Ryan Nadel and the art of getting somewhere

Ryan Nadel once offered a modest condition for spending a weekend in virtual reality: the dog would have to come too. In 2016, writing about conversational interfaces and headsets, he imagined asking a bot where to go snowshoeing. He preferred the actual forest. A simulated excursion from the sofa might become more appealing, he joked, if somebody developed VR for his dog.

It is a useful place to begin with a person whose career includes HoloLens, augmented playgrounds and artificial intelligence. The joke contains a preference: computers should help life happen. The destination matters. A walk, a game, an interview, a conversation that leads somewhere. Across his work, that preference supplies a more interesting through line than the succession of fashionable technologies.

Today, Nadel is a Seattle-based technical advisor at Microsoft. His earlier chapters include journalism in the Middle East, a Vancouver digital studio, an interactive companion to Art Spiegelman’s Maus, and a business trying to get independent films into cinemas. It is an unusual route into AI product work. It also offers plenty of practice at asking what happens after somebody looks at a screen.

The audience had other plans

During the 2006 Israel-Hezbollah war, Nadel was a young journalist moderating comments at the Jerusalem Post. He was surprised by the number arriving from evangelical Christians in Texas. A story filed in one part of the world was becoming a gathering place for people in another. The audience was doing something with the material, and that activity caught his attention.

By 2008, he had enrolled at Vancouver’s Centre for Digital Media. He graduated in 2010 and founded 8 Leaf Digital Productions that year, bringing design thinking into strategy and software development. Journalism had supplied the encounter with readers. Digital media gave him ways to build the encounters themselves.

One early assignment came with a considerable artistic obligation. Spiegelman’s MetaMaus needed a digital companion, and Nadel proposed taking over the project after graduation. His studio produced the DVD included with the book in 2011. The work involved existing material and roughly a year of production, bringing an artist’s archive into an interactive form.

That makes an instructive first chapter for a product builder. There was already a voice, a body of work and a standard to respect. The software had to carry them. Adding an interface could deepen the experience; it could also get in the way. The interesting challenge was deciding how a reader should move through someone else’s creative world.

Writing also had a family dimension. In a 2008 piece about Leonard Cohen’s visual art, Nadel identified the biographer Ira Nadel as his father and recalled tagging along while the biography was being written. He ended with a small scene of his own: reading the article’s opening to his father for feedback. Long before the later essays about agents and management, there was this more familiar arrangement for improving a draft. Read it aloud. Let another person hear what you meant.

A playground, with software attached

Nadel also founded Biba Ventures, which brought digital games onto physical playgrounds. Its premise gave the phone an unusual job. Instead of keeping a child occupied in one spot, mobile play could become a reason to use the equipment already outside. Augmented reality met the rather less negotiable reality of a playground.

By his account in 2022, Biba had reached about 5,000 playgrounds worldwide. He also noted its inclusion in TIME’s 2019 inventions selection. Those are historical markers, describing the venture at that point in its development. They give some scale to an idea that begins with a very ordinary location.

The playground is a revealing setting for this career. A digital feature must share space with an existing activity. People have somewhere to go and things to do with their hands and feet. The screen has to earn its place in that arrangement. The snowshoeing joke belongs to the same sensibility: the world outside the device gets a vote.

His work in film distribution put a different kind of real-world test around software. At 20 Year Media, which he cofounded, the team acquired Emerging Pictures in January 2015. The distributor offered a way to try ideas with cinemas and paying audiences. Nadel wanted the business to learn from selling tickets and working with exhibitors. A demonstration could look convincing; an empty seat had a more economical way of expressing disagreement.

Then the workplace became the setting

At Microsoft, Nadel worked on Movies and TV, followed by HoloLens and mixed reality, then Teams. The sequence moves from entertainment into the ordinary business of getting work done with other people. It also brings his interests in media, interaction and practical use into the same organization.

He worked on the HoloLens business applications program through commercialization and launch. He later described responsibility for the intelligence portfolio in Teams. In April 2024, his INNOVATEwest speaker biography identified him as a principal product manager leading Teams’ AI experiences team, including the integration of GPT-related technology into productivity applications.

A July 2023 episode of Inside Microsoft Teams brought him together with fellow product managers Alice Lu, Derek Snyder and Wendy Arnett to discuss Copilot. The subject was familiar office territory: meetings, chat and phone calls. These are places where a useful feature has to survive interruptions, accumulated context and the sometimes heroic effort required to work out what everyone agreed.

The shift in setting is significant. A playground and a meeting have different purposes, but both come with people already engaged in something. Introducing technology means understanding that activity well enough to help. Nadel’s route to workplace AI passes through a long series of those encounters.

The small matter of trusting the answer

His name also appears among the participants in Microsoft’s Appropriate Reliance Research Initiative, published in May 2024. Its focus is the balance between accepting AI output too readily and dismissing it when it would be useful. The initiative brings researchers and practitioners together around applied research, design guidance and practical interface patterns.

That puts a necessary complication beside the promise of easier work. Reducing effort is useful only if people can judge the assistance. An answer can arrive quickly and still require scrutiny. Nadel’s participation places him in a wider effort to understand how people and AI should work together, including the decisions around trust that an attractive interface alone cannot settle.

His own side project made the design question concrete. In January 2025, he introduced Career Nexus as a solo project that had grown from an evening coding exercise. It connected job applications, interview preparation and professional development around the user’s profile and the job in question. The point was to preserve context across related tasks.

He asked himself why someone would use the product when they could simply open a general AI assistant. His answer concerned the work of shaping an experience: remembering relevant information, organizing the steps and helping a person approach a particular goal. A blank chat window leaves quite a lot of product design to its visitor.

A kitchen for building with AI

In March 2025, Nadel described building Career Nexus with a culinary analogy. AI coding could feel like fast food: convenient, but unsatisfying without an understanding of the ingredients. Even as the tools improved, he argued, the equivalent of home cooking would retain its place. Sometimes the builder needs control over the recipe.

His process paired o1 for broader planning with Claude for implementation, debugging and interface work. When one struggled, he tried the other. He connected that practice to situational leadership: assigning work according to the kind of help needed, investigating problems and deciding when to override a suggestion.

By November, he was extending the management comparison to systems of collaborating AI agents. Drawing on Andy Grove and situational leadership, he considered how autonomy, context and feedback should vary. The question was how to arrange the work so the whole system could perform. Giving every agent the same instructions and freedom would miss the point of managing the arrangement.

Then, in December, he described starting projects by talking through ideas with Microsoft 365 Copilot. Voice let him explore assumptions while walking, with work conversations available as context. His workflow was becoming a continuous process involving several agents. The technical advisor was still making prototypes, now with a different division of labor.

“Create white space in your schedule”

Ryan Nadel, reflecting on five years at Microsoft

Leave room for the walk

The walking has a history. Reflecting on his fifth Microsoft anniversary, Nadel recalled the commemorative crystal the company sent him. He used the occasion to recommend curiosity, empathy and accepting unfamiliar opportunities. He also advocated leaving unfilled space in the day for walking, handwriting and thinking, rather than responding to every flashing demand on a screen.

There is a pleasing tension here. His work includes tools intended to help people do more; his advice includes resisting the urge to schedule every available minute. Both concern the conditions under which useful ideas appear. A calendar can be full while a problem remains entirely unconsidered.

In June 2026, he returned to the practical test in an essay about outcome engineering. He argued that builders should begin with the result a system must reliably deliver, then define evaluation, tools, constraints and stopping conditions. Engineers and product managers would have to decide what success meant and how to recognize it.

Read across the career, that argument has familiar company: an archive a reader can explore, a playground children can use, a cinema selling tickets, an applicant preparing for an interview. The technologies change, and the test keeps returning to the person doing something with them. Somewhere beyond the next interface, there is still a forest. Ideally, the dog is invited.