How to Structure One-on-One Meetings (Simple Agenda + 12 Questions)

Can I be honest for a moment? For a long time, my one-on-one meetings were really just status updates with coffee. I’d ask what they were working on, they’d tell me, I’d nod, and we’d both go back to our desks. Nobody grew. Nobody felt more connected. It was a box I checked.

Over the years – in hospitality, in higher ed, in nonprofits and now leading a church staff – I’ve learned that a well-structured one-on-one is one of the BEST tools a leader has. It’s where trust gets built, problems surface early, and people actually get developed. And, it doesn’t take a fancy system. It takes a simple structure you stick to.

Here’s how I structure mine today, plus a simple agenda and the questions I keep coming back to.

6 Keys to Better One-on-One Meetings

1. Meet regularly.

For some people this is weekly. For others it’s every other week or even once a month. But, it needs to be predictable. If it’s weekly, put it on the same day at the same time every week. How often you meet should depend on two things: how the person is doing (someone who is thriving may need less frequent check-ins) and the kind of work they do (a complex role that changes week to week needs more time than a role that repeats the same tasks). And please…don’t be the leader who cancels one-on-ones every time things get busy. When you cancel, your people hear “you’re not a priority.”

2. Make it personal.

I always start by asking how they’re doing – and I mean really doing. If the meeting is only about work, you miss a great chance to know your people and find out about outside pressures that might be affecting their work. Plus, it tells them you value them as a person.

3. Let them go first.

This one feels backwards. We want to make sure OUR items get covered. But, I’ve found that letting the other person start with their agenda puts them in the driver’s seat and sets the tone. Most of the time they cover the things I was going to bring up anyway. In other words, this is their meeting more than it’s mine.

4. Write it down in one shared place.

Back when I first wrote this post I used Wunderlist (RIP). The tool has changed, but the principle hasn’t. Keep one shared list or document for each person – Microsoft To Do, Asana, a shared Google Doc, whatever your team already uses. Add things during the week as they come up, then review them together. It gets the meeting started fast and makes sure nothing falls through the cracks.

5. Follow up.

I’ve heard it said that you have to inspect what you expect. If something got assigned last time, ask about it this time. For some people that just means glancing at the shared list. For others it means going to look at the project together. Either way, your one-on-ones are where follow-up happens. Without it, the list is just a wish list.

6. Get on the same page.

When tasks get passed along by email and text, it’s hard for people to see the bigger picture the way you see it. Use part of your one-on-one to share the “why.” Walk the building together, pull up an example of what you’re picturing, talk through where the organization is headed. Vision leaks…and one-on-ones are one of the best places to refill it.

A Simple 30-Minute One-on-One Agenda

Here’s the rhythm I use. Steal it!

• 5 minutes – Personal check-in. How are you doing? How’s the family? What’s on your mind?
• 10 minutes – Their agenda. Questions, ideas, roadblocks they brought.
• 5 minutes – Follow-up. Review last time’s action items on the shared list.
• 5 minutes – My agenda. Anything they haven’t already covered.
• 5 minutes – Growth and next steps. One thing they want to get better at, and who owns what before next time.

12 Good One-on-One Meeting Questions

You don’t need all of these every time. Pick two or three.

• How are you doing – really?
• What’s the best part of your work right now?
• What’s draining you?
• What’s one thing slowing you down that I could help remove?
• Is there anything you need from me that you’re not getting?
• What’s a win from the last couple of weeks we should celebrate?
• Where do you feel stuck?
• What’s one skill you’d like to grow this year?
• Is there anything about our team that’s frustrating you?
• What’s an idea you’ve had that we haven’t tried yet?
• On a scale of 1–10, how clear are your priorities right now?
• What’s one thing I could do differently as your leader?

That last one takes some courage to ask. Ask it anyway…and then just listen. If you want more on this, check out my 5 keys to giving feedback and the 4 keys of delegation.

3 Common One-on-One Mistakes

• Turning it into a status report. If it could have been an email, it shouldn’t take up your one-on-one.
• Doing all the talking. Aim for them talking at least half the time. More is better.
• Canceling when things get busy. Busy seasons are exactly when your people need it most. Shorten it if you have to, but keep it.

Quick Answers

How long should a one-on-one meeting be? Usually 30 minutes. Some people and seasons need 45–60, but 30 minutes held consistently beats an hour that keeps getting canceled.

How often should you hold one-on-ones? Weekly or every other week for most people. Monthly can work for experienced people in steady roles.

Do one-on-ones work with volunteers? YES. They may look different – a monthly coffee or a quick call – but volunteers who feel known stick around a whole lot longer.

The more you invest in your people this way, the better your relationships will be and the more productive your team will become. Make sense?

Do you hold regular one-on-ones with your team? How do you structure them? What question would you add to my list? Comment below…