How do you run a discovery session with a new customer?

30-second answerSay your answer out loud first, then reveal.

Prepare (research the company, industry and attendees), then lead with the business, not the AI. Ask what outcomes matter, which workflows are painful, who does them today, how often, how they measure success, what data and systems are involved, and what constraints exist (security, compliance, timeline, budget). Map the current workflow step by step, quantify the pain, identify decision-makers and the champion, and summarise back what you heard with proposed next steps.

Question bank

Area	Questions
Goals	What business outcome would make this project a success in 6 months? Who cares most?
Workflow	Walk me through how this task is done today, step by step. Where do people lose time?
Volume and value	How many cases per day? Time per case? Cost of errors?
Users	Who does the work? What tools do they use? How tech-savvy are they?
Data	Where does the information live? Formats? Quality? Access?
Constraints	Security, compliance, data residency, approval processes, budget, deadlines?
Past attempts	Have you tried solving this before? What happened?
Decision	Who signs off? What would make them say no?

Techniques

Observe the work (screen-share or shadow a user). People describe idealised processes; reality is messier.
Ask for examples: "Can you show me three real cases, including a difficult one?"
Quantify: "If this took 2 minutes instead of 15, what would that be worth?"
Listen for hidden requirements: audit needs, exceptions, union or HR concerns, legacy systems.

Output: a short written recap within 24 hours: problem statement, current workflow, candidate use cases, data inventory, constraints, open questions, proposed next step.

PreviousWhat does a typical FDE engagement lifecycle look like for an AI project?

Slow is fine. Stopping is the only problem.

How do you run a discovery session with a new customer?

Question bank

Techniques

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