Lenny's Podcast: Product | Growth | Career

How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

Jan 11, 2024

In this engaging discussion, Sam Schillace, Deputy CTO at Microsoft and creator of Google Docs, shares insights from his remarkable tech journey. He delves into the evolution of Google Docs, discussing the value of embracing risk and the joy of creative problem-solving. Sam emphasizes the importance of optimism and playful experimentation in innovation, reflecting on Microsoft's collaborative culture under Satya Nadella. He also touches on why asking 'what if' can spark breakthroughs, urging listeners to pursue their passions for career fulfillment.

01:27:50

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Episode guests

Sam Schillace

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Quick takeaways

Undervaluing things you're good at can lead to missing out on valuable and fulfilling work.

Embracing failure and taking risks is crucial for personal and professional growth.

The focus on simplicity, convenience, and collaboration played a significant role in the success of Google Docs.

The future of document technology envisions more dynamic and immersive experiences, with conversational and adaptive features.

Deep dives

The Value of Doing What You Enjoy

The speaker emphasizes that people tend to undervalue things they're good at and think work has to be unpleasant. They suggest doing the thing you enjoy, even if it feels easy and fun, because it can be valuable and fulfilling. The key is to do it to the best of your ability and with dedication.

What if AI works? What would you build?

01:15

Understanding the Real Value and User Proposition of Products

01:10

Achieving Extraordinary Returns in Your Career

01:25

The Radical Shift in the Software Industry

04:23

Intro

4min

The Evolution of Google Docs: A Case Study in Innovation

24min

The Evolution of Google Docs

15min

The Balance of Innovation: Playfulness vs. Purpose

5min

Embracing Risk for Innovation and Fulfillment

25min

Innovative Leadership and Creative Insights at Microsoft

9min

A Culinary Tech Anecdote

4min

Encouraging Innovative Contributions and Engaging with Ideas

2min

Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO. In this episode, we discuss:

• The journey of building Google Docs

• The importance of taking risks, embracing failure, and finding joy in your work

• The importance of asking “what if” questions vs. “why not”

• Why convenience always wins

• How, and why, Sam stays optimistic

• Inside Microsoft’s culture

• Why you should solve problems without asking for permission

• Early-career advice

• Why “pixels are free” and “bots are docs”

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace

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Where to find Sam Schillace:

• LinkedIn: https://www.linkedin.com/in/schillace/

• Newsletter: https://sundaylettersfromsam.substack.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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