A Customer Workshop Preparation Checklist

Choose a session with a clear purpose

Use this checklist for a discovery workshop, architecture review, or delivery planning conversation. It is a suggested coaching tool you can adapt to the person's experience and the customer's needs.

Choose an appropriate opportunity together. Someone leading their first workshop may need a rehearsal and an experienced colleague alongside them. Someone more experienced may only need a quick review of the decision and constraints.

• What should the customer understand or decide by the end?
• Who needs to attend, and who can make the decision?
• What will be written down afterward: requirements, options, decisions, or next steps?

Before: build a one-page brief

Ask the architect to prepare the brief. Review it together without rewriting it in your own voice. The preparation should reveal their reasoning and the gaps they need help closing.

• Customer goal: describe the business problem in the customer's words.
• Known facts: list the current environment, requirements, and sources of information.
• Open questions: separate what is known from assumptions that need confirmation.
• Constraints: capture relevant security, operational, budget, and timing considerations.
• Options: prepare the tradeoffs you can explain and the evidence you still need.
• Agenda: connect each discussion to the intended outcome and leave time to agree on actions.
• Support: agree when a colleague should step in and what can be taken away for follow-up.

Rehearse the difficult moments

A short rehearsal can be more useful than another pass through the slides. Ask questions a customer might reasonably raise. Listen for how the architect responds when the answer is uncertain.

• Why are you recommending this option?
• What would change your recommendation?
• How would the team operate this after implementation?
• What can we commit to today, and what needs further validation?
• If you do not know an answer, how will you acknowledge it and arrange a follow-up?

During: let the architect own the conversation

Confirm the goal with the customer at the start. Give the architect room to ask questions, check understanding, and adapt. If you are there as a coach, observe specific moments instead of taking over whenever you would phrase something differently.

• Check assumptions aloud before using them to justify a decision.
• Explain options in terms of customer consequences, including operational effort and risk.
• Record unresolved questions without turning guesses into commitments.
• Close with decisions, open items, named owners, and agreed follow-up dates.

After: turn feedback into the next opportunity

Let the architect reflect first: What went well? Where did they lose confidence or miss an opportunity to ask a question? Then offer specific observations. 'You checked who would operate the platform before recommending a service' gives someone a behavior they can repeat.

Choose one improvement to practice. Agree on the support they need and identify a next session where they can apply it. Keep the conversation focused on development rather than treating one workshop as a complete assessment of someone's ability.

• Observed strength: what happened, and why did it help the customer?
• Practice next: what one behavior would improve the next conversation?
• Support needed: rehearsal, technical review, shadowing, or clearer context?
• Next opportunity: which session will they lead, and when will you debrief?