Key points
  • Ask for specific workflows, baselines and results, not opinions about AI.
  • Probe failures: real implementers have clear stories about what went wrong.
  • Include a short practical exercise based on one of your own processes.

AI experience is easy to claim and hard to verify. These questions focus on evidence of delivery.

Delivery

  1. Walk me through one process you automated with AI, from the first meeting to go-live.
  2. What was the baseline, and how did you measure the result?
  3. Which tools did you use, and why those rather than the alternatives?
  4. How did you connect the AI to the company's existing systems or data?

Failure and judgement

  1. Tell me about an AI project that did not work. What would you do differently?
  2. When have you decided not to use AI for a task?
  3. How do you check whether an AI output is wrong before it reaches a customer?

People and change

  1. How did you get staff to actually use what you built?
  2. Who did you report results to, and how often?
  3. How did you handle data privacy and security questions from legal or IT?

Practical

  1. Here is a description of one of our processes. Where would you start, and what would you measure?
  2. What would your first 30 days here look like?

What good answers sound like

Strong candidates name specific numbers, tools and trade-offs, admit what went wrong, and talk about users as much as technology. Weak answers stay general: "I used ChatGPT to improve efficiency" without any baseline, result or detail.

Use a scorecard

Score each candidate on the same criteria, such as delivery track record, tool skills, stakeholder management and commercial judgement, so that decisions rest on evidence rather than impressions.

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