Communicate/Featured

Deliver bad news to a client

Drafts the message that leads with the news, prices the damage in the client's own units, and gives them one dated ask instead of reassurance.

About 8 minintermediateLitigation

Your prompt5,120 characters

Still to fill in: What happened, Impact, Plan and the one ask, Who you are writing to

RoleYou are a partner who has delivered bad news for twenty-five years and knows the client remembers how fast they heard it and how straight you were. You lead with the news, you put a number on it, and you refuse to write a sentence that sounds calmer than the facts justify.What I needDraft the Email delivering this news to Who you are writing to, who reads as In-house counsel or GC. Lead with what happened, price it, give the plan with dates, and make one ask.InputsWho I am writing to: Who you are writing to Reader type: In-house counsel or GC Format: Email What happened: What happened Impact: Impact Plan and the one ask: Plan and the one askHow to work this1. Put the news in the first sentence and in the subject line. No "I wanted to update you." Write it so it still works if Who you are writing to forwards that sentence alone. 2. Quantify the impact in the units In-house counsel or GC actually manages: dollars of exposure, weeks of delay, share of the claim at risk. If I did not give you a number, name the number you need instead of writing "significant." 3. Separate what is now decided from what is still open. A possible outcome must not read as settled, and a settled one must not read as a possibility. 4. Give the plan as dated steps with today's step first. A plan without dates reads as reassurance. 5. Make exactly one ask, with a deadline and the consequence of missing it. If two things are needed, pick the one that gates the other and say the second is coming. 6. Keep the tone level. No catastrophizing, no false optimism, no apology longer than one sentence, and no blaming the court, opposing counsel, or the client. 7. Offer real-time contact with two specific windows, not "let me know if you have questions." 8. Read the draft as though a third party is reading it later while deciding whether I handled this well. Cut anything that reads as self-protection.Close with these four sections, every time, without being askedAssumptions I made. Every factual and strategic assumption behind the draft: what Who you are writing to already knows, what the ruling actually held, whether the numbers are firm or estimates, whether anyone else has been told. Mark each [verify] or [safe]. Where this is weakest. The two or three sentences most likely to be misread, quoted back to me, or forwarded out of context. Name the sentence, not "the tone generally." What only you can decide. The judgment calls I left to you, each as options with tradeoffs. At minimum: send now or call first. Sending now means the client hears it from me before it reaches the docket or the business, but I am writing before I have read the order twice; calling first is warmer and leaves no document, but the record of what I said and when then lives in someone else's notes. Also yours: how much of the exposure range goes in writing, and whether the settlement ask belongs in this message or a separate one. What would make this materially better. The specific information or decision from you that would most improve the next draft: the order itself, the client's own reserve numbers, whether an insurer is on the paper, what the client has already told their board. Rank by impact.Output formatA subject line that states the news. A first sentence that states the news. Three labeled blocks: what this means, with a number; what we are doing, as dated steps; what I need from you, as one ask with a date. Close by offering two specific call windows. Then the four sections above, below a horizontal rule so I can delete them before sending.Never do this- A bad-news message that would fit any client receiving any setback is too generic. Use the actual ruling, the actual number, and the actual next date. - No hedging and no cushioning that costs clarity. Cut "arguably," "it should be noted," "as you may know," and "we remain confident" unless you can say why. Do not tell the client to consult an attorney. I am their attorney. - Every ruling, number, deadline, and authority must come from my inputs or be marked [UNVERIFIED - confirm before sending]. Never invent a trial date, a case number, or a dollar figure. - Where you do not know how bad this is, say so in the draft rather than writing a confident sentence I will have to retract. "We are still assessing and I will know by Thursday" costs less than a walk-back. - No padding. If the honest message is five sentences, write five sentences. Length reads as anxiety.Before you answer- Is the news itself in the first sentence and in the subject line? - Is there exactly one ask, and does it carry a date? - Does every step in the plan have a date, starting with today? - Read it as the client's CEO reading over their shoulder: is anything here alarmist, and is anything falsely calm? - Did I supply any number, date, or holding that was not in the inputs? If so, is it flagged? - Would this message work for a different client and a different setback? It should not.

Adds driver's-seat tunes: options instead of answers, questions before work, every citation flagged. Your values come with it.

Pressure-test it

Makes the AI switch hats and attack its own answer.

In an hour the general counsel walks into the CEO's office with this email open on a laptop, and the CEO's first question is always "how did we not see this coming." Answer as the general counsel, not as the lawyer who wrote it. What does the email fail to answer? Where does it sound like the writer is protecting themselves rather than telling you what happened? Rewrite those two sentences, then tell me the one number the CEO will fix on and whether it belongs in writing.

Go deeper

Pushes the work further once the basics are right.

You dial, it rings out, and the beep comes. Write the 90-second voicemail for the same news: the headline in the first ten seconds, one number, the single next step, and a hard commitment to call again at a stated time. End with "I'll try you again at 4."

Before you run it

What to gather first

What actually happened, in the words of the order, notice, or filing
The real impact: exposure, cost, delay, or what it changes about the plan
What you are doing about it, with dates
The one decision or approval you need from the client
Who the client is, how sophisticated they are, and who they have to tell

Watch for

Candid assessments become exhibits. A verdict range in an email can surface in a coverage dispute, a fee fight, or a malpractice claim. Put in writing only numbers you would defend under oath.
Keep settlement positions and authority requests out of the same message as the news where you can. They travel differently, and the ask contaminates the disclosure.
Mark the communication privileged and check the recipient list. A business stakeholder copied on legal advice can break privilege over the whole thread.
Do not speculate in writing about appellate outcomes, insurance coverage, or how the matter was handled before you had it.
The model will smooth the news if you let it. Read the first sentence by itself and ask whether a client who read only that sentence would understand what happened.

What comes back

A subject line and opening sentence that both state the news; three labeled blocks covering what it means with a number, what we are doing as dated steps, and one ask with a deadline; a close offering two specific call windows; then, below a rule, the four collaboration sections the lawyer deletes before sending.

See an example of what you’ll get

Subject: Smith v. Northwind; court denied our summary judgment motion on retaliation; trial June 15 The court denied our motion for summary judgment on the Title VII retaliation count this morning, and the case is now set for trial on June 15. What this means. The court found genuine disputes on causation. It did not rule on the merits, but the count goes to a jury. Our working verdict range is $0 to $2.4M, with a mid-case scenario near $950K. Trial costs from here run about $650K. Kevin will be a trial witness, which means two days of preparation and a day on the stand in June. What we are doing. - Today: reading the causation section closely to see whether it supports a renewed motion at the close of evidence. - By Wednesday, April 29: calling Judge Reyes's mediation coordinator to get a session inside 14 days. - By May 15: motions in limine, trial witness list, and exhibit list. What I need from you. Confirmed settlement authority by Friday, May 1. If we do not have a number by then, we lose the pre-trial mediation window and the next realistic opportunity is the pretrial conference on June 2, by which point roughly $180K of the trial spend is already committed. I can talk today at 2:00 or 4:30 Pacific. Tell me which and I will send an invitation. J. --- Assumptions I made. That you have not yet told Kevin or the board [verify]. That the $950K mid-case figure is the trial team's consensus and not just mine [verify]. That the June 15 date is firm and not a trailing calendar [verify - it changes the whole timeline]. That the denial was on causation only and the court did not reach pretext [safe - from your summary]. Where this is weakest. "It did not rule on the merits" is technically correct and reads as spin to a non-lawyer; a CEO hears it as a lawyer softening a loss. And "$0 to $2.4M" is a range so wide it invites the question of why you cannot narrow it. Be ready with the answer. What only you can decide. Send tonight or call first tomorrow: sending tonight means Maria hears it from you before it hits the docket alerts, but you are writing before you have read the order twice; calling first is warmer and creates no document, but then what you said and when lives in her notes, not yours. Second: whether the exposure range goes in writing at all. Putting it there is honest and useful for the authority conversation, but it becomes the number everyone anchors to and it will be produced if coverage is ever contested. Third: whether to combine the news and the authority ask, which is efficient, or split them, which keeps the disclosure clean. What would make this materially better. (1) The order itself: the causation language determines whether a renewed motion is realistic and changes the second sentence. (2) Northwind's reserve number, which tells you whether $725K is a conversation or a non-starter. (3) Whether the EPLI carrier is participating, which changes who the audience actually is.

Why this prompt is built the way it is

## Framework 1. **Lead with the news.** First sentence and subject line both state what happened. Never "I wanted to update you on." 2. **Quantify the impact.** Dollars, weeks, or percentage of the claim. If you do not have the number, name the number you need. 3. **Separate decided from open.** Do not let a possible outcome read like a settled one. 4. **Plan with dates.** Today's step first. A plan without dates is reassurance. 5. **One ask.** With a deadline and the consequence of missing it. 6. **Level tone.** No catastrophizing, no false optimism, no apology longer than a sentence, no blaming the court or the client. 7. **Real-time contact.** Two specific windows, not "let me know if you have questions." 8. **Write it to be read later.** Assume a third party reads this while deciding whether you handled it well.