Five strategy development traps and how to avoid them

Fall strategy sessions will be in full swing soon, but many teams fall into predictable traps that undermine their efforts.  Here are five I see frequently, and the questions that can help you avoid them.

Trap #1: Treating strategy development as a leadership only exercise. When strategy happens in isolation, you get predictable results: front-line teams feel disconnected from the plan, execution suffers from lack of ownership, and you miss critical insights from those closest to customers and operations.

Ask yourself: Who will be executing this strategy and how can we involve them in shaping it? What perspectives might we be missing by keeping the circle too small?

Trap #2:  Focusing on capabilities instead of market needs.  Starting with "what we do" instead of "what stakeholders need" leads to uninspiring mission statements, incremental thinking that avoids real innovation, and blind spots that go unnoticed.

Ask yourself: Who are our key stakeholders and what do they need from us?  What beneficial value can we provide to them?

Trap #3:  Avoiding difficult conversations.  When teams stay in their comfort zone, dodging tough questions about trade-offs, risks, or misalignment they end up with strategies that everyone can live with, but no one is truly committed to executing.

Ask yourself: What assumptions are we holding that might no longer be true? What’s the risk we haven’t discussed? Where are we not fully aligned? If we say yes to this, what are we saying no to?

Trap #4:  Rushing the process. Strategy development that feels efficient in the moment often creates expensive problems later: shallow understanding of market dynamics, surface-level alignment that crumbles under pressure, and missing voices that could have prevented costly mistakes.

Ask yourself: Given the stakes, how much time should we really invest in getting this right? What's the cost of a flawed strategy versus a thorough process?

Trap #5:  Skipping measurable outcomes. Without clear metrics, even brilliant strategies become accountability-free zones where teams can't tell if they're succeeding, stakeholders lose confidence, and course corrections happen too late to matter.

Ask yourself:  how will we know if we are succeeding? What mix of leading indicators (tracking activities) and lagging indicators (measuring outcomes) will keep us honest about our progress?

The best strategies emerge when teams are intentional about their process not just their outcomes. By asking the right questions up front, you can avoid these common traps and build strategies that stick.

I work with leadership teams to design and facilitate strategy sessions that avoid these pitfalls while building genuine alignment and commitment. Feel free to reach out if you'd like to explore how we might collaborate.