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How To Overcome 5 Common Challenges Leaders Face In Executing Strategy

Last Updated: September 26, 2023
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From communication to time management and beyond, learn how to make strategy execution a reality for you and your team.

67% of good strategies reportedly fail because of execution.  Five of the most common challenges to execution are: poor communication, lack of alignment, absence of structure, time management, and not having the right resources.  

Overcome these challenges by implementing practices that enable you and your team to execute effectively.

Communicate Intentionally and Constantly

One of the main challenges leaders face in team settings is effective communication. A team that fails to communicate also struggles to execute. Poor communication can result in doing the wrong thing, confusion over tasks, and unresolved issues, which make it hard for strategy to see the light of day. 

Practice these 5 things to increase the frequency and clarity of communication:

  • Use icebreakers to get to know your team: A team that’s comfortable around each other will communicate more easily. Make time for lighthearted engagement and commit to an ongoing process of developing relationships to help everyone feel at ease.
  • Connect activity to the overall strategy: Get in the habit of answering questions such as, “why we’re doing this” and “how this fits into our strategy.” These questions help connect the dots between an assignment and strategy and make it clear that each project has a purpose.
  • Always close the loop: Don’t let things float without a clear next step or owner. Train your team to always give tasks and projects a “date and driver” (i.e. a deadline and an owner). When a task or milestone is done, make it a habit to define and assign the next action that must occur.
  • Keep your team on the same page: Make sure everyone has the same definition of “done.” And use the power of visual explanation to eliminate confusion; tools like TechSmith, Lightshot, and Loom are great for providing feedback and instruction, while diagrams are powerful for helping your team see a path or important connections in their work.  
  • Communicate candidly: Above all, be human and strive for real dialogue to surface issues and different points of view.

Create Structure

Absence of structure creates a challenge to executing strategy because it eats at a team’s brainpower. If your team is constantly guessing at what needs to happen next or reinventing the wheel, you’re all wasting precious time and energy.

To combat this:

  • Define your goal clearly: What are you working toward? What does success look like? Why does it matter?
  • Take an “SOP” approach to translate your goals into an action plan:
    • Strategy: Where are we going and why?
    • Operations: how will we get there?
    • People: Who do we need on the journey?
  • Measure progress against goals and priorities to manage them.
  • Make the time to reflect after milestones are met or when something isn’t going to see what worked, what didn’t work, and what needs to adjust for a strategy to get implemented.

Create success structures by setting guidelines (e.g. “it’s up to you how to get it done within a $500 budget limit”), using templates (hint: many templates exist in your sent emails), standardizing processes where it makes sense,  and even automating repetitive tasks.

Audit Your Resources

Does your team have what it needs to successfully execute? Answer this question honestly with a reality check of budget, skills, time, tools, training, and authority. Ask your team what they need. Sometimes the money is there but teams don’t have “permission” to use it. Sometimes, a specialized skill is needed that doesn’t exist within your organization.

A special note on software tools: if you don’t know what you have and how it’s being used, conduct a tool audit. A tool audit will help you and your team understand what’s available and what is missing.  Make a list of each tool you have, what its purpose is, how much it’s being used, and note any features you could take advantage of to help you execute work. Eliminate unused or redundant tools and commit to the ones that help your team get work done.

Take Responsibility for Aligning Your Team with the Work

An unaligned team will find it hard to get projects done, spend time on the wrong things, and even abandon their work. They’ll struggle to achieve results simply because they don’t know what to focus on.

Enable your team to do their best work together by communicating the vision of where you’re headed, how their work connects to the vision and strategy, and addressing anything that is out of alignment, e.g. confusion around roles.  Ensure they always know:

  • Who is responsible for what
  • How to ask for help or identify hurdles
  • How and when to check in on progress 

Keep the purpose and path clear so your team can focus, move in the same direction, and get the right things done.

Manage Your Time

Poor time management means wasted energy and incomplete work. Even worse for leaders, poor time management can get in the way of your most important work, i.e. vision casting, strategy design, and people development.

Develop these 5 habits to own your time and set an example for your team to follow:

  • Prioritize: Define 3-5 priorities to focus your money, energy, and resources.
  • Distinguish between what’s important and what’s urgent. The Urgent-Important Matrix is a helpful tool.
  • Schedule your priorities: Set time aside to work on what’s important to you — and respect it just as much as you would a client or team call.
  • Say no: Identify what is taking time away from your priorities and learn to say no.
  • Use the Rule of Three to plan your day.

Successful Execution Starts with Purposeful Leadership and a Team Equipped for Action

Your most brilliant strategy will fail if you’re unable to implement it. This can be due to confusing priorities, unclear roles, and not having the structure or resources to complete work.

Overcome the common challenges to execution by building implementation habits that enable you and your team to get the right things done.

Related: How to Foster an Engaged Remote Team (Try These Leadership Tips) 

Want to build a stronger execution muscle in your business? Get the free download: 7 Leadership Habits for Effective Execution.

Leading Your Team and Business Shouldn’t Be Overwhelming

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