Document coach
The Hard Email
Say the hard thing in the first three sentences — and keep the relationship.
The difficult email — the bad news, the escalation, the professional no, the uncomfortable ask — fails in two predictable ways: too blunt, and the relationship pays; so hedged, the message disappears. This guided session works like sitting down with an executive communications coach who has un-sent a thousand career-damaging drafts. It starts where every hard email should: what do you actually want to happen after they read it? Then it builds the email around that outcome — the hard thing stated plainly up front, one genuine sentence acknowledging how it lands for them, exactly one ask with a concrete next step, and a close that survives the worst-case read. What you want and who they are stay beneath the draft as working notes; the email itself comes out short, clear, and kind — 150 to 250 words you can finally send.
What this expert will cover
- 2 questions
The Outcome
working notesWhat you actually want this email to cause — a working note for you and your coach, never part of the email. Complete means: the one thing you want to happen after they read it, and the acceptable second-best you would settle for.
- 4 questions
The Reader
working notesWho is on the other end — a working note that steers every word choice, never printed in the email. Complete means: the relationship and what it's worth, what they care about and fear in this situation, and how they are likely to react on first read.
- 1 question
Subject Line
The subject line the email sends under. Complete means: one plain line that tells the truth about what's inside — specific enough that it can't be mistaken for routine, calm enough that it doesn't detonate before they open it.
- 4 questions
The Point
The opening that says the hard thing. Complete means: the news, the no, or the problem stated plainly within the first three sentences, followed by the minimum context the reader needs — and, where it's yours to own, one plain sentence of ownership without groveling.
- 2 questions
Their Side
One genuine sentence that shows you see how this lands for them. Complete means: their likely objection or feeling named honestly — no flattery, no managing — plus, where needed, one sentence that holds your position so acknowledgment doesn't read as the decision reopening.
- 3 questions
The Ask
The one thing you're asking for. Complete means: exactly one ask, phrased so the reader could answer yes or no; a concrete next step naming who does what; a deadline where one is honest; and what happens — or what you can offer — if the answer is no.
- 3 questions
The Close
The last lines the reader carries away. Complete means: a forward-looking close that signals the relationship continues — no apology loop, no hedge that reopens the ask — and, only where true, one line of genuine appreciation.
The kind of questions it asks
- What do you actually want to happen after they read this email? Not how you want to feel sending it — the concrete thing they should do, decide, or accept once they finish reading.
- Who is this person to you, and what is the relationship worth after this email is ancient history? A client you need next year and a vendor you're done with get very different sentences.
- Give it an honest subject line — plain words that say what this is: "Update on the March deadline", "A decision on the Acme contract". No "Quick question" if it isn't one, and no alarm you can't back up in the first sentence. A working subject is fine — we'll sharpen it once the point is on the page.
Ready when you are.
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