Josh and Bob dig into the courage problem that runs through every layer of tech leadership right now. The courage to push back on your team. The courage to be honest with peers. And the hardest one, the courage to tell the people above you that the thing they want is the wrong thing.

They get into why most leaders are courageous downward but cave upward. Why fear of losing a job often costs you the job anyway. The "blinds" metaphor for how much truth you actually let out in the room. And the moment Josh told his boss "no" for the first time and watched the conversation turn into something better than he expected.

Then they bring it back to the current reality. Boards with youthful enthusiasm about cutting 50% of the workforce with AI. The agile-is-dead chorus. Senior leaders want fast answers to questions that deserve careful ones. And the leaders in the middle who quietly comply instead of saying what they actually think.

This is a challenge episode. If you've been swallowing what you really believe in leadership conversations, this one is going to sit with you.

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