3 Simple Ways to Boost Your One on Ones

Grumpy Manager
4 min readOct 15, 2023

A Manager’s Handbook to Effective and Useful One on Ones

Photo by Christin Hume on Unsplash

I briefly touched upon this topic in the previous article, ‘Meetings that don’t suck.’ It is a subject particularly close to my heart because I have wrestled with it, danced around it, and dodged it for quite some time. It has also surfaced in some of my meetings with other managers, leading me to realize that everyone grapples with finding effective ways to conduct one-on-one sessions with their reports.

I’ve encountered a variety of challenges in my one-on-one meetings. Some engineers wanted to delve into every intricate detail of their projects during our half-hour catch-up. Others struggled to find topics for discussion, often offering only single-syllable responses. I found myself in the position of needing to guide the conversation or prompt more specific questions to fill the half-hour. Additionally, a few desired more frequent meetings, while others considered it an obligation.. For example:

Me: “How’s everything going?”

Engineer 1, taking out the laptop and walking me through the entire code he wrote in the past week.

Engineer 2: “Good.”

What was happening here? Well, what was prominently absent in these meetings was clear expectations. When people are unsure about the purpose of the…