Going beneath the surface to have effective one-on-ones

Problem

Often, one-on-ones end up defaulting into being status updates. I see this a lot with new managers and people who don't have a lot of time. However, one-on-ones should be treated as a case-by-case system, as everyone has different goals and different things they want to get out of these meetings.

Actions taken

"If you're having comfortable one-on-ones, you're not pushing the envelope of the relationship." - The Art of the Awkward 1:1

There's a great blog post called "The Art of the Awkward 1:1" that suggests that if you're having comfortable one-on-ones, you're not pushing the envelope of the relationship. While an awkward one-on-one shouldn't involve someone saying something to deliberately make someone feel uncomfortable, it should be about pushing personal limits.

For example, question how people feel about your company's ultimate direction, their compensation, or the way your team's projects fit into your company's direction. Talking about things such as compensation may make people feel awkward. However, if one-on-ones become too comfortable, you're actually failing to use them effectively as a tool.

Managers shouldn't bring a complete agenda to a one-on-one. Instead, they should inspire team members to bring items they want to discuss to meetings. I use shared document to capture what we talk about, but also to present bullet points for agenda items for the next meeting. This allows engineers to update the document throughout the week before the meeting.

Lessons learned

Going beneath the surface is the real value of one-on-ones, and this should be the goal of every manager. Bring out hard-hitting questions, but also encourage the people you work with to bring their questions and thoughts to their one-on-ones. Being open and transparent with others encourages them to be open and transparent with you.