In April, when Duolingo’s CEO, Luis von Ahn, announced the company was going “AI-first,” he wasn’t just making a strategic decision. He was stepping into a spotlight few leaders envy. The decision was bold. The backlash was immediate and unexpected.

Critics called the rollout tone-deaf. Users deleted the app. Commentators flooded social media with post-mortems on what the CEO should have done differently. But here’s what most people missed:

They weren’t in the room when the decision was made.

They didn’t carry the weight of the trade-offs. They didn’t face the timeline, the internal debates, or the reputational risk. And they didn’t have to answer to stakeholders while trying to lead through ambiguity.

Every high-stakes leader faces this dichotomy. A pharmaceutical executive greenlight

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