The Wrong Questions, w/ Jake & Jason

Asking the Right Questions in Leadership

I just returned from a cruise with my family, and as I’ve reflected on the trip, I realized how much it taught me about leadership. When you travel with kids, you quickly discover the importance of setting expectations, asking the right questions, and guiding rather than dictating. That trip reminded me of something I see on construction projects every day: leadership often comes down to the questions we ask.

On the cruise, my kids would sometimes get restless. If I asked, “Why are you acting like that?” The question immediately created tension and blame. But when I shifted to, “What do you need right now?” or “How can we make this fun?” It changed the tone completely. Suddenly, we were working together instead of against each other. That small shift reminded me of a truth I have seen time and again in construction: poor questions create resistance, but good questions open doors.

I see the same pattern with project teams. A leader who asks, “Why are you behind schedule?” puts people on the defensive. It shuts down collaboration. On the other hand, if the question is, “What’s blocking us, and how can we remove it?” the conversation becomes productive. Instead of fear, it creates problem-solving.

One of my colleagues, Jake, often says that leadership is not about having all the answers but about creating an environment where the right answers can surface. That starts with the questions we ask. Are we asking questions that build trust, or ones that erode it? Are we using questions to support and empower, or to judge and control?

Looking back at my own leadership journey, I can see times when I defaulted to the wrong kind of questions. They came from a place of frustration or fear. Those moments did not inspire my teams, they shut them down. Over time, I’ve learned that asking questions with curiosity and care changes the culture of a project. It sets a tone of respect and partnership.

This is something I want to carry forward not only in my work but also in my family life. On that cruise, I saw how quickly the wrong question could derail a moment, and how the right one could bring us back together. In construction, the stakes are higher, but the principle is the same. Questions are powerful tools. Used poorly, they create barriers. Used wisely, they unlock collaboration, flow, and trust.

Key Takeaway:
Leadership is not about having the answers. It is about asking questions that build trust, remove barriers, and empower teams to find the right solutions together.