A Microsoft employee recently tweeted a cheeky dig at Windows, and instead of getting fired, he got attention. Ten years ago, that would’ve been unthinkable. But in today’s tech world, self-deprecating humour, platform agnosticism, and even public criticism are no longer career-ending moves. They’re part of the culture.

In this episode of Tech Talk, Rich Bradbury speaks with Matt Armitage from Kulturpop about what this moment reveals about Microsoft’s evolution, and what it says about Big Tech more broadly. Have we moved past the age of tech evangelism? Are meme-literate CEOs and collaborative platforms the new normal? And how are companies navigating the thin line between transparency and chaos?

This is a conversation about brand reinvention, employee voice, and why the ability to laugh, even at yourself, might just be Big Tech’s new superpower.

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