Ask the vendor to run your own contracts, not its samples, and to answer ten things: where the data sits, how accurately it reads clauses and dates, where each answer comes from, how it handles scans and variations, who sees what, how you export, what it costs, how you cancel and who migrates your files.
The pages that rank for this software are mostly enterprise contract-lifecycle vendors. Ironclad's home page, for example, lists 'Enterprise Class' in its navigation, shows large-company logos, publishes no prices and sends visitors to a demo request. A contractor's paperwork is different: signed subcontracts photographed on site, variations that change payment terms, insurance certificates that expire and retention (retainage) held until the defects period ends. The demo is where you find out whether a tool copes with that.
Prepare a test pack of eight contracts before the demo
A vendor's sample contract is typed, clean and has one version. Yours don't. Pull eight documents from your own files, redact client names if the vendor hasn't signed a confidentiality agreement yet, and use the same eight with every vendor so the scores can be compared.
| Document in the pack | Why it is there | What it tests |
|---|---|---|
| A prime contract with a client, typed PDF | The easy case | All ten fields |
| A subcontract scanned from a signed paper copy | Real life on most sites | Reading scans; dates and retention |
| A subcontract with two later variations | Terms change after signing | Which payment terms and value apply now |
| A photographed signature page and cover sheet | Phone photos of signed pages are common | Parties and signing date from a poor image |
| A supplier account agreement that renews automatically | Quiet cost traps | Renewal date and notice period |
| An equipment hire agreement | A layout you don't control | Dates and charges in an unfamiliar format |
| A subcontractor's insurance certificate | Not a contract, but you track it | Policy end date |
| A one-page order form | Short documents with little structure | Value and parties |
Score ten fields wherever they exist: the parties, contract value, start date, completion date, payment terms in days, retention percentage, the event that releases retention, notice periods for claims and termination, the defects or warranty period, and insurance requirements. Not every document has every field, so note how many were possible. That is up to 80 checks per vendor, enough to show a pattern and few enough to finish in an afternoon.
Send the vendor a short email a few days ahead, so the answers don't depend on a salesperson's memory:
Subject: Preparing for our demo
We will bring eight of our own contracts, including two scanned signed
copies and a subcontract with two variations. Please process them in a
trial account before the call, or live during it.
Please send in advance:
1. Your sub-processor list and data-processing terms
2. A sample export of documents and extracted data
3. Which AI features sit in which plan, and the all-in price for 150 active
contracts and 6 users over three years, including any onboarding,
migration and AI fees
4. Your standard renewal and cancellation termsA vendor that won't send these before the demo has told you how the same questions will go afterwards. The general method for running any AI software demo is in how to run an AI software demo so you see the real product; what follows is the contractor-specific part.
Questions 1 to 3: where data lives and whether the AI reads it right
1. Where does my data live, and does the AI learn from it?
Contracts hold prices, margins, bank details and the names of clients who may have signed confidentiality terms, and some prime contracts limit who else may see them. You need three separate answers, because a vendor can give a good one to the first and a vague one to the others: where the files are stored and whether you can choose; which company's AI model reads the text and where; and what that company keeps afterwards.
The last point is the one vendor pages often skip, because model providers set their own rules. OpenAI says API data isn't used for training by default. Anthropic keeps prompts and outputs on its most capable models for 30 days even for customers on zero data retention, and added an application route back to zero retention in September 2026. Neither rule is good or bad in itself. The point is that a vendor built on either should be able to say which one applies to your documents. Write the answers down in a table like this one, with invented answers to show the contrast:
| Answer to write down | Vendor A (clear) | Vendor B (vague) |
|---|---|---|
| Where files are stored | Named cloud provider; region chosen at sign-up | 'Secure cloud' |
| Which AI provider reads the text | Named model provider, processing in the same region | 'Industry-leading AI' |
| What that provider keeps, and for how long | 30 days, then deleted; in the data-processing terms | Not stated |
| Is my text used to train models | No, stated in the contract | 'We take privacy seriously' |
| What is deleted on cancellation, and when | All documents and extracted data within 30 days of the export window | Not stated |
Ask for the audit report, not the badge. ContractSafe's pricing page, for instance, lists a SOC 2 audit and ISO 27001 certification; any vendor claiming the same should hand over the report or certificate and the scope it covers. If you have customers in the EU, data-protection law such as the GDPR can apply to the personal data inside contracts, such as signatories' names and contact details. The vendor's data-processing terms are where that is dealt with, and a lawyer should read them before you sign.
2. How accurate is it on my own contracts?
Ask the vendor to process your eight documents and show every extracted field next to the page it came from. Then mark each field as correct, wrong, missing or invented (a value returned for something the document doesn't contain). These illustrative results cover seven of the ten fields for one vendor on a pack like the one above:
| Field | Possible | Correct | Wrong | Missing | Invented |
|---|---|---|---|---|---|
| Parties | 8 | 8 | 0 | 0 | 0 |
| Contract value | 7 | 7 | 0 | 0 | 0 |
| Start date | 7 | 6 | 1 | 0 | 0 |
| Completion date | 5 | 3 | 1 | 1 | 0 |
| Payment terms | 6 | 5 | 1 | 0 | 0 |
| Retention percentage | 4 | 2 | 1 | 1 | 0 |
| Notice periods | 5 | 3 | 0 | 2 | 1 |
| Total | 42 | 34 | 4 | 4 | 1 |
Thirty-four of 42 is 81%, which sounds acceptable until you look at where the misses fall. Parties and values are perfect, because they sit on page one. The weak fields are completion date, retention percentage and notice periods, which are the ones that cost money when they are wrong. Agree pass marks per field before the demo: 100% on parties and values, at least 90% on dates, and, more important than any percentage, every wrong or missing field flagged for a person to check instead of silently left blank. A tool at 81% that flags its misses is safer than one at 85% that stays quiet.
Run the same pack through a general assistant such as ChatGPT or Claude, on a business plan, as a free baseline. Anthropic's help centre says Claude analyses text and visual elements in PDFs of up to 100 pages, and only the text in PDFs of 101 to 1,000 pages. A scan is an image, so a long scanned subcontract is the case to test before you rely on the baseline. If a general assistant gets close to the paid tool's score, what you are buying is the tracking, reminders and permissions, not the reading, and you can judge the price on that basis.
3. Can I click from every answer to the clause behind it?
Ask the vendor to open any extracted field and show the exact clause, page and wording. Then pick three fields yourself, because a vendor will click the three that work. Compare two imagined screens. On the first, 'Retention: 5%' sits beside a link to clause 9.2 on page 14, which reads 'the Contractor shall retain 5% of each interim payment, reducing to 2.5% at practical completion'. On the second, 'Retention: 5%' stands alone.
The first screen shows why the link matters. The field holds one number, but the clause has two: 5% during the job and 2.5% after completion. Only the source text reveals that, and a person checking the answer can fix the record in seconds. Ask how the tool stores multi-stage terms, whether as two fields, a note or nothing. One construction-focused vendor's home page promises 'every flag traced to a clause'; ask any vendor for that standard, and ask what the screen shows when the AI isn't sure. Good answers include a 'needs review' status, corrections that stay corrected when the document is processed again, and a log of who changed what.
The software reads and flags; it doesn't give legal advice. For an unusual clause such as pay-when-paid, set-off or damages for delay, ask a lawyer who knows construction contracts. Which clauses AI flags and misses in construction contracts and what builders should test in contract review software go deeper on the review side, which is a different product from the repository this tutorial is about.
Questions 4 to 6: dates, scans and who can see what
4. Which dates does it find, and who gets the reminder?
For a contractor the value of the software is mostly in the dates. Ask which dates it extracts by default, whether you can add your own, who receives each reminder and how many days ahead. These are the ones worth testing:
| Date | Where it hides | What a miss costs |
|---|---|---|
| Retention release | Payment clause, plus the defects period | On an $86,000 subcontract at 5%, $4,300 sits unclaimed or late |
| Notice deadlines for delay or extension claims | Special conditions, sometimes a short window such as 14 days | The right to claim lapses |
| Insurance expiry | The certificate, not the contract | A subcontractor on site without cover |
| Auto-renewal and notice window | Supplier and hire agreements | A year of charges for something you stopped using |
| Option and extension dates | Hire, lease and framework terms | A rate you could have kept |
Test two awkward cases in the demo. First, relative dates: a defects period ends 12 months after the date on the practical completion certificate, which doesn't exist when you upload the subcontract. The tool should let you set the trigger later and compute the end date from it. Most tools capture fixed dates well and relative ones badly, so ask to see one created live. Second, who owns the reminder: ask what happens to reminders assigned to a project manager who leaves. If they die with the account, you have a quiet gap that nobody notices until a deadline passes. A shared mailbox or a role-based recipient avoids it. The same logic applies to certificates; tracking subcontractor insurance expiry with AI covers that side in detail.
5. How does it handle scans, signed copies and variations?
Ask the vendor to process the scanned subcontract and the one with two variations, then show the terms that apply today and the history behind them. A contractor's documents change after signing, and a repository that treats each file as separate will show you out-of-date terms. Here is the answer you should expect for a subcontract with two variations:
| Field | Original subcontract | Variation 1 | Variation 2 | What the tool should show now |
|---|---|---|---|---|
| Contract value | $48,000 | No change | Adds $6,500 | $54,500, with both variations listed |
| Payment terms | 30 days | 45 days for stage payments | No change | 45 days, from Variation 1 |
| Completion date | 28 June | No change | 12 July | 12 July, from Variation 2 |
If the tool shows $48,000, 30 days and 28 June, it is reading the original and ignoring the changes. If it shows the new figures but not where each came from, you can't check it. For scans and photographs, ask how it handles handwriting, initials, crossed-out text and a signature page photographed at an angle, and whether it tells signed copies from drafts. Ask to see what it does with the photographed signature page from your pack, since that is the document it is most likely to read badly. AI tools for subcontracts and change orders covers how those documents get produced in the first place.
6. Who can see and change which contracts?
A contract repository holds your margins and your clients' terms, so permissions matter more than they do for a shared drive. Ask whether access can be set per project or per contract type, whether shared links expire, and whether there is an audit log of who viewed, downloaded and edited, and whether you can export that log. A sensible setup for a firm of fifteen looks like this:
| Role | Should see | Should not see |
|---|---|---|
| Owner or director | Everything | No restriction |
| Project manager | Contracts for their own jobs | Other jobs' margins |
| Bookkeeper | Values, payment terms and dates | Full commercial terms, unless needed |
| Outside adviser | Selected contracts, read-only, for a set time | Anything not shared |
Then ask where the security features sit in the pricing. On ContractSafe's pricing page, for example, single sign-on starts on the middle plan and IP restrictions on the top one. A vendor can have the control you need and still not include it in the plan you are quoted. The question that exposes the most is about the audit trail: if someone changed 'retention 5%' to '3%' on a signed subcontract, would the log tell you who and when? If the answer is a vague yes, ask to see it happen.
Questions 7 to 10: getting out, paying, cancelling and starting
7. How do I get everything out, and can you show me now?
Ask the vendor to export a batch live, then repeat it yourself during the trial. A published answer worth matching: ContractSafe's pricing page says authorised users can download a backup of all documents at any time and offers a CSV of contract data and reminders. Anything vaguer than that deserves a test. In the trial, export 50 contracts and check:
- The originals arrive as ordinary files, with their original names.
- A spreadsheet has one row per contract and a column for every extracted field, including the dates and reminders.
- Your corrections are in the export, not only the AI's first pass.
- The notes and audit log come out too, or you are told plainly that they don't.
- The owner can do it without raising a support ticket, and it costs nothing.
Do the rehearsal in month three, not at cancellation. The first time you export shouldn't be the day you're leaving, and a quarterly export to your own storage doubles as a backup. If the vendor offers an API, ask which plan includes it; on the vendor above, APIs appear on the top plan.
8. What does it cost all in at my volume?
Contract software is sold on several meters at once: per user, per active contract, per page processed, per AI credit, per gigabyte, plus onboarding and migration fees. ContractSafe's page shows how many meters a single vendor can use. It lists unlimited users on every plan, counts only contracts in the repository and not archived files or attachments (a contract with three earlier drafts counts as one), puts AI data extraction on every plan but AI contract review on the top one, charges no implementation fee, and sells 'Jump Start' extraction services from $2.50 a contract. Get the equivalent list from every vendor, then price three years on one sheet. These two quotes are invented:
| Cost over three years, 150 active contracts, 6 users | Vendor A | Vendor B |
|---|---|---|
| Headline price | $5,400 a year, unlimited users | $60 a user a month, $4,320 a year |
| Onboarding fee | $0 | $2,500 |
| Migration of 300 legacy contracts | 300 at $2.50, $750 | Included |
| AI add-on | Included | $1,200 a year |
| Price rise after year one | None, price locked for three years | 8% a year |
| Three-year total | $16,950 | $20,420 |
Vendor B looks cheaper on the headline, $4,320 against $5,400, and costs about $3,500 more over three years once the onboarding fee, the AI add-on and the annual rise are counted. Vendor A's total is $5,400 times three plus $750; Vendor B's is $8,020 in year one, $5,961.60 in year two and $6,438.53 in year three. Ask each vendor to put its figures on the same sheet and to say in writing which of them can change during the term.
9. What are the renewal and cancellation terms?
Ask for the term, how it renews, the notice window, the refund position, and how long you have to export after cancelling. A common trap is the notice window. Suppose an annual term ends on 30 June and renews automatically unless you give 60 days' written notice. The deadline is 1 May; miss it by a week and you owe another year's fee, $5,400 at Vendor A's price above. Ask for a calendar reminder to be put in the contract record itself, which is a good test of the tool you are buying.
Ask also what downgrades cost. ContractSafe's page says upgrades take effect at once and are prorated, while downgrades take effect at the end of the subscription period, which is common and worth knowing before you choose the larger plan on trial enthusiasm. Wording worth asking a vendor to agree to, which a lawyer should check against your actual agreement:
Customer may export all Customer Data, including original documents,
extracted data, reminders and notes, at any time during the term and for
60 days after termination, at no charge. Vendor will delete all Customer
Data within 30 days after that period ends and confirm deletion in
writing. Fees will not increase by more than 5% on renewal.Think about the vendor's own survival too. Clockwise, an AI calendar tool, shut down on 27 March 2026 and deleted its users' data. Bench, an online bookkeeping service, shut down on 27 December 2024. A contract repository is a worse place to be caught out than a calendar. Ask how long the product has been on sale and who owns it, and set up a scheduled backup to your own storage so that a closure costs you a migration, not your records.
10. Who moves my existing contracts in, and how long does it take?
Ask who uploads the existing files, how long the first batch takes to become searchable, what you must supply, and what it costs. The honest answer for a contractor with 300 contracts in a shared drive named things like 'Scan0045.pdf' is that someone has to work out what each file is. Here is a realistic plan with illustrative hours:
- Week 1. Sort the 300 files into live jobs and finished ones, at about two minutes a file: 10 hours. Upload the 50 live contracts first.
- Week 2. Check the extracted fields on those 50 at about five minutes each: about 4 hours.
- Week 3. Set the reminders that matter: retention releases, notice windows and insurance expiries on live jobs.
- Week 4. Upload the 250 older contracts and spot-check one in five, 50 contracts at five minutes each: about 4 hours.
That is about 18 hours, or around $700 at $40 an hour, on top of whatever the vendor charges. Ask what the vendor's own help covers: ContractSafe's page, for one, lists data and document migration on every plan and sells its paralegal 'Jump Start' extraction separately, which for all 300 files would start at $750. Ask the vendor to show the first week working on your files during the trial, not on slides.
Integrations are the second half of this question. A logo wall says little. Ask to see a contract signed in your e-signature tool arrive in the repository without anyone filing it, and to see the contract value reach your job costing or accounting records, which links to the question of whether job costing needs construction-specific accounting software. If the link needs a person to retype anything, it is a feature of the brochure.
Scoring two vendors on one page
Score each question 0 for no answer or an unacceptable one, 1 for a partial answer, and 2 for something shown working on your documents. Weight the questions by what a mistake costs you. These scores are invented to show the sum:
| Question | Weight | Vendor A | Vendor B |
|---|---|---|---|
| 1. Data and AI training | 3 | 2 | 1 |
| 2. Accuracy on my pack | 3 | 1 | 2 |
| 3. Source citations and review | 2 | 2 | 1 |
| 4. Dates and reminders | 3 | 2 | 1 |
| 5. Scans and variations | 2 | 1 | 2 |
| 6. Permissions and audit log | 1 | 2 | 1 |
| 7. Export | 3 | 2 | 0 |
| 8. All-in price | 2 | 2 | 1 |
| 9. Cancellation and exit | 3 | 1 | 1 |
| 10. Migration and start | 2 | 2 | 1 |
| Weighted total, maximum 48 | 40 (83%) | 26 (54%) |
Vendor A scores 40 of 48 and Vendor B 26. The rule that matters more than the total: a 0 on any question weighted 3 rules a vendor out. Vendor B scored 0 on export, so it is out even if its extraction had been the best in the pack. Use the sheet to decide, and keep the written answers with it. If two vendors finish close, the tie-breaker is the question where a mistake is hardest to undo, which is nearly always export.
Red flags in the demo itself
- The demo runs only on the vendor's own sample contracts, and 'we'll process yours afterwards' becomes 'we can't share the results'.
- An AI answer appears with no source clause, and the presenter moves on when you ask for one.
- Data location, retention or model-training questions are met with 'we'll get back to you' and the follow-up never arrives in writing.
- Export is described but not shown, or needs a support ticket.
- 'Unlimited' appears in the pitch and a fair-use clause appears in the contract.
- A discount that expires today, on a product you have seen for forty minutes.
After the demo, get the answers in writing and compare them with what you saw. If you'd rather have someone go through the shortlist with you, that is what my AI implementation consultation covers: finding the jobs where AI pays off, adding AI to the tools the team already uses, and handing over something the business can run. The contact page has the form.
Questions contractors ask before booking a contract software demo
Does a small contractor need contract management software at all?
Not always. With a few dozen live contracts, a shared drive and a dated spreadsheet with calendar reminders can work. Software starts to earn its cost when dates are missed, signed copies are scattered across phones and folders, or several people need controlled access. Run the eight-contract test described above before paying, because the dates and variations are where cheap tools fail.
Can I just use ChatGPT or Claude to read my contracts?
For reading a handful of documents, yes, and they make a fair free baseline for the accuracy test. They don't track dates, set permissions or keep an audit trail, which is most of what contract software sells. Use a business plan, where content isn't used for training by default, and have a lawyer interpret any clause that carries real money or risk.
How many contracts should I bring to the demo?
Eight to ten of your own, chosen to be awkward: two scanned signed copies, one photographed signature page, a subcontract with variations, an auto-renewing supplier agreement and an insurance certificate. Use the same set with every vendor so the scores can be compared. Redact client names if the vendor hasn't signed a confidentiality agreement.
Is AI clause extraction accurate enough to trust?
Treat it as a fast first pass, not a verdict. Set pass marks per field before the demo: names and values should be near-perfect, dates need checking, and every miss should be flagged for a person rather than left blank. A tool that is 80% accurate and flags its misses is safer than one that is 85% accurate and silent about the rest.
What should I get in writing after the demo?
The answers to all ten questions, the plan each AI feature sits in, the all-in price over the full term, the renewal and notice terms, the data-export formats and the sub-processor list. Ask for it by email, not on a call. If a vendor's written answers differ from the demo, believe the written ones and ask why.
Further reads
- Questions to Ask Before Buying AI That Touches Client Data — Data questions that apply to any AI tool touching client files.
- AI Contract Review for Small Firms: What It Catches and Misses — What AI contract review catches and misses, outside construction.
- Can AI Review a Contract? What Small Business Owners Should Know — A plain-English view of what AI can safely do with a contract.
- AI Tools for Construction Project Management: RFIs, Logs, Reports — Where contract dates meet RFIs, logs and reports on site.
- Which AI Tools Should a General Contractor Buy? What to Skip — A buy-first order, a skip list with triggers, and a hours-it-must-save test for a general contractor, priced for a six-person remodelling firm.
- AI Tools and AI Development: The Complete 2026 Guide — the AI hub, including every tutorial in the AI-for-business series.
Sources: ContractSafe pricing page and FAQ (October 2026); Ironclad home page (October 2026); Document Crunch home page (October 2026); Anthropic and OpenAI data-retention documentation; Claude help centre article on uploading files (October 2026).