15 questions to ask AI about your business, and 5 to keep for a professional

A chatbot that can't see your records will still answer "who owes me money?", but it'll answer with advice about chasing invoices. The useful version reads your invoices and tells you the three clients and the amounts. That takes a connection to your data. The Model Context Protocol (MCP) is the open standard most assistants now use for this: Claude and ChatGPT both support it, and a business app exposes read tools the AI can call. Below are 15 questions that work when that connection exists, each with the kind of answer to expect, and 5 to keep away from AI.

Money

1. "Who owes me money?" Expect a list of overdue invoices with client, amount and days late, plus a total per currency. Example: "3 invoices are overdue for $4,150: Harlow $2,400 (18 days), Café Luna $950 (12 days), Ortiz $800 (3 days)."
2. "How does this month compare with last month?" Expect collected, invoiced and expenses for both months with the dates of each period. Example: "October so far: $6,200 collected, $7,900 invoiced, $1,140 in expenses. September: $8,050, $7,300, $980."
3. "How much did I bill Carla this year?" Expect one total and the invoices behind it. Example: "$12,600 across 5 invoices since January 1, all paid except INV-0041 ($1,800, due November 3)."
4. "Who are my best clients this year?" Expect clients ranked by what they paid, so you know who to protect. Example: "Harlow $18,400, Ortiz $9,200, Café Luna $6,750."
5. "How much will come in during November?" Expect a forecast in ranges, not a promise. Example: "Sure: $5,400 from sent invoices. Likely: $7,200 with your monthly retainer. Possible: $9,100 if one open quote is accepted at your usual rate."

Clients and work

1. "How many unbilled hours do I have on the Harlow project?" Expect hours and the amount at your rate. Example: "6.5 billable hours not invoiced, $585 at $90 an hour."
2. "How many hours did I work for Ortiz last month?" Expect a total by project. Example: "14.25 hours in September: 11 on the audit, 3.25 on calls."
3. "What did I charge for logos in the past?" Expect a range and a median from similar past jobs, or a clear "not enough data". Example: "You charged $1,800 to $3,200 for 4 logo projects (median $2,400)."
4. "Who hasn't signed the contract yet?" Expect each pending signature request with the signer and the date sent. Example: "Café Luna's services agreement, sent October 20, not opened."
5. "Did Ana open the proposal I sent?" Expect the date it was viewed, or that it hasn't been. Example: "Viewed twice, last on October 22, no answer yet."

This week and what's next

1. "What's pending this week?" Expect money owed, invoices due soon, unbilled time, quotes waiting and meetings. Example: "$950 overdue, $1,500 due Thursday, $585 unbilled, 2 quotes waiting, 4 meetings."
2. "What should I do first today?" Expect actions ranked by money at stake. Example: "1. Send the reminder for INV-0038 ($950). 2. Invoice the accepted workshop quote ($1,800). 3. Follow up on the Ortiz quote, viewed 4 days ago."
3. "Prepare me for my call with Ana tomorrow." Expect a short brief from your records. Example: "Second meeting. Owes nothing. Opened your $3,400 proposal twice. Asked about a payment plan in the booking form. Ask: start date, who approves, whether 50% upfront works."
4. "Which quotes need a follow-up?" Expect quotes viewed without a reply and ones never opened. Example: "Ortiz viewed 4 days ago; Lee sent 6 days ago, not opened."
5. "Which expenses this month have no receipt?" Expect a list you can fix in minutes. Example: "2 expenses: Figma $15 on October 3, Zoom $49 on October 9."

Each example above is illustrative. The real answer comes from your records, which is the point: ask for the invoices or months behind any number you plan to act on, and spot-check one.

5 questions AI shouldn't answer for you

• "Can I deduct this?" or "How do I lower my taxes?" AI can explain what a deduction is. Whether you can take one depends on facts a tax professional should weigh. The IRS publishes guidance on choosing a tax professional and checking credentials.
• "Should I form an LLC or elect S corp status?" That decision touches taxes, liability and state fees. Use AI to list questions for your CPA or lawyer, not to decide.
• "Is this contract clause enforceable?" Enforceability depends on the state and the facts. A plain-language summary is fine; a legal opinion isn't.
• "Where should I invest my savings?" or "Should I take a loan to cover the gap?" Your cash forecast can show the gap. The financing decision is yours, with an adviser.
• "Should I drop this client?" AI can show what a client paid, how late, and how many hours you spent. Weighing the relationship is your call.

Where the answers come from

Asking in SoloWOS, or from Claude and ChatGPT

In SoloWOS, open the assistant with Ask AI (or Ctrl/⌘ + J) and type the question. It reads your account through read tools for invoices and payments, a business summary for this month against last, hours by project and client, signature requests, notes, shared documents and their views, your week, the 90-day cash forecast, pricing history and meeting prep, and it answers with the period and currency of each number and links to the records. One question is one request: 10 a month on Basic, 500 on Solo and 1,500 on Team. Questions outside your business in SoloWOS are declined and don't count.

The same questions work from Claude or ChatGPT once you connect SoloWOS: the guide to connecting SoloWOS to Claude or ChatGPT has the steps. The connector is on every plan. You choose Read, which only answers questions, or Read and act, which can also create drafts; sending anything to a client still asks for confirmation, and deleting things or recording payments isn't possible through it.

What you ask and the records needed to answer go to Anthropic when you use the in-app assistant (under Anthropic's commercial terms that data isn't used to train their models). Through the connector, they go to whichever AI app you connected, under that app's terms. The assistant won't give tax or legal advice: it gives general information and suggests a CPA or lawyer. See the SoloWOS AI assistant for everything it does, and AI for freelancers for related posts, like finding money you forgot to bill. If you invoice through SoloWOS, you can also send invoices clients pay by card from the same place the answers come from.