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Business systems · 5 min read

Pick software you won't regret in a year.

An AI prompt that turns your needs into a fair comparison of software options (CRM, accounting, scheduling, project tools) with a scoring table and questions for demos.

Choosing a CRM, accounting tool or scheduling app usually goes one of two ways: you pick what a friend uses, or you spend weeks watching demos. Either way, you may end up paying for features you never use and missing the one you needed.

Start from your needs instead. This prompt turns them into requirements, a comparison table and the questions to ask in demos.

How to use it

  • List what the software must do, who will use it and what it must connect to.
  • Run the prompt, then check every claim on the vendors' websites. AI knowledge of pricing and features can be out of date.
  • Use the demo questions on two or three finalists, and always try a free trial with real data.
software-choice.txt
Help me choose [type of software, e.g. a CRM] for my business.

Business: [name], [what we do], [number of users]
Must do: [list]
Nice to have: [list]
Must connect to: [e.g. Microsoft 365 / Google Workspace, QuickBooks, our website, phone system]
Budget: [per month]
Who will use it and how tech-savvy they are: [details]
Options I am considering (optional): [list]

Give me:
1. My requirements as a checklist, ranked must / should / could.
2. 4 to 5 options that fit, with a comparison table: key features vs my requirements, integrations, ease of use, pricing model (mark as "verify on vendor site"), and any Canada-specific notes.
3. A weighted scoring sheet I can fill in after demos.
4. 10 questions to ask in every demo, including data export, contracts and support.
5. Red flags to watch for.

Be honest when you are unsure about current pricing or features.

Don't forget

  • Connections: does it work with your email, calendar, accounting and website?
  • Who owns the data and how you export it if you leave.
  • Canadian needs: CAD billing, sales tax (GST/HST), French if you need it, data location if your clients care.
  • The real cost: per-user pricing, add-ons and setup time.

AI tools may give outdated prices or features. Treat the comparison as a starting list and confirm details with each vendor.

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