I’ve been wrestling with why so many smart leaders get strategy completely wrong, and I think I’ve figured it out. Strategy work is psychologically brutal, so teams escape into activities that feel productive but avoid the real work entirely.
Here’s what I keep seeing: leadership teams gather for “strategy sessions” and spend hours crafting inspiring mission statements, setting ambitious financial targets, and creating roadmaps to achieve their vision. They leave feeling accomplished, like they’ve done important strategic thinking.
They haven’t. They’ve done everything except strategy.
Your mission statement isn’t strategy. Your revenue goals aren’t strategy. Your three-year plan isn’t strategy. These are the comfortable substitutes teams create to avoid confronting what strategy actually demands: identifying what’s broken and designing a way through it.
Real strategy starts with admitting what’s not working. It forces you to face the challenges you’d rather ignore and work backwards from constraints rather than forward from dreams. This feels negative, so teams instinctively avoid it.
I’ve watched executive teams (where I have been asked to be a “fly-on-the-wall” advisor or coach) spend entire retreats discussing their “vision for the future” while carefully sidestepping the fundamental challenges threatening their business. It’s strategic theater—all the motions of strategy work without any of the substance.
Benjamin Franklin understood this distinction. When he wanted to unite the American colonies, he didn’t craft inspiring statements about unity and cooperation. He identified the specific problem: lack of communication and coordination. Then he built the postal service to solve it.
When he wanted to improve civic life in Philadelphia, he didn’t create mission statements about community safety. He identified the specific challenge: no organized fire protection. So he created volunteer fire companies.
Franklin consistently started with the challenge, not the aspiration. He worked backwards from what was broken, not forward from what would be nice to achieve.
Modern leaders do the opposite. They start with where they want to go and assume the path will become clear. But strategy isn’t about destination planning—it’s about obstacle navigation.
The teams that actually do strategy work look different. They spend time diagnosing what’s really preventing progress. They identify the core challenge that, if addressed, would unlock the most value. They design specific actions to overcome that challenge, not generic initiatives to “drive growth” or “improve performance.”
This requires brutal honesty about current reality. It means acknowledging that your product isn’t as differentiated as you thought, or that your operational capabilities can’t support your ambitions, or that your competition has advantages you haven’t admitted.
Most leadership teams avoid this work because confronting challenges feels like dwelling on problems rather than focusing on solutions. But you can’t solve challenges you won’t acknowledge, and you can’t create strategy around problems you refuse to name.
The psychological comfort of mission statements and goal-setting keeps teams busy while avoiding the hard questions: What’s the specific challenge we must overcome? What’s preventing us from winning where it matters most? What constraints must we design around rather than ignore?
Strategy isn’t about declaring what you want to become. It’s about diagnosing what’s stopping you from getting there and designing a coherent response.
The next time your team gathers for “strategic planning,” try this: spend the first half identifying and diagnosing your biggest challenge. Don’t set goals or create visions. Just name what’s broken and understand why it’s broken.
Only then can you begin the actual work of strategy.