3 questions to ask in every 1-on-1 with your direct reports

Question 1: “What's on your mind?”

This question opens up the floor to your direct report to talk through what they're thinking about and what's bothering them, whether it's project-related, work-related or otherwise. Asking the question this way, versus “what do you want to talk about?”, opens up space for them to be able to talk to you more freely. I have found that when I just ask “what do you want to talk about?”, my direct reports will often give me a deer in the headlights look, because for the most part people don’t come to 1-on-1s with tons of material prepared.

Asking “what’s on your mind?” allows the person’s brain to be a little bit more open and think about what is actually going on with them versus just whether they had topics that they wanted to bring up to the conversation. You'll find that it establishes greater trust with your direct report when you ask this question.

Question 2: “What do you want to accomplish this week?”

One of the goals of a 1-on-1 is to talk through priorities. What is this person supposed to be doing? What do they intend to deliver over the course of the next week? This question can spark a conversation where you talk through what actually makes sense for them to be focused on if you're not aligned. It will also help ensure that you’re both on the same page about what needs to happen, in what order, their bandwidth, and any issues they foresee.

Question 3: “What can I unblock for you?”

Your job as a manager is to get problems or blockers out of your direct report’s way. You're supposed to be an “offensive lineman”, blocking and tackling so that they can run freely with the ball. Asking them if there's anything you can help unblock for them will help them think about what is getting in their way when trying to do the work they’re focused on. It will also open up the opportunity for them to request your help in a way that they might not be comfortable with otherwise.

BONUS: “Let’s review what happened last week”

If you have time, talk through what happened last week. Hopefully you are documenting the contents of your 1-on-1s. Did everything get done that you agreed on last time you met? If not, what did get done? What didn’t? What else was worked on that wasn’t part of the initial plan you’d made? If there's a difference between what you agreed on and what actually happened, talk through it. Don’t approach it in a way that tries to figure out if they did something wrong. Ask questions to understand what happened. What got in their way? How can you as a manager help them so that that blocker isn’t a problem in the future?