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Overcoming the Top Obstacles to Strategic Planning


May 10, 2023

The history of strategic planning ranges from elaborate processes with minimal customer and stakeholder involvement and team insight to grandiose goals that are disconnected from the financial and operational realities of the organization. If the purpose of strategic planning is to create a system to enhance competitiveness and to have a sustainable competitive advantage, then for most organizations there is work to do.

There are significant opportunities for the strategic planning process to evolve into a system of continuous virtuous improvement to meet and anticipate all stakeholder needs over time.

Due to accelerating technology, business, culture, and society transformation strategic planning needs to adapt and include a more agile data-driven improvement system. This will foster alignment of the customer, stakeholder, competitive, and market insights, vision, and purpose, financial and operational realities as well as talent and culture development.  The descriptions of the top five obstacles to overcome are based on the twenty-plus years of guiding more than 250 organizations to lead the transformation toward higher performance.

Obstacle 1

“Even though we know that we can’t manage what we are not measuring, it is not easy to get the right measures.”

This includes disagreement around key measures, incompletely defined key metrics, and lack of external data as well as operational focus on key measures as an executive team. The impact is a lack of focus on the largest gaps in competitive insight, customer perception, and organization performance to be addressed in the plan.

Agile strategic planning assumes that data on current external competition and customer data, as well as operational performance, is defined and available.  If this is not the case, incorporated in the plan is the process to define and measure key performance data and confirm it as a baseline for measuring the success of the plan and the performance of the organization.

Three strategies that address and overcome the lack of a data dashboard on current key performance measures:

  1. Ensure executive team members agree to vital key measures in the business and create/update the data dashboard as a baseline.
  2. Insist all aspects of key measures are included both qualitative and quantitative.
  3. Create continuous processes for gathering external data so decisions can be made throughout the life cycle of the plan.

Obstacle Two

There is not currently a culture of consistent, competitive, customer data collection:  to ensure a customer-informed and involved strategic planning process.

This can include a lack of history in seeking customer input to gather data, report on data, and understand customer changes. The impact is planning can take on a path of its own and lack focus on what customers need, want, and would solve their biggest challenges.

An Agile strategic planning process is built upon intimate customer insight and access to customers to provide vital feedback to inform, influence and confirm a plan, and to involve in rapid cycle change during implementation.

Three strategies that address the lack of consistent, competitive and customer data collection:

  1. It is important to have a dashboard on the most important customer data that is informed by customer feedback as a baseline.
  2. It is imperative to have continuous customer engagement to understand your customer’s rapidly changing environment to be able to quickly adapt to meet changing needs.
  3. Finally, it is optimal to involve customers directly in the planning, pilots, and improvements to become more agile and real-time data and feedback to inform plan development and project implementation.

Obstacle Three

A lack of involvement among key internal and external constituents:

First, inform, engage, and be involved, so that buy-in from all constituents is accomplished as a deliverable within the plan.  This often involves organization structure, talent, and the system’s current reality.  People will not support what they are not asked to help create.

An Agile planning system includes new technology and processes for giving all internal and external constituents a “voice” in the development and assessment of current operations, talent, and systems as well as the opportunity to respond to the strategic themes of a plan before it is implemented.  Also, the details of three-year objectives, one-year goals, strategies, measures, and responsibilities are a must to set the team up to succeed with the plan. 

Three strategies that address the lack of involvement of key internal and external constituents:

  1. First, consider a Customer/Client Advisory council that is designed to provide feedback and planning, new products, pricing, and changes.
  2. Second, think about how to engage Senior Leadership and all of leadership to define strengths and weaknesses as well as organizational capacity review.
  3. Third, envision an encompassing process to gain team member perspectives via surveys and targeted focus groups on topics defined by customers and leaders.

It takes unusual curiosity and courage to seek feedback that may include information that is hard to hear and vital to future growth: a good planning process accomplishes both and engages all constituents.

Obstacle Four

Lack of understanding that transformational plans are only possible if organizational values and culture are defined:  

It is essential to understand strengths and opportunities based on the current culture and future-defined values.  Stepping over a review of current and future values and a culture assessment will dramatically limit planning potential.  Culture eats all change, especially strategic plans, for breakfast.

A culture assessment and review of values is an intrinsic part of an effective strategic plan. The intentional transformation of culture is the best way to help executives to socialize the mindset and skillset shifts that will be needed to succeed with the plan and to perform at the next level.

Three strategies to consider:

  1. Include updated values: We know values are the foundation of enhancing culture also known as the organization’s social system. Often when creating a plan, new values such as adaptability, innovation, and enterprise thinking are needed. This is to help leaders and the team to understand what is required in the shift to create a future environment for success.
  2. Assess current culture: If culture is about what the team experiences, then what is more important than revisiting culture during the planning process as well as assessing strengths and culture readiness on the path ahead?
  3. Define culture shifts needed: Involve key stakeholders in the planning process and give input on the aspects of alignment, collaboration, empowerment, and innovation. Also, to assess specifically what emphasis is needed to update values and define the “from and to” of the desired culture to pave the way for understanding, buy-in, and support of the future environment that will be needed to succeed with the plan.

Obstacle Five

The propensity to overcomplicate the review and revision of vision and to undervalue the importance of developing a purpose-driven mission:  to engage all constituents in the plan.   This calls for a level of clarity that is a true differentiator when well-articulated.

If executives have not experienced the profound impact and momentum that a compelling vision and mission can create, they often undervalue the importance of framing the organization’s unique value proposition as a differentiator.  It also limits the impact on customer perception and buy-in as clarity and communication are less focused and intentional.

Three things that matter about vision, mission, and communication:

  1. With more volatility, uncertainty, complexity, and ambiguity (VUCA) than ever before organizations must revisit the vision and focus on strategist differentiators in a compelling statement or words for the industry and competitive marketplace. It is vital to keep the message broad enough to allow for agility while providing direction for strategic growth.
  2. While vision captures core competitive differentiators, the mission is a purpose statement and reason for being. When the mission is well-articulated it guides decision-making to ensure the purpose is aligned within operational leadership. This will enable leaders to cultivate an optimal culture with the best-talented people.
  3. Finally, and perhaps most important is the capacity to communicate the strategic vision and to operationalize the mission to ensure alignment among leadership and with teams. People feel valued when they clearly understand how their own contributions are making a difference and it is more important than ever for leaders in a talent-driven economy to make these connections. The momentum we see is the energy that leaders can leverage with a new vision and mission to inspire people. This is why we do this work. So rewarding!


Written by Diane Egbers, Founder and CEO of Leadership Excelleration, Inc. (LEI) and author of The Ascending Leader, engages with clients and guides a consulting team to provide all aspects of executive coaching, organizational consulting, and leadership programs. Diane understands her client’s needs by leveraging experience serving more than 250 organizations and her prior role as VP of Human Resources.