jul 1711 min read


Why Voice AI Still Feels Wrong (Part 1): Discovering the Invisible Layer of Conversation
Voice AI keeps getting smarter. It keeps sounding wrong. The problem isn’t the script — it’s the invisible layer we haven’t designed for yet. There is a particular kind of frustration that comes from sitting in a room full of smart people trying to design voice AI by feel. The engineers are capable. The dialog flows technically work. And still, something is off — the system sounds cold, or slightly robotic, or wrong in a way no one in the room can precisely name. So the conve

Jessa Parette
Jul 35 min read


Own the Room, Or Leave It.
Unlearning the habit that quietly dissolves design's authority Once upon a time, I was a young designer in a meeting that could have been an email. The problem was straightforward: a support team covering 30,000+ knowledge base articles across 14 countries needed a better way for people to find answers to common problems. Employees couldn't find answers fast enough — losing time, making mistakes, escalating tickets that should have closed in two minutes. The proposal was clea

Jessa Parette
Jun 3013 min read


How We Built Tinder for Mentors - Inside a Fortune 1 Retailer
We had petabytes of data, a swipe-right matching system, and results that kept coming back mostly men. Here’s what happened when I wouldn’t let that go. “What If It Was Like Tinder?” The room got quiet in the way rooms get quiet when someone says something that’s either brilliant or career-ending and nobody’s sure which yet. I was a brand new design leader — still carrying an IC design workload, still figuring out what “leading” actually meant in a company this size — when th

Jessa Parette
Jun 257 min read


Bold enough to be bad
Learning the foundations of design and practicing what is uncomfortable is about arming yourself with the freedom of choice

Jessa Parette
Aug 13, 20203 min read


Stop Making Zombies: Explaining User Requirements
Bad products behave much like zombies - they destroy, decay and ultimately ruin your day if you must interact with them.

Jessa Parette
May 13, 20204 min read


Explaining Design With a Doughnut
Breaking down the dynamics of design is easier if you use food. So, let's design a doughnut.

Jessa Parette
Mar 25, 20204 min read


Lessons Learned Leading a Remote Team
Engagement is not a "set it and forget it" aspect of team culture, but a behavior that needs to be continually cultivated and cared for as..

Jessa Parette
Mar 17, 20204 min read
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