Email Basics
5 Questions to Ask Yourself Before Sending a Sensitive Personal Email
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Would I say this in person? Am I avoiding confrontation by sending this email?
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Did I reread this and look for errors or other problems that could potentially cause misunderstandings? If so, did I clear them up?
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Is this email really necessary? Would a phone call be better? Do I really need to send it, or did composing the email itself let off enough steam?
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Am I sending this to the right person? Is there anyone else who should be involved (human resources, managers, etc.)?
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Will I regret this?
5 Questions to Ask Yourself Before Sending a Sensitive Personal Email

