The Strategic Playground helps leaders and teams think bigger—on purpose.

This bold, immersive experience makes strategic thinking practical, energizing, and accessible to every level of the organization—not just the top. Participants walk in with real challenges, and walk out with practical tools, sharper instincts, and a mindset shift that transforms how they think, work, and lead.

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Program Description

Strategic thinking isn’t just a C-suite skill. It’s a competitive advantage that belongs to everyone—and The Strategic Playground is here to build it.

Born from the belief that strategy shouldn’t be intimidating, exclusive, or overly theoretical, The Strategic Playground is a bold, energizing development experience designed to help leaders and teams think and work more strategically—on purpose. It was built for people who want to stop reacting and start leading. For teams who want to think bigger and contribute more. For organizations that know strategy lives and dies in everyday decisions, not just annual plans.

This isn’t a lecture. It’s an active, modular, real-world experience. Participants practice thinking differently about the work they already do—spotting patterns, challenging assumptions, seeing beyond the obvious, and framing smarter solutions. Through hands-on workshops, scenario-based learning, coaching, and on-the-job application, they learn frameworks they’ll actually use and develop habits that stick.

The Strategic Playground is built on five core principles:

• Strategic thinking can be taught (and should be).

• Leaders at every level deserve access to it.

• Teams learn best by doing—not by theory.

• Play and curiosity fuel great thinking.

• Big impact starts with small, practical shifts.

The result? A practical mindset shift that transforms how leaders see their role, their challenges, and their opportunity to lead. The Strategic Playground empowers teams to not just do more—but think better.

Who It’s For:

This program is for leaders, high-potential talent, and cross-functional teams who are ready to stop reacting and start leading. It’s perfect for organizations that want to build a deeper strategic bench, expand their decision-making capability, and help employees think more critically and act more boldly in their day-to-day roles.

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 includes a series of modular workshops that can be delivered as full sessions, short sprints, or embedded into existing development tracks. Each module builds on the last to create continuous, digestible learning experiences that spark growth without overwhelming busy teams.

To support long-term impact, the program also includes:

• Practical assessments to benchmark and track growth

• Reinforcement sessions that deepen learning and sustain momentum

• Toolkits and discussion guides that leaders can use with their teams to keep strategic thinking alive on the job

Organizations can integrate the full program into their internal learning and development offerings, allowing internal teams to scale the experience and bring the tools, language, and frameworks to more leaders over time.

It’s hands-on, real-world, and built 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 awareness, surfaces hidden habits, and equips participants with simple mindset shifts to sharpen everyday thinking.

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 organizational pushback.

The Bigger Picture: Spotting What’s Next

Strategic thinkers don’t just react—they anticipate. In this module, we zoom out to build strategic awareness, explore external trends, and spot signals hiding in plain sight using tools like PESTLE analysis.

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.

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.

Eliminating Bias and Assumptions in Decisions

Bias is sneaky—and costly. This module gives your team tools to test assumptions, reduce blind spots, and make smarter, clearer decisions grounded in reality, not habit.

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.

Not Your Average Leadership Program.

This is strategy—with sticky notes, stretch thinking, laughter, and bold ideas. We take play seriously, because it unlocks the best thinking in people.

And we believe strategic thinking shouldn’t be reserved for the C-suite. It should be part of how everyone shows up.

Need a broader learning strategy to support your talent goals?

VP CLIENT STRATEGY AND SERVICE, B2B MARKETING AGENCY

“I came away feeling like I know several more avenues to consider, a bigger way to think about things, and questions to ask before I make a decision or a conclusion or an assumption. I learned some fantastic tools I never tried before.

CHIEF OPERATIONS OFFICER, MANAGEMENT CONSULTING GROUP

“What a wonderful class!! I really liked the content - such great reminders of actions that can be taken to 'think" strategically and/or probe others. I can see how this would be perfectly aligned for the executives we support!”

DIRECTOR OF LEARNING AND DEVELOPMENT, MAJOR BEEF PROCESSING COMPANY

“I loved the session! The experience challenged me and pushed me out of my comfort zone and made me engage in different ways than I typically do. I felt like after every exercise I had something I could take away and really use. I’ll definitely be using this with my team! And the Powerful Questions really helped me drive a clarifying conversation about my vision. I’ve been using those questions since I got them and asking them is helping people think a little differently!”

We’re proud to have delivered custom workshops for many respected clients. Here are some of the organizations we've worked with.

Mary Rapaport is on a mission to democratize strategic thinking.

As the creator of The Strategic Playground, an energizing development experience that helps leaders and teams build the thinking that drives the business, Mary works with well-known companies to develop real-world strategic thinking capability—not just check-the-box training.

Learn more about Mary here: https://xceleratebiz.com/about

Interested in bringing the Playground to your organization?