Align on AI strategy, governance, and value creation

Facilitated workshops that turn AI hype into a practical roadmap, clear guardrails, and accountable leadership.

About StarCIO Workshops

Bring teams from across the organization to learn, collaborate, question, challenge, and reach consensus.

Formats: Workshops can be conducted in half-day sessions for small groups, one or two days for larger ones, or scheduled quarterly. They are conducted on-premises, virtually, or in a hybrid format.

AI Strategy & Governance Workshop

Objectives include: Creating or updating AI strategies, governance, roadmaps, technology selections, and experiments.

Audience: Boards, C‑suites, and senior business, technology, digital, data, and risk leaders who oversee AI responsibly and drive measurable outcomes.

Why workshops: Accelerate alignment and decision-making for new AI investments, prepare for board meetings, create or iterate on strategy, improve governance, and streamline AI experiments.

Workshop outcomes: StarCIO’s AI Strategy and Governance workshops help a leadership team align on a pragmatic AI vision, define clear guardrails, and establish a responsible path to value. Participants will leave with shared priorities, decision frameworks, and practical next steps tailored to your organization’s AI ambitions.

Workshop facilitator: All StarCIO workshops are facilitated by Isaac Sacolick.

20-year startup CTO and transformational CIO
Grounded in StarCIO ‘s 200+ digital and AI transformation best practices
Bestselling author on digital transformation
1200+ articles on StarCIO, CIO.com, and InfoWorld
Trusted by transformation leaders, CXOs, and boards to navigate AI, data, and governance decisions

Learn more about Isaac Sacolick

Testimonial

“StarCIO was an invaluable thought partner, and their expertise made a huge contribution to the progress we have made and the successes we have started to stack up.”

— Michael Betz, Chief Digital Officer, Covista

Sample StarCIO Advisories for AI workshops

Typical one-day workshops address 3–5 Advisories, while two-day events can cover 5–8, depending on the desired depth of discussion.

Defining and updating vision statements for AI, covering strategy and select initiatives.
Driving digital transformation with AI, and seeking opportunities beyond efficiencies or productivity improvements, including revenue, product development, and customer experience.
Learning industry-specific opportunities for using AI. Where the competition is heading, and what can be learned from leading industries.
Creating a product management function for projecting business value from AI investments and managing the P/L, strategies, and roadmaps.
Diving into department-specific opportunities for using AI and AI agents in operations, marketing, technology, customer experience, finance, HR, and other areas.
Evaluating opportunities and capturing business value. Prioritizing experiments, POCs, and learning activities.
Reviewing and updating AI governance, including policies, procedures, standards, and related data governance.
Discovering AI Agents to capture big opportunities and identify short-term, low-hanging-fruit objectives.
Revisiting Agile for AI initiatives, with a focus on improving speed to delivery, quality, and feedback while driving efficiencies in agile/scrum using AI capabilities.
Defining release readiness criteria for when AI capabilities are production-ready, including data, testing, user acceptance, and security factors.
Updating knowledge management to engage subject matter experts, address tribal knowledge issues, and enhance AI with the organization’s intellectual property.
Establishing change management programs in AI initiatives that grow adoption, address detractors, and capture feedback.
Redesigning the organization, including rewriting departmental missions, roles/responsibilities, career paths, and learning objectives for areas most impacted by AI.
Selecting KPIs/OKRs for the genAI era to focus teams on what matters around growth, efficiencies, customer needs, compliance, and other strategic drivers.
Elevating AgenticOps, or how operational teams in IT, security, and risk management monitor AI in production and manage incidents.

2026 Workshop Series

World-class IT in the GenAI Era - Unifies IT teams on AI’s impact on innovation, Agile, DevOps, and IT Ops. Align on the IT Org structure and revisit the digital operating model to deliver innovations fast, efficiently, and with operational resiliency.
AI Strategy and Governance - Bluesky thinking the organization’s objectives and governance for using AI to deliver short-term ROI and longer-term growth.
Transforming to a Leaner, Faster Agile - What happens when you downsize, and your “scaled” agile no longer works? Learn StarCIO’s Agile, product management, continuous planning, and change management for a leaner and faster delivery model.
10 Steps for Technology and AI Selections - A workshop to recast the technology research, POC, and procurement process. Align architecture, procurement, and delivery functions to a faster selection process, more efficient production rollouts, and smarter change management practices.

Department and Team Building

Digital leadership and transformation—A leadership workshop on defining strategy, developing missions, and aligning mindsets to drive transformation.
Executing Digital Strategy with Product Management - A workshop that helps product teams align product roadmaps with digital strategy, define "MVPs" and create a methodology on working practice with customers, stakeholders and end users.
Digital Planning -> Execution: Product, Agile, & Data - Focuses on aligning business, technology, digital, and marketing organizations on defining agile culture, developing roadmaps, and establishing planning practices.
Design Thinking - Brainstorming solutions, persona development, journey mapping, and other techniques. Incorporate design thinking practices into product management, agile, data science, and a culture of innovation.
Change management - Turn a weakness into a strength by educating digital transformation leaders on bringing change management practices into their innovation practices.
Driving the Data-Driven Organization - A workshop for business, data, IT leaders, and top data practitioners on the tools and practices to become more data-driven. Establish "data governance" and define an "agile" practice for asking questions and answering them with data.
Agile Architecture - Redefine the roles and responsibilities of architecture teams. Apply agile methodologies to technology selections and POCs. Define standards working with agile development teams
Agile for Stakeholders - Helps stakeholders to agile teams understand their role in representing customers, defining requirements, and inputting on priorities. Initial steps for non-IT to apply agile methodologies in other departments.
DevOps and IT Transformation- A technical workshop for developers and engineers on establishing both an "agile" and "stable" mindset and operating platform. Develop a consensus on tools and roadmap for CI/CD, IaC, monitoring and other DevOps practices.