The art of one-on-one meetings: a useful guide

A few years ago, I showed up for my weekly one-on-one with my manager armed with an iced coffee and absolutely no idea what we should talk about. We stared at each other for a full minute before someone said, “So… how’s it going?” It was awkward. It was pointless. It was 30 minutes of small talk that neither of us needed. Sound familiar?

One-on-ones shouldn’t feel like a blind date with your boss. When done right, they’re a chance to build trust, tackle real problems, and make sure no one’s silently drowning in work or in questions they’re too shy to ask.

You’re in the right place if you’re a manager, a founder, a freelancer growing your team, or just someone typing “one-to-one conversation examples” into Google. This is your no-fluff, real-talk guide to making the most of one-on-one meetings.

What even is a one-on-one meeting?

A one-on-one (or 1-on-1) meeting is a regular check-in between a manager and a direct report. It’s not a performance review. It’s not a status update. It’s a space where the employee gets to talk, ask, vent, share ideas, and be heard. But it only works if both people show up prepared.

The art part: making it meaningful

Think of your one-on-one as a really good conversation over coffee. You want it to feel natural but still go somewhere. That’s where a simple one-on-one meeting agenda can help. You don’t need a 10-slide deck—just a few talking points to keep things focused.

Start with questions that open the door. What’s been going well? What’s been challenging? Is anything slowing you down? This is where those “one-on-one meeting with manager questions and answers” you see online come in handy if you use them to spark real talk, not just tick boxes. And don’t forget to flip the script. Managers can and should ask for feedback too. Trust goes both ways.

Templates are your friend, not your boss

You’ve probably searched for a “one-on-one meeting template” at some point. Templates are great to get you started, but they’re not law. Think of them like IKEA instructions: helpful, but you can still build the bookshelf your way.

Is a big project going on? Focus the meeting on that. Just hired someone new? Make space for questions. Long week? Maybe it’s a shorter, more casual check-in. It’s your meeting. You’re allowed to adapt.

Real talk: what makes a one-on-one actually work?

Here’s what people really appreciate in a 1-on-1: Feeling heard. Having space to ask questions. Knowing it’s okay not to have all the answers. A little humor (yes, even in finance). And a plan for what happens next.

Consistency matters too. It’s hard to build trust if you keep rescheduling. You don’t have to meet for hours. Just often enough that your team knows you’re paying attention.

One-on-one meetings with employees: not just a manager thing

Let’s clear something up. One-on-ones aren’t just for managers. Freelancers running client projects, nonprofit teams juggling deadlines, educators mentoring staff—they all benefit from better conversations.

If you work with people, one-on-ones are your secret weapon. They help you catch issues early, spot growth opportunities, and stop communication breakdowns before they turn into epic Slack threads.

Final thought: meetings don’t have to be messy

Now, scheduling these magical meetings? That’s where things often fall apart. Between full calendars, time zones, and the never-ending back-and-forth of “Does Tuesday work for you?” it’s easy to let them slip.

That’s why Doodle exists. With tools like 1:1, you can offer time slots, let the other person choose what works for them, and skip the email ping-pong. It’s simple, saves time, and makes you look like you’ve got it together (even if you’re still wearing pajama pants).

So go ahead—make the most of your one-on-ones. Ask better questions. Have real conversations. And if you’re still scheduling by smoke signal, maybe give Doodle a try.