The Biggest Barriers for any Director of Strategic Initiatives


When a company has ambition, vision, objective, and goals it is the Director of Strategic Initiatives who bring these aspirations of an organization into reality. 

They create the plan and develop programs to guide the organization in the right direction. Every company has a strategic plan to focus on their weakness and on key areas which will impact the business outcomes. 

But unfortunately, 68% of the formulated strategies are never realized due to poor execution. In another study conducted by PMI, 61% of the employees think that their firm often struggles to bridge the gap between strategy formulation and day-to-day implementation. 

Due to this, the Job of Director of Strategic Initiatives is crucial since they have to bring ideas, plans, and strategies to fruition by overcoming the challenges that are associated with strategic implementation. 

In this article, we discuss some of the most important challenges that Director of Strategic Initiatives typically face and how to overcome them. 

  • Goal Setting
  • Small Milestones 
  • Shortage of Resources  
  • Ineffective Training  

Goal Setting 

Formulating a strategic goal could be difficult as there are multiple factors like location, culture, organizational objectives, resources, and skillset that have to be considered. 

To achieve this, you have to opt for a particular goal-achieving methodology that sits well with the DNA of your organization and not the one you are comfortable with. 


You have to do a SWOT analysis, Benchmarking, and analyze last year's goals before selecting a particular goal planning method or framework. 

There are numerous goal-planning frameworks like SMART Goals, OKRs, BHAG, Backward Goals, One Word Goal, Goal Pyramid, etc. 

But you may ask which framework is efficient to ensure success? 

Well, there is no particular framework that can help you achieve your goals unless you stick with it till the very end. It depends entirely on your organization’s needs and is context-specific. Selecting a particular framework and religiously following it will help you achieve your goals. 

Small Milestones  

By now we understand that for a successful implementation, day-to-day execution of tasks is essential. It is ideal to set the right expectation across all the departments and set small milestones on the way that will help you and your employees to stay on track. It also gives a sense of success and acts as a source of motivation.  


You can use project management tools that will not only help you to set the micro tasks and milestones but will also help you to track how you're approaching the ultimate goal. 

This way your implementation will head in the right direction with minimum hiccups. 

Shortage of Resources  

This is a common problem in organizations. It is important to understand what kind of dependencies can arise and what kind of role is required to fulfill those dependencies.  

The challenge is not limited to Human Resource, but it is also associated with a digital resource which helps the employees and management to achieve their goals. 


The organization must plan what kind of software and infrastructure is required to begin the strategic initiatives. 

86% of stakeholders say that prioritizing and funding the right initiatives is important to stay competitive and it is also necessary to manage resources efficiently rather than holding it because of poor allocation of budget. 

It is always better to start within a focus group and scale it as you start seeing results, this way you won’t exhaust your resources in one go and could save it from getting wasted on initiatives which might not provide expected results. 

Ineffective Training  

Strategic initiatives run on a tight timeline and to make it a success it is necessary that your employees are trained properly and know their way through the new process. 

Unfortunately, because of the forgetting curve employees tend to forget 70% of what they learn in a matter of 24 hours and this could reach up to 90% in a span of one month. 


The key is to reinforce the training but using traditional training methods only delays the process of adopting the new process. 

No doubt traditional training method is effective, but it is not scalable. Further, traditional training is not feasible in the new normal since most of the employees are working remotely. 

The modern training method is the answer to overcome the forgetting curve. You can use training tools like Apty which is a Digital Adoption Platform that guides your employees from one step to another and helps them accomplish their tasks in no time. 

It helps you to train your employees within any web-based application and they get familiarized with the new application and process from day 1.  

It is not just another walkthrough solution - rather a training method that helps you to identify and fix how your employees from different departments and locations are using the application. Based on that, you can create not only the contextual walkthroughs but also other supporting content like Video, PPTs, PDFs, and SCORM. 

Strategic Implementation is no easy task... it could be challenging. Formulating a strategy is one thing and implementing it is an entirely different thing. It is important to segment the goal into micro-milestones and to manage the resources judiciously.  

At last, the success of the strategic implementation lies in the hands of your employees. You have to train them with a training tool like Apty which not only helps you meet your deadline but also ensures that the new process is adopted in an intended manner.

Overcome the Strategic Implementation Challenges with Apty

Krishnan Kaushik
Written by Krishnan Kaushik

Krishnan works at Apty. He is passionate about Marketing and in love with Google SERPs. You can find him on Twitter @IAM_krish_v and can challenge him for a match of chess.

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