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

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” — Brought to you by Teal—Your personal career growth platform: https://tealhq.com/lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny | Ahrefs—Improve your website’s SEO for free: https://ahrefs.com/awt Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace Where to find Sam Schillace: • LinkedIn: https://www.linkedin.com/in/schillace/ • Newsletter: https://sundaylettersfromsam.substack.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Sam’s background (03:45) The first Google Docs file (06:45) Disruptive innovation (10:11) First-principles thinking (11:00) Recognizing disruptive ideas (13:17) Examples of first-principles thinking (15:46) The power of optimism (19:47) Sam’s motto: Get to the edge of something and fuck around (21:53) User value and laziness (24:31) People are lazy (and what to do about it) (28:36) Building Google Docs (31:06) The evolution of Google Docs (37:15) Finding product-market fit (39:52) The future of documents (44:57) The value of playing with technology (47:58) Taking risks and embracing failure (49:21) Thinking in the future (53:48) Finding joy in your work (01:01:20) Just do the best you can (01:02:34) The transformational power of AI (01:09:27) Advice for approaching AI (01:13:07) The culture at Microsoft (01:16:51) Closing thoughts (01:17:32) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Sam SchillaceguestLenny Rachitskyhost
Jan 10, 20241h 27mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Sam Schillace on optimism, play, and building truly disruptive products

  1. Sam Schillace, Microsoft deputy CTO and creator of Writely (Google Docs), talks through how disruptive innovation actually happens, drawing on his experience building browser-based apps before they were considered viable.
  2. He contrasts "why not" thinking (finding reasons something won't work) with "what if" thinking (exploring upside), arguing that optimism, cheap experimentation, and comfort with failure are core to breakthrough products.
  3. Sam explains why user value and convenience always trump cool tech, how to recognize truly disruptive ideas (strong love and strong hate), and why people should lean into work that feels almost guilty to get paid for.
  4. He also shares his view that generative AI is a category shift as big as the internet, predicts conversational, agentic software will replace static apps, and describes how Microsoft’s culture and leadership are navigating this shift.

IDEAS WORTH REMEMBERING

5 ideas

Disruptive ideas feel dumb at first—and polarize people.

Sam notes that every truly new idea initially looks wrong or toy-like; the strongest signal of real disruption is a bifurcated response where some people love it and others absolutely hate or dismiss it, rather than broad indifference.

Shift from "why not" to "what if" when evaluating new tech.

"Why not" questions list obstacles (cost, reliability, edge cases), but "what if" questions force you to imagine the upside if it works—an essential muscle for spotting opportunities in things like browser apps back then or AI now.

Optimize for user value and convenience, not clever technology.

Users are lazy and only adopt products that clearly make their lives easier; Sam argues you must look beyond how cool something is and obsess over how much effort it takes to discover, learn, and habitually use your product.

Make experiments cheap so optimism can be practical.

You’ll always be wrong in your head; the only way to learn is to try things. By sharpening tools and designing small, fast experiments (as he did with early Writely prototypes), you lower the cost of being optimistic and curious.

Follow the work you’d feel guilty getting paid for.

People undervalue what comes easily to them and assume work must be unpleasant; Sam recommends leaning hard into the activities that are fun, energizing, and valued by others, as that’s where outsized career impact tends to come from.

WORDS WORTH SAVING

5 quotes

You should go do the thing that you feel guilty to get paid for, and do the hell out of it.

— Sam Schillace

There’s just not that much of a prize for being pessimistic and right. It’s much better to be optimistic and wrong than pessimistic and right.

— Sam Schillace

Every new idea looked dumb at first. Unfortunately, the dumb ideas also look dumb at first.

— Sam Schillace

Users are lazy. Nobody cares that you’re friendly or nice or the logo is pretty—they care about making their life easier.

— Sam Schillace

AI isn’t a feature of your product. Your product is a feature of AI.

— Sam Schillace

The origin story and evolution of Writely/Google Docs"Why not" vs. "what if" thinking in innovationOptimism, risk-taking, and learning through experimentationUser value, convenience, and product adoption dynamicsCareer strategy: doubling down on work you enjoy and excel atHow to practically explore and apply generative AIMicrosoft’s culture, Satya Nadella’s leadership, and the future of software

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