Maria Giudice & Christopher Ireland
Rosenfeld Media
Published in
4 min readDec 13, 2022

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Designer of Change: John Maeda

John Maeda, VP of Design and Artificial Intelligence, Microsoft

John has crafted a unique career path, exploring and explaining the role of design in academia, startups, venture firms, and corporate settings. He is open and adventurous in his choices, and always groundbreaking. We interviewed John in the earliest stage of research for our latest book, Changemakers. Here’s a brief glimpse of his inspired wisdom.

John, you’ve braved many career changes. How did you approach them? Were you initially cautious or optimistic in taking on a new challenge?

I’m never truly optimistic. If you do your best, the result comes out more favorable, but people who are overly optimistic are seeking success as their goal. I don’t seek success. I don’t expect anything. I seek learning experiences. I love the age acceleration of hard jobs. I’m wiser and less deterred after them.

In most of the roles I took on, I was super naive at first. Two quotes that I’ve lived by helped me survive in those situations. The first is Nelson Mandela’s “Don’t judge me by my successes. Judge me by how many times I fell down and got back up again.” The second is Mr. Rogers’ philosophy to “always look for the helpers.” When I joined Kleiner Perkins, I looked for the helpers. My first day, I met Jackie Xu. We were both new, but she was so kind, and she explained to me how Silicon Valley worked. She didn’t have to do that, but she did, so whenever I could, I would help her back.

Even with helpers, entering these environments where you’re naive or inexperienced must take incredible courage. Do you think of yourself that way?

One time at a conference I was asked to explain the difference between audacity and courage. I initially gave a lame answer, but I was intrigued by the question so I studied the topic further. What I learned is that courage is knowing what you’re getting into but still proceeding. Audacity is the opposite of that. You proceed despite not knowing what you’re getting into. Generally, younger people are good at audacity because they have nothing to lose. Part of my ability to navigate different environments is that I’m still able to be audacious, but then I switch to being courageous soon enough to not die.

You’ve sought to lead change in academia, venture, startups and corporate institutions. Is there anything you’ve seen work in all situations?

I’ve always tried to build a culture based on Kim Scott’s concept of radical candor. This doesn’t just mean being transparent. There’s transparency and then there’s clarity. I’m always driving toward clarity in roles and relationships and accountabilities. I don’t always succeed, but on a regular basis, I’ll share with the company, hey this is how I suck and here’s how I’m trying to improve. This also gives me a chance to explain why I’m not going to stop doing something. I don’t like bottling up “anti-John” energy. I’d rather share it and explain how I think about it.

How has this shaped your relationships?

The problem of being a creative person is you like being a lone wolf traveling with your pack. Leading across is hard because it goes against your training to be independent. But by working with Kleiner Perkins, I began to rethink what it means to be a partner. I like thinking of everyone as my partner. I wasn’t like that before. What makes a good partner is recognizing what you can do for your partner. Now I ask myself how I can be a better partner. It’s not about my pack–it’s about my team.

Many of us have learned from you. I’m curious who you learn from?

As a leader, I’m fascinated by the coaching profession even though I’m not a sports person. If you think like a designer, an engineer, or a thought leader, you’re screwed. But I was able to meet a few coaches and I was really impressed by how they think. For example, Pat Summitt, the college basketball coach, said:

“The absolute heart of loyalty is to value those people who tell you the truth, not just those people who tell you what you want to hear. In fact, you should value them most. Because they have paid you the compliment of leveling with you and assuming you can handle it.”

This is what you expect from your direct reports and the people around you, but I expect it from everyone. People are always going to be withholding to some extent. But if I can move them from 90% withholding to 50% withholding, that’s like venture scale growth. I index it toward as much as I can, even though I know the toxins will always be there.

Thanks, John!

Find more interviews and insights like these in our latest book, Changemakers: How Leaders Can Design Change in an Insanely Complex World. Available now on Amazon or Rosenfeld Media.

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