The Strategic Playground: Where Better Thinking Begins
Democratizing strategy. Energizing learning. Unleashing possibility.
The Strategic Playground is a bold new approach to leadership development—one that makes strategic thinking accessible, exciting, and practical for every level of the organization.
This isn’t an academic course. It’s a real-world, high-energy development experience that helps people use strategic thinking frameworks in the context of their everyday work. Through interactive workshops, benchmarking assessments, peer learning, coaching, and on-the-job application, participants build the habits and confidence to think and act more strategically—on purpose.
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Program Description
The Strategic Playground is a comprehensive development program designed to help teams and leaders strengthen their strategic thinking muscles. The program blends assessments, real-world scenarios, group coaching, application assignments, and hands-on practice to create lasting capability. Participants leave with tools they can use right away, and a mindset shift that lasts long after the session ends.
Who It’s For:
Leaders, high potentials, and teams who are ready to stop reacting and start thinking ahead. Perfect for organizations who want to build their strategic bench, elevate critical thinking, and empower employees to make smarter decisions every day.
How the Program Works
The Strategic Playground uses a hands-on, real-world approach to build strategic thinking capabilities that stick. Participants don’t just learn frameworks—they use them. The program blends high-energy workshops, real work application, peer learning, and coaching to create an engaging experience that drives impact where it matters most: on the job.
Each module is designed to activate strategic thinking through interactive activities, reflection, and scenario-based learning. Participants practice spotting assumptions, framing complex challenges, analyzing data, and exploring options in ways that connect directly to their everyday roles. The program’s flexible format allows it to be delivered in full sessions, sprints, or embedded into broader development efforts.
No theory for theory’s sake—just practical tools, sharp insights, and a bold shift in how participants think, act, and lead.
Strategic Approaches to Real Business Challenges
Think Like a Strategist
In this engaging module, we'll delve into the art and science of strategic thinking, empowering you to overcome common barriers and cultivate a strategic mindset. By the end of this module, participants will be equipped with the tools and mindset to tackle complex challenges strategically and drive organizational success.
Bias Busting; Thinking Beyond the Silo
Challenging hidden assumptions and biases in thinking is key to unlocking more innovation and creativity. The module introduces a range of powerful concepts, including The Arena Map, PESTLE Analysis, Game Theory, and Time Zero Analysis that will help participants build their analytical skills and learn to frame their challenges through the lens of current trends from an outside-in perspective.
The Art of Strategic Decision-Making: A Framework Approach
Participants are equipped with a collection of decision-making frameworks, examine each framework, appreciating the strengths and use of each tool, and then apply their knowledge in an interactive exercise, identifying the most suitable frameworks for specific situations and considering what audiences may appreciate each. Participants consider how each these frameworks may help them strengthen their approach to their own strategic challenges.
Cultivating an Analytical Mindset
Identifying patterns in data, being able to develop and leverage insights from stakeholders, and building a deep understanding of business context - and bringing an analytical approach to problem-solving is key to making sound strategic decisions. Participants will learn approaches to gathering and reviewing important data and information and approach challenges with greater business acumen for a more strategic approach.
Transforming Strategic Insights into Actionable Plans
For strategic thinking to make an impact, it must drive action. This module introduces practical tools to help participants translate their strategic thinking into actionable plans. Participants will build skills that help them identify strategic options. prioritize actions. and navigate critical next steps translating strategic thinking into tangible results.
Building a Strategic Thinking Culture
Strategic thinking requires organic reinforcement in an environment that rewards. recognizes and continuously encourages strategic thinking at every level. Leaders and individual contributors at every level will learn strategies to cultivate a culture of strategic thinking within their organization.
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
Creator of the Strategic Playground Workshop and the Chief Xceleration Officer at Xcelerate, LLC.
Mary Rapaport is on a mission to democratize strategic thinking. She believes it's not just for the elite few, but for everyone in an organization. When everyone channels a strategic mindset, the business culture thrives, teams become more creative, and employees lean in and engage more. Cultivating this mindset helps leaders create a better (and more fun) place to work, fostering a stronger culture of creativity and innovation.
As a strategic thinking architect, Mary empowers leaders and teams across all functions and levels to think, act, and lead more strategically. As the founder of Xcelerate, she builds learning strategy, designing and delivering immersive learning experiences that ignite "aha moments" and drive tangible business results.
Mary's passion extends beyond individual development. She champions inclusive growth through the Minority Business Growth Alliance, a non-profit providing invaluable coaching and support to BIPOC entrepreneurs. She holds an MBA, a BA in International Business, and is a certified leadership and sales trainer.
