Entrepreneur Series #4: Should I Tell My Boss About This?


This is part 4 of a series of 18 articles I wrote for Entrepreneur.com.


Every manager has been blindsided at some point. Someone asks them about a situation they know nothing about, and suddenly they’re standing there looking uninformed. It’s not a great look.

The principle is simple: never leave your lead in the dark. That doesn’t mean forwarding every Slack thread. It means running three quick mental checks before deciding whether to escalate: Could my leader be asked about this? Is this high-value information? What’s the blast radius if they don’t know?

If the answer to any of those is “yes,” share it. But share it strategically — your boss doesn’t need the play-by-play. They need enough context to not get caught flat-footed.

Read the full article on Entrepreneur.com


Previously: Help Others Think Big | Next up: Why You Have to Let People Fail