Take control of AI in your work.
Artificial intelligence is reshaping how organizations work — but most teams are navigating these changes without a clear roadmap. The question is no longer simply whether to adopt AI, but how to make thoughtful, strategic decisions about where AI fits, where it doesn't, and how to bring your people along for the journey.
AI Strategic Planning is a two half-day workshop series designed to equip your leaders with the frameworks, facilitation skills, and ready-to-use tools needed to build a comprehensive AI strategy — one that is grounded in your organization's mission, values, and real-world context.
Participants leave workshop-ready to lead their own strategic planning process from day one.
Who Should Attend
These workshops are open to any professional who wants to think more strategically about AI in their work. Managers, directors, and senior executives will receive the greatest direct benefit, as they are best positioned to champion and lead a strategic planning process within their teams or organizations. Department heads, project leads, and those responsible for organizational development, HR, or technology adoption will also find immediate application.
No prior AI expertise is required — only a commitment to thoughtful, inclusive leadership.
The Workshop Series at a Glance
Workshop 1: Foundations & Discovery | Half Day
Setting the stage and gathering the intelligence you need
- What does good look like? Understanding what a complete AI strategic plan looks like — its essential components, what it must address, and how it gets used
- Stakeholder mapping: Mapping stakeholders: who needs a seat at the table, how to identify voices that are often left out, and how to structure inclusive participation across levels and roles
- Creating safety: Designing a psychologically safe environment where people can express fears, enthusiasm, skepticism, and questions about AI honestly — without judgment
- Gathering raw materials: Selecting and deploying data-gathering instruments — surveys, structured interviews, and focus groups — to surface the real landscape of AI awareness, use, concerns, and aspirations in your organization
- Workshop activity: Hands-on practice: participants draft a stakeholder map and customize a data-gathering survey for their own team or organization
Workshop 2: Strategy & Stewardship | Half Day
Building, measuring, and sustaining your plan over time
- Facilitated alignment: Running structured, facilitated conversations about AI adoption: how to guide your team through aligning on mission, vision, values, goals, and objectives as they relate to AI — and where legitimate disagreement should be honored
- Risk & benefit analysis: Assessing risks and benefits: frameworks for evaluating AI adoption across dimensions including efficiency, equity, ethics, cost, culture, data privacy, and competitive positioning
- Measurable outcomes: Developing SMART outcomes and evaluation metrics: how to define what success looks like in 90 days, one year, and three years, and how to know if your strategy is working
- Governance & accountability: Building your AI governance model: who is responsible for AI decisions, how are policies communicated and enforced, and how do you handle exceptions or emerging tools
- Planning for change: Living strategy: how to build in regular review cycles and adapt your plan as AI technology and your organization's needs evolve — without starting over from scratch
- Workshop activity: Hands-on activity: participants outline their organization's AI mission statement and draft a set of strategic goals with accompanying metrics
What Participants Take Home
Every participant receives a comprehensive toolkit of boilerplate and template materials ready to customize for their organization:
Planning Process Templates
- AI strategic plan template (full framework)
- Stakeholder mapping worksheet
- Process timeline and project planner
- Facilitator guide and agenda templates
Data Gathering & Measurement Tools
- Staff AI readiness survey
- Leadership interview guide
- Focus group facilitation guide
- SMART goals and evaluation metrics worksheet
Conversation & Alignment Resources
- Mission/vision/values alignment activity guide
- Risk and benefit assessment matrix
- Psychological safety self-assessment
Governance & Ongoing Review
- AI governance charter template
- Annual plan review and revision guide
- Communication plan template for rollout
Why This Approach Works
Most AI training focuses on tools and technology. This workshop is different. It treats AI adoption as an organizational and human challenge as much as a technical one. Participants gain practical skills in facilitation, stakeholder engagement, and strategic planning — skills that will serve them beyond AI, in any context where thoughtful change leadership is needed.
By focusing on process ownership rather than prescribing answers, this workshop respects that every organization is different. There is no one-size-fits-all AI strategy. The goal is to give your people the capability to build the right strategy for your context — and the confidence to lead that process themselves.
Format & Logistics
| Format | Two half-day sessions (3.5–4 hours each), delivered virtually |
| Group Size | Available as private cohorts for a single organization (additional fees apply) or open-enrollment cohorts shared across multiple organizations |
| Delivery | Instructor-led with facilitated discussion, individual reflection, and hands-on activities |
| Materials | All templates and boilerplate materials provided digitally; participants customize during the workshop |
| Pricing | Starting at $500 per participant — contact us for group and private cohort rates |
| Follow-On | Optional post-workshop coaching available to support your planning process implementation |
Ready to help your organization think strategically about AI?
Contact Dan Sholler to schedule your workshops or learn more about how AI Strategic Planning can be customized for your industry, organization size, or specific needs.