An in-person workshop is the most visible part of bringing Claude into an organization, and it is easy to buy on reputation alone. The COO, CHRO or department head who signs for one should have a short list of questions ready, because the answers show whether people will leave with new habits or with a pleasant session behind them. Here are the questions we would ask if we were on the other side of the table.
Whose Documents Will People Practice On?
The best test of a workshop is the material. A session built on sample files teaches people to operate a screen, while a session built on your own documents teaches them to do their work better. Ask the facilitator to work from a board summary, a client letter, a policy memo or whatever each department really produces, and ask how redacted copies will be handled when the originals are restricted. If the answer is a polished demo deck, the workshop will not change how anyone works.
Who Will Be In The Room, And Who Is Not?
A workshop for one department works better than one for everyone at once, because colleagues who share documents and approval paths can agree on habits together. Ask whether the session is built for a single department and who from IT, legal or HR will join. Ask too which leaders have been through their own briefing first. People learn less when their manager has never used Claude and cannot say what is welcome.
What Will The Facilitator Say About Mistakes?
AI can be fluent and wrong. A good workshop shows that on the department's own papers: an invented citation, a figure that does not match its source, a summary that drops the one caveat that mattered. Ask to see how the facilitator handles an error live. Participants should leave knowing what to check and trusting their own judgment more, not less.
Who Reviews What, And Is It Written Down?
Every output that leaves a department needs a person who stands behind it. Ask whether the workshop ends with a named reviewer and a short checklist for each kind of document. Agents and assistants draft, check and flag, and a person your organization names decides. If the session never settles that, people will settle it individually, and no two will do it the same way.
What Does The Workshop Say About Your Policy?
Staff will ask what they may paste in, and the facilitator should read your acceptable-use policy before arriving. Ask how the exercises stay inside it, and what happens to a question the policy cannot answer. A workshop that ignores the rules makes the policy harder to enforce, while one that teaches the rules on real documents makes it easier to follow.
How Will The Learning Reach Other Offices?
A single room cannot teach everyone. Ask what the department keeps: tested prompts, a short guide, a list of checks and the names of colleagues who could coach others. Those become the start of a leader network and a shared playbook, which carry the training into other offices without the facilitator in the building. A workshop that leaves nothing written down is over when the room empties.
Who Is Leading It, And Will They Stay Involved?
Ask who the facilitator is and whether the same person will work with you through later departments. A named lead who knows your documents, your reviewers and your systems is worth more than a rotating cast. Ask also what happens when a new release changes how Claude behaves, and who will tell your coaches.
What Leaders Should Expect To Hear
Good answers are specific. They name your documents, your reviewers, your policy and your offices, and they admit what AI gets wrong. Weak answers are general, promise that everyone will master it and never mention who checks the work. A workshop is also only the first piece, since the policy, the leaders and the playbook are what make it last.
If you are weighing a workshop, bring us the department you would start with and the questions you worry about most. We will say where we agree, where we would look again and which leader should sit in the room, and the decision stays with you.