Why Leadership Teams Fail at Strategy Execution and How to Fix It

I’m thrilled to sit down with Ling-Yi Tsai, a renowned HRTech expert with decades of experience guiding organizations through transformative change using technology. With her deep expertise in HR analytics and the integration of tech solutions across recruitment, onboarding, and talent management, Ling-Yi has a unique perspective on how leadership teams can bridge the gap between strategy and execution. In this conversation, we dive into the persistent challenges of strategy execution, the importance of distinguishing strategic from operational priorities, the power of focused goals, and the structures that drive accountability and measurable success.

How do you see the persistent struggle with strategy execution impacting organizations, even when they start with a strong vision?

The struggle with strategy execution is a pervasive issue, and it often stems from a disconnect between planning and action. Even with a compelling vision, many leadership teams fail to translate that into consistent, measurable progress. This gap can erode trust within the organization, as employees start to see strategic plans as mere rhetoric rather than actionable commitments. Over time, it impacts performance by stalling growth and innovation, and it can damage culture by creating frustration and cynicism. When strategies fail to materialize—whether due to poor communication or lack of focus—organizations miss opportunities and lose credibility, both internally and externally.

What are some of the root causes behind this gap between strategy and results that you’ve observed in your work?

From my experience, several root causes stand out. First, there’s often a lack of alignment across the organization—leadership might understand the strategy, but if it’s not communicated effectively to employees, execution falters. Research shows that a staggering 95% of employees don’t even understand their company’s strategy. Second, leaders frequently get bogged down by day-to-day operational fires, leaving little time for strategic priorities. Lastly, there’s a tendency to overcommit to too many goals, diluting focus and resources. Without clear prioritization and accountability, even the best strategies become wishful thinking rather than reality.

How can leaders better distinguish between working on daily operations versus focusing on long-term strategic goals?

It’s about mindset and intentionality. Working “in the business” involves handling immediate, operational tasks—think resolving customer issues or managing budgets. Working “on the business,” however, means stepping back to focus on the bigger picture—innovating processes, building partnerships, or shaping culture. Leaders can distinguish these by regularly asking themselves: ‘Am I solving today’s problem, or am I building tomorrow’s foundation?’ It’s also helpful to audit how they spend their time. If most of their day is consumed by urgent tasks, they’re likely stuck in operations. Creating dedicated time blocks for strategic thinking, free from interruptions, can shift that balance.

Why do you think operational urgencies so often overshadow strategic priorities, and how can leaders counteract this?

Operational urgencies feel immediate and tangible—they demand attention with visible consequences if ignored, like a missed deadline or a client complaint. Strategic priorities, on the other hand, often seem abstract or distant, even though they’re critical for long-term success. Leaders can counteract this by building structured rhythms, like recurring meetings focused solely on strategy, where operational updates are off the table. Treating this time as non-negotiable sends a signal that strategic work isn’t optional. It’s also about cultivating discipline to say no to distractions and empowering teams to handle operational issues independently.

Why is it so challenging for leadership teams to narrow down their strategic goals, and what’s the consequence of taking on too many?

Narrowing down goals is tough because every leader often feels their own projects or initiatives deserve priority. There’s also a fear of missing out or a desire to please stakeholders by saying yes to everything. But when teams take on too many goals, resources and attention get spread thin. The consequence is exhaustion and mediocrity—nothing gets done well. Focus gets lost, and employees become confused about what truly matters. I’ve seen organizations where too many priorities lead to stalled progress, missed targets, and even burnout, as teams chase too many rabbits and catch none.

How can leaders decide which strategic goals are truly worth pursuing?

Leaders need a clear set of criteria to evaluate goals. I recommend looking at whether a goal requires cross-functional collaboration, if failing to achieve it would significantly harm future success, and if it demands leadership oversight and resources. These filters help identify what’s truly mission-critical. It’s also important to align goals with the organization’s core purpose and long-term vision, ensuring they’re not just trendy or reactive. Engaging the team in honest discussions about impact versus effort can also bring clarity, helping to prioritize the few goals that will drive the most meaningful outcomes.

What role does a strategy scorecard play in turning plans into measurable results?

A strategy scorecard is a game-changer because it makes progress visible and tangible. It connects abstract goals to concrete metrics, so everyone knows whether they’re winning or losing. Without it, teams often focus on activity rather than outcomes, mistaking busyness for progress. A good scorecard tracks both strategic goals—like growth or innovation—and organizational health metrics, such as employee engagement or financial stability. When updated and shared regularly, it fosters alignment, keeps priorities top of mind, and drives accountability across all levels of the organization.

What should an effective strategy scorecard include, and how can leaders ensure it remains a useful tool?

An effective scorecard should be simple and focused. It needs to include key metrics for strategic goals—think measures of culture, partnerships, or efficiency—and a handful of organizational health indicators, like financial performance or learning opportunities, ideally no more than 5 to 12 metrics total. Overcomplicating it with too much data defeats the purpose. To keep it useful, leaders should review it at every strategic meeting, ensuring it’s visible to employees and stakeholders. Sharing it openly builds connection and clarity, and regularly updating it prevents it from becoming a static document that’s forgotten.

How does a clear governance structure support strategy execution, and what does it look like in practice?

Governance is like the operating system for strategy execution—it defines who does what, how decisions are made, and how progress is tracked. Without it, you get chaos or the classic trap of ‘everyone is responsible, so no one is accountable.’ In practice, a clear governance structure spells out who owns each strategic priority, who approves changes, and how cross-functional challenges are resolved. It might involve specific roles, like a strategic coordinator to keep things on track, and regular check-ins to monitor progress. This clarity ensures follow-through and prevents initiatives from falling through the cracks.

What advice do you have for our readers who are looking to improve their leadership team’s approach to strategy execution?

My advice is to start with ruthless focus. Execution fails when everything feels like a priority, so limit your strategic goals to just a few high-impact ones. Protect time for strategic work—treat it as sacred, not something to squeeze in between crises. Build visibility and accountability with a simple scorecard, and make sure everyone knows their role in the governance structure. Above all, communicate relentlessly. If your team and employees don’t understand the strategy, no amount of planning will save it. Execution is a discipline, not a one-time event, so commit to consistent habits that turn vision into results.

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