Keeping emails concise and taking the bosses written approvals in a simple Yes or No can be helpful. Make sure the text is to-the-point, with suggested solutions, so that the boss can answer quickly.
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The most productive one-on-ones have some kind of structure, which requires you to do some prep beforehand. Basically, don’t just show up and chat—you’ll lose precious time in rambling conversation...
Our natural bias is to start by imagining all the things that will go horribly wrong if we disagree with someone more powerful. Yes, your counterpart might be a little upset at first, but most like...
You may decide to hold off voicing your opinion if you want to gather your army first. People can contribute experience or information to your thinking — all the things that would make the disagreement stronger or more valid.
Also, delay the conversation if you’re in a meeting or other public space. Discussing the issue in private will make the powerful person feel less threatened.
Before you share your thoughts, think about what the powerful person cares about. You’re more likely to be heard if you can connect your disagreement to a “higher purpose.”
State it overtly then, contextualizing your statements so that you’re seen not as a disagreeable underling but as a colleague who’s trying to advance a shared goal.
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