Sample report for an invented law firm. See the leader brief. Get your own free AI assessment. Other samples: Wealth management practice · Accounting firm · Trades business · Engineering firm
Sidekick Orchestration Sidekick Orchestration
Free AI assessment

Sample report · invented firm

Where AI fitsBrennock Ashdale

// AI assessment Law firm

At a glance

Where to start

Finance and admin: pre-bills ready for review.

What it costs today

About $14,400 a month.

Book 30 minutes with Chase

Book 30 minutes with Chase: cal.com/chase-sidekick/intro

The two-minute version

Where you stand
A few people use AI on their own. No approved tool or written rule yet.
The main risk
Information about your clients, such as privileged legal files, going into personal AI accounts your firm can't see.
A sensible first move
Two-step sign-in for everyone, then partners first: one approved tool your firm controls, one page of rules, and a month on finance and admin.
What you'd report at day 90
Lawyer hours per pre-bill, and days from month-end to bills out, before and after.

Top opportunities, in your order

Opportunity 1

Pre-bills ready for review

You ranked finance and admin first. Vague entries get written down or queried. Pre-bill notes let lawyers review instead of reconstruct, so bills go out sooner.

Vague entries get written down or queried.

SummaryExample

Pre-bill notes for one matter

PRE-BILL NOTES · September
Pellworth v. Greyhaven
For Isla Brenmoor. Rewording gives a clearer narrative of the same recorded work; hours stay the same. Additions come from emails and memos, for the timekeeper to accept.

Reworded Entries

  1. Sept 8 · JT · 1.4 h: "call w client re docs" becomes "Telephone call with client regarding documents."
  2. Sept 10 · AM · 3.2 h: "research + memo" becomes "Legal research; drafting memorandum."
  3. Sept 14 · IB · 0.8 h: "misc". NEEDS DETAIL from you.

Possible Additions For The Timekeeper To Accept

  • Entry 1: JT's Sept 8 email lists outstanding documents. Add "for our list of documents"?
  • Entry 2: AM's Sept 10 memo covers the limitation defence. Add "re limitation defence"?

For Your Decision

  • Sept 22: JT and AM each billed 2.0 h to "review Greyhaven's list of documents". Both needed?

Draft fees: $11,240, plus taxes.

Draws from
Your practice-management system (through an export or connector IT sets up) and the matter's emails and memos.
Reviewed by
Each timekeeper accepts an addition only if it describes work actually done; the responsible lawyer approves the bill.

Opportunity 2

Client updates drafted for the lawyer

You ranked client service second. A monthly draft from the matter file keeps clients informed before they ask, without costing a lawyer an evening.

A monthly draft from the matter file keeps clients informed before they ask, without costing a lawyer an evening.

Draft letterExample

DRAFT FOR ISLA BRENMOOR. Not sent.

Monthly litigation update

Subject
Pellworth Timber's claim against Greyhaven: September update

Dear Ms. Ferreira,

Done since our last update

  • We served our list of documents on September 11.
  • Greyhaven's list arrived September 18; we're reviewing it.

Coming up

  • Examinations for discovery: November 18 and 19, at a court reporter's boardroom in Vancouver. Greyhaven's lawyer will examine you on the 18th as Pellworth Timber's representative.

What we need from you

  • The 2023 crane maintenance invoices your office manager mentioned on September 8.

Fees

  • Billed on this stage: $18,600 to date (September bill to follow), against our $24,000 estimate.

Isla Brenmoor

Draws from
The matter's filed emails, calendar and documents, and fees billed.
Reviewed by
The responsible lawyer edits, adds any advice, and sends it herself.

Opportunity 3

A Monday matter brief for the partners

You ranked leadership reporting third. Partners see a near deadline, an overrun or a stalled matter early, so the meeting starts on decisions instead of catch-up.

Partners see a near deadline, an overrun or a stalled matter early, so the meeting starts on decisions instead of catch-up.

BriefExample

Monday matter brief

MONDAY MATTER BRIEF · Week of September 28
From your practice-management system. Your copy shows only matters you can open; screened matters stay screened.

DEADLINES, NEXT 14 DAYS (6; 4 more, on track, not shown)

  • Tessaro share purchase: closing Oct 6. D. Lam. Two closing tasks open.
  • Pellworth v. Greyhaven: review of Greyhaven's documents due Oct 9. I. Brenmoor. On track.

Needs A Partner'S Eye

  • Over fee estimate (3): Kinsale lease, Brightwater supply, Morrow shareholder.
  • No time recorded in 30 days (4): list attached.
  • Unbilled time over 60 days: $42,300 across 9 matters. Largest: Brightwater, $11,900.
Draws from
Your practice-management system, through a connector IT sets up.
Reviewed by
The partner, before the meeting. Lawyers confirm flags on their own matters. Your calendar and docketing system stays the record of deadlines.

Where else AI fits

  1. Quotes and proposals

    Today
    Engagement letters adapted from the last one.
    Set up once
    Your approved templates and intake fields.
    Then runs
    A first draft for each new matter.
    You still decide
    Scope, fee estimate and the signature.

  2. Operations and projects

    Today
    Assistants retype intake into conflict and ID checklists.
    Set up once
    Your intake form, conflict fields and ID checklist.
    Then runs
    Each intake fills the conflict search and ID checklist.
    You still decide
    Whether to act; a lawyer signs off conflicts and ID.

What this time costs today

You told us 20 to 50 hours a week across your team on finance and admin; we used 35. That's time spent today, not a promised saving.

  1. 35 hours × $95your numbers
  2. $3,325a week
  3. $14,400a month
  4. $173,000a year

35 hours × $95 = $3,325 a week ≈ $14,400 a month ≈ $173,000 a year

Your data and AI

You hold privileged legal files and confidential client business information. You're not early. Others who hold this kind of information handle it in layers: limit what AI can reach, limit what it can do, write the rules down, and have a person read everything that leaves.

In this order

  1. Step 1Status: To do

    Accounts first

    Turn on two-step sign-in for everyone first. None of the security problems we've seen at clients came from AI.

    Start here. Only some of your people use two-step sign-in. None of the security problems we've seen at clients came from AI. They came from weak passwords, phishing and risky links on accounts without two-step sign-in. Turn it on for everyone in Microsoft 365, keep passwords in a password manager, and give people a quick refresher on phishing. A connected AI assistant makes a stolen password more costly, so this comes first.

  2. Step 2

    Know what's sensitive and where it lives

    List what's restricted, then keep it out of reach.

    List what's restricted, in plain words, and where each item lives. You told us you hold privileged legal files and confidential client business information. Many AI connections can reach everything your login can open, so decide one system at a time rather than file by file. Keep restricted files out of what AI can reach, or behind a separate account, and confirm it with a quick test. IT can check who can open what before anything is connected.

  3. Step 3

    Then choose the tool

    You run Microsoft 365, so Copilot is the natural place to start: it works inside the sign-in and permissions IT already manages. Check your agreements first; one that bans outside processing means a private model. A ChatGPT or Claude business plan is the alternative.

    Choose the tool last, after accounts and your restricted list. What decides it: your agreements with clients, any rule on where data is stored, the systems you already run, and what your people will actually use. Once nothing rules a tool out, a decent tool that gets used every day beats a perfect tool that never gets picked up. Mandate one people dislike and they drift back to personal accounts with no oversight.

Your tool options

You run Microsoft 365, so Copilot is the natural place to start: it works inside the sign-in and permissions IT already manages. Check your agreements first; one that bans outside processing means a private model. A ChatGPT or Claude business plan is the alternative.

  • Copilot in Microsoft 365. Works inside the sign-in and permissions IT already manages; Microsoft says it only shows people what they can already open.
  • A ChatGPT or Claude business plan. OpenAI and Anthropic each say they don't train on business data by default. Both connect to Outlook and SharePoint with admin approval.
  • If data has to stay in Canada. Microsoft stores Copilot prompts and responses in Canada when your Microsoft 365 data location is Canada, which is set at sign-up. OpenAI offers Canadian storage at rest for eligible new ChatGPT Enterprise workspaces. For Claude, Canadian residency runs through cloud platforms; ask Anthropic about its own plans. Storage in Canada doesn't always mean processing in Canada, so get each commitment in writing.
  • A private model on your own hardware. Open models can run on an office computer, so data can stay in the building. But they're usually less capable, someone must patch and secure the machine, and connecting email, calendar and other systems is slow work. A business workspace that doesn't train on your data covers the main worry behind the Law Society's private-tool point; this is for when an agreement bans outside processing.

Settings to ask for

  • Training off, in a business workspace the firm owns. Use a business workspace so the firm owns the accounts and data, training is off by default, and you control which apps people connect and can remove access the day someone leaves.
  • Connections need approval. In Microsoft 365, IT can require admin approval before anyone connects an AI app to email or files. That way every connection is a decision someone made.
  • Web search off for sensitive work. Turn off Copilot web search for the people who handle work for clients. It's one admin policy, set per user or group, and people can't turn it back on.
  • Drafts only, to start. Where the tool allows it, leave send and edit permissions off to start. AI prepares the email and a person sends it. That also limits the damage if an email or web page hides instructions aimed at the AI. Check the actual connection, because instructions alone aren't a lock.
  • Keep sensitive work out of chat memory. Many AI tools remember past chats. For sensitive work, use a temporary chat or turn memory off. On some personal plans, rating a reply can still send that conversation for training, even with training off.

The Law Society of BC's guidance on generative AI (prepared October 2023) keeps lawyers responsible for all work product they oversee. It says client confidential information would ideally stay out of AI tools, that a private tool using only firm information can avoid some of those concerns, and that clients should know how you use AI.

What stays with you

  • Legal advice and opinions. Strategy and merits stay a lawyer's judgment; AI gathers the file.
  • Authorities you cite. Check every case at the source before it goes into anything you file.

What could go wrong, and how to prevent it

  1. Information your clients trust you with

    How it's prevented
    Put written rules in the AI's settings from day one, and widen what it can reach one system at a time as it earns trust.
    Do this week
    Ask IT two questions: who can open what in your shared files, and whether anyone uses a personal AI account for work.

  2. Wrong answers going to clients

    How it's prevented
    The responsible person stays accountable, so check citations, figures and sources: a public tracker lists over 2,000 court decisions worldwide involving AI-invented content.
    Do this week
    At your next team or partners' meeting, agree: nothing AI-drafted leaves until the responsible person has read all of it.

  3. Staff using unapproved tools

    How it's prevented
    Give people an approved tool that beats the free one, and block unapproved AI apps on firm devices.
    Do this week
    Send a two-line note: no information about clients in personal AI accounts. Then ask, with no penalty, what people have been using.

Rules here were checked against their sources in September 2026. Your partners confirm how they apply to your firm.

What it takes

  • Partners first

    You and up to five partners use it first: about 3 hours of yours over two weeks, then 30 minutes a week. Others follow.

  • Turning it on

    IT does it, with Chase or from his checklist: partners first, web search off for client work, data storage checked, file permissions tidied.

  • A one-page AI-use policy

    Which tool, what goes in, and who reviews before anything leaves.

  • Your insurers

    Ask the Lawyers Indemnity Fund (BC lawyers' mandatory coverage) and any excess or cyber insurer what they want to know about your AI use.

A first project for you

Try this yourself, before your team does.

Use the firm's business AI account, on templates, past work or your inbox, with names taken out.

Starting instruction

Here is our month-end checklist as it stands today. Rewrite it as one page in order, with an owner and a day for each step. Then list every step that depends on one person. [paste your checklist; no names, amounts or account numbers]

How to check it

Walk through last month against the new checklist. Anything it missed goes back in before you share it.

If it saves you time, that's the case for your partners.

How Chase would help

  • Solo for Execs

    Start with yourself. AI leadership in 30 days: AI set up around your own work, plus what you need to lead it in your firm and answer the questions your partners, team and clients ask.

    CAD 2,900 once

  • Fractional leadership

    Chase leads AI adoption with your leadership team for 90 days: first two weeks meeting your leaders and showing AI on your firm's own templates and past work (not client files), then agreed measures reviewed every 30 days. Teams come in once leaders use it.

    From CAD 6,000 a month

    Scaled to how many leaders and teams are involved.

Who sets it up
Chase works with your IT provider directly, or gives them a checklist, your choice. Your IT provider turns it on.
If it isn't working
Fractional: measures agreed up front and reviewed every 30 days; if a milestone slips because of us, we keep working at no extra fee until it's delivered.
You keep everything that's built.

Chase signs your confidentiality agreement and never logs in to your systems or asks for client files. He doesn't give legal advice.

30 minutes with Chase to walk through your report and decide where to start.

You ranked finance and admin first and worry about client data. We'd start there.

Book 30 minutes with Chase

Book 30 minutes with Chase: cal.com/chase-sidekick/intro