Ask, the built-in assistant
Ask your vendor records a question. Approve the answer.
Ask is the AI assistant built into ShowMeTheDocs. You type a question in plain words, such as which vendors are missing a certificate or what expires this month. Ask answers from your own vendor records and drafts the follow-up work for you to review: reminders, requests to insurance agents, bulk edits, new vendors and requirements read from a subcontract. It never sends or changes anything until you approve.
Included in every plan. Optional: admins can switch AI off. Daily message limits depend on the plan.
What you can ask
Real questions Ask handles today, grouped by what you are trying to do.
Find out where you stand
Answers from your own records, with a sources row and the date they were read.
- “Brief me on what needs attention today”
- “Which vendors have a missing certificate right now?”
- “What certificates expire in the next 30 days?”
- “Why is Apex Roofing not compliant?”
- “Compare Apex Roofing and Cedar Electric”
Chase the paperwork
Drafts for you to review. Emails go out only after you approve.
- “Remind everyone expiring this month”
- “Ask the brokers of everyone expiring this month for their certificates”
- “Send a reminder to Ridgeline Electric”
- “Record a payment check for Ridgeline Electric, pay app 3”
Report and prepare
Plain-language summaries from exact numbers, ready to forward.
- “Write my month-end report”
- “Prepare for the insurer audit”
- “Which vendors worry you most?”
- “Who will probably be late renewing?”
- “Any patterns I should know about?”
Set up and clean up
Review the card, tick what you want, undo within 24 hours.
- “Add these vendors: Apex Roofing apex@example.com, Cedar Electric cedar@example.com”
- “Change the trade of all my electricians to Electrical”
- “Do I have duplicate vendors?”
- “Set up my business with a starter pack and two sites”
How Ask keeps you in control
- Answers come from your records
- Counts, dates and names are computed by the app, not guessed by the AI, and each answer says where it came from and when the records were read. When Ask cannot see something, it says so and points to the page that would show it.
- Nothing happens until you approve
- Ask drafts a reminder, a request to an insurance agent, a bulk edit, new vendors or requirements from a contract and shows you exactly what will happen. Emails go out only after you press Approve. Bulk edits and requirements drafted from a contract can be undone for 24 hours.
- You control what it may do
- Admins can switch AI off entirely, or switch off file reading, answers from your records and drafted actions one by one. They can also limit approval to admins. Every approval is in the activity log.
- Sensitive numbers are masked
- Social Security numbers, tax IDs, card numbers and bank account numbers typed into Ask are masked before anything is sent to the AI provider. The provider does not train on your content and deletes it within 30 days.
- It never judges compliance for you
- Ask does not approve documents, change statuses, give legal or insurance advice, or say a policy is sufficient. Readings and drafts are suggestions you check against the document.
Drop in files, photos and contracts
Drop a certificate into Ask and it suggests the vendor, the end date and the cover amount, with a short summary of what it found and what it cannot judge. Drop up to 10 files at once and check them in one table. On a phone, take a photo of a paper certificate. Drop a subcontract PDF and Ask drafts the insurance requirements it finds, quotes the clause, and creates only the ones you tick. The reader can misread, so you confirm every value before anything is saved.
Questions about Ask
What is Ask?
Ask is the assistant built into ShowMeTheDocs. You type a question in plain words and it answers from your own vendor records, then drafts the follow-up work for you to approve: reminders, requests to insurance agents, bulk edits, new vendors and requirements read from a subcontract.
Can Ask send emails or change data without my approval?
No. Every email, edit or import is shown as a card first, and nothing happens until you press Approve. An admin can limit approval to admins. Emails cannot be taken back, so each card says so. Bulk edits and requirements drafted from a contract can be undone for 24 hours.
Where do Ask's numbers come from?
From your records. Counts, dates and names are computed by the app and match your dashboard, and each answer shows where it came from and the date the records were read. When Ask cannot see something, such as the fine print of a document, it says so.
Is my data used to train AI models?
No. Ask sends your question and, when you ask about your records, the relevant vendor names, trades, requirement names, statuses and dates to the AI provider. The provider does not use this content to train its models and deletes it within 30 days. Social Security numbers, tax IDs, card numbers and bank account numbers typed into Ask are masked before anything is sent.
Can I turn the AI off?
Yes. An admin can switch all AI features off in Settings, or switch off reading files, answers from your records and drafted actions one by one. Everything else in the product keeps working without AI.
Does Ask decide whether a vendor is compliant or a policy is enough?
No. Ask reports what is on file: dates, amounts and the wording the reader found. It does not approve documents, change statuses, or give legal or insurance advice. Check readings against the document and ask your insurance agent or lawyer about wording.
How many questions can I ask?
Each plan has a daily message limit that resets at midnight UTC. The Free plan allows 10 messages a day, Starter 30, Growth 60 and Pro 120.
What kinds of files can Ask read?
Certificate PDFs, and photos or scans when scan reading is switched on, up to 10 MB each as PDF, PNG or JPEG. You can drop up to 10 files at once, take a photo with your phone, or drop a subcontract PDF with a text layer to draft its insurance requirements.
Try Ask on your own vendors. Start with a 14-day free trial, no credit card required.