Senior leaders in every industry share a common frustration: the persistent, costly gap between a well-crafted strategy and its real-world results. According to a 2016 analysis cited in HBR, an estimated 67% of well-formulated strategies fail due to poor execution. This statistic haunts boardrooms and derails ambitious goals, whether in hospitality, technology, or for teams focused on critical health, safety, and sustainability targets.
The conventional wisdom that treats strategy as a fixed plan handed down from the top for others to implement is not just outdated; it is a direct cause of this failure. The gap between a plan and its outcome often stems from a flawed mental model of what strategy and execution truly are in a complex, fast-moving world.
A close look at the work of today’s leading strategic thinkers reveals five counter-intuitive truths that, when taken together, reveal a new operating model for leadership. These insights challenge long-held assumptions and reframe the strategy-execution gap not as a problem of implementation, but as a failure to learn.
Leaders often turn to “big, hairy, audacious goals” to resuscitate a struggling division, believing that a management moonshot will reignite momentum. But this is the stretch goal paradox: research shows this is precisely the wrong approach for a team that’s already down.
The core finding is that stretch goals are most effective for organizations that are already successful and have slack resources. These “thriving but complacent” organizations have the capability and resilience to see an audacious target as an opportunity. For organizations experiencing weak results, however, a stretch goal is far more likely to be perceived as a threat. This can "foster employee fear and helplessness, kill motivation, and ultimately damage performance."
As researchers Sim B. Sitkin, C. Chet Miller, and Kelly E. See discovered in their work on this paradox, the organizations best positioned for these goals often avoid them.
"The companies that could benefit from pushing themselves—those with strong recent performance records and resources to spare—avoid stretch goals, because success has made them risk-averse."
For struggling teams, a more effective strategy is to pursue "small wins." This approach builds momentum, energy, and resources, fostering the learning and confidence required to take on more ambitious goals later. This focus on learning from tangible progress highlights a recurring theme: effective strategy is grounded in reality, not just aspiration.
As executives climb the corporate ladder, their focus often narrows. A leader's attention is naturally pulled inward toward "resolving conflicts, reconciling budgets, and managing performance." The result is a dangerous insularity that ungrounds strategy from the external world.
Data from a 10-year longitudinal study supports this observation: "85% of leadership teams spend less than an hour per month discussing strategy," and a full "61% of executives told us they were not prepared for the strategic challenges they faced." This internal focus makes it impossible to learn from the market or treat strategy as the dynamic process it needs to be. Leaders lose their deep understanding of the competitive landscape, evolving customer needs, and emerging trends, rendering their strategies internally coherent but externally irrelevant. Â
As one executive candidly confessed to researcher Ron Carucci: "We all fake it till we make it."
This outward focus naturally leads to the next insight: if strategy must be grounded in external reality, then the traditional top-down planning model is backward. True strategy emerges from learning on the ground.
In one of the most radical shifts in strategic thinking, Harvard’s Rosabeth Moss Kanter argues that a strategy is never excellent in and of itself; its brilliance is revealed only through the quality of its execution.
This perspective rejects the idea of strategy as a complete script handed down from on high. A more effective model is "improvisational theater," where the strategy is shaped by real-world actions and feedback. In this mental model, execution isn't the rote implementation of a plan; it is the act of learning what works.
"A strategy takes shape from what actors do in front of audiences that provide feedback."
This means strategy often emerges from thoughtful planning followed by on-the-ground experiments. For leaders, the key takeaway is to "encourage innovation, begin with execution, and name the strategy later." Rather than waiting for a perfect plan, savvy leaders foster a culture of rapid learning and modification, allowing the most effective strategy to reveal itself through action. This reframes execution as the engine of strategic discovery.
Harvard’s Amy C. Edmondson and Solvay’s Paul J. Verdin argue that the widely accepted view that strategy and execution are separable activities is a primary cause of failure. The dramatic breakdowns at Wells Fargo (cross-selling) and Volkswagen (clean-diesel) are powerful examples of what happens when a fixed, top-down strategy is not altered based on new information discovered during execution.
They propose a radical alternative: treat strategy not as a plan, but as a hypothesis that must be constantly tested. In this model, execution is the process of generating the critical data needed to validate or refine the strategic hypothesis. For a hotel chain testing a new sustainability initiative, early feedback from housekeeping staff on recycling processes is not an "execution problem"—it is invaluable data for refining the strategic hypothesis. The people with the most valuable data are those on the front lines.
"The people who create and deliver products and services for customers are privy to the most important strategic data the company has available."
Closing the strategy-execution gap is therefore not about better execution, but about "better learning." This requires creating a continuous dialogue—a learning loop—between senior leaders and operational teams. If strategy is a hypothesis tested on the front lines, then it follows that the people conducting those tests are not just implementers—they are strategists. This leads to the final, and most radical, reversal of conventional wisdom.
In the traditional model, strategy is the C-suite's domain and execution is the organization's task. Roger L. Martin, one of today's most influential strategic thinkers, argues that to be effective, leaders must completely reverse this polarity.
He contends that "execution" is not choiceless doing. At every level of an organization, from the manufacturing floor to the sales team, people make critical choices to move forward. Those choices—about how to prioritize tasks, serve a customer, or solve a problem—are strategy. This creates a "cascade" of strategic choices that flows throughout the company.
In this model, the CEO’s primary job is not just to formulate the top-level plan, but to execute the entire strategic process. This requires designing and overseeing the system through which choices are made at every level. As Verizon executive Andres Irlando brilliantly redefined it:
"Wouldn’t you call execution the act of setting up that series of choice cascades, identifying the manager responsible for the choices in each cascade, and following up to ensure that they make the choices for which they are responsible?"
This profound mindset shift places the responsibility for any "strategy-execution gap" squarely with top leadership. It is not a failure of those "below" them, but a failure to effectively orchestrate the cascade of choices that brings a strategy to life.
The overarching theme of these five truths is clear: effective strategy in today's world is less about creating a perfect, static plan and more about fostering a dynamic system of learning, adaptation, and shared responsibility. The old "Plan-then-Do" mental model is obsolete.
For leaders in hospitality, safety, sustainability, and beyond, this represents a fundamental call to rethink how strategy is made and managed. Success depends not on rigid compliance with a plan, but on creating an organization that can learn and adjust in real time.
As you look at your own organization's ambitious goals, which of these truths most challenges your current approach? Perhaps the biggest takeaway is that the gap between strategy and execution isn’t a problem to be solved, but a space where constant learning must happen.
References- Harvard Business Review. "The Gap Between Strategy and Execution." HBR Insight Center Collection, 2017. Available at: https://hbr.org/insight-center/the-gap-between-strategy-and-executionÂ
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