Beyond Small Talk: Five Powerful Questions for Impactful One-on-One Conversations

The Owl and The Beetle: Thursday Memo

When I started my career as a manager, I adopted a common practice in the company: regular one-on-one meetings with my team members.

In business, one-on-one conversations are essential for building relationships, understanding needs, and addressing concerns. Asking the right questions during these conversations can help you gain valuable insights into your employees' needs and concerns and help you build a stronger team.

However, my one-on-ones quickly became dull, repetitive, and overall useless.

I looked at my calendar, which was booked solid with conversations leading nowhere, and had little to no impact on the business.

My frustration was reaching its peak, and I was on the brink of giving up. However, I made a breakthrough by utilizing powerful questions, drastically altering the results of the conversations.

I stopped asking people, “How are you?” or “What’s going on?” at the beginning of our conversations. These questions are so ordinary, expected, and dull. They set the whole conversation on a low note.

I also stopped asking people about the state of their projects. All I needed to know, as a manager of a distributed company, was already available to me on our project management tracking system.

I focused my conversations on calibrated questions to get to know my people deeply. I wanted to explore their motivators and struggles and find ways to help them.

This essay will explore five powerful questions to ask during a one-on-one conversation in a business environment.

Let’s get going!