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. Yancey is also the co-author of “Leading Performance… Because It Can’t Be Managed: How to Lead the Modern Workforce,” and a frequent keynote speaker. Reach him at teleiostrategy.com. 

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

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resist the temptation to tweak current offerings in response to customer or client feedback that might be incomplete or outdated.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.

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. 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. If your Association isn’t willing to explore uncomfortable ideas, it risks losing relevancy and, ultimately, revenue.

3. Focusing on the Rear-View Mirror 

Associations that spend too much time reflecting on past successes are at risk of missing future opportunities. 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

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 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.

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.

8. Relying 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.

9. ‘Strategic’ vs. ‘Stakeholder Value’ Plans

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. This shift emphasizes that the ultimate goal of any strategic initiative should be to create value for stakeholders.

By prioritizing areas that will have the highest impact on stakeholders and transforming these 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.

‍10. Focusing on Strategic ‘Priorities’

One of the most dangerous things a business leader can possess is an extensive list of “strategic priorities.” Having 20 “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.

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.

Strategic planning challenges abound, but with the right mindset and proactive measures, companies can turn potential obstacles into opportunities for profound growth and innovation. | AC&F |