What are the best approaches to speaking truth to power?

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Is it better to stand quietly and wait for an initiative to fail or to speak up and annoy people without getting much credit for steering away from the rocks? Perhaps my approach is wrong.

social skills

equality

psychology

understand

tynamite

So basically, someone is crucial enough in a team or power structure to manage, run, maintain and create initiatives, and you want to tell them that their efforts are absolute rubbish? Who wouldn't be offended? When I was in a group that elected a leader we didn't like for being ignorant, would it be a good idea to tell him we wanted a new leader, if he was trying his best?

There is no best way to speak truth to power. Someone somewhere is going to feel offended and insecure if they are trying their best and you say their attempts are rubbish. You can say it in a nice and tactful way when no one else is around so you're not undermining them publicly, and it's up to them not to react, as it would be childish and infantile in their part if they reacted in that way.