An AI strategy workshop for a leadership team should end with four written things: a shortlist of workflows worth changing, a named owner for each, the open data and hosting questions, and one decision taken in the room. If it ends with a slide of trends and a list of ideas, it was a briefing, not a working session.
#Key takeaways
- A leadership AI workshop is worth running when it ends in decisions with names attached, not in a list of ideas.
- The people in the room should own budgets and processes: the COO, finance, the heads of the busiest departments and whoever owns it and data.
- Pre-work matters more than the agenda: each leader brings the tasks that eat the most hours in their team and the tools those tasks run on.
- The outputs are a ranked shortlist of workflows, an owner for each, the open data and hosting questions, and one first decision.
- A workshop alone is enough when the first workflow is obvious and someone inside can run it; otherwise it is the start of an audit.
#Who should be in the room for an executive AI workshop?
Decision-makers and the people who know where the work happens. In a mid-sized operations company that usually means the COO or head of operations, the finance lead, two or three department heads with the heaviest manual workloads, and whoever owns it, data and security. Leave vendors out.
#What pre-work should leaders do before the workshop?
Ask each leader to answer the same written questions in advance, so the room starts from facts rather than opinions.
- Which three tasks in your team take the most hours, and how often do they repeat?
- Which systems do they run on: SAP, Odoo, Microsoft 365, Excel, Salesforce, HubSpot, Zendesk, WhatsApp?
- Where does work wait for someone to approve, check or re-key something?
- Which AI tools does your team already use, approved or not?
- What should an AI system never send or decide without a person checking?
The Microsoft and LinkedIn Work Trend Index, may 2024 found that 75% of knowledge workers use AI at work and 78% of those users bring their own tools. Your leadership team is not starting from zero. It is starting from unmanaged use.
#What does a sample agenda look like?
A working agenda has five blocks and no keynote.
- The facts: a one-page summary of the pre-work, grouped by department.
- The filter: score each workflow on volume, how rule-based it is, the cost of a mistake, whether the data is reachable and who would approve the output.
- The shortlist: cut to three to five workflows, with the person who owns each process named next to it.
- The open questions: where the data lives, which hosting rules apply and who signs off on AI output.
- The decision: agree one next step with an owner, such as an audit of the top workflow or a trial of a tool you already have.
#What should the workshop produce on paper?
Four written outputs. A ranked shortlist of workflows with the reason each made the cut. A named owner per workflow. A list of open data and hosting questions, such as whether personal data may leave the country or whether an old ERP has a usable API. And one decision the leadership team has taken, not deferred.
The criteria for choosing the first workflow are in how to pick the first process to automate with AI. If the board then wants a full plan, what a good AI roadmap for a mid-sized company contains describes the next document.
#When is a workshop alone enough?
When the first workflow is obvious, the data is reachable and someone inside the company can configure an existing tool or run the first build. Many teams leave with a step that needs no consultant: switch on a feature they already have, write a usage policy, or train one department.
You need more when leaders disagree on the order, when nobody can say what a workflow costs today, or when hosting rules are unclear. Gartner expected 30% of generative AI projects to be abandoned after proof of concept, with unclear business value among the causes (Gartner, july 2024).
#How does Stennir run an executive workshop?
At Stennir the executive workshop is part of AI consulting. It usually sits inside the AI Opportunity Audit: we interview the people who run the work first, then bring the ranked workflows to your leadership team to pressure-test the order and agree an owner for each.
The audit returns five ranked workflows, each with a cost and a payback case, and one recommended build with its scope and hosting region. The report is yours whether or not you build with Stennir. If you go ahead, the same people take the first workflow into AI implementation.
We are
Stennir runs a leadership working session that ends in a ranked shortlist, named owners and one decision.
We aren't
Stennir does not run an inspiration session on AI trends, or a vendor demo presented as strategy.
#What should a COO do next?
Send the pre-work questions above to your leadership team and read what comes back. For a quick read on where you stand, take the free readiness assessment. See AI for operations for typical workflows, or book a 30-minute call to talk through a workshop.
#Common questions
What do you need from us before an AI strategy workshop?
A sponsor who can make decisions, written pre-work from each leader on their heaviest tasks and the systems they run on, and access to a few of the people who do that work every day. Without pre-work, the session collects facts instead of deciding.
Should the CEO attend the whole workshop?
Not necessarily. The CEO matters most at the decision point, when the shortlist and owners are agreed. The earlier blocks need the people who know the work: operations, finance, department heads and it. A CEO at the decision keeps it honest about what gets funded.
Can the workshop run in Arabic?
Yes. Stennir runs sessions in Arabic and English, and the written outputs can be in either or both. What matters more is that the shortlisted workflows include the Arabic documents and messages your teams actually handle, because that is often where the hardest data questions sit.
What could go wrong with a leadership AI workshop?
The common failure is a session that ends in enthusiasm and no owner. Another is a shortlist shaped by whoever spoke loudest or whichever vendor presented. Written pre-work, a shared scoring filter and one decision taken in the room are the guards against both.
