by Drew Yancey, PhD,Founder & CEO at Teleios Strategy and co-author of “ Leading Performance… Because It Can’t Be Managed: How to Lead the Modern Workforce”
As executives gear up for the 2025 strategic planning season, the process can feel like a balancing act. Developing a strategic plan that both drives meaningful change and satisfies stakeholders is a complex task, made even more challenging by the fast-evolving landscape of marketplace needs, industry trends, and technological advancements.
However, many leaders unknowingly fall into common pitfalls that can derail their planning efforts. To avoid these, it’s crucial to approach strategic planning with intentionality, foresight, and a willingness to embrace change. Based on insights drawn from value proposition redesign practices and real-world business challenges, here are some of the most common strategic planning pitfalls to avoid.
1. Starting with Products and Services, Not Marketplace Needs.
One of the most frequent missteps in strategic planning is jumping straight into product and service enhancements without first taking the time to understand the modern market’s evolving needs and challenges. This misalignment can lead to investing time and resources in offerings that don’t resonate within the marketplace.
Association leaders must resist the temptation to tweak current offerings in response to customer or client feedback that might be incomplete or outdated. Instead, focus on uncovering the deeper, underlying needs of your target market by conducting thorough research, listening to stakeholder pain points, and analyzing trends in your industry.
A valuable framework to use here is the Jobs-to-Be-Done (JTBD) approach, which focuses on understanding the motivations and desired outcomes that drive customers to engage with your company. By first identifying what your audience is truly seeking to accomplish, you can tailor your offerings to meet those specific needs and deliver greater value.
2. Incrementalism: The Trap of Small Tweaks.
Incremental improvements — small, conservative changes to existing programs or services — are tempting because they feel safer and easier to implement. However, this approach often keeps Associations stuck in the status quo, unable to generate the breakthrough innovations that the marketplace craves.
For example, a common sign of incrementalism is allocating resources primarily toward existing programs, while overlooking opportunities to invest in new and innovative initiatives. While there may be pressure to avoid risk, Association executives need to think big and bold to stay relevant and provide distinctive value in a competitive landscape.
One way to avoid this trap is to ask yourself whether your current strategic plan is simply aimed at maintaining the status quo or driving transformative change. Big, bold ideas are uncomfortable because they challenge the way things have always been done. But if your Association isn’t willing to explore uncomfortable ideas, it risks losing relevancy and, ultimately, revenue.
3. Focusing on the Rear-View Mirror Instead of the Windshield.
Associations that spend too much time reflecting on past successes are at risk of missing future opportunities. While celebrating past accomplishments can be beneficial for morale, it can also blind you to the changes and challenges on the horizon.
Your strategic plan must be forward-thinking. Instead of concentrating solely on what has worked before, actively look for new trends, disruptions, and future opportunities within your industry. Be willing to question current assumptions and take a proactive stance in identifying where your Association could be heading.
A key way to do this is by conducting regular environmental scans — assessments of external factors such as economic conditions, technology trends, and regulatory changes — that could affect your Association in the future. The goal is not just to adapt to these changes but to position your organization to lead them.
4. Overemphasis on Risk Avoidance.
A conservative approach to strategic planning, driven by a fear of failure or desire to avoid risk, can lead to stagnation. Many Association leaders, especially in times of uncertainty, focus heavily on maintaining stability rather than pursuing opportunities for growth.
However, organizations that prioritize short-term stability over long-term innovation tend to struggle with customer retention and engagement. Bold moves are necessary to stay ahead of the curve, even if they involve some level of risk. To break free from the risk-avoidance mindset, it’s essential to build a culture where calculated risk-taking is encouraged, and failure is seen as part of the learning process.
One way to manage risk without stifling innovation is to adopt a dynamic feedback loop. By continually testing and refining new initiatives based on marketplace feedback, you can make adjustments early, minimizing risk while still pursuing meaningful change.
5. Benchmarking Only Against Similar Organizations.
Benchmarking — comparing your Association’s performance to that of similar organizations — can be helpful, but it should not be the sole basis for your strategic planning. When Association executives rely too heavily on what their peers are doing, they risk blending in with the crowd rather than standing out.
The more valuable approach is to look for inspiration outside your immediate sector. Explore what leading organizations in other industries are doing to innovate and create value for their customers or stakeholders. By bringing fresh ideas and perspectives into your strategic planning process, your Association can differentiate itself and offer unique value propositions not found elsewhere in the marketplace.
6. Failing to Allocate Resources Toward Innovation.
A common pitfall in strategic planning is the disproportionate allocation of resources toward maintaining existing programs, leaving little room for investment in innovation. While it’s important to sustain core functions and services, innovation must be an explicit priority to ensure future relevance.
Leaders often struggle with bias toward the familiar. Innovation, however, requires rethinking traditional resource allocation models. Consider setting aside a percentage of your budget specifically for new initiatives, even if it means trimming less impactful programs. The key is to strike a balance between sustaining what works today and building the capacity for what’s needed tomorrow.
7. Prioritizing Short-Term Gains Over Long-Term Vision.
In the race to show immediate results, many Associations fall into the trap of prioritizing short-term wins at the expense of long-term strategic goals. While quick wins can boost morale and offer evidence of progress, they can also distract from the bigger picture and lead to unsustainable growth or missed opportunities for lasting impact.
As you build your strategic plan, it’s essential to maintain a clear focus on your Association’s long-term vision and objectives. This requires the discipline to make decisions that may not show immediate results but will set the foundation for future success.
8. Relying on Feedback Loops Focused Only on Current Services.
Another common pitfall is over-reliance on feedback loops that center solely on evaluating current services rather than exploring potential new offerings. Feedback is essential for assessing the effectiveness of your current initiatives, but it should not limit your Association’s ability to innovate.
To avoid this trap, ensure that your feedback loops include mechanisms for identifying unmet customer needs and exploring new value creation opportunities. Encourage your existing customers to think beyond what they currently receive from the company and consider what they might need in the future. By shifting the focus of your feedback mechanisms, you can uncover valuable insights that will guide innovation and help you stay ahead of the curve.
Strategic planning is more than just an annual exercise. It’s an opportunity to take stock of where your Association is today and where it needs to go in the future. By avoiding these common pitfalls, you can ensure that your 2025 plan not only positions your Association for success but also delivers meaningful, lasting value to your customer base.
9. Functioning with ‘Strategic’ vs. ‘Stakeholder Value’ Plans.
As we transition toward year-end, many organizations are realizing their strategic goals are significantly off track. This isn’t a rare occurrence; in fact, it’s almost expected. The natural momentum that kicks off a new year often dwindles as daily operations take precedence, leaving ambitious strategic plans largely unexecuted. Statistics suggest that most organizations fail to implement 70% of their strategic initiatives. Take this opportunity to toss out your ‘strategic’ plan… what you need is a ‘stakeholder value’ plan. Traditional strategic plans tend to be more of a generalized wish list than a targeted, actionable roadmap. They frequently lose sight of the very people they’re supposed to benefit: the stakeholders.
Redefining strategic plans as “stakeholder impact plans” is crucial pivot. This shift emphasizes that the ultimate goal of any strategic initiative should be to create value for stakeholders. An effective plan needs to clearly articulate how it will deliver new value to key stakeholder groups. Of course, it’s fundamentally essential to recognize who they are. At their core, successful organizations serve at least two primary stakeholder groups: customers or clients (external stakeholders) and employees (internal stakeholders). You can even go a step further by including suppliers (another critical external group) and ownership (an additional internal group) as key stakeholders.
Stakeholders are not afterthoughts, but rather are the foundation and focus of the planning process. It’s about understanding the “jobs to be done” for these stakeholders — identifying what they rely on your organization to achieve, assessing where your organization is meeting these needs, and pinpointing where it falls short.
By prioritizing areas that will have the highest impact on stakeholders and transforming these priorities into concrete objectives with measurable results, your strategic plan transforms into a dynamic tool. It becomes more than a list of hopes; it turns into a driving force that fosters sustained action throughout the year.
This new perspective not only revitalizes the planning process but also ensures that the plan remains relevant and impactful long past the initial enthusiasm of the new year. Adopting a stakeholder value plan is not just about changing terminology — it’s about rethinking how strategic planning can fundamentally drive the success of your organization by truly serving those who matter most.
10. Focusing on Strategic ‘Priorities.
One of the most dangerous things a business leader can possess is an extensive list of “strategic priorities.” Traditional strategic planning tends to overemphasize long lists of these while underemphasizing concrete plans for executing on those priorities. As a result, a shocking 60-90% of strategic plans fail to fully materialize. The problem lies not with planning itself — identifying strategic priorities is vital — but rather with the lack of clear execution protocols to activate those priorities.
Leaders often compile inventories spanning dozens of critical priorities across growth opportunities, operational improvements, customer initiatives, and more. However, having twenty “top strategic priorities” is equivalent to having none at all. Attempting to actively pursue such a wide array simultaneously stretches resources too thin. Without adequate focus, it becomes challenging to achieve critical mass on any specific initiative, causing frustration and initiative fatigue across teams.
Moreover, priorities trick leaders into complacency, fostering the false belief that merely identifying something as “important” will somehow guarantee execution. Like overly ambitious New Year’s resolutions, priorities rarely catalyze change without concerted plans for accountability and follow-through. Despite good intentions, only 8% of people fully achieve their resolutions each year. Similarly, while leaders excel at strategizing priorities, 60-90% of organizational strategic plans fail largely due to flawed or total lack of execution protocols.
Endeavor to transform priorities into quantifiable, actionable objectives centered on specific execution plans. For instance, rather than just identifying “improved customer retention” as a priority, leaders must drill down to concrete goals like “reducing customer churn by 2% within 6 months.” This clarity of purpose fuels strategic discipline. In today’s disruptive business landscape, both planning and execution are indispensable. However, leaders must resist conflating priorities with outcomes. A paradigm shift focused on execution-based strategic management is crucial for channeling priorities into real-world impact and results. Just as resolutions without concerted action plans go nowhere, strategic priorities minus execution equal zero.
As business leaders prepare for the 2025 strategic planning season, avoiding these common pitfalls and undertaking the alternate best practices will foster a more forward-thinking, adaptable blueprint that drives real impact. Strategic planning challenges abound, but with the right mindset and proactive measures, companies can turn potential obstacles into opportunities for profound growth and innovation.
Drew Yancey, PhD is Founder & CEO at Teleios Strategy, a premier strategic planning, leadership development, executive coaching and succession planning advisory firm. With a proven track record in high-performance team building and strategic execution for over 15 years, Yancey solves challenging problems at the nexus of growth, strategy, and innovation. He is co-author of “ Leading Performance… Because It Can’t Be Managed: How to Lead the Modern Workforce” .
