I try to keep it somewhat casual and try build trust with my reports. Taking in issues or blockers they are experiencing on their respective projects and such.This guide covers every aspect of how to have effective and meaningful one-on-one meetings from both the employee and manager perspective. Your first one-on-one meeting with a direct report is a great opportunity to think about the projects and tasks that you can delegate to them in the future. Your first one-on-one with the direct report is a little different for three main reasons: firstly it's an opportunity to establish clear expectations. One-on-one meetings help managers and team members stay informed and build a healthy relationship. Absolutely you can have meetings with 30 reports. The question now is how often do you do . First, work with your direct report to identify five to eight people who'd be able to provide input.