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What does it mean to Challenge Directly?

This involves telling people when their work isn’t good enough — and when it is; when they are not going to get that new role they wanted, or when you’re going to hire a new boss instead of promoting them; when the results don’t justify further investment in what they’re working on. Delivering hard feedback, making tough calls about who does what on a team, and holding a high bar for results — isn’t that the job of any manager?

But most people struggle with doing these things. Challenging people generally pisses them off, and that doesn’t seem like a good way to build a relationship or to show that you Care Personally. And yet challenging people is often the best way to show them that you care when you’re the boss.