How Leadership Drives Strategy Execution from Start to Finish

In the State of Strategy Execution 2025 report, we surveyed over 250 senior leaders to uncover the latest strategy trends and statistics. Over half of the respondents said that the biggest obstacle to strategic success was a lack of leadership.

This finding underscores the importance of leadership and strategic alignment, something we consider to be one of the six core pillars that impact successful strategy execution along with collaboration, accountability, progress tracking, continuous improvement, and data and technology.

In this article, we’ll look at why consistent leadership engagement from the initial stages of strategic planning through to finalizing its implementation is vital and how strategy teams can create this within your own organization.

Why leadership engagement in strategy execution falters

All too often, leadership engagement in strategic initiatives peaks during the initial planning phase and then dwindles or dies out once execution gets underway. This usually means infrequent check-ins, a lack of active participation in progress reviews, and an overall detachment from the day-to-day workings of the plan. When leaders aren’t consistently present and visibly invested, the entire organization can lose momentum and the strategic plan risks becoming a forgotten document. There are three main reasons why this drop-off in leadership involvement tends to occur.

First of all, there’s a common misconception among some leaders that their role in strategic initiatives concludes once the plan is formulated and priorities are set. They participate in the initial sessions, offer their insights, and then delegate the execution to their teams. But the role of leadership in strategy is more than just high-level. Leaders have an important part to play in guiding, supporting, and course-correcting the strategy as it unfolds.

Secondly, the daily demands faced by organization leaders often push strategic execution down their priority list. Many leaders fail to establish regular meetings dedicated to reviewing the progress of strategic initiatives and key performance indicators. If meetings are set, they’re often postponed or canceled, and once this happens a couple of times, the strategic plan can fade into the background entirely. The rest of the team could see this and feel like the plan isn’t a priority for leadership. This negatively impacts motivation and accountability at all levels.

Third, some leaders may feel disconnected from the strategic plan itself, particularly if they weren’t actively involved in its development. If the planning process excluded the input of certain department leaders, they may not feel a sense of ownership toward it or fully understand the rationale behind the objectives. This lack of connection can make it difficult for them to champion and consistently support the execution phase.

Finally, periods of uncertainty and disruption can exacerbate this issue. During uncertain times, such as economic downturns or significant market shifts, the long-term strategic plan can feel less urgent than immediate operational concerns like managing costs or adapting to new regulations. While it’s understandable that leaders need to address pressing issues, they often fail to revisit and realign the strategy once the crisis subsides. At this point, the strategy is totally abandoned.  

Making leadership a constant in your strategy execution process

A fundamental shift in leadership’s approach to engagement is necessary. We need to redefine what leadership involvement in strategy execution looks like — continuous participation, active oversight, and consistent communication. Your leadership team needs to actively drive the strategy forward. The following five key steps provide a practical framework for embedding this consistent leadership engagement.

Involve the entire leadership team from the start

Set the tone for active leadership engagement by including key leaders in the strategic planning process. Encourage open dialogue and ensure diverse perspectives are heard and genuinely considered during the formulation of the plan. This fosters a sense of ownership and collective responsibility. 

Explain how everyone’s input is valued and contributes to the overall strategic direction from the outset. It’s equally important to be transparent and set realistic expectations by explaining that, while all suggestions are considered, not every individual idea can be implemented. This is an honest and inclusive approach that helps build initial buy-in and sustains commitment across the leadership team, even as challenging conversations and difficult decisions arise during the planning process.

Set execution expectations and commitment 

It is important to clearly define the operational rhythm and expectations for strategy execution at the planning stages. Establish specific timelines for regular updates — for example, you’ll require monthly progress updates on the last Friday of every month. 

Schedule rolling review meetings with leadership to discuss progress, address roadblocks, and make informed decisions based on the data. These meetings should be mandatory. Develop a communication process, such as a regular summary email from the executive sponsor, outlining key discussion points and recognizing achievements. Set these “rules of the road” and you ensure that strategy execution remains a consistent priority, fosters accountability and demonstrates visible leadership engagement across the organization.

Appoint an executive sponsor

Designate a high-level executive to champion your strategic execution process. While the CEO is the ideal candidate, any member of the executive committee with significant influence and passion for the strategy can serve this crucial role. 

The executive sponsor acts as the owner or champion of the strategic plan. They continuously reinforce its importance within the organization. They become the key voice in progress meetings, advocating for the plan’s priorities and ensuring that strategic discussions and actions remain on track. This is a great way to drive accountability at the highest level within the organization.

Communicate your results to the rest of the organization

Constant communication of strategic execution results is vital for transparency and reinforcing leadership engagement. After leadership review meetings, share progress updates, celebrate successes, and communicate any action plans with the rest of the organization. 

This shows that the strategy remains a priority to leadership and that they are actively monitoring its trajectory. Highlighting successes and acknowledging challenges fosters a culture where everyone understands the strategic direction, even as it evolves, and sees tangible evidence of leadership’s ongoing commitment. 

Collect regular feedback

Leaders should actively seek feedback from across the organization regarding their involvement in strategic planning and execution. If you’re about to start a new plan, gather insights on leadership engagement in previous initiatives. What worked well, and what could be improved?

Use things like surveys, informal discussions, or dedicated feedback sessions to gather this sentiment. Be prepared to acknowledge, own and act upon any negative feedback. If the sentiment is that leadership doesn’t care, address this directly and communicate the steps you will take to improve engagement moving forward. This demonstrates a commitment to continuous improvement and reinforces the importance of leadership in driving strategic success.

Facilitate leadership engagement from start to finish with AchieveIt

Ensure consistent leadership engagement throughout your strategic initiatives with AchieveIt. From collaborative planning tools that involve leaders from the outset to real-time dashboards providing clear visibility into progress and KPIs, AchieveIt keeps leadership connected and informed at every stage. By centralizing strategic data and fostering communication, AchieveIt empowers leaders to actively guide execution, make data-driven decisions, and drive successful outcomes with informed oversight.

Ready to empower your leaders and transform your strategy execution? Request a free demo today.