Strategist Thinking Amidst Execution Pressure with Mary Rapaport

Ever feel like you're stuck in the weeds, too busy with daily tasks to think about the big picture? In this episode of Owlcast, we dive into the world of strategic thinking amidst execution pressure. Join host David Morelli and co-host William Oakley as they speak with Mary Rapaport, founder of The Strategic Playground. Mary shares her unique approach to "democratizing strategic thinking," showing how it's not just for the C-suite. Learn why we get stuck in a "doing" mindset, the telltale signs of a strategic thinking gap, and how you can start cultivating this critical skill today—all without adding a single minute to your workweek.

You’ll explore how:

• Strategic thinking is a priority, not a time issue. The excuse "I don't have time for strategic thinking" is often a reflection of how we prioritize tasks and a deeply ingrained cultural bias toward rewarding execution over ideas.
 • A "strategic thinking gap" can be identified. Warning signs include being disconnected from the company's overall strategy, constantly fighting the same problems, and an absence of genuine "Aha!" breakthroughs.
 • Strategic thinking can be democratized. It's not a skill reserved for executives. Anyone at any level can cultivate a strategic mindset by connecting their daily work to the company's broader goals and asking questions that challenge assumptions.
 • Strategic thinking is a definable skill. It involves being future-focused, understanding how different parts of a system are interconnected, incorporating external perspectives and data, and being willing to adapt.