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How do you strike the balance between investing in buzzy tech for tech's sake vs tech that is strategically valuable/critical?

It's really hard to know a priori. Eg the architectural concept of the network PC was clearly recognized as important in the 90s, but it didn't materialize in a successful way until 15 years later as the Chromebook.

Same for Java's write once, run anywhere. Java failed at that but the concept was successfully realized in Ajax web apps. Betting on Java would have been the wrong answer but I imagine that was far from obvious at the time.

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Super interesting question. I wish there was a good answer that doesn’t sound as obnoxious as the one I’m going to offer. The lesson I learned working in Silicon Valley and watching this play out is that there are people that “just know” and they are “right”. The real success comes from letting that person decide and own execution because while they know, they won’t have all the details right and will need to change along the way but will change in the “direction of goodness” (old NASA expression).

I know it is ridiculous to say “they just know”. But time and again what I’ve seen is that within every company (or product line) facing a big decision, there’s someone who knows what to do, has a plan, and understands all the arguments in every direction and deeply understands the technology and “product”. They might be in any number of roles. But there’s literally a single person or small tight knit group.

In hindsight, that’s what really played out at Microsoft over time. The Windows 1.0 team, Word, Excel, Office, Windows NT, Internet Explorer and so on. Where the team did not know there was also no one who knew and the team went in circles for years.

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That's an interesting answer, thanks for engaging on the question! I guess instinct and pattern recognition play a significant role.

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