Lenny's Podcast: Product | Career | Growth

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

January 11, 2024

AI Summary

5 min read

Sam Schillace, deputy CTO at Microsoft and creator of Google Docs via his startup Writely, shares lessons from building disruptive products amid resistance. He emphasizes psychological barriers to innovation, like undervaluing easy, fun work, and practical ways to experiment while prioritizing user convenience.

Overcoming Why-Not Thinking

Disruptive ideas trigger "why-not" objections—doubts about feasibility, like browser limitations for Google Docs or connectivity fears—rooted in worldview threats. Schillace counters with "what-if" questions: imagining extended possibilities, such as cheap reusable rockets or AI as cognitive surplus. Engineers' natural pessimism risks missing opportunities; he chooses optimism consciously, noting little reward for being pessimistic and right, especially now. This growth mindset fosters receptivity to surprises from experiments, as in multi-agent AI systems that improved via shared "whiteboard" memory.

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What you'll learn

1 `* (00:00) **Intro and Google Docs Origin Story**`
2 `* (04:00) **Disruptive Innovation Mindset: Why-Not vs What-If**`
3 `* (13:00) **First-Principles Thinking and Optimism**`
4 `* (19:00) **User Laziness and Frictionless Onboarding**`
5 `* (31:00) **Google Docs Creation and PMF Journey**`
6 `* (42:00) **Future of Documents and AI Experimentation**`
7 `* (49:00) **Cultivating Innovation: Embrace Failure and Flow**`

+ Full timestamped outline available in the app

Show 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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