The right greeting isn't a rule you memorize — it's a setting you re-check every time the relationship in front of you changes.
Promote someone on Monday and by Wednesday their old teammates are still signing off with "thanks so much!!" and three exclamation points — to their new boss. Nobody told them the dial had moved. Formality in email is a setting you adjust each time who you're writing to changes, and most people never notice it needs adjusting at all.
Before you type a greeting, answer three quick questions: How well do we actually know each other? Who has more power in this relationship? And what am I asking them to do? A stranger you're pitching cold gets more formality than a stranger who just introduced themselves at a conference. Get any one of these wrong and the email feels off before the reader hits sentence two.
Everyone obsesses over "Dear" versus "Hi," but the sign-off is the more honest signal. "Best regards" opens a door back to formal at any point in a thread; "Thanks!" closes it. If you're easing a relationship from formal to familiar, move the sign-off first — it's lower-risk than the greeting and the other person will follow your lead within a reply or two.
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Is "Hi" ever okay for a first email to a stranger?
In fast-moving industries, yes — but "Hello [Name]" is the safer default until you've read the company's own tone in a reply or on their site.
When can I drop "Dear" with a client I've worked with for months?
Mirror their last message. If they've already switched to a first-name, casual sign-off, follow them there.
My boss emails casually — can I match that tone back?
Seniority sets a ceiling, not a floor. Staying a notch more formal than your boss is safe; matching their casualness exactly can read as presumptuous until you know them better.
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