Finding the Cracks

Strategy never fails on paper.

It fails in execution, in assumption, or in resistance that no one wanted to name out loud.

The board’s role isn’t to write the strategy but to interrogate it. Not with cynicism, but with curiosity. Our job as a director is to look for the hairline cracks. The ones that may not be visible now, but that risk becoming fault lines later.

Here are three ways I’ve seen boards strengthen their strategic oversight by looking for what’s not being said, and translating that into meaningful questions about risk and resilience.

1- Scan for Assumptions Disguised as Certainty

Every strategy has baked-in assumptions. Some are explicit. Most aren’t. Directors need to listen for the “we just assumed…” moments.

Ask:

• What assumptions must stay true for this strategy to work?

• What would we do differently if that assumption shifted by 10%? By 50%?

• Where are we overconfident? Where are we underestimating friction?

Cracks form when assumptions go untested. Strategy isn’t just about direction, it’s about durability.

2- Translate Strategy into Risk

It’s not enough to ask, “What are the risks?” Boards need to ask, “How is this strategy creating new risks?”

Ask:

• What risks are we creating by choosing this path—even if it’s the right one?

• What does this strategy require us to stop doing? What’s the risk of that?

• How does this strategy show up in our risk register—and where might it not?

Boards add value when they connect the dots between opportunity and exposure, ambition and trade-offs.

3- Look for the Gaps in Story and Signal

Sometimes, the strategy sounds great but the organizational signals don’t match. That’s where cracks form: between what leadership says and what the culture reinforces.

Ask:

• How are employees experiencing this strategy?

• Where is resistance showing up? What’s being misunderstood or quietly challenged?

• What metrics will tell us this strategy is working before the financials do?

The earlier you catch misalignment, the easier it is to fix. The longer you wait, the more expensive it becomes.

Final Thought: Strategy is Never the Whole Story

Strategy documents are tidy. Reality isn’t.

Boards don’t need to know every detail but they do need to sense where the seams are stretched. Where the culture is creating drag.

The most effective directors don’t just ask about the plan, they find ways to test the foundation underneath it.

Because cracks don’t show up when everything’s going right.
They show up when no one’s looking for them.