How to Run an Effective Remote 1-on-1 Meeting

Hey there! 👋

I had my monthly 1-on-1 with my manager last week that lasted exactly 12 minutes. We covered my current projects, he asked if I had any questions (I said no), and then we both sat there in awkward silence until he said, “Well, I guess that’s it!”

Sound familiar?

Remote 1-on-1s can feel like pulling teeth. Without the natural flow of in-person conversation, they often devolve into status updates or uncomfortable small talk. I’ve been on both sides of these meetings—as a supervisor and as a direct report—and I’ve learned that the problem isn’t the technology.

It’s the lack of intention.

What Makes Remote 1-on-1s Different 🤔

Here’s what I’ve figured out: In-person 1-on-1s benefit from body language. They also gain from casual moments before and after the meeting. Additionally, there is an ability to read the room. Remote meetings strip all of that away.

But here’s the thing—that constraint can actually be a gift. When you can’t rely on those natural conversational cues, you’re forced to be more thoughtful about structure and preparation.

The best remote 1-on-1s I’ve experienced felt more focused and productive than their in-person counterparts. They just required a different approach.

Four Elements That Transform Remote 1-on-1s

After running hundreds of these meetings (and enduring plenty of awkward ones), here’s what consistently works:

1. Start With the Human Check-In

Skip “How are you?” and try something more specific. “What’s been on your mind this week?” or “What’s been energizing you lately?” These questions invite real conversation instead of automatic responses.

Give this 5-7 minutes. Sometimes the most important insights come from how someone answers this question.

2. Use the “What, So What, Now What” Framework

Structure the main discussion around three questions:

• What happened since we last talked? (Updates, challenges, wins)
• So what does this mean? (Impact, patterns, concerns)
• Now what should we do about it? (Next steps, support needed)

This prevents the meeting from becoming a random brain dump and ensures you’re moving from information to action. It can also lead to some pretty interesting conversations.

3. Make It a Shared Document

Create a running agenda document that you both contribute to before each meeting. Include sections for their updates, your updates, discussion topics, and action items.

This does two things: it makes preparation easier and creates a record of what you’ve discussed over time. Plus, when someone adds something sensitive to the agenda, you know it’s important to them.

4. End With the “One Thing” Question

Before you wrap up, ask: “If you could change one thing about how we work together, what would it be?” or “What’s one thing I could do to better support you this week?”

This question often surfaces the most valuable feedback. And because it’s focused on just “one thing,” it feels less overwhelming to answer.

Your Challenge This Week 🎯

If you’re a manager: Try the shared document approach for your next 1-on-1. Create a simple agenda template and share it with your team member 24 hours before the meeting.

If you’re a direct report: Before your next 1-on-1, think about what you actually want to discuss beyond project updates. What support do you need? What feedback do you have? Come prepared with one specific topic.

I’m curious—what’s your biggest frustration with remote 1-on-1s? Are they too superficial, too long, or do they just feel awkward?

Hit reply and let me know. I’ve been collecting stories and strategies from managers across different industries, and your experience might help someone else.

Talk soon, Tim.

P.S. The 12-minute meeting I mentioned? I followed up with my manager and suggested we try a shared agenda approach. Our next 1-on-1 was 45 minutes of actually useful conversation. Sometimes you just need to take the first step.