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The One Question Every Leader Should Ask at the Start of the Year

Not a goal-setting exercise. Not a reflection on revenue or market share. One question. Direct and uncomfortable. The kind that tells you more about the state of your organization than any financial r

KEVIN J. WOLSKO  ·  JANUARY 28, 2026  ·  FORWARDTHINK, LLC

Not a goal-setting exercise. Not a reflection on revenue or market share. One question. Direct and uncomfortable. The kind that tells you more about the state of your organization than any financial report you have looked at in the past twelve months.

The question is this: if your best three people left tomorrow, how would the organization perform in six months?

Sit with that for a moment. Not the recruiting plan you would activate. Not the relationships you would personally take over. What would the organization actually look like, operating without the people it most depends on?

Why This Question Matters

The answer tells you everything about the health of your people infrastructure. If the honest answer is that the organization would struggle significantly, that is not a talent problem. It is a development problem, a documentation problem, a succession problem. The value of the organization is concentrated in too few people, which means the organization is fragile in a way that no financial metric captures.

Resilient organizations can absorb the departure of key people. Not without disruption, but without existential risk. They have built depth. They have developed the next layer. They have documented what matters. They have distributed ownership rather than centralizing it.

What to Do With the Answer

If the answer makes you uncomfortable, that discomfort is information. It tells you where the work needs to happen this year. Not the revenue plan. Not the product roadmap. The people infrastructure that makes everything else possible.

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