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Chris Rosato

Founder, Outpace

Chris Rosato is a product thinker, designer and engineer. He runs Outpace, his New Zealand product and AI practice, working with organisations on where AI is worth using, how a defined job can run with agents, and which product decisions to settle before anything is built.

More than two decades working across disciplines, from agile coaching and learning design to product and engineering. A founder of Orion Group.

Writes about AI adoption, Agents, Product strategy, Design and Engineering.

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Written by Chris

The words "Is your job safe?" on a bright blue background above the Claude, Cursor and GitHub Copilot logos12:34

Will AI Replace Designers?

A designer of 29 years on the line that decides it: whether your week is spent producing things, or being accountable for how they turn out.

AI for Work · · YouTube
Illustration of a lone figure in silhouette against an orange sky, facing a vast bank of white and slate-grey cloud.

The Comfortable Fog

In most organisations, coordination stands in for progress. Why comfort beats clarity, and what changes when AI moves the bottleneck.

Chris Rosato ·
A white-haired man in a black and white striped suit surfing a board across a wave of glowing green code.

Onboarding an AI Teammate: The First Five Days

In January 2026 we gave an AI agent a name, a seat and a job at Orion Group. This is what the first five days actually looked like, broken permissions included.

Chris Rosato ·
Illustration of laboratory glassware in orange and blue, with a gloved hand adjusting a flask on a bench.

Stop Planning, Start Probing

A tidy change roadmap feels like control, but complex work doesn't follow it. Small probes teach you more, faster, with less collateral damage.

Chris Rosato ·
Illustration of a man standing in the shadow of a doorway, watching butterflies cross an orange and blue sky.

Change Does Not Hurt, Losing Does

People don't resist change. They resist losing things. Until you name what they're giving up, your change story sounds like propaganda.

Chris Rosato ·
Teresa Torres and Peter Yang either side of a mocked-up post reading "Claude Code runs my life"49:37

Build Your Personal OS with Claude Code

Teresa Torres shows her actual week with an agent: the daily list, the writing she won't hand over, and the notes that stop her repeating herself.

Teresa Torres (Peter Yang) · · YouTube
Illustration of a man sitting on a chair on top of a red block beside a small speaker, its cable trailing into blue water, against a flat red background.

Amplified: How AI Shortens Time

AI turns small signals into fast shifts. How to spot the early friction, pace your response, and place changes where they stick.

Chris Rosato ·
Illustration of a woman seen from behind, turning her head, as white wave lines rise across her shoulders against a deep blue sky.

What AI Can't Fake

Generative AI hasn't killed the expert. It has changed what expertise means: how fast you learn now matters more than what you already know.

Chris Rosato ·
Illustration of a woman in profile resting her chin on her hand, against a yellow background of pipes and line drawings.

Beyond Transactions

Faster answers are the smallest thing AI offers. The bigger opportunity is using it to think, create and lead better.

Chris Rosato ·
A man in glasses with folded arms beside floating blue cubes joined by thin lines on a pale background.

The Future is AI, the Future is Human

AI is poised to change the nature of management. The risk isn't AI replacing managers. The risk is managers failing to evolve while the world around them changes.

Chris Rosato ·
Simon Sinek speaking to a large audience in black and white, with the words "Don't try to convince others, do this instead."7:59

How to Create Change

Simon Sinek on why change stalls when you try to convince the sceptics, and why a rollout should start with the early adopters.

Simon Sinek · · YouTube
Roger Martin in a blue jacket against a green background, with the title "Quick Study: A Plan Is Not a Strategy" and the Harvard Business Review wordmark.9:32

A Plan Is Not a Strategy

Roger Martin on why a list of planned activities isn't a strategy, and why the comfort of planning is exactly the problem.

Roger Martin (Harvard Business Review) · · YouTube
Eddie Obeng on the TED stage in an orange shirt, arms spread wide, holding a sheet of paper.12:37

Smart Failure for a Fast-Changing World

Eddie Obeng on what happens when the pace of change outruns the pace of learning, and why smart failure deserves better treatment than it gets.

Eddie Obeng (TED) · · YouTube