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Virtual One-on-One Meetings: How to Build a Better Connection

Virtual One-On-One Meetings Provide Direction And Connection

One of the simplest, most cost-effective ways to build trust and improve performance in your virtual team is a deliberate and well-executed cadence of virtual one-on-one meetings. Here are six topics both high-performing and struggling employees tell us they’re yearning for in their virtual one-on-one meetings.

Your Employees Are Yearning For More in a Virtual One-on-One Meeting

Even before this transition to remote work, when we would ask employees about their experience with one-on-one meetings, we often heard nervous laughter and responses like these:

  • “One-on-one meetings, what are those (hahaha)?”
  • “She has an open door. She tells us to come by whenever we want. (Of course, she’s never there. Hahaha). “I just wish she could carve out some dedicated time.”
  • “I just count on windshield time with my manager between client visits. He’s so busy, that’s the only time I know I’ve got him captive (hahaha).”
  • “He just leaves me alone. I do a good job. I guess he would tell me if I was screwing up (hahaha).”

Obviously, these responses are less than ideal, but it’s even harder to wing it now. So much is changing—and fast.

In the last few months, when we’ve asked employees about their one-on-one meetings, the tenor of the conversations has changed from nervous laughter to deep concern.

Employees are yearning for MORE DIRECTION and CONNECTION in their virtual one-on-one meetings.

We explore this concept further in our Asking for a Friend series:

“Dear Boss, Here’s What I Need Most In Our Virtual One-On-One Meeting…”

Here we share what we’re hearing employees need most right now in their one-on-ones.
We encourage you to share this article with your team and to talk about what’s working in your remote one-on-ones and what you can do to take them to the next level.

(And psst…Dear Leader…if life without human-centered practical leadership training is getting a bit too edgy for your liking – or your strategies just aren’t working like you need them to – visit our Virtual Leadership Development page to learn how to build and sustain company-wide change.

clarity - help employees understand and create clarity

1. Clarity: Help Me Understand What’s Most Important Right Now

“I understand that you don’t have all the answers. Priorities change.  But please give me a fighting chance of working on the right things, because quite frankly, I’m feeling overwhelmed and I don’t have time for rework or wasted effort. Please use our one-on-one meeting to ensure I know what matters most this week, and what I need to do to be successful.”

2. Caring: Show Me I Matter More Than My KPIs

“It’s been a rough week. I’m tired. I signed up to be a working parent, but not a working parent with no daycare!

I know you’re busy, but before you jump right in and talk about the project, can you take a minute to see me and check-in to see if I’m doing okay?”

caring - show employees they matter in virtual one-on-one meetings
consistent cadence of one-on-one meetings they can expect

3. Consistency: Give Me a Cadence I Can Count On

“I know your heart is in the right place and that you’re being pulled in a million directions too. But this is the third time you’ve canceled our one-on-one meeting. I had my list all ready to cover with you. And now I’ve got to track you down.

I scheduled my one-on-one meetings with my team AFTER ours so I would have answers for them. Now I’m heading into those with unanswered questions which is embarrassing and is slowing all of us down.”

4. Credibility: Be Real With Me, So I Can Be Real With You

“You know what made me feel great, that one time when you opened up and really shared how you were feeling. It made me feel so much better to know that you’re scared and tired too. But since then, you’ve just been so perky and positive—and I wonder, are you for real?”

add credibility - be real in your virtual one-on-ones
capacity - ask how you can support employees in one-on-ones

5. Capacity: Ask Me What Support I Need

“What I need to hear more than anything right now is: ‘How can I be most helpful?’

I have ideas about how you can help. But, it’s frustrating to have to always be the one initiating that conversation.”

6. Curiosity: Ask Me For My Ideas

“I’m learning a lot and I’ve got some great ideas about how we can do things better. But, I feel awkward sharing my ideas if I’m not asked.’

‘Boss, I really care about you, this company, and our success. I’d love to have some time to pull up with you each week in a quick online one-on-one meeting to share as we work through this important time together.’


Your courageous employee.”

cultivate curiosity ask employees for their ideas

How to Hold a Better Virtual One-on-One Meeting: Free Tools

Whether you’re the manager looking to hold better remote one-on-ones, or an employee yearning to get the support you need from your manager. These easy-to-use one-on-one meeting tools work wonders.

One-on-One Meeting Template

This one-on-one meeting template helps you create a more meaningful one-on-one strategy for each team member.

Use this to add variety and a broader range of support to your one-on-one meetings.

MIT Check-In

It’s a staple in our live-online leadership development programs, and both managers and employees tell us a using it each week to structure remote one-on-ones creates focus, connection, and helps to prioritize what matters most.

It works like this. You schedule 10 minutes a week and ask your employees to and come prepared to discuss the following:

First, start with connecting at a human level. Be sure they’re feeling seen at a human level.

  • What’s the Most Important Thing you accomplished last week?

    (This gives them an opportunity to ensure you  are aware of the good work they are doing)

  • What’s the Most Important Thing you’re working on this week?

    (This helps clarify expectations and ensure alignment)

  • What support do you need?

    (This gives your employee a structured time to ask for help AND also makes it easier for them to keep a running list of anything that’s not urgent and can wait.)

In fact, here at Let’s Grow Leaders, we’ve automated these questions in Basecamp, our project management tool. Every Monday each team member (including the executive team!) answers these questions so that everyone can see and understand their biggest priorities, and offer support.

Of course, automation is not a substitute for great one-on-one meetings, it’s a jumping-off point for deeper conversation.

Our clients tell us it’s exactly this kind of real-life leadership experience that brings LASTING VALUE to their training. We’re all about practical, relevant ways to learn and implement leadership skills.

This is no cookie-cutter, stale-off-the-shelf program. Every Virtual Leadership Training we provide is customized…designed specifically to meet your team where they are.

You can download the free MIT Check In here.

Your Turn:

What would you add? What’s working well in your remote one-on-ones?

P.S. This article was featured in CTO Universe MVP Best Articles of 2020 Awards.

See Also:

How to Overcome One of the Biggest Challenges from Working From Home

How to Hold an Effective Mid Year Review in a Pandemic

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leading virtual and hybrid teams
building great team cultures
practical leadership skills
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