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Three Strategy Execution Problems We Keep Seeing in Practice

Developing a strong strategy can be a difficult endeavour on its own, but making it work across an organization can be even harder.

In our research with senior leaders, the barriers to successful strategy execution rarely stem from a lack of ideas. Leaders pointed to challenges that emerge as strategies move into action, with priorities competing for attention, alignment becoming harder to maintain, and progress becoming more difficult to see.

We see these same challenges in our client work, often reinforcing one another in ways that make execution increasingly difficult.

Three patterns come up consistently in both our research and our work with clients: prioritization, alignment, and measurement. Each has important implications for leaders working to build strategies that stick.

1. Prioritization: Making strategic choices requires deciding what will deliberately NOT get done

76% of leaders said a lack of or inconsistent prioritization got in the way of successful strategy delivery.

Strategy naturally generates possibilities, with new initiatives, investments, and capabilities all competing for finite capital and internal resources. When too many of those possibilities become priorities, organizations can quickly spread their resources too thin.

Deliberate choice is fundamental to strategy. Leaders must make explicit trade-offs on where the organization will concentrate its resources and what it is prepared to defer, reduce, or stop.

This becomes especially important when an organization is already operating close to capacity, because adding new priorities without changing existing commitments makes it increasingly difficult to execute any of them well.

We saw this at one home-services organization, where new initiatives continued to emerge throughout the year. Teams had limited visibility into what others were working on, capacity became stretched, and the strategy began to lose momentum.

Working with department-level leaders, we introduced a two-quarter planning cadence and developed a dashboard to provide a clearer view of upcoming initiatives across the organization. Leaders could see what was already in flight, assess competing demands, and make more informed decisions about where to focus resources. Moving away from an annual planning view also allowed priorities to be revisited as circumstances changed and new initiatives emerged.


A question for leaders:
When something new becomes a priority, is your organization equally clear about what will receive less attention as a result?

2. Alignment: Agreement in the room does not guarantee commitment and shared ownership outside of it

67% of leaders identified internal misalignment as a barrier to successfully delivering their strategy.

Misalignment often becomes visible during execution through inconsistent messages, conflicting decisions, and teams moving in different directions. While these issues can appear to be communication problems, they often reflect how people were involved in developing the strategy in the first place.

People need meaningful opportunities to understand the evidence behind strategic choices, contribute their perspectives, and work through areas of disagreement before decisions are finalized. The goal is to build enough shared understanding and commitment that people can move forward consistently once a decision has been made.

We saw this at a cold-storage and 3PL organization experiencing rapid growth. Strategic decision-making had historically been concentrated among a small group of executives, and as the organization grew, implementing new strategies became increasingly difficult.

We brought together people from across functions and levels of the organization to help define a focused set of ambitions. Bringing more perspectives into the process helped shape a practical plan grounded in what the organization needed, while giving those responsible for execution a clearer understanding of the choices being made and the rationale behind them. Having participated in the process, they were better positioned to carry those choices forward in their own areas of the organization.


A question for leaders:


Have the people responsible for delivering your strategy had the opportunity to understand, challenge, and ultimately own the choices behind it?

3. Measurement: What gets measured needs to change as strategy moves through the organization

74% of leaders said not measuring or managing progress significantly hindered their strategy’s success.

Organizations can have strategic measures in place and still struggle to sustain momentum in execution. Measures that are useful to the executive team do not always give the people responsible for day-to-day execution the information they need to make decisions. Long-term outcomes such as customer loyalty, culture change, or revenue growth are important, but they often move too slowly to show whether the work underway is having the intended effect.

As accountability moves through the organization, measures need to become more specific and actionable so that teams can see how their work contributes to the broader strategic outcome.

Consider customer loyalty. An organization might track Net Promoter Score as an enterprise-level measure, while operational teams need measures that are closer to the work they control.

Customer Support might track first-contact resolution or wait times, while Product could monitor issue-resolution speed or feature satisfaction. These measures give teams a more immediate view of performance and help them understand how their day-to-day work contributes to the organization’s longer-term goals.

They also give leaders an earlier indication of whether the work underway is moving the organization toward the results it wants to achieve.


A question for leaders:
Can your teams see the connection between what they measure regularly and the results the organization ultimately wants to achieve?

The Patterns Are Connected

Prioritization, alignment, and measurement can look like separate execution challenges, but in practice, they often reinforce one another. Poor prioritization makes alignment harder when teams receive competing signals about what matters, while weak alignment can make measurement less useful because ownership is unclear. Without useful measures, leaders have less visibility into whether the strategy is progressing as intended and where adjustments may be needed.

Many of these execution challenges can be addressed during the strategy development process itself. Decisions about who is involved, how priorities are set, where ownership sits, and how success will be measured all influence an organization’s ability to carry the strategy forward.

When these elements work together, people across the organization have greater clarity about what matters, what they are responsible for, and how their work contributes to the strategy.

A strategy starts to stick when those individual decisions reinforce one another, giving people across the organization the clarity and commitment to turn strategic intent into action.

At Level5 Strategy, an award-winning boutique management consulting firm based in Toronto, we help leading Canadian organizations navigate challenges in strategy execution with the right tools and insights. Whether you’re exploring our approach to strategic alignment or strategy measurement, our experienced team delivers the hands-on support needed to drive lasting success. For more expert perspectives on strategy consulting services, explore our latest thinking or connect with our team.

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