Difficult Message → Sent

The problem

The message you need to send — a pushback, a bad-news update, a boundary — sits in drafts for two days and gets worse the longer it waits.

The workflow — 5 steps

1. Step 1

   Separate the facts from your feelings

   Write it out unfiltered, then have the model split observable facts from your interpretations. Most difficult messages go wrong by sending interpretation as fact.

   Below is my unfiltered account of a situation. Split it into: (1) Observable facts, (2) My interpretations, (3) My feelings, (4) What I actually want. Do not advise me yet.
   
   """
   {vent here}
   """

2. Step 2

   Decide the one outcome

   Messages that carry three asks get zero. Pick the single outcome and make everything else subordinate to it.

   Given those facts, list the three possible outcomes I could push for, with the likely cost of each to the relationship. Then recommend one and say why.

3. Step 3

   Draft it short and unhedged

   Length signals anxiety. Ask for a hard word limit and explicitly ban softening language, then add warmth back deliberately if needed.

   Write the message. Under 120 words. State the position in the first two sentences. One reason. One concrete next step. Ban: 'just', 'sorry to bother', 'I hope', 'a bit', 'kind of'. Tone: respectful and direct.

4. Step 4

   Pre-load the likely responses

   Rehearsing the three most likely replies is what stops you from conceding in the moment.

   Predict the three most likely responses to this message, including the most defensive one. For each, draft my two-sentence reply that holds the position without escalating.

5. Step 5

   Read it as the recipient

   One final pass from the other side catches the sentence that reads as an accusation.

   Read this message as the recipient on a bad day. Which sentence would sting most, and what is the minimum edit that keeps the meaning but removes the sting?

What changes when you run it

Free prompts used in this workflow

Prompts are the ingredients; this workflow is the recipe. Each of these is free to copy.

• Professional EmailQuick, clear emails that get a reply
• Polite DeclineSay no without burning the relationship
• Follow-up NudgeRe-open a stalled thread without nagging
• Difficult FeedbackDeliver hard feedback with care
• Meeting RecapTurn raw notes into a clean recap
• Cold OutreachPersonal first message that lands

Related workflows

• Inbox → Triage & RepliesWriting & communication
• Discovery Call → Client ProposalClient & sales work
• Meeting → Action PlanMeetings & decisions