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Advice / Succeeding at Work / Management

How to Have One-on-Ones That Actually Matter

I’ve done it. You’ve done it. We’ve probably all done it. Fallen into that trap where one-on-one meetings with your boss or direct reports become stale and feel like they’re not that useful.

Especially for teams that work together like a well-oiled machine, these regular meetings can seem redundant. After all, if all your projects are on track and you really have nothing to check in on, why should you meet?

I’ll tell you why: Because one-on-one meetings aren’t just about checking in on daily work. They’re about getting to know the people you work with better. They’re about discussing higher-level things: feedback, career goals, professional development, and the like. And, ultimately, they exist to help you figure out how you can make good employees happy and keep them around.

So how can you take these meetings from a weekly necessity to potentially the most valuable 30 minutes of your week? In a recent blog post on popforms, Kate Stull addresses just that. Check out some of my favorite tips below along with a few pointers I’ve picked up on having one-on-ones that really matter.


1. Ask the Right Questions

One good way to get more out of your employees than, “So how’s that project going?” Ask better questions! Try and think about open-ended, thought-provoking, and big-picture questions that you can pull out when you find yourself needing a conversation starter.

popforms actually offers a newsletter that sends you two questions every week to ask your team; everything from “What is one thing I could do to make you more productive?” to “What did you want to be when you grew up?” You can even sign your employees up so they have time to think about their answers ahead of time. While the newsletter is good, it’s also helpful to simply open your mind a little more about what you could really be hitting on during this time.


2. Don’t Run the Meeting

One of my favorite tips from Stull is to have your employees run the meeting, not you. After all, this time is largely about people getting face time with you, asking questions, addressing issues, and the like. Since you can’t read minds to plan out the agenda that will best suit each employee, why don’t you have them run the meetings, instead? Not only does this allow your staffers to get the most out of the time, they’ll gain skills in setting an agenda and running an effective meeting.

If your employees are a little nervous or you find the meetings lagging, at least make it clear that this is meant to be a conversation. That way everyone knows that they can bring things to the table.


3. Have a Backup Plan

Nothing to talk about? Have a backup plan to get the conversation rolling. popforms suggests some ideas from Rands in Repose, including a mini performance review or “my current disaster:”

Chances are, in my professional life, something is currently off the rails. It’s selfish, but if you’re leading with status and I can’t find an interesting discussion nugget, let’s talk about my current disaster. Do you know how many open reqs we have that we can’t hire against? Who is the best hiring manager you know and what were their best moves? The point of this discussion is not to solve my Disaster, the point is that we’re going to have a conversation where one of us is going to learn something more than just project status.

Talking about a problem you’re facing gives your employees a little more insight into your job—and may even give them a chance to contribute on bigger picture things.


4. Get Out of the Office

One of the things I’ve found most helpful in having beneficial conversation during a one-on-one? Get out of the office.

When you’re sitting in the conference room where you meet for work-related tasks every day, it’s too easy to fall into the habit of just talking about projects and the like. Or, depending on the setup of your office, the concern of being overheard could keep your employees from really opening up. So, at least once every month or two, get out of the office. Go to a coffee shop. Go for lunch. Have a walking meeting around a nearby park. Whatever it is, break up your routine to really give your team members space to talk.



One-on-ones don’t have to be a drag—in fact, they can be a really powerful time to strengthen your relationship with your boss or employees and make everyone’s work lives better. Read the rest of the popforms post if you want more tips, and get ready to make your meetings matter more, starting now.