Don't confuse a wish list with a winning strategy

In many organizations, the annual strategic plan reads like a fundraiser’s wish list—growth targets, new initiatives, culture shifts—yet progress remains elusive. It wasn’t unusual for teams to recite lofty goals in boardrooms while no one could define the actual barrier to success. One marketing director once confessed he didn’t know whether poor sales were due to an outdated product, a cluttered website, or a misaligned pricing model. As months passed, the goals sat on a dusty slide deck, gathering cobwebs and excuses.

Contrast this with a nonprofit I advised that wanted to double volunteer hours. Rather than set another stretch target or pump up staff motivation, we gathered the team to ask, “What exactly is keeping offices from signing up volunteers?” The answer was bottlenecks in orientation processes and scheduling software that crashed. By naming these barriers, the group identified a proximate objective: cut orientation time in half and upgrade the booking system by month’s end. When the challenge was clear, the board approved funding for an online training portal and a new calendar app, and volunteer hours actually doubled in two months.

Naming obstacles is more than a semantic trick; it unleashes disciplined problem-solving. When you ask “What’s stopping us?” you diagnose rather than defer. You replace abstract ambitions with concrete needs. This shift is at the heart of strategic thinking: goals become challenges to conquer, not dreams to hope for.

By recasting your agenda as a cluster of clear problems—recognizable and solvable—you create the foundation for coherent policies and coordinated action.

You start by listing the top three unhindered goals you can’t stop mentioning, then, for each, you mindfully pause and ask yourself “What’s stopping us?”—letting that very question reshape your thinking and focus your next moves. You dive into your most pressing desired outcome and convert it into a precise strategic question, challenging the assumption that more effort alone will get you there. This simple reframing builds the bridge from wishful goals to the real-world obstacles you must solve, giving you clarity and momentum to finally make progress.