Executive AI Workshop
AI Training for Executives: A Hands-On AI Fluency Workshop for Leadership Teams
A half-day or full-day session for founders and leadership teams, built from pre-session interviews. Each executive leaves with AI configured in their own account and a plan the team agreed on.
Why AI training for executives has to be hands-on
Leaders make the AI decisions: which tools to buy, which workflows to change and how much risk is acceptable. Many make them without using AI seriously in their own work. Section's AI Proficiency Report 2026 found that 57% of executives say AI is integrated, versus 18% of individual contributors. When leaders and the people doing the work see adoption that differently, companies end up with licenses nobody uses and pilots aimed at the wrong problems.
The Executive AI Workshop closes that gap from the top. Each leader uses AI on their own material, learns to judge its output and works with peers to pick pilots the business can actually run. The session follows the 4D AI Fluency Framework (Delegation, Description, Discernment and Diligence), developed by Anthropic with Rick Dakan and Joseph Feller, because delegation and diligence are leadership decisions before they are tool settings.
What each executive leaves with
A configured executive briefing assistant
A Claude Project or ChatGPT plugin in the executive's own account, loaded with approved strategy documents, KPI definitions and context. It prepares briefings, summarizes reports and pressure-tests decisions.
A 4D self-check
A short scenario-based check on Delegation, Description, Discernment and Diligence, taken before and after the session, so each leader knows where to focus.
A shortlist of 3–5 pilots
Candidate AI pilots scored on value, effort and risk, each with an owner and a measure of success.
A 30/60/90 plan
What the leadership team will do in the next 90 days: pilots, training, policy decisions and the dates you will review results.
Before the workshop: pre-session interviews
Scoping call
We agree on goals and format (half or full day, in person or virtual) and confirm which tools and accounts executives will use.
Executive interviews
A 30-minute interview with each executive about their week, their decisions and where AI could help or hurt.
Document and account prep
Each executive approves the documents their briefing assistant may use. We confirm accounts and plan settings with your admin.
Pre-build
We pre-configure every briefing assistant, so the session is spent using and refining it rather than setting it up.
Executive AI workshop agenda (full day)
The half-day version keeps the same arc with shorter hands-on blocks. Governance and the 30/60/90 plan are never cut.
| Block | Session | Output |
|---|---|---|
| 1. Where you stand (60 min) | Interview findings, the 4D framework and a live look at what AI does well and badly in your business | A shared baseline |
| 2. Delegation (75 min) | What leaders should hand to AI, what to keep and which mode fits: automation, augmentation or agency | A delegation list per executive |
| 3. Description and Discernment (90 min) | Hands-on with each briefing assistant on a real question: checking output, catching errors, refining instructions | A tested briefing assistant |
| 4. Diligence and governance (60 min) | Data rules, approved tools, disclosure and who is accountable for AI-assisted work | Decisions for your AI use policy |
| 5. Opportunity mapping (75 min) | Scoring candidate pilots on value, effort and risk across functions | A shortlist of 3–5 pilots |
| 6. The 30/60/90 plan (45 min) | Owners, dates and measures, plus the repeat 4D self-check | An agreed 30/60/90 plan |
An executive AI workshop that is not a slide deck
Most AI training for executives is a keynote with a demo at the end. Leaders nod along, then go back to email. In the Operator Intelligence Executive AI Workshop, slides are kept to a handful. Executives spend most of the session using AI on their own documents, with the facilitator alongside, and debating real trade-offs with each other. The briefing assistant they leave with is the one they used all day, so the habit starts in the room.
Board and Fortune 1000 variant
For boards and for leadership groups inside Fortune 1000 companies, the workshop shifts from personal productivity to oversight. Sessions focus on the questions a board or division leader should ask about AI risk, governance, vendor choices and measurement, and they run inside your enterprise-approved tools and existing security review. The format also works as an AI leadership offsite session. Leaders who want an ongoing peer forum can apply to The Taible, our invite-only executive AI roundtable.
What we need from you
- An executive sponsor who owns the outcome
- 30 minutes with each executive for a pre-session interview
- Business-tier AI accounts for each executive, or help choosing a plan
- Three to five approved documents per executive for their briefing assistant
- A room with screens, or cameras-on attendance for virtual sessions
- An admin or IT contact to confirm accounts and settings
- Time on the calendar for 30-, 60- and 90-day check-ins
How we measure the workshop
We judge the Executive AI Workshop by what happens after it, and leadership teams that want someone to own that follow-through can add a fractional chief AI officer. We compare each executive's 4D self-check before and after the session, track use of each briefing assistant at 30, 60 and 90 days, and check how many shortlisted pilots have started with an owner and a measure. The 30/60/90 plan doubles as the scorecard: at each check-in, the leadership team reviews what shipped and what stalled.
What comes after the workshop
Most leadership teams follow the workshop with one of three steps: a Team AI Bootcamp to bring the next layer of the company up to speed, an AI Workspace Setup to configure instances for priority teams, or a quick-win pilot through our AI enablement practice. Not sure where you stand? The free AI readiness assessment takes about five minutes.
Who facilitates
The workshop is led by Operator Intelligence co-founder Chad Westleigh, who completed Anthropic's AI Fluency: Framework & Foundations and Teaching AI Fluency courses (certificates of completion), holds an MIT Professional Education certificate in Applied Agentic AI for Organizational Transformation and has nearly 20 years in digital strategy. For operator-heavy leadership teams, co-founder Luke Freeman, a serial entrepreneur with $500M+ in career sales, joins to keep the conversation on margins, people and execution.
Frequently asked questions
Should we book a half-day or a full-day workshop?
A half day suits leadership teams that already use AI and want a plan. A full day adds hands-on time and a deeper opportunity-mapping session, which most teams new to AI need. We recommend a format after the pre-session interviews.
Can the executive AI workshop run virtually?
Yes. Virtual sessions use the same agenda in shorter blocks, with cameras on and each executive working in their own account. In-person sessions suit offsites and leadership retreats.
Do executives need technical skills?
No. The workshop assumes no technical background. Executives work in plain language with tools configured for them, and the technical setup happens before the session.
Is our confidential information safe?
Executives choose which documents their briefing assistant may use, and everything stays in your business-tier accounts under your admin's controls. The governance block covers data rules and disclosure, and we align with your existing AI policy.
What does an executive AI workshop cost?
Cost depends on format, the number of executives, in-person versus virtual delivery and how many assistants we pre-build. We don't publish fixed prices; see how we price and request a scoped proposal.
How is this different from an AI keynote or university course?
Keynotes and open courses teach AI in general. This workshop uses your documents, configures AI in your accounts and ends with pilots and a plan for your business, with follow-up at 30, 60 and 90 days.
Book an executive AI workshop
Tell us about your leadership team and what you want AI to change. We'll propose a format and schedule the pre-session interviews.
Book a leadership sessionRelated
AI Training & Fluency
All programs, from executive workshops to team bootcamps.
Team AI Bootcamp
The hands-on follow-on for the teams below the leadership group.
AI Workspace Setup
Configured instances for priority teams in two to four weeks.
The Taible
An invite-only executive AI roundtable.
Chad Westleigh
Instructor background and credentials.
AI implementation roadmap
Turn workshop priorities into a 30/60/90 plan.
AI upskilling program
Take workshop priorities company-wide over 90 days.