Sam Schillace
Deputy CTO & CVP, Microsoft · 1 appearance on the record.
computed by AI from the episodes · how this works → · full disclaimer →
executiveengineerfounderinvestorauthor
Sam Schillace is Deputy CTO and Corporate Vice President at Microsoft. He previously co-founded Upstartle, creating the web-based word processor Writely which became Google Docs, and served as Head of Engineering at Box.
22statements → 9claims → 3claims resolved → 100%fully supported → 3.68/5average certainty → 2.36/5average debate potential → ≈4.5/5argument clarity, estimated →
3 supported 0 partly supported 0 contradicted 6 not checkable as stated how the 9 claims stand · each chip opens the sources
4 predictions · 5 assertions · 1 opinion · 11 insights · 1 disclosure · every statement was checked. The predictions and assertions are the 9 claims: statements the public record can support or contradict. 3 are resolved, and 6 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how Sam argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable supported claim
Schillace: Physicians paired with AI diagnostic tools perform worse than AI alone
“There's a study I saw a while ago that compared like an AI based system, AI only physician only and AI plus physician An AI plus physician did worse than AI only. The physician kind of dragged the AI down because they didn't trust it.”
How they sound: not measured why? →
We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Sam Schillace on measured tape to publish a rate. This says nothing about how they speak.
Everything Sam Schillace said on In Depth that made the record, most notable first. Filter by type, assessment or year in the ledger →
Schillace: Google Docs has become a complicated, bloated version of Microsoft Office
“To be honest, like, I'm a little bit sad at the state of Gdocs these days because I think they're losing sight of the idea that, you know, they're kind of turning it into Office and like making it very complicated to use again. And I find lots of things broken…”
Schillace: Failing early is better than failing late in technology
“Failing on the early side, you at least have a chance to, like, course correct, right? Because if you don't spend all your resources and burn out completely, you can keep going, and maybe the world catches up to you, or maybe you make the world catch up to you…”
Schillace: There is no prize for being pessimistic and right in tech
“There's not really much of a prize for being pessimistic and right about these things. Ok, you get a ribbon. Who cares? The prize is for being optimistic and right.”
Schillace: You cannot short broad technological revolutions
“You can't go short on, like, technical, technological revolution, right? You can't, like, short solar or some crazy shit like that. It tends to be wrong. We tend to figure stuff out over time. You know, at best, you're right for a little while, and eventually …”
Schillace: AI tooling will expand engineering ambitions rather than shrink team sizes
“Programmers are definitely going to get more effective. We're going to get more agentic programming tools. So you're going to get higher and higher leverage, but I don't think it's going to make the team smaller. I think it's just going to make the ambitions b…”
Schillace: AI will make creating pixels free, radically altering software applications
“I have the suspicion that the nature of applications is going to change radically in the next five to 10 years. And so I think, you know, this idea that just in the same way that the internet made the distribution of information essentially free, AI, generativ…”
Schillace: Many businesses will be disrupted because their models rely on pixel expense
“I think there are lots of businesses out there that don't fully understand that they're predicated on the expense of creating pixels. And so similar disruption is in the works.”
Schillace: Engineers should think with AI models but plan with code
“The easy way to understand this is when I say you should think with the model, but plan with code because the models are, they're stochastic and fuzzy. And so if you want something reliable, you should build kind of a scaffold around it in code, something exec…”
Schillace: High-value LLM applications work like a cryptographic trapdoor
“The things that work well with LLMs have this shape almost like a cryptographic trapdoor. There are like things where it's started work for the human to create the work, but easy for the human to validate the work. Those are the things that tend to have high v…”
Schillace: Waiting for tech to get easier guarantees too much competition
“The mistake people make the most is, you know, they'll be like, well, that's a cool idea, but it's really hard. Let's wait three years till it's easier. When it's easier, there'll be a million people doing it and there's path dependencies in there and stuff li…”
Schillace: Enterprise software de-emphasizes UX once it clears the CIO's checklist
“There's less of an emphasis on end user experience, I think in the enterprise space, because once you're kind of over the line where the CIO says, okay, that's on the checklist of things that your software does, anything above that doesn't really matter very m…”
Schillace: Durable AI value will accrue to trusted personal data holders
“So that's kind of where that durable value will wind up being, I think, over time. It's kind of the holders of the data and the companies that we can trust to, you know, hold that data and trust to give us the right answers are probably where their value is.”
Schillace: Physicians paired with AI diagnostic tools perform worse than AI alone
“There's a study I saw a while ago that compared like an AI based system, AI only physician only and AI plus physician An AI plus physician did worse than AI only. The physician kind of dragged the AI down because they didn't trust it.”
Schillace: Successful software projects feel slightly out of control
“Most of the successful software projects I've seen Have the same feeling of sort of slightly out of control, but not too much of a disaster as chasing a three year old down a slight incline in a park.”
Schillace: Google Workspace and Microsoft Office are reaching market stasis
“And I think it's hard for either one company to fully become what the other one is and take, take the whole market. So I think we're getting close to stasis on this actually.”
Schillace: AI chatbots should be managed and edited like documents
“We have this idea that these chatbots should be treated like documents. I say bots or docs a lot. So meaning that they have individual names and you can edit all the pieces of them and you can save them and share them and delete them and all this copy them and…”
Schillace: Incumbents must assume AI blockers get solved and reassess value propositions
“Whatever it is that's in the way of this disrupting your business. Now, like assume that that gets solved. What's your business look like after that gets solved? And then what do you do? What is the thing that your business is about? What value are you deliver…”
Schillace: Over one billion people use Google Docs today
“There's like more than a billion people use gdocs today.”
Schillace: Microsoft's experimental AI team explores agent mechanics instead of shipping products
“I've got a team right now at Microsoft that's This sort of experimental prototyping team. It's just the whole thing is like a jazz ensemble. It's really wild. We don't really ship products. We're trying to explore the space and understand some deep things abou…”
Schillace: Microsoft cloud tools must preserve desktop compatibility, unlike Google Docs
“They're trying to keep the cloud very strongly competitive roundtrip, or very strongly compatible, you know, roundtrip compatible with the desktop. That's a design point Google does not care about, but Microsoft does care about.”
Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Goo | Jun 6, 2024 | 54m |