A Brief History of Design

How I came to appreciate Microsoft’s design roots

It is easy to question everything designed before you when you join a new company. I mean, why the heck would a scroll bar be red in Windows 2.0 … what could they have possibly been thinking?! But while it may be fun and easy to criticize the past, it is crucial to ask the question “why?” To realize that those who came before were pretty damn cutting-edge, and that each design decision carries the baggage of late nights, pulled hair, teamwork, innovation, and expertise.

In January 2016, I joined Microsoft all bright-eyed and ready to design incredible experiences for third-party developers. When I was told my first project was to create the Microsoft Design timeline for //build2016, I would be lying if I said I was ecstatic. But as I engaged in the project, and continuously learned about the rich history, I realized I’d been given a valuable, fascinating first assignment.

My hope is that after reading this, you’ll realize your own interest and appreciation for the design choices in your company or industry. In the meantime, here’s a brief history of design at Microsoft.


A need arises

Microsoft’s first PC operating system, MS-DOS, was a simple setup that only required three components: a keyboard for input, a monitor for output, and a PC to run the OS. A simple time for a simple machine. Graphic design wasn’t a consideration until the arrival of the graphical user interface (GUI), which introduced the mouse as a new way to interact with the OS.

Within Windows 2.0, engineers did the design work. Design wasn’t even a discipline in software development yet. That meant it was engineers who made the call to expose all eight colors in the UI as a feature. This was a fine way to show off the range available, but it created odd effects like a bright red scroll bar and a visual hierarchy that didn’t map to user interaction. It was sort of a mess, really. But who was willing to force a change?

(Left to right: MS-DOS Screen, Virginia Howlett, Bitmap font, Windows 2.0 + the red scroll bar, the infamous 8 colors)

Design takes shape

In 1987, a Microsoft print designer named Virginia Howlett recognized the gap. Engineers were already seeking her advice — it was time for design to have a seat at the table. She wrote to Bill Gates about the importance of design within software development, outlining the competitive advantages and the far-reaching effects of a rich interface.

Shortly after, Virginia joined the User Interface Architecture Group, the first software design and usability team at Microsoft. The team comprised Tandy Trower as Program Manager, Mary Dieli as Usability Researcher, and Virginia Howlett as Graphic Designer for Information Architecture. They immediately began work on Windows 3.0 which launched in 1990.

Windows 3.0 (design gets a seat at the table)

The result was a stronger and more consistent hierarchy, made possible by the thoughtful use of color and meaningful icons. In fact, the iconography work was completed as part of a collaboration with Susan Kare, famed designer of Apple’s trash icon.

Meanwhile, typography technology improved and started to push us out of the bitmap era. Microsoft and Apple both worked to develop TrueType, an outline font standard that controls how fonts are displayed, which lead us to our first font team being formed in 1990. These combined efforts resulted in a dramatically improved product, reflected by massive sales increases of the Windows OS.

As design efforts took shape in Microsoft’s software, it also started to creep into our hardware. Steve Kaneko, Microsoft’s first industrial designer, created Microsoft’s first ergonomic mouse in 1993 and led us down a new path that would advance our devices and inputs for years to come. We continued to innovate in the software and hardware space, but were still figuring out how to bring everything together into a cohesive experience.


A point of differentiation

The Windows 95 launch was our apex. It was the most heavily user tested product in Microsoft history. It introduced users to our signature Start button and the task tray. The response was overwhelmingly positive and resulted in a record-setting 7 million copies sold within the first five weeks. During a code review in 1995, Steve Ballmer spoke to design as a point of differentiation, and made clear that we should discern ourselves from the competition through typography. The impact design was having on the product was apparent and our executives were starting to take notice.

Evolving our design thinking

The design of Windows continued to evolve, but some of the core design problems in the operating system hadn’t yet been solved. Design was focused on what looks good, but wasn’t necessarily answering the question of why we design — the thoughtfulness of actual user interaction. To that end, our use of typography could be described as overzealous and the color palette was limited by the technology of the time. Interaction design, visual design, and typography were not yet acting as a unified team, causing further misalignment.

(Left to right: Windows 95 Start button, Tahoma typeface, Windows Vista Business, Bill Flora, Window Media Center, inspiration for the unification of Microsoft’s Design Language)

Bill Flora, hired by Virginia in 1992, started addressing those issues while leading Encarta 95, Windows Media Center, and Zune. Through his leadership, teams simplified the visual design and brought motion designers and design integrators into the fold to help create a more cohesive experience focused on content.

Microsoft, even at that time, was a large and complex company with many products. Design’s influence could only go so far and hadn’t yet breached the seams. To achieve that, we needed a significant culture change.


A shift in culture

Enter Bill Buxton. Bill joined Microsoft Research in 2005 and kick started a shift in the design culture. Bill didn’t belong to a product group and reported to an Executive Vice President. Because of that, he could be a direct design advocate to executives. He formulated best practices that let designers focus more on user feedback, and urged designers to learn fast and often from the people who were using our products. The result was a strengthened design culture and a unification of Microsoft’s design language. In 2006, Windows Vista introduced Segoe UI typeface, reducing our typography set to one. Segoe UI was born out of insights in user research and proved to be more efficient on system performance. This new era influenced a movement toward simplified and intentional design, often referred to as flat design, which became even more apparent in the release of Windows 7 in 2009. We were moving the needle forward, at exponential speeds.

(Left to right: Windows 8, inspiration for the unification of Microsoft’s Design Language, Segoe UI typeface, Windows 10, Cortana logo, Albert Shum, Microsoft HoloLens)

Simplicity and scalability

Windows 7 ushered in a new era of design at Microsoft, characterized by the need to embrace natural inputs like touch as well as scaling to more screen sizes. Windows 8 built on the momentum in Windows 7, but some of the bigger risks, such as heavy focus on touch, didn’t quite land broadly with users at the time. A core principle of design at Microsoft is listening to customers early and often, but it became clear, we had no mechanism to do this well. For Windows 10, programs like the Windows Insider Program helped keep a clear and consistent feedback channel allowing us to respond much more quickly to feedback.

With Windows 10, the need to scale across devices is commonplace and a core focus in creating a consistent design language. We’re adapting to people’s lives the way they live them across experiences; not expecting them to adapt to us. Within that goal, Microsoft is dedicated to progressing the goals of accessibility and inclusive design to reach the greatest number of people with our technology.


Closing thoughts

This exploration only begins to scratch the surface of the rich design at Microsoft. There are thousands of specialized, talented designers here creating the next big thing, and working tirelessly to improve our technological world as it stands. Windows 10 is our most successful operating system to date, and I credit our focus on customers — from our entrepreneurial roots of A PC on every desk to our current mission of empowering every person and organization on the planet to achieve more. As for our future, it’s bright, volumetric, creative, and ever-evolving. And we’re pretty damn excited about it.

Tell me a story. What do you love about your team’s design ethos? What would you change?


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Thank you to all of the incredible people who made this article possible through telling their story, creating the visuals, and refining the words:

Amit Bapat
David Betz
Bill Buxton 
Kristian Davila
Bill Flora
Alex Gough
Greg Hitchcock
Virginia Howlett
Nate Jones
Steve Kaneko
Eddie Mays
Danielle McClune
Sarah Morris
Amy Stevenson
Janet Thompson