Strategy Isn’t a Comprehension Problem—It’s a Courage Problem
tl;dr: Most strategic planning failures aren’t intellectual. Leaders understand what strategy requires—the hard part is having the courage to say no to good ideas that don’t serve the strategy. Organizations prefer complexity because it gives permission to do everything. Strategy is subtraction with conviction, and that’s an emotional challenge, rather than a cognitive one.
Heads at different schools and different contexts share the same pattern with me:
Their trustees understood the strategic plan. They nodded at the priorities. They asked smart questions about implementation. But when it came time to choose, they wanted to add initiatives, not subtract them. In the end, not much changed and the plan became a 50-item wish list.
The problem wasn’t comprehension. It was courage.
The Story We Tell Ourselves
We blame consultants (I certainly have in the past!). We say strategic planning is broken. We complain that boards don’t get it, that plans sit on shelves, that execution is the real challenge.
All of that is sometimes true. But it’s not the root cause.
The root cause is that strategy asks you to disappoint people. It asks you to say no to good ideas. It asks you to make tradeoffs where both options have merit. And most organizations would rather live with the exhaustion of doing too much than face the emotional labor of choosing.
I’ve watched this pattern repeat for many years. Boards hire consultants to give them strategic clarity. The consultants deliver frameworks, priorities, roadmaps. And then the boards—full of really smart, accomplished people—struggle less with understanding the strategy and more with the courage to follow through.
Clarity, Discipline, Accountability
Brené Brown names three things that leaders consistently avoid: clarity, discipline, and accountability. I’ve seen this play out in more boardrooms than I can count.
Clarity is the hardest because it requires choice. I watched a head of school spend forty-five minutes last month trying to explain why a beloved program had to end. She knew the answer. Everyone in the room knew the answer. But saying it out loud—”This program doesn’t fit who we’re becoming”—meant watching faces fall. Clarity creates consequences. That’s what makes it hard to say out loud.
Discipline follows clarity. Once you’ve chosen, you have to stay chosen. Every week, new opportunities emerge. Every month, stakeholder groups advocate for their initiatives. Discipline is the organizational muscle to keep saying “not this year, maybe not ever” to things that would be good in isolation but don’t serve the strategy.
Accountability is the courage to measure whether your choices worked. If you said this initiative would improve retention, did it? If you committed resources here, what’s the return? Most leaders fear being wrong more than they fear being vague. So they stay vague.
The sequence matters. You can’t have discipline without clarity. You can’t have accountability without both.
