40 questions to ask your construction data in Claude or ChatGPT
By the Junction team · Published 24 October 2026 · 4 min read
The short answer
- Good questions are specific: name the measure (committed cost, over/under billing), the scope (open jobs) and the period.
- Below are 40 you can copy, grouped by finance, project management, operations and owners. Swap in your own job numbers.
- They work once your systems are connected to your AI tool. Check the first few answers against reports you already trust.
An assistant is only as useful as the questions it is given. People new to it either ask something vague ("how are we doing?") or something it cannot answer without the right data. These are written the way a controller or project manager would phrase them, and each one maps to something an accounting or project system actually holds.
Finance and accounting
Ten questions for controllers, CFOs and AP/AR teams
- What is our over/under billing across all open jobs, largest first?
- Which vendors have invoices unpaid for more than 45 days, and how much is owed to each?
- Show committed cost against budget on every open job.
- Which jobs have costs ahead of billings?
- What is our accounts receivable aging, grouped by customer?
- Which subcontractors are owed retention, and how much?
- Which jobs closed in the last 90 days, and what was the final margin on each?
- How does this month's job cost compare with the same month last year?
- Which vendors did we pay more than once in the last 30 days for the same amount?
- What is our total open commitment with each subcontractor?
If you are new to over and under billing, our guide to reading a WIP schedule explains the arithmetic, so you can judge the answer you get.
Project management
Ten questions for project managers, engineers and superintendents
- Which jobs are over budget on labor this month?
- Which subcontracts have no approved change order but cost above the original amount?
- Which RFIs on my projects have been open longest?
- Which issues assigned to my projects are overdue?
- What are the pending change orders on each of my jobs, and their total value?
- Which jobs have cost-to-complete above the remaining budget?
- List open purchase orders on job 1042 by vendor.
- Which submittals are late, and who is holding them?
- What changed on my jobs' budgets since last Friday?
- Which activities on the schedule start in the next two weeks?
Operations and leadership
Ten questions for executives, operations managers and estimators
- Which jobs are trending over budget across all our systems?
- How much have we committed with each subcontractor this year?
- Where do we stand on open change orders by project?
- Which five jobs hold most of our open payables?
- How is backlog split by customer and by project type?
- Which jobs had the biggest swing in forecast margin this quarter?
- What did we spend on equipment last quarter, by job?
- Which vendors account for most of our spend, and has that changed?
- How many jobs are open in each region, and what is the contract value of each group?
- Which estimates are due this week, and who owns them?
Owners and capital programs
Ten questions for owners, owner's reps and program managers
- Which capital projects are over their approved budget?
- Which invoices have waited longest for approval?
- What are the open change orders on each program?
- How much of each project's budget is committed, and how much is spent?
- Which contractors have the most outstanding pay applications?
- Which projects have no activity logged in the last 30 days?
- What is forecast cost at completion against approved budget, by program?
- Which contracts are approaching their end date with unbilled balances?
- Which projects hold the most retention?
- What was approved and paid last month, by project?
Make the answers trustworthy
- Ask for the source. A useful answer names the system and the kind of record, and says when the data was last updated.
- Check one figure by hand. Compare a single number with the report you already run before relying on the rest.
- Be explicit about scope. "Open jobs" and "all jobs" give different totals; say which you mean.
- Keep sensitive data out. Payroll and personal records should not be reachable by a general-purpose assistant at all.
These questions need the assistant to reach your systems. How to connect Claude to your construction accounting data covers the setup, and our systems list shows what Junction connects to or plans to.
Frequently asked questions
- What should I ask ChatGPT or Claude about my construction data?
- Ask specific questions about measures you already track: over/under billing, committed cost against budget, overdue payables, change orders and overdue issues. Name the scope (open jobs) and period, and compare the first answers with a report you trust.
- Can ChatGPT read my Vista or Sage 300 CRE data?
- Only through a connector. ChatGPT and Claude reach outside systems via MCP servers, so something has to connect to your accounting system, return only what each person is allowed to see, and tell the assistant where the numbers came from.
- Are AI answers about job cost reliable?
- They are as reliable as the data and the connection behind them. Verify a few figures against your own reports, ask for the source and date of the data, and treat the assistant's arithmetic as something to check, not accept.
Keep reading
Ask Claude or ChatGPT about your own systems
Junction connects Claude and ChatGPT to construction accounting, project and property systems. Early access, set up with you.