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How does one develop "certainty" without limiting one's perspective?

I have noted that in all offices, bosses want certainty and not the hard truth or complex problems. The higher up one goes,they are supposed to solve more complex problems. But it seems that in most offices, the higher ups just don't want to deal with any part of complexity. So, for navigating this weird path, certainty is key and there is no scope for doubt. Has anyone developed this mindset? If yes, how difficult was it and what were the kind of risks you were willing to take in the interest of that certainty in communication?

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