How to connect strategy to execution

by The Smartsheet Team

January 16, 2024

7 key steps for connecting strategy to execution


PPM Blog Visual #1


A sound strategy is critical to the success of any business, but executing on that strategy is the real challenge. Consistent execution is also what sets the strongest companies apart. If your organization isn’t hitting its targets, deadlines, and KPIs, it’s time to figure out where the gaps are and why.

Here, we detail the signs of a strategy-execution gap and outline seven important steps to help your organization follow through and deliver on its goals.

What are the signs of a strategy-execution gap?

Strategy-execution gaps occur when an organization’s real-time execution fails to meet the goals the team developed during the planning phase. As businesses grow and evolve, the process of identifying these gaps–and, more importantly, preventing them in the first place–becomes more complicated. There are several indicators of an execution gap, including:

  • Missed targets and objectives
  • Lack of progress or difficulty tracking progress on critical initiatives outlined in the strategic plan 
  • Employees and teams are unclear about their roles and responsibilities in relation to strategic objectives 
  • Inadequate allocation of resources, including time, labor, and budget 
  • Misunderstandings and misalignment among different levels of the organization
  •  Delayed time-to-market

7 crucial steps to for successful strategy execution

Incorporating the following steps into your planning process will help you develop a strategy that’s set up for success from day one. 

1. Start with a sound strategy.

Starting with an executable strategy might seem like a given. However, many organizations charge straight into the execution phase without subjecting the strategy to the necessary stress tests. It’s vital to step back and evaluate whether the strategy can be executed–and whether it should. Consider the following questions as you build your strategy:

  • Is the strategy aligned with the realities of the organization? The strategy needs to reflect what is actually possible given current capabilities, people, resources, and time.
  • Is the strategy clear, specific, and understandable? People at every level of the business need to be able to understand how the strategy applies to their role and their day-to-day work.
  • Does the strategy include perspectives from across the organization? The collective wisdom of employees at all levels can uncover insights, ideas, and potential pitfalls that may not be apparent from a top-down perspective.


PPM Blog Visual #2

2. Create a shared vision.

Just as an architect needs to gather input from the engineers, builders, and craftsmen who will bring a blueprint to life, it’s important to engage the people and teams who will be implementing the strategy on a day-to-day level. Communicate the “why” behind your strategy so that your team has both a greater understanding of the root cause and a deeper connection to the work. While leaders might have the best intentions during the planning phase, the executors of the strategy are likely balancing a variety of priorities and obligations that could affect every aspect of the process. Getting everyone on board enhances ownership, commitment, and alignment. 

3. Clearly define metrics of successful execution.

Without clear KPIs, strategy execution becomes a guessing game. These metrics provide the yardstick for measuring progress and alignment with strategic objectives. Clear and quantifiable KPIs not only establish a common understanding of success, but also enable teams to track their performance in real-time, identify areas needing improvement, and make data-driven decisions. They also serve as a navigational tool, helping teams stay focused on strategic priorities.

4. Establish effective channels of communication.

Communication is the backbone of strategy execution. Transparent communication ensures that every member of the team understands the overarching goals, their role in achieving them, and how their work contributes to the bigger picture. It enables employees to make informed decisions, ask questions, and provide valuable feedback, while preventing misunderstandings and misalignment. Clear communication channels also allow leaders to convey changes, updates, and adjustments to the strategy as they happen.

PPM Blog Visual #3

5. Empower decision-making at all levels.

The timeline from strategy to execution can get stalled completely by a top-heavy decision-making structure. By decentralizing decision-making, leaders not only accelerate the process, but also tap into the collective intelligence, creativity, and expertise of the entire team. Invest in developing leadership and managerial skills at all levels, and ensure employees have a very clear sense of what they are and are not allowed to decide.

6. Build in contingency plans.

Contingency plans are designed to address unexpected events and risks that may arise during the execution of a strategy. Including contingency plans in your strategy is not a sign of pessimism, but rather a strategic necessity for smart risk management and resilience in an unpredictable environment. These plans allow the organization to respond effectively to unforeseen challenges, reducing the impact of disruptions and protecting the portfolio's objectives.

 7. Foster continuous learning and adaptation.

Successful strategy execution requires both agility and adaptability. Facilitate a culture of continuous learning, where the team is encouraged to acquire new skills, keep track of the competition, and stay updated on industry trends. Monitor the execution process regularly and be open to making adjustments to the plan when necessary. Learn from both successes and failures, and use those insights to refine the execution strategy.

To gain a better understanding of where your team stands today in terms of strategy execution, take the Smartsheet Project and Portfolio Management Maturity Assessment


PPM Blog Visual #4