Walk into any community pool on a summer afternoon, and you'll notice something interesting: the shallow end is packed with splashing, frantic activity—lots of movement, lots of noise, but nobody is actually getting anywhere. On the deep end, however, there’s very little activity, even though that's where the real swimmers develop their stroke, build their endurance, and actually move expertly across the pool.
You might have noticed this same phenomenon in conference rooms across the corporate world every day. Teams thrash around in the shallow end of thinking—busy, reactive, constantly in motion—while the deep waters of careful, strategic thought remain largely unexplored. Ouch, right? Mary Rapaport, founder, creator, and CEO of The Strategic Playground, argues that this isn't just a productivity problem; it's an existential threat in the age of AI. She explored this theme in a recent webinar aptly titled: In the Age of AI, Equip Leaders to Think, Not Just Do
The Harvard Business Review reveals just how crowded that shallow end has become: 96% of leaders report a lack of time for strategic thinking, while 43% can't even articulate their own strategy. Meanwhile, 44% spend their time firefighting instead of building capabilities for the future. Yikes. We've created organizations full of people who know how to keep their heads above water but have forgotten how to swim toward deeper, more valuable outcomes.
When Staying Afloat Becomes the Goal
The strategic thinking gap manifests in predictable patterns across organizations. Teams find themselves constantly treading water—reactive rather than proactive, focused on staying busy rather than making meaningful progress. Innovation feels out of reach, replaced by incremental improvements that barely create ripples in the competitive landscape.
Problems are often addressed quickly, but the underlying issues that create these problems remain unaddressed. Leaders search in vain for thought partners who can dive beneath surface-level symptoms to explore root causes. When you can't find colleagues capable of swimming in deeper analytical waters, you know your organization has a fundamental capability problem.
This shallow-water mentality didn't emerge overnight. Classic business practices like Frederick Winslow Taylor's scientific management (Taylorism) and Lean Six Sigma methodologies consistently rewarded staying comfortable and predictable. The 2008 financial crisis pushed this trend further when organizations eliminated their strongest swimmers—the experienced strategic thinkers who commanded higher salaries—leaving behind teams that could execute routine tasks but struggled to stay afloat in deeper strategic waters.
AI Changes the Depth Requirements
The rise of AI has fundamentally altered the waters we all swim in as professionals. Machines excel at the shallow-end activities that were once very prevalent (routine analysis, pattern recognition, and standardized problem-solving). But as AI takes over these capabilities, the only valuable real estate left is in the deep end, where uniquely human skills, like creative problem-solving, systems thinking, and strategic insight, become the primary differentiators.
Organizations that help their people become comfortable in these deeper waters see remarkable results. Research shows a 30% increase in productivity when leaders deliberately develop strategic thinking capabilities. Teams that venture beyond surface-level brainstorming generate five times more ideas, with 4.5 times more of those ideas representing genuine innovation rather than incremental tweaks.
Learning to Swim in Strategic Waters
Strategic thinking isn't an innate talent that some people possess while others are doomed to splash around in the shallows for eternity. It's a learnable skill set built on four foundational elements: future orientation, systems thinking, data-informed analysis, and adaptability to changing conditions.
The transformation begins with building business thinkers rather than functional specialists. This means helping teams understand the deeper currents that drive organizational success—the growth strategy, competitive pressures, and stakeholder priorities that create the undertow that carries daily activities. When people understand these deeper dynamics, they can have a more profound impact.
Now, we have to learn how to dive deeper. Instead of asking surface-level questions like, "How can we increase sales?" teams learn to probe deeper: "What's preventing customers from seeing value in our solution?" or "How might we make our offering feel essential rather than optional?"
This shift from symptom-focused questions to root cause, possibility, or paradigm-shifting inquiries opens up entirely different solution spaces. Like learning to hold your breath and explore the vast expanse underwater, it initially feels uncomfortable but reveals a whole world of possibilities that simply can’t be seen from the surface.
Making Deep Thinking Part of Daily Work
Strategic thinking doesn't necessitate a complete deviation from business as usual. It's about approaching existing work with more thought and intention. Turn routine meetings with shallow status updates into deeper explorations of challenges and opportunities.
The key is creating structured opportunities to dive below the surface. Post-project reviews that explore underlying patterns rather than just immediate outcomes. Stakeholder interviews that uncover what keeps partners awake at night. Research assignments that bring external perspectives into internal discussions.
Leaders play a crucial role by modeling comfort in deeper waters. When they ask provocative questions that push beyond easy answers, reward execution as well as insights, and create psychological safety for exploring uncertain territory, they signal that the organization values swimming ability over merely staying afloat.
Building Your Team's Swimming Capability
The transformation happens through consistent practice and proper coaching. Recognition—from the top down—becomes particularly important. Leaders have to publicly celebrate the team member who identifies hidden patterns. The colleague whose question changes the project's direction deserves a pat on the back. And the individual who connects seemingly unrelated information needs to get their kudos. These acknowledgments help shift cultural norms from rewarding busy work to valuing thoughtful contribution.
Just as swimming instructors gradually guide students into deeper water, strategic thinking development works best as a progressive capability-building process rather than a sudden leap into complexity.
Your Strategic Swimming Coach
At ELB Learning®, we understand that developing strategic thinking capabilities across your organization requires more than good intentions and occasional deep-end exercises. Our learning and development consulting services help you design systematic approaches that build these critical skills progressively and sustainably.
We partner with your team to assess where strategic thinking gaps are limiting performance, then create targeted development experiences that help your people become comfortable operating in deeper analytical waters. From initial capability assessment through program design, implementation, and measurement, we help you build the thinking capacity your organization needs to thrive as AI handles the work at the shallow end.
Our consultants work with your team to identify the specific strategic thinking capabilities you need, then design learning experiences that create lasting behavioral changes instead of temporary demonstrations of skill.
If you’re ready to help your team venture beyond the shallow end and develop the deeper strategic thinking capabilities that drive real business impact, watch the full webinar below to explore these concepts in detail and get the specific tools you need to implement them immediately.
Want to learn more about how ELB Learning® can help you build strategic thinking capabilities across your organization? Learn more about our strategic learning strategy consultative services.
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Disclaimer: The ideas, perspectives, and strategies shared in this article reflect the expertise of our featured speaker, Mary Rapaport. Be sure to follow her on LinkedIn to explore more of her insights.
