Learning from Strategy Execution

By Hubert Saint-Onge

This is my fourth article on how to develop and execute strategy amid the ambiguity created by high turbulence in rapidly changing environments with compounding complexity. The initial article reviewed the sources of ambiguity and their impact on the business environment. It also pointed out that long-term strategic planning often falls short in times of ambiguity. A different toolkit is required to navigate rapidly shifting market dynamics; this is where the Emergent Strategy framework comes into play.

The second and third articles outlined the unique approach of the Emergent Strategy framework, which is supported by identifying market dynamics with sense-making and resulting narratives. This approach elucidates market dynamics and points to the outlines of emergent strategies. However, the results of these efforts are often too incomplete to form a solid base for strategy execution. In highly ambiguous environments, the assumptions initially generated from the sense-making process must be more thoroughly tested when executing changes under these assumptions.  This explains why the Emergent Strategy framework rejects the myth of the “perfect plan.” Instead, it treats strategy and execution as interdependent processes, where real-world action generates insights that reshape the first outlines of strategy.

Organizations cannot afford to separate ‘planning’ from ‘doing’ in a fast-moving, volatile world. For example, companies like Spotify and Amazon thrive by treating strategy as a hypothesis to test, not a blueprint to follow. This approach acknowledges that uncertainty is inevitable—but by learning from execution, organizations turn unpredictability into a source of innovation. The key lies in creating strategies that capture feedback, adapt quickly, and align teams around shared learning goals.

This fourth article explores how learning during execution catalyzes strategic evolution, fostering resilience and innovation in unpredictable environments.  Emergent Strategy challenges the traditional top-down approach by integrating strategy development with execution, treating them as a continuous, adaptive loop.

It focuses on how to leverage real-time learnings from the execution phase to refine and sharpen overall direction continuously. It shows how the Emergent Strategy framework treats strategy development with execution as a continuous loop, focusing on short planning cycles, rapid experimentation, learning, and constant adaptation.

I. The Dynamic Relationship Between Strategy and Execution

The Emergent Strategy diagram below illustrates how the Strategy Development and Strategy Execution cycles evolve in tandem, continuously informing each other, unlike in the traditional ‘strategic planning’ model, where planning is completed before moving to execution work. This implies that the strategy development cycle takes on a certain plasticity to allow changes engendered by the learning achieved in the execution cycle. When this learning is shared across people, teams and functions, it becomes the organizational learning that underpins the breadth and complexity of the collective focus and depth of understanding required for effective strategy-making.  When applying emergent strategy principles, organizations learn from real-time execution to refine their strategy and its implementation rather than rigidly adhering to a predefined plan. As teams act on strategic initiatives, they encounter unforeseen challenges, opportunities, and stakeholder feedback. Reflection on these experiences transforms raw data into actionable knowledge. For example, an underperforming marketing campaign might reveal shifting customer preferences and result in a strategic pivot.

This principle is the basis for the above diagram, which shows bridges (in dark blue) connecting

learnings from the four stages of the ‘strategic execution cycle’ to the corresponding stages of the ‘strategy development cycle.’ The learning that emerges in each Strategy Execution stage feeds directly back to each Strategy Development stage. The interactive forward and backward linkages between the two cycles are designed to enable learning and generate agile responses. By institutionalizing reflective practices like after-action reviews, organizations turn execution into a learning laboratory.  It is no longer possible to separate planning from executing.  Although it is always valid, this principle is even more pertinent in times of ambiguity. Given the speed and complexity of change, learning is essential in a turbulent market environment to connect strategy development and execution.  This learning produces a more profound knowledge of market dynamics based on the realities encountered.  A validated, well-grounded strategy emanates from this knowledge.  Learning also leads to enhancing the strategy with new ideas.  An innovative approach will out-distance the competition to win in the marketplace.

Typically, the Strategy Execution stages often receive less prominence in current practice, but in times of ambiguity, they provide critical feedback to refine the strategy. These stages include launching initiatives, executing a road map, embedding the necessary organizational changes, and interpreting and leveraging the outputs and results. In the “Launch Initiatives” stage, the execution work is divided into project teams responsible for laying the foundations for implementing the new strategy and testing the validity of different aspects. The second stage involves introducing changes to prepare the organization for execution, and the third one consists of interpreting and leveraging the initial outcomes. Learning is key to all three stages.   

Organizational learning generates the capabilities to compete effectively in the marketplace. It drives the ability to adapt quickly to dynamic conditions and changing demands in the business context. It produces strategies to innovate, breakthrough, and outdistance the competition. A key source of this learning is the dynamic feedback at the interface between the strategic development and execution cycles.  The inability to learn blindfolds an organization and engenders a downward spiral. Organizations require emergent structures, just as they require emergent strategies: when possible, start marginally, tentatively, and let experience take it from there. In other words, it allows structures, like strategies, to be learned before being planned. Even though rapid changes in the market are not readily recognizable, staying abreast of meeting customer needs means adapting capabilities such as structures, processes, and systems must take place with the shortest possible delays.

II Building Execution Teams with an Iterative Learning Orientation 

A learning-oriented culture is essential for bridging execution and strategy refinement. This requires psychological safety, where teams feel empowered to share failures and experiment without fear of blame. Leaders must prioritize curiosity over compliance, encouraging questions like, “What did we learn?” rather than “Who is at fault?” Tools such as agile methodologies or adaptive frameworks embed learning into daily workflows, ensuring insights from execution inform real-time strategic decisions.  

1.  High-Order Learning

a. Assumptions

One key area for learning is to discover through strategic initiatives what key assumptions have proven right through their early work on execution in the market interacting with stakeholders and which ones were found to be off base. The first task is to identify the assumptions underlying the strategic orientations and goals identified in the preliminary work in the strategy development cycle. Having tested the market from an execution perspective, Strategic Initiatives teams must identify and assess the assumptions in the initial strategic thinking produced in the Strategy Development Cycle.  These are questions that must addressed:

1.         What assumptions were made during the initial strategy work?

2.         What assumptions were validated in interactions with stakeholders?

3.         Which assumptions have proven invalid or need to be re-calibrated?

4.         What were the surprising findings in this inquiry?

5.         What new assumptions need to be researched and tested through the execution process?

6.         How did stakeholders (customers, employees, partners) react to the new strategic orientation?

7.         What are the most valuable suggestions made by stakeholders?

8.         What are the initial signs of marketplace changes that could eventually represent a threat?

The initial strategic thinking might be viable if the assumptions are on the mark or only require minor adjustments. However, if a whole new set of assumptions is necessary to underpin a potential strategy, it might be beyond the ‘elasticity’ of the organization’s collective thinking. At that point, a more profound organizational approach to learning must be architected to take place over a longer timeline.

b. Capabilities

Another key area of inquiry for the Strategic Initiatives teams is to determine what capabilities will be required to execute the different elements of the new strategy, either in the market-facing space or in the internal workings of the organizations, such as new processes and supporting systems. In my experience, organizations tend to assume their current capabilities can support a new strategy when this is nowhere close to the mark.  For instance, if the strategy requires an advanced level of customer centricity but the culture is not conducive, it might take too long to get there. These are the questions that should guide this inquiry:

1.         What are the dimensions of the new strategic orientation where the organization's capabilities represent a market advantage?

2.         What capabilities are currently missing?

3.         What capabilities could be acquired or developed within the required time window?

4.         How accurate are the leadership assessments of the current organizational capabilities on how they can support newly emerging strategies?

5.         If new capabilities are required, how can they best be developed or acquired?

If the required capabilities are outside the organization’s potential to be brought to bear, adjustments would have to be made to the strategic aspirations, or potential partnerships or alliances could be explored. However, many organizations cannot partner effectively to make this work.  Depending on the importance of this capability for the organization's success, supporting work might be required before launching new strategies.

c. Culture and Mindsets

Organizations that have been successful for many years develop strong views on how to run their business. The drive is to preserve the management principles that have contributed to its success. However, these principles often become mindsets integral to the culture. Over time, they can hinder the changes required by new marketplace realities.

Individual mindsets and collectively held assumptions are the main obstacles to generating new insights, considering the need to deal effectively with internal and external dynamics. Both mindsets and resulting assumptions were acquired through experience and were, at one point, well-suited to the business context. The problem is that they are rendered obsolete and counter-productive with accelerated change: the responses they trigger by route are no longer effective. The challenge is that once acquired, they are difficult to renew to fit a new context

For instance, if the findings of the Strategic Initiatives Teams point to the need for a strategy that strongly emphasizes customer-centricity, there might be some resistance at the outset by leaders who see this as a step too far. Their mindsets may initially keep them seeing the organizational culture as incapable of supporting the customer-centricity initiatives necessary to bring the desired strategy direction to fruition. For instance, they might see this initiative as adding costs the market cannot support. Renewed mindsets and assumptions give team members new lenses for assessing market dynamics and possible responses. Adopting new collectively held mindsets and assumptions makes it possible to see the possibility of adopting and implementing new strategy choices.

The questions that need to be answered in such a case are …

1.         What collective mindsets stand in the way of adopting a proposed strategy?

2.         Does the organization's leadership have the foresight and the courage to tackle this significant culture change? How do you make the business case to justify this chance

3.         What is the most effective way to facilitate this change?

4.         How do we ensure the leadership’s full commitment to the strategy and the culture change that will ensure its success?

This is where organizational learning plays a pivotal role. Experience has taught us that the best way of realigning mindsets and assumptions to a new reality is to create a high-trust container where people who respect one another constructively share their different points of view.  The best way to engender the learning required is to arrange a well-facilitated, trust-based conversation that allows participants to set aside the objections generated by their mindsets. The purpose of these discussions is to transition from defensive to productive reasoning.

The learning mechanism is straightforward: if colleagues whom I respect see strong potential in the proposed market strategy and believe it will allow us to capture new market growth, I will gradually come to terms with the need to start questioning my established beliefs and consider supporting customer-centricity as a vital new element of the culture.  

These deliberations will occur in the ‘Embedding the Change’ stage of the Strategy Execution cycle. With more discussions over time, leaders realize the potential of this strategy and commit to the changes needed to win in the market. This significant cultural change will remove the most critical constraint on moving the new strategy forward and pave the way for a successful new intervention in the marketplace. 

2. Foundational Learning

To harness the power of execution-driven learning, it is essential to start small: pilot reflective practices in one team, redefine metrics to include learning outcomes, and celebrate adaptive wins. Strategy is no longer a static document—it’s a journey shaped by every step taken.  

a. Conduct after-action reviews (AARs) after key milestones:

The After-Action Review is a structured debriefing method following a market intervention to test the potential impact of a strategy. This is a collaborative process that Strategic Initiative Teams can use to identify where there is a strategy fit and where changes are required.  It involves gathering participants to evaluate a strategy’s potential impact by comparing the intent versus potential outcomes, analyzing how the strategy would be received in the market and identifying the steps required to enhance the strategy.  These are the key questions addressed by this process:

1.           What were the targeted outcomes of the trials?  

2.           What actually happened?  

3.           Why were the gaps identified?   

4.           What will need to be retained or changed?

5.           What did we learn?

b. Feedback Loops:

Strategic Initiatives Teams establish robust feedback loops to gather insights from the execution phase. This involves collecting data and observations from various stakeholders, including team members, customers, and partners. Regular check-ins, surveys, and feedback sessions help capture real-time information about what's working and what isn't. This feedback is crucial for validating or reshaping the strategy as it provides direct input from those involved in or affected by the execution.

c. Iterative Processes:

Adopting an iterative approach allows teams to continuously test, learn, and adapt. By breaking down the execution into smaller, manageable phases or sprints, teams can experiment with different tactics and assess their effectiveness. This iterative cycle of planning, executing, reviewing, and adjusting helps refine both the strategy and the execution approach based on real-world outcomes and learnings.

d. Cross-functional collaboration:

Encouraging collaboration across different functions and departments can lead to a more comprehensive understanding of the execution process. When teams from diverse backgrounds and expertise come together, they can share unique perspectives and insights. This collaborative environment fosters a culture of learning and innovation, enabling the strategic initiatives team to identify areas for improvement and potential opportunities.

e. Data-Driven Decision Making:

Leveraging data analytics is vital for harvesting learnings from execution. By analyzing performance metrics, customer feedback, and market trends, teams can make informed decisions about the strategy and its execution. Data-driven insights help identify patterns, understand customer behaviour, and predict future trends, which are invaluable for strategy validation and adaptation

3. Adaptive leadership as a condition for enacting execution learnings

Most strategies promulgated by senior leadership are not executed successfully. The rigidities of the strategic planning approach are primarily responsible for separating strategy and execution. The Emerging Strategy requires “strategic plasticity”—bending without breaking. Strategy teams closest to execution often spot trends first. Empowering them to suggest strategic pivots accelerates adaptation but is impossible without adaptive leadership

Adaptive leadership and a learning-oriented culture are essential for bridging execution and strategy refinement. This requires psychological safety, where teams feel empowered to share failures and experiment without fear of blame. Leaders must prioritize curiosity over compliance, encouraging questions like, “What did we learn?” rather than “Who is at fault?” By listening to the feedback generated through these learning tools, leaders can identify misalignments between the strategy and customer needs, leading to fine-tuning their customer interactions, audience targeting and products.

Leaders play a crucial role in fostering an environment where learning from execution is prioritized. Adaptive leaders encourage experimentation, support risk-taking, and are open to changing course based on new insights. By modelling a learning-oriented mindset, leaders involved in both the Strategy Development Cycle and Strategy Execution Cycle inspire their teams to seek ways to enhance strategy and execution continuously.

 By utilizing these learning tools, Strategic Initiatives Teams and their colleagues involved in other stages of the Strategy Execution Cycle can effectively harvest the learnings needed to validate or reshape their strategy and execution approach, ensuring they remain agile and responsive in ambiguous and turbulent environments.

Conclusion

Execution is not merely the implementation of a strategy—it is a source of critical insights. As teams implement strategic initiatives, they encounter unforeseen challenges, opportunities, and stakeholder feedback. Reflection on these experiences transforms raw data into actionable knowledge. For example, an underperforming marketing campaign might reveal shifting customer preferences, prompting a strategic pivot. By institutionalizing reflective practices like after-action reviews or agile retrospectives, organizations turn execution into a learning laboratory.  

In Emerging Strategy mode, execution is not the end of planning but the beginning of learning. Organizations cultivate agility, responsiveness, and creativity by treating strategy as a living process. Integrating learning into execution ensures strategies remain relevant amid complexity, turning ambiguity into a strategic advantage. Ultimately, organizations that listen, learn and adapt can thrive and grow—not despite challenges but because of them.