A bold, immersive experience designed to make strategic thinking practical, energizing, and accessible at every level—not just the top.
Participants bring real challenges and leave with actionable tools, sharper instincts, and a more strategic mindset that transforms how they think, work, and lead.
The Problem
When teams are stuck in constant execution mode, strategic thinking disappears.
Deadlines, competitive pressure, and rapid change push teams into reactive decision-making instead of thoughtful leadership.
✓ Opportunities are missed
✓ nnovation slows down
✓ Decisions prioritize short-term fixes over long-term impact
Without space to think ahead, teams respond to problems instead of preventing them.
The Solution
Strategic thinking shouldn’t be limited to the top—it should be a capability at every level.
The Strategic Playground™ transforms strategy from a theoretical concept into a practical, energizing skill set.
Through immersive, real-world experiences, participants:
✓ Work on real challenges
✓ Learn to spot patterns early
✓ Challenge assumptions with confidence
✓ Apply strategic thinking directly to their day-to-day work
The result: stronger decisions, better alignment, and a more strategic way of working—every day.
Program Description
Strategic thinking isn’t just a C-suite skill—it’s a competitive advantage that should exist at every level.
The Strategic Playground™ is designed to build that capability—turning strategy from something abstract into something practical, engaging, and actionable.
Built on the belief that strategy shouldn’t feel intimidating or exclusive, this immersive experience helps leaders and teams move beyond reactive work and start thinking and leading more intentionally. It’s for individuals who want to think bigger, contribute more, and make better decisions in real time—because strategy lives in everyday actions, not just long-term plans.
This is not a lecture. It’s an active, modular, real-world experience. Participants work on real challenges, learning to spot patterns, challenge assumptions, and frame smarter solutions. Through hands-on workshops, scenario-based learning, coaching, and on-the-job application, they develop practical frameworks and lasting habits they can use immediately.
Core Principles
✓ Strategic thinking can be taught—and should be
✓ It should be accessible at every level
✓ People learn best by doing, not by theory
✓ Curiosity and exploration fuel better thinking
✓ Small, practical shifts lead to meaningful impact
A practical shift in mindset that changes how leaders think, approach challenges, and make decisions—empowering teams to not just do more, but think better.
Who It’s For:
How the Program Works
The Strategic Playground™ is more than a workshop—it’s a flexible, end-to-end development experience designed to build lasting strategic capability across your organization.
The program is delivered through a series of modular workshops that can be run as full sessions, short sprints, or integrated into existing development initiatives. Each module builds progressively, creating focused, digestible learning experiences that fit into the rhythm of real work.
To support long-term impact, the experience also includes:
✓ Practical assessments to benchmark and track progress
✓ Reinforcement sessions to deepen learning and sustain momentum
✓ Toolkits and discussion guides that help leaders apply concepts with their teams
Organizations can integrate the full program into their learning and development strategy, enabling internal teams to scale the experience and extend its impact across the business.
It’s hands-on, real-world, and designed to shift how people think—not just what they know.
Strategic Approaches to Real Business Challenges
The Strategic Playground is more than a workshop—it's a toolkit for building sharper minds and stronger teams. Each module focuses on a specific dimension of strategic thinking, blending practical tools with fresh perspectives. Whether you're looking to expand your team's mindset, spark better decisions, or build action plans that actually drive change, these modules are designed to be applied, not just admired.
The Strategic Mindset
Uncover what it really means to think strategically — and what gets in the way. This module builds self-awareness, surfaces hidden habits, and equips participants with practical mindset shifts to sharpen everyday decision-making.
Problem Framing
Better problems lead to better solutions. This module gives leaders powerful question frameworks and tools to reframe challenges, break through stuck thinking, and open up new possibilities.
Bust Silos, Increase Impact
Help your team think beyond their own lane. This module shows how to move from tactical to strategic, align with stakeholders, and measure what really matters — while navigating cultural and organisational pushback.
Eliminating Bias and Assumptions in Decisions
Bias is sneaky — and costly. This module gives your team practical tools to test assumptions, reduce blind spots, and make smarter, clearer decisions grounded in reality, not habit.
The Bigger Picture: Spotting What's Next
Strategic thinkers don't just react — they anticipate. Expand strategic awareness, explore external trends, and surface hidden signals using tools like PESTLE analysis.
Seeing Shifts Early: Making Future-Focused Decisions
Most people miss the early signs of change. This module teaches how to map potential shifts, track patterns, and prepare for inflection points before they hit — so your team stays a step ahead.
Building Strategic Action Plans
Ideas are great. Action is better. This hands-on module brings it all together with a clear process for translating insight into forward-looking, high-impact plans using tools like TOWS analysis and strategic design principles.
Not Your Average Leadership Program
Strategy is built here—through hands-on exploration, bold thinking, and purposeful experimentation.
It’s an environment where curiosity fuels insight, and practical thinking drives real impact.
Strategic thinking isn’t reserved for the C-suite—it’s a capability every team should develop and apply every day.
Looking for a broader learning strategy to support your talent goals?
VP, Client Strategy & Service
B2B Marketing Agency
“I left with a broader perspective, new avenues to explore, and better questions to ask before making decisions or assumptions. The tools I gained were practical, immediately useful, and unlike anything I had used before.”
Chief Operations Officer
Management Consulting Group
“This was an incredibly valuable experience. The content provided practical, actionable reminders for how to think more strategically and ask better questions. I can clearly see how this would strongly benefit the executives we support.”
Director of Learning & Development
Major Beef Processing Company
“I found the experience both challenging and highly engaging. It pushed me beyond my usual ways of thinking and working, with each exercise providing practical takeaways I could immediately apply. The ‘Powerful Questions’ in particular have been incredibly valuable—helping me clarify my vision and guide more thoughtful, strategic conversations with my team.”
Mary Rapaport is on a mission to democratize strategic thinking—making it practical, accessible, and impactful at every level of an organization.
As the creator of The Strategic Playground™, an energizing and immersive development experience, Mary helps leaders and teams build the thinking capabilities that truly drive business performance. Her work goes beyond traditional training, focusing on real-world application rather than check-the-box learning.
She partners with leading organizations to develop strategic thinking as a daily practice—not just a concept. Through her approach, individuals learn how to navigate complexity, challenge assumptions, and make more thoughtful, effective decisions in real time.
Mary’s work is grounded in the belief that strategy isn’t reserved for the top—it’s a capability that should exist across every level of a business. By combining practical tools, experiential learning, and a strong focus on application, she helps organizations build stronger thinkers, more confident leaders, and more aligned teams.
Interested in Bringing The Strategic Playground™ to Your Organization?
