Leadership and Life Essentials: Stop Wasting Your 1 on 1s: Better Questions, Better Conversations

Most one-on-ones are wasted because leaders default to surface-level check-ins like 'How are you?' and project status updates—conversations that could easily be handled by email. Jackie Serginer-Galeoni argues that these meetings are one of the most powerful tools a leader has, not for managing tasks, but for uncovering hidden friction, building trust, and preventing small issues from becoming crises. The real problem isn't the time spent—it's the lack of meaningful questions. She reveals four specific, high-impact questions that shift the conversation from logistics to insight: what one thing about how you work together could be different, what could I do to make your job easier, when do you feel most energized or drained at work, and what’s getting in the way of your best work? These aren’t checkboxes—they’re invitations to deeper connection. Jackie emphasizes that the real skill isn’t asking perfect questions, but having the patience to listen, the courage to dig deeper, and the discipline to follow up on patterns across the team. When done right, one-on-ones become a feedback engine, a trust builder, and a strategic advantage. The episode dismantles the myth that one-on-ones are optional or time-wasting. Instead, Jackie reframes them as non-negotiable leadership rituals. She warns that skipping them or doing them poorly sends a message: 'You don’t matter enough to my time.