Executing strategy is inherently challenging, and leaders can sometimes make it even tougher without realizing it. In our work with global leaders and their teams, we frequently observe common, yet avoidable, strategy execution missteps that leaders should learn to recognize and address.
Here are eight pitfalls that even highly capable leaders often encounter:
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Believing that communication equals execution. Leaders may assume that once they have communicated their strategy—sometimes only once—execution will follow naturally. In reality, strategy requires sustained attention and reinforcement.
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Starting with the easy action. Many leaders begin with quick, straightforward steps, thinking that easy wins will build momentum. However, the easiest actions might not offer the market insights or organizational learnings needed to refine a strategy. Tackling smaller, unknown challenges could unlock significantly more value.
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Never saying “no.” While good leaders understand their strategy, they may overlook the importance of balancing capacity. Failing to prioritize actions or saying “no” to less critical initiatives can stretch resources too thin. In "Why Strategy Execution Unravels—and What to Do About It," a 2015 piece at Harvard Business Review, Donald Sull, Rebecca Homkes, and Charles Sull note that only 11% of leaders surveyed feel that all their company’s strategic priorities have the resources they need for success.
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Believing that today’s skills will create tomorrow’s vision. The adage “what got you here won’t get you there” holds true in evolving markets. Recognizing the need for new skills and phasing out outdated ones is essential for progress in execution.
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Getting caught up in urgent matters. Day-to-day operational demands, often referred to as “firefighting" or the “Whac-A-Mole” approach, can pull leaders away from focusing on strategy execution. Maintaining strategic clarity amidst daily pressures is key.
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Stakeholders diverging over time. Even with initial alignment, stakeholders may gradually drift in execution focus. Successful leaders proactively realign stakeholders throughout the execution process to maintain momentum.
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Focusing on activities instead of results. A focus on “checking the box” on a project plan can cause leaders to miss important cues that strategy needs adjustment based on market changes. True progress comes from staying adaptable to achieve desired results.
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Acting as if it's everyone’s business. Without clear accountability for strategic outcomes, dispersed ownership can slow progress. Leaders must ensure decision-making responsibilities are well-defined and aligned with strategic goals.
We see strong leaders face these challenges, even in a business simulation environment where time is compressed for learning purposes. Strategy execution is rarely straightforward—opportunities are often ambiguous, teams process information differently, and strategic trade-offs require careful navigation. However, by recognizing and addressing these pitfalls, leaders improve their ability to execute strategy effectively. It's not about following a formula, but rather developing judgment.
Business simulations offer leaders the opportunity to gain perspective, reflect, and adjust their approach to execution. Contact us to learn more about our learning solutions.
Jean Williams
Jean Williams has more than 20 years of experience in executive and leadership development and management consulting. She is a professional facilitator and a certified executive coach, and she has years of experience designing, developing, and delivering educational programs for executives and senior managers. Jean’s delivery work with Insight Experience focuses on leadership development, strategy execution, and behavioral observation and coaching.