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

Lenny's Podcast: Product | Growth | Career

notes

NOTE

Importance of asking 'what if' questions

The speaker emphasizes the importance of asking 'what if' questions rather than 'why not' questions. They recall how early skepticism towards Google Docs was based on 'why not' questions, such as concerns about browser readiness and cloud trust. However, the speaker advocates for considering 'what if this does work' and using imagination to explore the potential positive implications. They reflect on the pessimistic nature of engineers but argue that it's more beneficial to be optimistic and wrong than pessimistic and right, particularly in the current moment.

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Transcript

Episode notes

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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