Debbie’s Story

Debbie was the kind of CEO who thrived on long-term strategies and visionary goals. She had built her company from the ground up, guiding it through periods of rapid growth and successfully positioning it as a market leader. Her leadership style was big-picture, and she often found herself immersed in planning the next big move, tackling major partnerships, and handling investor relations.

Her top managers—each leading key departments—were experienced and competent. Debbie trusted them to run their teams and deliver results, and as a result, she didn’t feel the need to micromanage. She would check in with them in high-level meetings, but she didn’t prioritize regular, one-on-one catch-ups. She assumed that as long as things were running smoothly, there was no need for frequent check-ins. After all, the business was thriving, and the company’s metrics spoke for themselves.

But over time, Debbie started noticing subtle signs of disconnect. Some of her managers began to withdraw during meetings, offering more terse updates, and when they did speak, they often seemed frustrated. Small issues started slipping through the cracks. The marketing campaigns weren’t as cohesive as they used to be, operations weren’t running as efficiently, and there were complaints about communication between departments.

Debbie brushed it off, thinking the managers were just caught up in the day-to-day grind of their work. She remained focused on long-term goals, assuming the problems were temporary and that the managers were perfectly capable of resolving them on their own. But when a major product launch failed to meet expectations, Debbie realized that the cracks had turned into something bigger.

The fallout from the launch was significant. The team was stressed, morale was low, and customer feedback was poor. Debbie called an emergency meeting with her top managers to address the situation. During the meeting, it became clear that the managers were not on the same page, and several underlying issues had gone unaddressed for months. Some of the managers felt they hadn’t had a clear direction in recent months and had become frustrated by a lack of communication from Debbie. They felt unsupported and disconnected from her vision.

One of the managers, Jason from operations, spoke up: “Debbie, we’ve been running in different directions. You’ve been so focused on the big-picture vision that you’ve left us to handle everything on our own. We need guidance and support, not just targets to hit.”

It hit Debbie hard. She realized that in her quest to scale the company and drive growth, she had neglected one of the most essential parts of leadership: staying connected with her team. She had trusted her managers to run their departments without providing the ongoing support and feedback they needed. In her drive to lead from the top, she had created a disconnect that was now affecting the entire organization.

That day, Debbie made a commitment to change. She scheduled regular one-on-one meetings with each of her top managers—something she had previously deemed unnecessary. During these meetings, she didn’t focus just on performance or metrics; she took the time to listen, understand the challenges her managers were facing, and offer support. She encouraged open dialogue and made it clear that her door was always open for feedback and ideas.

Debbie also made sure to involve her managers more deeply in the strategic planning process, recognizing that their insights were vital to shaping the company’s future. These regular check-ins allowed her to stay in touch with the pulse of the organization and gave her managers the opportunity to voice concerns and celebrate successes.

Within a few months, the shift was noticeable. The team felt more unified, communication improved, and the work environment became more transparent and collaborative. The marketing department refined its strategies, operations became more efficient, and employee engagement rose. Debbie’s commitment to staying connected with her team created a culture of trust and support that enabled her top managers to feel empowered and aligned with her vision.

When the company faced another major product launch, the result was a complete turnaround. The product not only met customer expectations but exceeded them, and the managers worked together seamlessly to ensure its success. Debbie had learned that leadership wasn’t just about managing from a distance; it was about maintaining strong, ongoing connections with those who helped make her vision a reality.

Moral: Effective leadership is built on strong relationships and communication. Regular check-ins with your team, especially your top managers, creates alignment, build trust, and ensure that everyone is moving in the same direction. Never underestimate the power of connection.