One-on-one meetings can be one of the most valuable tools for managers and employees. They can also be an absolute waste of time.
I’ve had both, and plenty in between.
I once had a manager (name withheld to protect the guilty) who scheduled weekly "one-on-ones," but they weren’t really one-on-ones. They were task-tracking meetings in disguise. The entire conversation revolved around what was on the board, what was getting done this week, and what was falling behind. If I brought up anything else (career growth, roadblocks, team dynamics) it got pushed to “later.” And by later, they meant annual review season (which, shocker, is too late to actually fix anything).
So not only did I have to stop what I was doing and context switch to go to a meeting that could have been done by looking at the damn Agile board, I had to do it every. single. week.
On the flip side, I’ve also had a manager who I possibly never had a formal one-on-one with. And you know what? I never missed it. Why? Because we were always talking; they checked in frequently, casually, and in real-time. If something came up, we addressed it right then and there. No waiting weeks to bring it up in a structured meeting, and the casual nature of it made it easier to bring up the trickier stuff.
Both approaches taught me a key lesson: It’s not about the meeting itself. It’s about the connection. Your one-on-one is just a tool to build that.
One-on-Ones Are for the Employee, Not the Manager
The best one-on-ones aren’t about project status updates (there are better places for that). They’re dedicated time for an employee to talk about what they need. That could be:
A problem with a teammate
A career goal they want support on
A process that’s making their job harder
An update on how they’re doing—stressed, motivated, or burnt out
A personal situation that may affect work
Managers: If you treat 1:1s like your time instead of theirs, you’re missing the entire point - making your life harder.
One-on-ones aren’t just another meeting on your calendar. They’re one of the few structured opportunities where your employees get to drive the conversation. If you monopolize that time with your priorities (project updates, team metrics, or whatever fire you’re putting out that week) you’re sending a clear message: Their needs come second.
When employees don’t feel like they have a dedicated space to bring up challenges, career goals, or roadblocks, those problems don’t disappear; they just go unresolved until:
They start disengaging and doing the bare minimum.
They burn out and then you find out they were struggling.
They quietly start job hunting.
Ask yourself:
Do your employees feel heard?
Are they getting value out of these meetings?
Or are you just checking a box?
Because if your employees aren’t getting anything from your one-on-ones, neither are you.
Common One-on-One Mistakes (You’re Probably Making at Least One)
Cancelling too often.
Your employee may not always need the meeting, but they should be the one to decide that. Constant cancellations and reschedules send a clear message: "I don’t have time for you."
Turning them into project updates.
This is the biggest mistake I see. Yes, work will come up. But if your 1:1 is only about tasks and deadlines, you’re missing the bigger picture. Talk about the person, not just the work.
Talking more than listening.
If your employee only speaks for five minutes, while you're flapping your lips for the rest of it, you’re doing it wrong. You should be listening way more than you’re talking.
Letting them become therapy sessions.
(This is a trap I fall into a lot.) Yes, be empathetic. Yes, be supportive. But you are not their therapist. Your job is to listen, help where you can, guide, and empower; not be their emotional crutch (whether it's about work or not).
Not following up on issues.
If an employee brings up a concern, and you never follow up, you’re showing them that talking to you is pointless. Accountability goes both ways.
Forcing the same structure on everyone.
Some employees love one-on-ones and come with a list of things to discuss. Others (looking at you, dev with your favorite hoodie and noise-cancelling headphones [also me]) would rather not be interrupted. Adapt the structure and frequency to what actually works for each of you.
How to Make Your One-on-Ones Not Suck
Let the employee drive the conversation. Sometimes people aren't as open or ready to speak. Have some good questions to help them think and get to know each other better in your pocket.
Prepare in advance. Don't make them watch you fumble through notes and programs to start the meeting.
Be transparent. If they’re burnt out or struggling, they need to feel safe enough to say it.
Give feedback in real-time. Don't wait for 1:1s to offer praise or constructive input.
Hold them regularly. Don’t go weeks (or months) without checking in. Even if it’s just 15 minutes, it matters.
For Employees: Be Honest
Managers can’t fix what they don’t know. If you’re feeling stuck, burnt out, or just want to grow, say something. A good manager will want to support you. If you don't trust your manager enough to open up in that way; get to their manager and/or refresh that resume.
For Managers: It’s Not About You
Your job isn’t to talk at your employees for 30 minutes. It’s to support, guide, and listen. A great one-on-one builds trust, and trust is what builds great teams.