Voices of Remote Work
4 min

Seven Tips to Have Effective One on One Meetings with Investor and Writer Tom White

For Walking Meetings & Remote Work

One-on-one meetings present an opportunity to laugh with a colleague, chatter about various goings-on at work, and discuss everyday life. While meant to be productive, one-on-ones can quickly go south and create unnecessary anxiety when done without guardrails or a clear purpose.

So, what goes into running effective one-on-one meetings? 

We asked Tom White—a Writer, Investor, and Explore Advisor at On Deck— to share some tips that all managers should keep in mind. 

1. Use the Right Tools

Before you plan an agenda or create talking points, it’s critical to ensure you’re using the right tools to facilitate a proper one-on-one, especially if you work remotely.

As Tom said, “A lot of communication and nuance is lost via remote work, particularly through disjointed text and video. As for Zoom, it’s scientifically shown that it’s tiring for us to make sense of another individual over a video screen. The cognitive overwhelm is exhausting.” 

In a remote setting, he feels strongly that effective one-on-ones to are best conducted without video and preferably while walking. 

He continues, “For those working from home, just like you need a designated place to do your work, you need a different place from which to host your one-on-one meetings—a space where you connect human to human.” 

Spot, for instance, encourages users to walk while talking (which does wonders for your creativity) and takes notes in real-time so you can reference them later. You can also find tools for brainstorming, ideation, organizing projects, and more.  

2. Build a Relationship 

The most important goal of effective one-on-one meetings is relationship building. Meeting with your employees is your opportunity to get to know them without anyone else — or any distractions — around. 

As Tom said, “When you divorce yourself from your computer or desk, you don’t have those other distractions, like Slack pings or emails coming in. You can focus on the conversation at hand rather than the peripheral stuff.”

You can ask your direct report questions like: 

  • What are their short and long-term career goals? 
  • Are they happy at work/with life?
  • What systems and processes are working for them, and which could use improvement?
  • How are their relationships with other team members?
  • What are sources of friction you can address as a manager? 
  • What are other ways you can support them better? 

Per Tom, “Showing a genuine interest in others is super important and mitigates the many challenges in remote work communication.” 

Ask questions about life outside of work too. This will help you develop a stronger rapport with your direct report and allows you to understand if there’s anything going on in their lives that may impact their work or well being 

3. Set an Agenda — Together 

Resist the temptation to plan the agenda in isolation. The one-on-one meeting is for your direct report. It is their time

This is their opportunity to openly share what’s on their mind. In advance of the meeting, you both should write down what you’d like to address in your shared organization or project management tool. If you’re using Spot, be sure to populate the Agenda and Shared Notes with anything you’d like to discuss or review during the call. 

4. Get a Status Check

Similar to Ariel Camus’ Stoplight Technique, Tom recommends getting a status check at the beginning of one-on-one meetings. Asking your direct report to share if their day is Red, Yellow, or Green sets the foundation for the meeting and allows you as their manager to guide how the conversation should go. 

He continues, “If your report says ‘Green’, it indicates that everything is going well. They’re most likely in the right frame of mind to have a more in-depth conversation about something. But if they say ‘Red’, then perhaps you could hold off on bringing up that issue you wanted to discuss until the next meeting.” 

5. Make Them Consistent 

Ensure that your one-on-ones are consistent. Rescheduling or running them on different days of the week could derail any good, important personal/professional progress being made. . 

Put simply, erratic and unpredictable meetings can cause stress and increase the likelihood of miscommunication. Consistent meetings establish a rhythm that helps harmonize the motions of work. 

6. Keep Your Notes Organized 

Write down the important details from your conversation or use an automated tool to simplify the process. It’s frustrating for both you and your employee to talk about something important only to forget what either of you said later, so having detailed notes to reference for a reminder (especially for continuing a conversation the next week or implementing feedback about a project) will save time and energy. 

7. Prioritize One-on-Ones

To your direct reports, one-on-one meetings can be even more valuable than team gatherings because they have your undivided attention. To them, the one-on-one is an opportunity to address their concerns and ask questions without fear of judgment or running out of time to raise their points. Because one-on-ones are so beneficial, it’s crucial to prioritize them. Show up on time and listen carefully. 

Tom summarized it best, “Remember that you have two ears and one mouth for a reason. As a manager, your role is not to dictate, but to listen.”

One-on-ones will be much more effective if your employees feel comfortable around you. Let them ask questions, raise concerns, and admit mistakes without fear of condemnation and be sure to offer plenty of praise. 

Effective one-on-one meetings are a cornerstone of a healthy, functioning team. 

For more information about tools that facilitate one-on-one conversations and simultaneously boost creativity and physical health, head over to Spot’s blog

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