Leading an AI-Native Organization AI Strategy Working Session for Senior Leaders

Most organisations have AI ambition. Few have a shared view of what to do first, how much to invest, or who owns what.

Senior leaders are being asked to fund, govern, and accelerate AI initiatives, often without a shared language for the decisions involved or a clear framework for prioritising investment against measurable outcomes. Strategy conversations stall between vision and execution because the people who control budgets, governance, and workforce decisions aren't yet aligned on the basics.

This course exists to close that gap: giving senior leaders the fluency, the frameworks, and a structured day to align on priorities, make decisions, and commit to next steps.

This course is suited to General Managers, Directors, and senior leaders who are accountable for funding, governing, or directing AI initiatives across an enterprise. It is designed for the level where AI investment decisions are owned — not delegated.

• General Managers, Directors, and senior leaders with P&L responsibility where AI initiatives are stalling between vision and execution
• PMOs and transformation sponsors aligning AI investment with enterprise strategy
• CIOs, CTOs, and technology leaders responsible for AI platform and data decisions
• Anyone who must evaluate, approve, or manage AI initiatives across the enterprise

No technical background required. This is a leadership session, not a technology course.

After the session, you'll be able to:

• Articulate your organisation's AI-Native maturity across strategy, workforce, governance, data, technology, culture, and agility
• Set AI investment priorities grounded in P&L impact rather than hype
• Define governance guardrails and responsible AI ownership that enable progress without inviting unnecessary risk
• Shape a workforce upskilling plan that connects AI-Native training to the roles and value streams where it matters most
• Commit to a 30-60-90 day AI leadership roadmap with named owners and specific next steps

This is a working session. Everything you produce is built around your organisation's context.

• An AI-Native Organisation heatmap diagnosing your current maturity across seven dimensions
• An AI Money Map linking AI investments to specific, measurable business outcomes
• A Responsible AI Governance and Risk Plan covering the first 90 days of your highest-value initiatives
• A workforce upskilling plan identifying who needs to become AI-Native first and how
• A 30-60-90 day AI leadership roadmap with prioritised initiatives, named owners, and explicit decisions on what to pause

Pretty Agile is the AI-Native Charter Partner for Australia and New Zealand, selected by Scaled Agile from over 80 applicants globally.

What Pretty Agile brings to the delivery:

• facilitators who work with senior leaders on AI strategy, governance, and investment decisions in live enterprise contexts, not trainers reading slides
• facilitation grounded in how Australian and New Zealand enterprises are actually navigating AI at leadership level, including the governance questions, funding trade-offs, and workforce decisions that come up in practice
• scenario work and artefacts built around the decisions this audience owns

Designed by Scaled Agile. Delivered by Pretty Agile. Focused on helping senior leaders turn AI ambition into funded, governed, measurable progress.

Morning: Fluency, context, and strategic alignment

AI Challenges and Opportunities: Surface the real threats and opportunities facing your business model, cutting through hype to focus on what's strategically meaningful.

AI Fluency for Leaders: Build a shared executive AI lexicon (LLMs, GenAI, RAG, agents) so leadership conversations start from common ground.

AI Organisational Model in Our Context: Diagnose your organisation's AI-Native maturity across seven dimensions: strategy, workforce, governance, data, platforms, culture, and agility.

AI Vision and Strategy: Define your AI Strategic Intent, the leadership team's motivation and desired impact as it relates to your AI journey.

Afternoon: Investment, workforce, governance, and roadmap

AI Value Patterns and Priorities: Build your AI Money Map, a prioritised portfolio connecting every AI investment to a specific measurable return.

AI Workforce: Determine who must become AI-Native first, and shape an upskilling plan that includes AI-Native Foundations and Change Agent pathways.

Human-Centric AI Culture: Explore how to build an environment where AI augments human judgement and creativity, and how to lead the cultural shift that makes adoption stick.

AI-Empowered Agility: Identify the legacy planning, funding, and governance practices that prevent your organisation from moving at the speed AI requires.

Responsible AI: Assess governance exposure and define the guardrails, ownership, and policies required to scale AI responsibly.

AI Technology Investments: Evaluate build-versus-buy trade-offs, align on starting platforms, and understand why curated data and operational AI technology set the ceiling on AI-Native performance.

AI Leadership Roadmap (30-60-90): Commit to a unified roadmap that names owners, accelerates high-value initiatives, and explicitly pauses lower-value work.