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Jon Friedman (MDes ’03) had been interning as a designer at Microsoft for many months before being pulled into a so-called “interview loop,” a process where he would undergo interview after interview to determine whether the company would hire him full-time.

The interviews were going well, until the last one. A senior engineer offered him a whiteboard and a test: design software for a theoretical call center.

“I can’t start designing it until I go to the call center to see the problems with the software they currently have,” Friedman remembers replying.

“Yeah, yeah, just imagine you did,” he remembers the engineer telling him.

“No, that’s the point, dude. I can’t imagine that I did. I have to actually go see it because I don’t know what the problems are. I could make up problems, but then I’m just making up problems, and what’s the point?” Friedman says he replied.

The discussion escalated into a heated argument. The two parted.

The next day, Friedman received a job offer.

“I was surprised,” Friedman says. “I’m not someone who argues, but he was running over the idea of human-centered design—the thing I was passionate about....It was a culture shock for me and probably for Microsoft to have me there.”

That shock has propelled Friedman on an upward trajectory ever since. He built and led the design team that transformed Microsoft’s Outlook web application into a modern product serving hundreds of millions of active users, as well as becoming the foundation of what is now the company’s premier cloud suite service, M365. Now, as Microsoft’s corporate vice president of design and research, Friedman is the highest-level design executive the company has ever had.

When he started at the company more than 20 years ago after graduating from 91�ؿ� Tech’s Institute of Design, “there were industries where design was very respected and well-formed: architecture and furniture design. But not in software,” Friedman says.

Friedman took it upon himself to nurture the massive tech company’s almost nonexistent design culture—a task the company had once assigned to product managers.

“[Those PMs] are the ones who realized that we need someone to draw this stuff,” Friedman says. “They said, ‘The software doesn’t look right. Let’s get someone to draw it and pick the colors.’”

“Make it look pretty,” Friedman says he was sometimes told. Beyond that, many added: stay in  
your lane.

“They were over-functioning as designers because they didn’t understand what a designer could do,” Friedman says.

SUCCESS FROM FAILURE

Ironically, it took a product that was widely seen as a failure for Friedman’s message—that designers could do more than make apps “look pretty”—to finally hit home.

Friedman was pulled onto a project to create the Microsoft Kin: a mobile phone the company was working on around the same time that the iPhone came out. Friedman was the first designer assigned to the project and was able to secure a design team to tackle hardware, software, and branding.

“It was not, ‘Make this look pretty.’ I got super excited because I got to think holistically about a product—from packaging to industrial design to software,” says Friedman, who spent his childhood in Skokie, 91�ؿ�, sketching and designing, even doodling designs in the margins of the Talmud during a short stint at a religious boarding school.

In the past, tensions often arose between designers and engineers who just wanted a pleasing package for some product’s function. But designers could help with function, too, he argued. Were those functions even solving anything that needed solving?

It’s true that when the Kin was released, it was pulled from shelves after six weeks. The failure was attributed, Friedman says, to a variety of factors from product market fit to costs.

But the multidisciplinary process utilized in making it allowed engineers—for the first time on a big project that Friedman saw during his time at the company—to see design in a different light.

“The product design work was awesome, and the culture of product building was the thing that ended up having a lasting effect on my career...propelling me. A lot of learning and failure, and a lot of mistakes made,” Friedman says.

A BETTER FIT

A short time after the Kin project, former Microsoft Corporate Vice President Harv Bhela was put in charge of a project wherein a fledgling web application called Outlook—used almost solely by information technology workers to remotely access from their home computers—was targeted for expansion. The company wanted to transform Outlook into a mainstream email app used by everyone.

But it wasn’t designed for everyone.

“The bigger change was that the web was becoming important, mobile was becoming important—not just desktop. It changes a design problem in a very big way,” Bhela says.

Design still wasn’t part of the mainstream company culture yet—there were maybe four or five design leaders in all. Bhela asked around about who he should have to help design it, and Friedman’s name kept coming up. He invited Friedman to talk to his team.

“And I thought that was going to be easy!” Friedman laughs. “I mean...these people thought I was a nutbag. It was like I was from a different planet.”

Friedman worked on the product for months, which turned into years. And the small penetration he’d made with Kin finally pierced the cultural divide.

Adds Bhela, “Engineering is always very suspicious of everyone else. When you’re trying to change the culture, it’s important to collaborate well with other functions—functions that haven’t worked with design before.

“Jon has that in spades.”

Now, under Friedman’s years of leadership, design has become a pivotal part of the product development process at Microsoft. Friedman has taken an “editor-in-chief” role in Microsoft 365 Copilot, continuously tweaking it to make it more accessible for the average, everyday user.

In the age of artificial intelligence, Friedman says, “I think for the first time ever, computing can go from being a tool to being something that truly adapts to you. Something that you no longer have to adapt to, but understands you and your motivations, and gets out of the way at the right moment to help you accomplish your goals.

“That is no longer you having to learn systems, that is systems learning you.” —Tad Vezner