Leadership Series: Strategic Decision-Making in the AI Era

Strategic Decision-making gives leaders the ability to make quicker more appropriate decisions in the AI era.

Many leaders have an incomplete decision support system and framework with which to lead. In this era of AI they skip understanding who’s affected, what people need, and why they should care. So decisions fail, not because they’re wrong, but because the implications of implementing them have not been fully understood.

In an AI world, good data is easy to get, however, its retrospective. Good decisions require understanding people, context, and values and the impact of resolving the problem. Is it a complex or even chaotic situation? Who will help resolve it? Who will be affected most if we change course?

This course supports informed decision-making for human-centered outcomes particulalry in non-linear, uncertain environments.

What You’ll Learn

“Ethical, diagnostic, stakeholder-centered decision-making for uncertain times.”

Methodologies & Frameworks 

Rich Picture Mapping
Understand the situation from multiple perspectives. Map stakeholders, their needs, constraints, and how they see the problem. Use this to avoid making assumptions.

Critical Systems Heuristics (Ought Questions)
Ask the boundary-critical questions that bring ethics and values into problem-framing:

• Who ought to benefit from this decision?
• What ought to be improved?
• By what means ought improvements be achieved?
• Who ought to be involved in deciding?

This ensures you’re not just solving the problem — you’re solving it the right way.

CATWOE Analysis
Define the real problem (not the assumed one) by mapping: Clients (who’s affected), Actors (who decides), Transformation (what changes), Weltanschauung (worldviews), Owners (accountability), Environment (constraints).

Estuarine Mapping
Assess problem complexity. Determine if your decision is simple/obvious, complicated, complex, or chaotic. This determines how you’ll involve people and make the decision.

Stakeholder Involvement Framework
Based on problem type and stakeholder needs — grounded in what ought to happen — decide who should be involved in the decision and when. Different decisions require different involvement models.

Implementation & Adoption Strategy
How to move from decision to action so it actually sticks. What needs to happen for people to adopt it?

What Particpants Leave With

✓ Rich Picture Map — how to map situations across multiple stakeholder perspectives
✓ CATWOE Analysis — a comprehensive problem definition framework (not the assumed one)
✓ Problem Complexity Assessment — a tool to map where decision sits on the simple-to-chaotic spectrum
✓ Stakeholder Involvement Plan — who decides, when, and how
✓ Implementation & Adoption Strategy — how to make it actually happen
✓ 12-Month Toolkit — templates, frameworks, community of 200+ practitioners

Who This Is For

• Leaders making decisions with high stakes and uncertain outcomes (strategy, AI adoption, major investments, organizational change)
• Teams navigating trade-offs between efficiency and ethics (sustainability, customer fairness, employee wellbeing)
• Decision-makers who’ve made analytically sound choices that still failed in practice (because people didn’t believe in them or implementation revealed unforeseen costs)
• Organizations trying to embed ethical reasoning into their decision architecture

Note – This course integrates established methodologies from Systems Thinking (Checkland’s SSM, Ulrich’s Critical Systems Heuristics), complexity assessment (Snowden’s Cynefin), and covers key principles of Design Thinking.