In ongoing companies there are always hard questions, and they often don’t get asked because there aren’t any good answers and that makes people uncomfortable. But this is precisely why they should be asked—to keep the team uncomfortable. Better for that discomfort to come from friendly fire than from a competitor intent on killing you for real—as Eric learned at Sun. If there aren’t good answers to the hardest questions, then there is at least a silver lining. Those hardest questions that have no easy answers can be very effective in mitigating the risk-averse, change-fighting tendencies of
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