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Chapter 4 · How do I choose the best tools?
00 Introduction 3 lessons
  1. 0.1 Who this guide is for and how to read it
  2. 0.2 The eight questions every lawyer asks
  3. 0.3 Survival glossary
01 How can AI help my practice and day-to-day work? 5 lessons
  1. 1.1 What is AI really?
  2. 1.2 Chat vs. agent
  3. 1.3 Where skills, MCP and plugins fit in
  4. 1.4 What lawyers are actually using AI for right now
  5. 1.5 Does it really save time?
02 Can I trust it? 5 lessons
  1. 2.1 Hallucinations
  2. 2.2 What is the answer based on?
  3. 2.3 When the model tells you what you want to hear
  4. 2.4 What a benchmark score really tells you
  5. 2.5 Test it on your own matters
03 Am I allowed to use it? 7 lessons
  1. 3.1 The three questions behind the question
  2. 3.2 What happens to the documents I upload?
  3. 3.3 Who can access, store or reuse my data?
  4. 3.4 Anonymisation and pseudonymisation
  5. 3.5 Professional rules by jurisdiction
  6. 3.6 Sovereignty and compliance
  7. 3.7 Other risks
04 How do I choose the best tools? 6 lessons
  1. 4.1 Same brain, different bodies
  2. 4.2 Subscription vs. API access
  3. 4.3 Legal AI tool or general-purpose assistant?
  4. 4.4 Open-source vs. closed, from the buyer's seat
  5. 4.5 Panorama of tools
  6. 4.6 Questions to ask before choosing a legal AI tool
05 How do we make it work across the firm or legal team? 7 lessons
  1. 5.1 Why one enthusiast is not an adoption strategy
  2. 5.2 Choosing a first pilot
  3. 5.3 Training the team
  4. 5.4 Measuring time saved and quality
  5. 5.5 Who maintains the tools and the shared know-how?
  6. 5.6 Change management
  7. 5.7 Working with IT, security and procurement
06 How do I get better results? 3 lessons
  1. 6.1 Give it better context
  2. 6.2 Turning your methods into reusable instructions
  3. 6.3 Watch out for AI slop
07 What does this mean for my career and my firm? 4 lessons
  1. 7.1 Which skills should lawyers develop?
  2. 7.2 What does a legal engineer do?
  3. 7.3 How AI may change fees, staffing and client expectations
  4. 7.4 What an AI-native firm might look like
08 Where and how do I start now? 4 lessons
  1. 8.1 Starter kits by profile
  2. 8.2 Classic mistakes to avoid
  3. 8.3 Section 1 recap
  4. 8.4 Staying current without drowning

Lesson 4.6 How do I choose the best tools? 4 min read

Questions to ask before choosing a legal AI tool

You have a shortlist. Send each vendor the same questions below and ask for written answers with supporting documents. Copy the template into an email to compare their responses.

Template

The questions to send any vendor

19 questions, by criterion. Copy them into an email or a document.

Security

Gate

Ask for: Data processing agreementSub-processor listAudit or penetration test report

  1. 1 Which plan covers our data, and will you sign a data processing agreement (DPA) for it?

    A good answer:A DPA for the plan that you buy, with the terms of GDPR Article 28.

  2. 2 Where do you store our data, and how long do you keep our documents, prompts and outputs?

    A good answer:Named regions, and a period in days.

  3. 3 Do you, or any sub-processor, train or improve models on our data?

    A good answer:No, in the contract, for each link in the chain.

  4. 4 Which security audits or penetration tests cover this product?

    A good answer:A current SOC 2 Type II report or ISO 27001 certificate whose scope includes this product. Otherwise, a recent penetration test report from a recognized organization covering this product.

Accuracy

Test

Ask for: The method behind each accuracy figure

  1. 5 Can we test the tool on our own past documents before we sign, under the data terms of the contract?

    A good answer:Yes, with the same data terms.

  2. 6 Which model and version run the product?

    A good answer:A named model and version.

  3. 7 For each accuracy figure that you quote: which test set, which configuration and which definition of correct?

    A good answer:A written method, run on the configuration that you would buy.

Integration

Test

Ask for: List of supported systems

  1. 8 Does the tool work inside Word and Outlook, and write tracked changes?

    A good answer:Yes, without copy and paste.

  2. 9 Does it apply the permissions of our document management system, matter by matter?

    A good answer:Yes. Ethical walls stay in place.

  3. 10 Do you support single sign-on, so that access ends when a person leaves?

    A good answer:Yes.

Price

Test

Ask for: Price scheduleRenewal terms

  1. 11 What is the price per user or per use, and what are the minimum seats and term?

    A good answer:A written schedule that states the minimums.

  2. 12 Which setup, training or usage fees come on top?

    A good answer:Fixed amounts, in the order form.

  3. 13 Does the contract renew automatically, and is there a cap on price increases?

    A good answer:A notice period that you can manage, and a cap in percent.

Support

Contract

Ask for: Service level agreement

  1. 14 Who is our contact, and which response times are in the contract?

    A good answer:A named person, and response times by severity.

  2. 15 What notice do we get before the model changes, and can we stay on the current version while we test?

    A good answer:Notice in days, in writing, and a period on the current version.

  3. 16 Describe your last serious incident. When did customers hear, and what changed after?

    A good answer:A specific account, with dates.

Viability

Contract

Ask for: Termination clauseA sample export

  1. 17 Who owns the company, and how is it funded?

    A good answer:Direct answers, under a non-disclosure agreement if necessary.

  2. 18 When the contract ends, how do we get our data out, in which formats, and within how many days?

    A good answer:A full export in standard formats, 30 days or more, then certified deletion.

  3. 19 Can we export our instructions, templates, workflows and the record of what the tool did on each matter?

    A good answer:Yes, in plain text or another open format, with a sample.

The copied text contains the questions and the documents to ask for, not the good answers. It collects the main questions of lessons 4.1 to 4.5.