Bridging the Strategy Execution Gap

Strategy making and execution are essential to organizational success. However, many organizations are continuously challenged with bridging the gap between the two. Over the years, research has shown a good deal of time and resources are spent building strategies. Too often though, when strategies are translated into project-based work—the projects, programs and portfolio efforts that enable forward momentum—there is a break down, resulting in failure to achieve the organization’s strategy.

There are a number of factors that contribute to the gap between strategy and execution. One of the most significant opportunities to bridge the gap lies in empowering and upskilling the teams and leaders responsible for the execution of your project-based work.

Upskilling vs. Hiring New Talent

According to a recent TwentyEighty Strategy Execution Project Manager Salary and Talent study1, 83 percent of project organizations reported that they were understaffed, and 44 percent of the open positions were for senior project professionals. This number will continue to rise as demand for talent in the marketplace continues to increase.

Add talent challenges to external factors such as increased regulation and compliance, emerging technologies, rising globalization and the constant acceleration of business, and the case for increased investment in talent management practically writes itself. We know from research and experience that organizations actively working to develop and retain their talent maintain significant competitive advantages.

Bridging the Strategy Execution Gap

Successfully aligning and executing project-based work requires a strong mix of skills. Skills, or the lack thereof, directly impact the ability to execute projects and realize your strategies.

If successful strategy execution alignment is seen as a “roadway” that enables two-way flow between strategy making and strategy execution, it becomes easier to talk about the knowledge and skills required to improve organizational performance by strengthening strategy execution alignment.



In order to bridge the gaps and create alignment, leaders need to evaluate teams across a range of technical and relational skills that support strong strategy execution alignment. If you think of strategy execution as the “roadway” on a bridge, which enables seamless two-way flow of information between strategy and the required technical and relational skills as the pillars that support the roadway, you can more easily plot the various knowledge and skills required for your success. From there, it is much easier to look at where your organization—and your people—need to improve in order to achieve a higher state of strategy execution alignment.

We first break the skills into two pillars:

  • Technical skills are the ability to perform a specific job function or task, such as documenting a plan as part of a project or program management role.
  • Relational skills refer to how people interact with and analyze information, as well as personal relationships, such as strategic thinking and change management approaches used to lead a project or program’s execution.

This provides a structure to help an organization begin to answer a range of questions, including:

  • Are there gaps on the technical side—project performance, budget management, or governance issues for example?
  • Are there gaps on the relational side—effective communication, situational analysis or customer satisfaction?
  • Is the challenge simply having a good mix of team members who demonstrate strong technical as well as relational skills?
  • Where should you invest for the greatest and fastest impact?

The two skill pillars can further be broken down into foundation, mechanics and advanced.

Recognizing the required technical and relational skills as the pillars that support the “roadway” allows you to do more than identify where the gaps are. It helps facilitate determinations around the skill gaps that should be prioritized for investment.

What If Your Strategy Had Context?

A key benefit of having team members with a strong balance of skills is their ability to see, understand and communicate the context of the strategies driving their project-based work, as well as the organization’s strategic intent. And, more importantly, how the two fit together.

To be successful, your strategy needs to be developed and managed based on an ever-changing environment. This means your workforce needs to make decisions and take actions based on situational context—while still being able to drill down and get the work accomplished.

How skilled is your current workforce at navigating through the challenges and barriers created by internal and external forces that affect performance and outcomes? Can they answer the hard questions? Can they help chart a critical path to success?

Combine the right skills with context and your people will gain a more holistic perspective to strategy making, strategy execution and alignment. This fresh perspective will help make your organization’s execution more adaptive and successful.

What If All of Your People Thought Like You? Like Leaders?

Today’s business climate requires project-based work to be executed with more coordination and agility than ever before. People at all levels of the organization are being asked to take on more leadership and decision-making responsibilities. Enabling your people through the development of their relational skillset enables them to fulfill this “leadership at all levels” need. To build a team that can lead at any lead you need to:

  • Build and enable decision-makers who understand and can execute with appropriate risk.
  • Ensure people have the right skills to make improved decisions.
  • Create a culture where teams aren’t afraid to make a mistake and, importantly, can apply lessons learned for rapid insights that improve results.
  • Grow peoples’ relational skills enabling them to persuasively communicate needs, ideas and recommendations – up, down and across.

Enabling leadership at all levels drives innovation, breaks down barriers and enables your organization to proactively identify and resolve issues that can impact successful achievement of your strategic objectives. It also helps to make your organization more versatile and dexterous.

Bridging the strategy execution gap starts with people. First, you must understand what skills, resources and leadership are needed to execute complex strategies. Then evaluate what areas that need improvement and invest in upskilling and empowering your team. Having the right skilled people in place will have a powerful impact on your organization’s ability to align strategy with execution and transform the way you do business.


1. Study: Twenty Eighty 2013 Project Manager Salary & Development Survey,


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Tim Wasserman
Tim Wasserman is the chief learning officer for TwentyEighty Strategy Execution and the program director for the Stanford Advanced Project Management (SAPM) program. He is responsible for leading the strategy and content of all Strategy Execution learning solutions. Mr. Wasserman is an expert in the successful implementation of large-scale organizational behavior change, with more than 25 years of experience developing and implementing enterprise-wide initiatives for Fortune 500 companies. He has led design and implementation teams to improve execution capabilities for organizations including Cisco, Google, Medtronic, Nordstrom, Prudential, and Boeing. He has delivered workshops globally and is on the SAPM faculty delivering on campus at Stanford on the topics of organizational change and transformation and global team effectiveness.