Explore Hugh MacLeod’s illustrated guide to life inside Microsoft


Drawing for me is a way of processing thoughts,” said cartoonist Hugh MacLeod. “I use lines to join the dots in my mind.” Those dots he refers to cut to the core of office environments. They help capture, within a drawing, the essence of a company’s aspirations. It’s “motivational art that doesn’t suck,” or so says his company’s website. Prescriptive and inspiring is what pops into my head. You kind of have to be if you’re striving to change the business culture within an organization.

Typically artists and business people operate in different worlds, where never the twain shall meet. MacLeod however is an artist obsessed with the business environment. He provides a right hemisphere brain perspective of the left side. “I find business interesting,” said MacLeod “It’s the art of getting stuff done, of creating something out of nothing. You’re building possibilities.”

Recently, MacLeod has made it his mission to document a moment of major transition at Microsoft’s Redmond campus, where a new CEO and fresh thinking across the company are quietly transforming the 40-year-old organization.

Every day is a moon shot.

“Attaching art to business outcomes can articulate deep emotions and bring things to light fast,” said MacLeod. To get there requires MacLeod immersing himself within a company, so he can look for what he calls “freaks of light”—epiphanies about a company that express the collected motivations of its people. “My cartoons make connections,” said MacLeod. “I create work in an ambient way to tweak people in the right direction.”

Talking to MacLeod, I get the sense that inside he’s floating in a sea of abstractions—about people, the way they operate, and how they do business. Oftentimes, he’ll jump ahead to the next thought before completing the current one. He’s like a master detective in an Agatha Christie novel who switches cases without identifying the murderer. Some might find that maddening, but with his personality and Scottish accent, I find it an endearing quirk.

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