Email & messages
The hard part of an email is almost never the words. It is deciding what you actually want, putting it in the first two lines, and resisting the urge to soften it into something the reader can ignore. These prompts are written around that: they move the ask to the top, cut the throat-clearing, and flag the hedges and apologies that quietly invite a no. Several of them refuse to draft anything until they have told you what your message is really doing, and one will tell you plainly that your draft is already fine to send.
36 prompts in 5 groups
Email & messages21 categories
Outreach and chasing
Writing to people who owe you nothing, and nudging the ones who never wrote back.
- Write a cold email that gets a replyLongReaching out to someone who has no idea who you are and owes you nothing.
- Follow up without being annoyingLongSecond or third nudge on something they genuinely might have missed.
- Ask a busy person for somethingLongEmailing someone whose time costs more than yours.
- Chase a thread that has gone quietLongThree unanswered messages and you still need an answer.
- Introduce two people over emailLongA double opt-in intro where both sides should know why they are here.
- Chase this politelyShortA second nudge on something they genuinely might have missed.
- Chase it or let it go?MediumA thread that has gone quiet and you cannot tell what the silence means.
Hard news and conflict
Bad news, apologies, angry replies, boundaries and feedback that has to survive in writing.
- Deliver bad news in writingLongA slipped deadline, a cancelled project, a decision that will land badly.
- Apologise properly, onceLongYou got something wrong and the apology needs to land before the excuse does.
- Reply to an angry messageLongSomething landed in your inbox that made your heart rate go up.
- Set a boundary in writingLongMessages at midnight, creeping scope, or a pattern you need to name once.
- Give difficult feedback in writingLongThe conversation has to happen in text and you get one shot at the wording.
- Write a resignation or offboarding noteLongYou are leaving and the note will outlive the feelings you have today.
- Bad news in the first lineMediumA slipped deadline or a cancelled plan that somebody will be unhappy about.
Declining and negotiating
Saying no cleanly, and putting a number or a counter-offer in writing.
- Say no without leaving the door ajarLongDeclining a request you are genuinely not going to do.
- Write the negotiating messageLongCountering on price, scope, or terms without blowing up the deal.
- Ask for a raise or a rate increaseLongPutting a number in writing to a manager or a long-standing client.
- Decline a meeting without damageLongAn invite you should not accept, from someone you cannot simply ignore.
- Decline this kindlyShortSaying no to something you are genuinely not going to do.
Drafts and replies
Turning notes, long drafts and tangled threads into something short enough to read.
- Cut this email in halfLongYou wrote five paragraphs and the ask is somewhere in paragraph four.
- Write a subject line that gets it openedLongThe email is written and the subject line still says "Quick question".
- Summarise this thread into a decisionLongForty replies deep and nobody can say what was actually agreed.
- Turn these bullets into a readable messageLongYou have rough notes and they need to become something a person will read.
- Halve this, keep every factShortA message that grew a paragraph at a time while you were writing it.
- Put the ask firstShortFour paragraphs of context and the request hiding at the bottom.
- Subject line for thisShortThe email is written and the subject line still says "Quick question".
- Reply to this in one lineShortA message that needs answering, not a thread that needs extending.
- What is this email really doing?MediumBefore rewriting a draft you have already rewritten twice.
- Rewrite this for a phone screenMediumA long message going to someone who reads everything on the move.
- Draft the reply to thisMediumA message with four questions in it that you keep putting off.
Tone check
Reading a draft back before you send it: too cold, too soft, too annoyed.
- Check the tone before I send thisLongYou wrote it while irritated and it is addressed to someone who matters.
- Same message, warmerShortA reply written in a hurry that reads colder than you meant it.
- Make this more directShortA draft so softened that the reader could reasonably ignore it.
- Am I being too passive here?ShortWhen you suspect you buried the point to avoid saying it.
- Does this sound annoyed?ShortYou wrote it while irritated and it is going to someone who matters.
- Two versions, firm and warmMediumA message where you cannot decide how hard to push.
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