Overcoming Roadblocks to Strategy Execution

Most organizations conduct a periodic process called strategic planning.  Oddly, these exercises tend not to be strategic and few produce anything resembling a plan.  Even if the process establishes a solid plan, there are many obstacles ahead. These problems can stop your project in its tracks or veer it seriously off course.  Avoiding execution roadblocks and minimizing the ones you cannot avoid are key to a successful strategy implementation.  Consider the following issues and suggested solutions when planning your strategic initiatives.

For more on Strategy gone wrong, check out these Deadly Sins of Strategic Planning

13 Strategy Execution Roadblocks

  1. Plan Is Too Big
  2. Strategy is Misaligned to Corporate Culture
  3. Conflicting Initiatives
  4. Not Enough Time
  5. No People Available
  6. Tech Cannot Support the Project
  7. Inconsistency Across Projects
  8. Nobody Knows What is Going On
  9. Are Making Progress?
  10. Lost Momentum
  11. Repeating Mistakes
  12. Are We Solving World Hunger Now?
  13. Won’t This Project Ever End

Plan Is Too Big

Strategic planning processes often produce broad directions or concepts but cause roadblocks by skimping on defining how to get there.  An example of a common strategy is international expansion.  Sounds straightforward but there are a number of interim steps that need to occur on the path.  To combat this roadblock, break the plan down into actionable initiatives that can be addressed within one year or less.  These are the specific steps that move toward the strategic goal.

Strategy Culture Misalignment

Once the strategy is broken down into initiatives, check that these fit with the organization’s culture.  Often, strategy can require a change in corporate culture, but that change does not happen without a plan of its own.

For example, if your organization has low transaction volume and the strategic initiative envisions a product line or customer set with very high transaction volume, the initiative will need to include systems, resource and cultural change components.

For more on Strategy Culture Misalignment, check out Value of Culture and Strategy Alignment

Conflicting Initiatives

Strategy initiatives cannot succeed if they are competing with a number of existing projects.  Strategic projects tend to have longer term goals so naturally folks will want to focus on shorter term projects first.  To combat this roadblock, include in the planning process a review of existing or upcoming projects.  Determine priorities and if necessary, terminate or delay other projects.  If that is not possible, then reassess starting the strategic project.

When it comes to strategic initiatives, if you can’t finish them, don’t start them!

No Time

These initiatives require efforts that can interfere with existing operations and cause roadblocks.  In these cases, there are two choices; either add resources or decrease workload.  Before initiating a strategic project, check that time is available and if it is not then look for low value tasks to eliminate or bring in some temporary help to manage day to day tasks.  Avoid using temporary help for the strategic project.  Let them handle present workload and focus staff expertise on the future.

No People

This roadblock occurs when you do not have the right resources to complete the project.  Perhaps there is a missing skillset or the staff in a particular area is already overwhelmed.  To overcome this, while planning the project, ask for information on planned staff outages for medical reasons or upcoming retirements.  Also check for crunch times during the project timeline when groups may be unavailable and identify any critical missing skillsets.  Plan tasks around resource availability and ensure skill gaps are filled via consultants or educational programs.

Tech Issues

Strategic projects tend to have large scopes which may lead to technology limitations. For example, the goal of the project is to increase web interaction, but the current system capacity cannot handle the high-side potential volume.

These issues should have been identified when resourcing the project, but if not, the plan may need to be altered to include a technology solution.  Altering a project mid-stream requires a reassessment of the plan, resource budget and priority.  Do not simply add a significant project deliverable without a formal review of the change.


Often there will be more than one strategic initiative occurring simultaneously. The roadblocks come when staff are shared across multiple projects and they receive different guidance on expectations.  This can cause confusion and frustration.  To avoid this issue, build centralized planning and review processes. This includes clear consistent reporting by project leaders and status reviews.  During the reviews, look for different expectations and management styles in the project leaders and work to standardize.

Nobody Knows What is Going On

Project teams falter when they do not receive clear instructions or when there is no clear plan for the steps ahead.  These issues can result in duplicate efforts, incomplete tasks, bottlenecks and team aggravation.

To avoid this issue, communicate the plan clearly to all team members, stakeholders and those impacted by the plan.  Do this early and often to get everyone on the same page and keep them there.  In addition, there should be one overall project leader or steering committee, so that significant issues can escalate to one place.

Are We Making Progress?

Nothing slows a project down more than the perceived lack of progress.  This issue can be caused by either an unresolved issue or an insufficiently detailed project plan.

Unresolved issues are a project killer. If a significant issue arises, put together a plan to address it and assign an amount of time.  Do not let it linger.  If the issue cannot be dealt with in a reasonable amount of time, then the project may need to be reassessed.  Do not overanalyze as it will mire the project.

Developing a project plan can be challenging, especially when there are unfamiliar steps.  This can lead to large general tasks with long implementation times.  In these cases, it becomes hard to tell if the project is actually moving forward.  Avoid these chunks by breaking down any project step that requires more than a few weeks to complete.  Find interim milestones or subcomponents.

Lost Momentum

Sometimes even the best run project hits doldrums.  They may come at a stress point, soon after a major accomplishment or as the result of an issue outside of the project.  These low energy times can diffuse focus or decrease the team’s enthusiasm and attention to detail.

Overcome this roadblock by reengaging the team regularly.  Review progress on the project, celebrate successes, do some creative problem solving or team building exercises.  Consider taking a short break from the project.

If the issue is external to the project, for example, if there is a major issue with the organization, then stop to check that the issue does not impact the project.  Discuss with stakeholders and determine that the project should continue.  If the external issue requires the project be put on hold, then ensure documentation is up to date and set a time to reassess the project in the future.  Don’t forget to recognize the team for their efforts.

Repeating Mistakes

Teams that do not learn from their mistakes can easily derail an initiative project. Frustration and finger-pointing are indicators of this roadblock and there are two common causes.  Either the mistake is covered up or the mistake is not adequately assessed.

If a team member uncovers a significant error, enact a communication and assessment process.  For this to be effective the process must be learning-based not blame-based and it must be transparent.  Complete a root cause assessment of the error with the team and implement corrections that will ensure the issue does not recur.

Are We Solving World Hunger Now?

One of the most difficult roadblocks is scope creep, which happens when the project expands from its initial size or objectives.  This can happen when the project finds related issues or opportunities.  These are added informally as additional steps in the project plan and appear to be insignificant, but they are like project crack.  Once the project is altered without proper oversight, it becomes easier to justify larger changes.  Suddenly, the project has taken on a life of its own and the original outcomes are forgotten.

Luckily, this roadblock is easily dealt with in its early stages.  Instill solid change control procedures in your project plan.  Any change, no matter how small should be reported to the project leadership or steering committee for pre-approval.

If scope creep takes hold of your project and it is not stopped early, it becomes much harder to control.  Once you identify an advanced case pause and conduct a project reassessment.

Won’t This Project Ever End!

Much like this post, some projects seem to linger.  This may be an indicator of scope creep, but it may also be a symptom of another roadblock, perfectionism.  Strategic projects rarely have clean end points, more likely they move the organization in a direction and measure progress via key metrics.  Sometimes these projects have action loops with steps to be done if certain metrics are not met and those loops can create a never-ending project.

Knock down this metric by establishing directional metrics with ranges so that there is less possibility one missed measure will not keep the project going.  Set a time expectation for the project and conduct periodic assessments of the value to proceeding.

Bonus Roadblock

As initiatives are completed, recognize the project team staff, as well as those who were maintaining day to day operations.  This avoids one of the worst project roadblocks, namely a staff unwilling to take on projects due to lack of recognition of past efforts.

Bottom Line

Strategic planning is tough and even the best plans face challenges during implementation.  Establish proactive resolution processes and watch out for competing priorities, scope creep and never-ending projects.  Engage and listen to your team and don’t forget to celebrate and recognize accomplishments. Be prepared to face roadblocks along the way to ensure successful execution for your strategic initiatives.

What roadblocks have you overcome when implementing your strategic plans?  Please share your thoughts in the comments section.

About the author:

Michael F. Cade is an advisor and executive coach, taking the nonprofit sector Beyond the Numbers.  He is a leadership pathfinder, helping nonprofits optimize operations and strategy to attain long-term viability and relevance.  His Framework for Fiscal Sustainability is an innovative approach to evaluating organizational health and ensuring the ongoing successful delivery of mission.

Mr. Cade speaks on nonprofit and strategy topics, has authored several articles on financial and nonprofit leadership, as well as guest blogs and podcasts. He publishes the nonprofit leadership blog  Not for Profit Beyond the Numbers

If you have questions or would like a consultation on a nonprofit leadership or operational issue, contact him at:  mfcade@nfpbeyondthenumbers.com