You don’t need to know every technical answer. Knowing which questions to ask is a very good place to start.
01 / AI & AUTOMATION
Start with the task, then consider the tool.
When someone suggests AI for your business, ask what specific piece of work it will improve. “Use AI” is a technology choice; “reduce time spent preparing a draft” is an outcome you can assess.
For a trial, the questions are practical: what information will be used, who is allowed to use the tool, who checks the result and how will you decide whether it helped?
A useful question
“What would a successful, limited trial look like for our business?”
A useful proposal connects the technical work to the problem it is intended to solve. Ask what is included, what remains your responsibility and what you will need to keep paying for.
Check the setup costs, ongoing charges, support scope and any overlap with existing services. If the explanation is hard to follow, ask for a simpler one before deciding.
A useful question
“Which part solves our actual problem, and what are the alternatives?”
Make “it’s looked after” something you can explain.
Confidence is easier when responsibilities are visible. You can ask who owns the device list, who deals with alerts, what maintenance has been agreed and what happens when an issue is found.
For backups, discuss what is included, what is excluded and what restore checks have actually been completed. Keep the answers with your business documentation.
A useful question
“Can you show me what is covered, what was checked and what still needs attention?”
A business can have several technology providers and still have nobody coordinating a problem that crosses between them. The owner then ends up carrying messages between technical teams.
An agreed IT representative gives that coordination a home. Define who can contact providers, share the relevant technical detail, approve changes and report back to you.
A useful question
“Who is coordinating this issue, and what happens next?”
I’ve worked with business IT since 2007, across networks, virtual environments, cloud services, phones and the day-to-day systems people depend on. I enjoy solving the awkward problems and making the answer easier to understand.
Born in New Zealand, based in Western Australia since 2004. Outside technology: aviation and motorcycles.
