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Using AI To Draft A Hard Email You've Been Avoiding
By Nigel Guy · 2 min read
The hard email — the one declining something, pushing back, delivering bad
news, or asking for something uncomfortable — is usually the one sitting in
drafts the longest, because the blank page makes the discomfort worse
before it makes anything better. People avoid starting it, which is
understandable, and then avoid it a bit longer because the avoidance itself
starts to feel like the safer option.
The rule: use AI to get past the blank page, not to say the hard thing for
you — the draft should give you something to react to and edit, never a
message you send without changing the parts that matter.
The mechanism
- State the actual message in one honest sentence to yourself first,
before drafting anything. "I'm declining this," "I'm pushing back on
this," "I need to say no to this" — clarity here makes everything after
it easier.
- Ask for a first draft from that one sentence, plainly stated, rather
than describing the situation at length and hoping a good email emerges
from the description.
- Read the draft checking for two things specifically: does it soften
the actual message so much that it's no longer clear, and does it say
anything you wouldn't actually say. Both are common failure modes in
AI-drafted hard messages.
- Rewrite the opening and closing lines in your own words, even if the
middle stays close to the draft — these are the two places tone matters
most and where a draft most often sounds like nobody in particular.
- Send only once you'd be comfortable with the recipient reading it
aloud back to you. If a sentence would make you wince hearing it in
their voice, it needs another pass.
What to skip
Skip asking the tool to make the email "as diplomatic as possible" as your
only instruction — that reliably produces something so hedged the actual
message disappears, which defeats the point of finally sending it. Skip
sending a full draft unedited just to get the dreaded email off your plate;
speed at this stage isn't the win, saying the actual thing clearly is.
Guardrails
- A draft can sound reasonable and still misjudge the relationship or the
history you have with the recipient — you know context a tool doesn't,
and it's your job to catch where the draft ignores it.
- If the email involves something with real consequences — a formal
complaint, a resignation, anything that might be read back later in a
dispute — get it reviewed by someone who understands that specific risk,
not just edited by you.
- This helps you get past the avoidance, not past the discomfort of the
actual conversation the email opens. Some of these emails are just
genuinely hard, and a good draft doesn't change that.
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