The Power of Asking "What Keeps You Awake?"

The question "What keeps you awake?" is often considered cliché when posed to senior leaders. However, in my experience, asking this question consistently yields valuable insights, enabling me to serve customers better.

I recall a situation involving the CEO of a large forestry products company based in South America.

With a revenue of $14 billion, they were a customer of my employer at the time. The CEO, his CFO, and a strategy expert visited our facility in Silicon Valley.

Upon arrival, I invited the CEO to share his reasons for visiting. He candidly felt like a "prisoner" due to his heavy reliance on our products and perceived lack of alternatives. He believed our company prioritized their won interests, especially pricing, support, and promised capabilities.

After discussing his concerns, I asked the key question: "What keeps you awake?"

His response was both surprising and personal. He was most concerned about the safety of his thousands of employees working in the forests, cutting down trees, and transporting them to processing plants.

He stressed the importance of their safety and well-being and the need to comply with strict government regulations.

During his visit, he hoped to find a solution for truck drivers who faced challenges driving long distances on unpaved roads, often falling asleep at the wheel. He sought technology to detect driver fatigue, alert the central office, and monitor drivers' temperature and pulse using wearable sensors.

Before the CEO's visit, I researched the company, its business challenges, cultural nuances, and potential benefits from our solutions.

I encouraged my colleagues to abandon traditional PowerPoint presentations to engage in whiteboarding sessions. I also urged industry experts to honestly assess whether we could solve the CEO's primary problem without resorting to selling "vaporware."

At the end of the visit, I asked the CEO how his feelings had changed since his initial sense of being a prisoner.

He expressed gratitude for our empathic conversation and candid approach, stating that he now saw us as a true partners.

This experience highlights the importance of asking, "What keeps you awake?" as it can reveal critical concerns and help you focus on providing meaningful solutions.

Three months later, the CEO signed a deal worth $1,250,000!