The critical questions every business leader should answer before investing in AI. Covers business case, data readiness, and vendor evaluation.
Who this is for
Business owners and IT leaders evaluating an AI initiative and wanting to ask the right questions before committing budget.
Question this answers
What should we assess and what questions should we ask before starting an AI project?
What you'll leave with
Most AI projects that fail don't fail because of bad technology. They fail because the business problem wasn't well-defined, the data wasn't ready, or the expectations didn't match reality.
Asking the right questions upfront costs nothing and can prevent expensive mistakes. Here are the questions we ask every client before recommending an AI approach.
If the answer is "we want to use AI" rather than a specific problem, step back.
Understanding the current process reveals what AI needs to improve.
Time saved? Cost reduced? Quality improved? Define it before you start.
If you can't measure it, you can't prove it worked.
Every AI system makes mistakes. Plan for error handling and human review.
Usage patterns determine whether the investment makes sense.
Multiple systems? Spreadsheets? Email? The more scattered, the more prep work.
Inconsistent formats, duplicates, and gaps all need fixing before AI can use it.
Not all AI needs big data, but RAG systems need sufficient content to be useful.
This determines whether you need a one-time pipeline or ongoing sync.
Healthcare, financial, or personal data adds requirements.
Meet the person
This guide comes from real projects. If it raises a question about your own system, you can ask the founder directly.
HELLO PEOPLE designs, builds and looks after AI, software, app and data solutions for Australian businesses, with senior expertise on every project and a scope agreed before work starts. For AI, that means working on your own data, with a person able to check every answer.
Since 2007, HELLO PEOPLE has delivered more than 100 projects from Perth for small and medium businesses across Australia: custom software and apps, system integrations, data migrations, reporting and dashboards, and AI that works inside the systems a business already runs.
I lead every engagement myself. I trained in accounting before moving into IT, hold accounting and IT professional qualifications and an MBA, and bring more than 20 years of experience across sales, service delivery, inventory and compliance. I am also a PhD candidate in AI at Curtin University, researching retrieval-augmented generation (RAG), so the technology is always judged by what it does for the business.
Small and boutique. The person who scopes your AI project is the person who builds it, and the same person checks its answers before your team relies on them.
No ticket queue and no account manager in between. You hear back within one business day, usually sooner.
The first AI project is the start, not the end. When you need the next system, integration or report, you call the same person, who already knows your business.
Ask the author
Ask it here and it comes straight to the founder. No sales call, no obligation, and a real answer even if the answer is that you do not need us.
Kasun Wijayamanna
Founder, replies within one business day
Tell us what you are comparing, replacing, or trying to improve. We will come back with a practical recommendation and realistic scope.
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