STRATEGY

How Do You Choose an AI Workshop for Your Team? The Questions to Ask Before You Sign

5 min read

Choose a workshop by what the team will do differently the week after, not by the list of tools it promises to cover. Before you sign, ask seven questions: what material you will work on, which process gets built all the way through, in which tools, what the scope is, what happens to sensitive data, who owns what comes next, and how you will know it worked.

"We want an AI workshop for the team" is a good starting point, but it is not a brief yet. Two workshops with the same title can leave a team in very different places, and most of the difference is decided before the workshop begins.

What actually happens in an AI workshop for a team?

In a good workshop the team builds, on its own real work, a workflow it can run the next morning. You start from the team's material, build a foundation in writing requests that return something you can work with, and then take one real use case and build it together all the way through.

In my workshops we use the tools the team already has, whether that is ChatGPT, Claude, Gemini, Perplexity or NotebookLM, because what we are building is the process. And we build in stages: from a single prompt, to a workflow that repeats, to an automation, and sometimes to an agent. Not every team needs to reach agents. Every team needs to understand the difference, because without it you buy the wrong thing.

Do we work on our own material or on generic examples?

On yours: a real brief, real leads from the pipeline, the document someone on the team writes every week. That is the only way to leave with something that goes into the work instead of an exercise that stays in the room.

In a workshop for a BDR team at a technology company, every exercise ran on real leads from the team's pipeline: researching companies and people, building lists, qualifying leads and writing outreach. The workflows were in use that same week. The full story.

It also means there is preparation beforehand: choosing together which process to build, and checking where people are. A team at mixed levels is the normal case. The more advanced get depth in the build, beginners get the foundation, and everyone leaves with a shared language.

How long does an AI workshop for a team take?

Length and scope follow what the team needs: how many processes you build and how deep you go. A focused workshop builds one process for one team, a full workshop covers several processes for a whole department, and a workshop series connects teams from different departments.

Sometimes the answer is more than one workshop. A global sales team I worked with, some of them sceptics and some who had never touched AI, went through two workshops on their own material. By the end they had a complete sales process, from account research to follow-up with a shared action plan. Today there is no step in their workflow that happens without AI. The full story.

What determines the price of an AI workshop?

Scope and format: how many processes you build and how deep you go, and whether it is a workshop, an adoption program or ongoing partnership. After a short intro call you get a clear proposal with a fixed price, with no surprises along the way.

When you compare proposals, compare what the team leaves with: how many processes are built, on which material, and what happens in the weeks that follow.

What about our sensitive data?

The risk is less the workshop itself than the day after, when someone in a hurry pastes an internal document into a personal account. So ask up front which accounts you will work in, what is allowed in, and what happens to the material afterwards.

In my workshops we work only inside the organization's approved accounts, decide what comes in before we start, and I delete the material afterwards. NDA on request. What to check on the tools' side is covered in AI and privacy in organizations.

How do you measure whether an AI workshop worked?

After 4 to 6 weeks, with one question: is the team still using the processes it built, in day-to-day work, without anyone asking? The feedback form at the end of the workshop measures the workshop. Adoption is measured in the weeks after it.

One workshop does not change behaviour. It opens a window, and if nobody asks and nobody measures in the weeks that follow, the window closes. So every workshop I run ends with two decisions: who owns what comes next, and what gets measured. Some organizations take it from there on their own, some continue with me.

Remote or in person, Hebrew or English?

Both work. In person in Israel, remote for global teams, in Hebrew or English. What matters is whether the team can bring its real material and work on it during the session.

Which questions should you ask before you book a workshop?

The seven questions from the opening, with the answer that shows the workshop will be built for your team:

What to askAn answer that shows it will be built for your team
What material will we work on?Yours: briefs, leads, real documents
Which process gets built all the way through?At least one defined process, chosen with you before the workshop
In which tools?The tools you already have and that your organization has approved
What is the scope, and what sets it?How many processes and how deep, based on what the team needs
What about sensitive data?Approved accounts, agreed in advance, deleted afterwards, NDA if needed
Who owns what comes next?Two decisions at the end of the workshop: who owns it, and what gets measured
How will we know it worked?A check after 4 to 6 weeks: is the team still working this way

When is a workshop not the answer?

When you are looking for an inspiration session, when the team cannot bring real material, or when the main need is to tick a box. A hands-on workshop is built on the team's real work, and without that it will not give you what you are after. And when the question is how what happened in one team reaches the rest of the organization and stays there, you are looking at an organizational program.

If you have a team and a process you want to build, here is how my team workshops work and what comes out of them. If the question is already organization-wide, my organizational programs are built for exactly that.

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