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AI Strategy Workshop for Leadership Teams

Get your leadership team aligned on AI in one day — and leave with a prioritized 90-day roadmap, not a parking lot of opinions.

What is an AI strategy workshop?

An AI strategy workshop is a facilitated working session where a leadership team builds a shared, realistic view of where AI creates value in their specific business and converts it into a plan. ChatGPT.ca runs workshops for Canadian leadership teams structured around our Canadian AI Strategy Framework: level-set on real capabilities, score your workflows live, prioritize a 90-day roadmap, and set a governance baseline covering PIPEDA and Quebec Law 25. The deliverable is written and dated — not a whiteboard photo.

The agenda

Four working blocks. No trend decks, no vendor pitches.

Level-set (60-90 min)

What current AI actually does, demonstrated on your real documents and workflows — not vendor slides. Myths killed, capabilities grounded.

Opportunity scoring (90-120 min)

Your workflows scored live by the room: frequency, pattern-strength, cost of error, payback. Disagreements surface and get settled in session.

Roadmap prioritization (60-90 min)

Top opportunities sequenced into a 90-day plan with owners, budget ranges, and decision gates. What to deliberately not do gets written down too.

Governance baseline (30-45 min)

The one-pager: PIPEDA and Quebec Law 25 posture, acceptable use, what never goes into public tools, and who approves exceptions.

What you walk away with

Aligned leadership

Everyone leaves with the same picture of what AI does, what it costs, and what you are doing about it.

Written 90-day roadmap

Delivered within a week: prioritized initiatives, owners, budget ranges, and success metrics.

Governance one-pager

A defensible starting policy your team can follow the next morning.

Formats & pricing

Half-Day (Remote)

$2,500
3.5 hours + pre-work
  • Up to 8 attendees
  • Pre-work interviews (2)
  • Live opportunity scoring
  • 90-day roadmap in 1 week
MOST POPULAR

Full-Day

$4,500
6-7 hours, remote or on-site
  • Up to 12 attendees
  • Pre-work interviews (4)
  • Breakout scoring by department
  • Roadmap + governance one-pager
  • On-site in most Canadian cities

Workshop + First Build

From $6,500
Workshop + 2-4 weeks
  • Full-day workshop
  • Top roadmap item built and shipped
  • Team handover and training

Frequently Asked Questions

What is an AI strategy workshop?

An AI strategy workshop is a facilitated working session — half-day or full-day — where a leadership team builds a shared view of where AI creates value in their business and leaves with a concrete plan. Ours has three parts: a level-set on what current AI actually does (demos on your real documents, not slides), a live opportunity-scoring exercise across your workflows, and roadmap prioritization. The deliverable is a written 90-day plan, not just alignment.

Who should attend the workshop?

The people who own decisions and workflows: owners/executives, operations leads, and one or two front-line managers who know where the time actually goes. The sweet spot is 4 to 12 attendees. Larger leadership groups work as a full-day format with breakout scoring.

How much does an AI strategy workshop cost?

Fixed price: $2,500 for the half-day remote workshop, $4,500 for the full-day (remote or on-site in most Canadian cities; travel billed at cost outside major centres). Both include pre-work interviews, the facilitated session, and the written 90-day roadmap delivered within one week.

What do we walk away with?

Four things: a shared leadership understanding of what current AI can and cannot do for your business, a scored map of your workflows by automation potential and payback, a prioritized 90-day roadmap with owners and budget ranges, and a governance one-pager (PIPEDA posture, acceptable-use rules, what never goes into public AI tools). Plus the session recording and materials.

Is this a training session or a strategy session?

Strategy first, with enough hands-on demonstration to ground the decisions. If your goal is teaching staff to use ChatGPT or Claude day-to-day, that is our AI Training service — many clients run the leadership workshop first, then staff training once the roadmap says which tools are coming.

Can the workshop be delivered remotely?

Yes — the half-day format was designed remote-first and works well over Zoom or Teams with live collaborative scoring. Full-day sessions run remote or on-site anywhere in Canada. Bilingual delivery (English/French) is available for Quebec teams.

Leadership team circling AI without landing?

One day in a room settles it. A 15-minute call scopes the right format for your team.

Book a Workshop Date