Guide
How to send a hard email at work
May 1, 2026 · 2 min read · 20 min
The companion guide to The Email You Should Have Sent, condensed for the Tuesday morning where you’ve already been at it for half an hour.
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1 Name your actual goal in one sentence
Before you open the draft, write down what you want to be true after the email is read. Not what you want to say — what you want to change. "I want to be looped in earlier on staffing decisions" beats "I want to express that I felt excluded."
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2 Lead with the issue, not the feelings
Open with the concrete situation — what happened, what you observed, what's at stake. Save the emotional context for later in the email, if at all. People can absorb a hard message faster when they know what the message is before they get the texture around it.
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3 Make the ask specific and small
Vague asks ("more communication") create vague replies. Specific asks ("a 15-minute sync before staffing decisions go final") create either a yes or a renegotiation. Both beat a polite acknowledgment that changes nothing.
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4 Cut every sentence that's just for you
Re-read the draft and flag every clause that exists to make you feel better about sending it — the over-apologies, the throat-clearing, the "I just wanted to flag." Cut them. The remaining email is shorter, clearer, and easier for the recipient to act on.
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5 Wait one cycle, then send
Sleep on it if you can; take a walk if you can't. Re-read with fresh eyes. If anything makes you flinch, fix it. If nothing does, hit send and close the tab. Don't re-read it after it's gone.
From the essay: Read the full piece →
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