The single greatest challenge any organization will face Meaning Factcheck Usage

Context

In the book, he’s talking about how companies with a clear sense of purpose—a clear “Why”—outperform and outlast everyone. But he points out that as they grow and succeed, there’s a dangerous drift. They often start focusing on the “What” (the products) and the “How” (the metrics), and they forget the “Why” that inspired them initially. The success itself becomes the distraction.

Usage Examples

Think about a startup that just landed a massive round of funding. The immediate challenge isn’t the money—it’s the culture shift that comes with it. Are they going to start adding layers of management that stifle innovation? Are they going to get risk-averse? This quote is a perfect warning for them. It’s also incredibly relevant for established market leaders who feel their innovation slowing down. They succeeded, and now they’re being disrupted because they’re not challenging their own model anymore. It’s for any leader who feels their team is getting a little too comfortable.

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Common Questions

Question: Isn’t failure a bigger challenge than success?
Answer: Failure is obvious. It’s a clear threat that rallies people. Success is an invisible, slow-acting toxin. It’s a much harder problem to diagnose and solve because it doesn’t feel like a problem.

Question: How do you prevent success from becoming a challenge?
Answer: You have to be relentlessly intentional about protecting your culture and your “Why.” You have to keep asking the hard questions, even when things are going well. Celebrate the win, then immediately ask, “How do we get better?”

Question: Can you give a real-world example of this?
Answer: Look at some of the tech giants. They dominated for years, but then they became so big and focused on protecting their turf that they missed the next wave of innovation. Their past success made them blind to new, disruptive ideas.