Twelve things a solicitor can ask Copilot before the kettle boils
Practical Microsoft 365 Copilot prompts for legal work — chronologies, deadlines, bundle prep, contract comparison and handover notes — plus the four requests that do not work, and why.

Most Copilot training for legal teams is a demonstration of what the product can do. What people actually want is a short list of things worth typing on a Monday morning, on their own files, that return something they would have had to do by hand.
These are the ones that survive contact with real matters. Every one assumes the content is already in your tenant and that you can already open it — Copilot answers from what you have access to, and nothing else.
Before a hearing or a meeting
1. The chronology
Build a chronology of events on the Harlow matter from the emails and documents in this folder. One row per event: date, what happened, source document. Flag anything where the date is ambiguous.
The last sentence is what makes it useful. Without it you get a confident chronology with invented precision in it. With it you get a chronology and a short list of things to check.
2. The read-in
I am picking up this matter tomorrow. Summarise where it has got to, who the parties are, what the last three pieces of correspondence said, and what appears to be outstanding.
3. The other side's position
From the correspondence in this thread, set out the other side's position and the points they have conceded. Quote the sentence each one comes from.
"Quote the sentence" is doing the work again. A summary you cannot trace is a summary you have to redo.
4. The meeting you missed
Summarise this Teams meeting recording. List the decisions, the actions with owners, and anything raised that nobody answered.
Running the matter
5. Deadlines out of correspondence
List every date or deadline mentioned in the emails on this matter in the last three months, with what it relates to and who raised it.
Treat the output as a prompt to check your diary, never as the diary. It finds dates that were mentioned; it cannot know which ones were superseded by a phone call.
6. The thread you were copied into on Thursday
Summarise this thread in five bullets and tell me specifically whether anything is being asked of me.
7. What has gone quiet
From my sent items on this matter, list anything I asked for that has not been answered.
8. The file note
Draft a file note of this call recording in our house style: attendees, what was discussed, what was advised, what was agreed, next steps.
Drafting
9. Version comparison in plain English
Compare these two versions of the agreement and tell me what changed in substance — ignore formatting and numbering. Group the changes by clause and say which side each change favours.
The second half is the part people forget to ask for, and it is the part that saves the time.
10. The first draft of something routine
Draft a client care letter for this matter using the attached precedent, taking the parties and scope from the matter file. Leave anything you are unsure about as [TO CONFIRM].
Asking for explicit placeholders beats asking it to be accurate. It will not know what it does not know; it will follow an instruction to flag.
11. The plain-English version
Rewrite this advice for a client with no legal background. Keep every qualification. Do not simplify anything that changes the meaning.
The administrative hour
12. The time you did not record
From my calendar and sent items yesterday, list what I worked on, grouped by matter, with how long each took.
Not a time entry. A prompt for one, which is the difference between a useful tool and a compliance problem.
Four that do not work, and why
Worth knowing before somebody tries them in front of a client.
- "Find me case law on…" Microsoft 365 Copilot answers from your tenant and, where enabled, the web. It is not a legal research tool and has no authoritative view of case law. Use the tools your firm subscribes to, which cite because they are built on a citable corpus.
- "Is this clause enforceable?" It will answer. The answer is a plausible-sounding paragraph, not advice, and its confidence does not vary with how right it is. This is the request most likely to embarrass somebody.
- "Summarise everything on this client." Too broad to be useful and, in a firm with unreviewed permissions, the request most likely to surface something from a matter the asker should not be reading. Scope it to a matter.
- "How much have we billed on this?" Unless your billing data is in the tenant in a form Copilot can reach, it will reason from correspondence about money, which is not the same thing and is worse than no answer.
The one rule
Everything above produces a draft, and a draft is a starting point that has to be checked by somebody who knows the file. That is not a disclaimer bolted onto the end — it is the operating model. The time saved is in the assembling, not in the judging, and the judging is the part the firm is paid for.
Two practical habits make the difference between a team that gets value and one that quietly stops using it:
- Ask for sources, every time. "Quote the sentence", "name the document", "say where this came from". A traceable answer can be checked in seconds; an untraceable one has to be redone.
- Tell it what to do when it is unsure — flag, bracket, list separately. Left to itself it will fill the gap smoothly, and a smooth gap is the hardest kind to spot.
One more thing worth settling before any of this reaches a fee earner's desk: Copilot answers from whatever that person can already open, which in most firms has never been audited. That is the check to run first.
If you want this as a session for your team rather than a blog post, we run it on your own matters.




