This isn't a chance to catch up on current work

It's very easy to get into a habit of just talking about whatever work is currently being done whenever you have a 1 on 1 meeting. This however isn't the time to cover that, there should be plenty of work touchpoints in your schedule. This meeting should focus on other items that affect an employee's work life. Be candid with the other person in this meeting, it's ok to talk about the weather or lunch or what you did last weekend. We don't want to force anyone to share something that they aren't comfortable with but we can make them at ease and build trust by talking about ourselves.

The idea isn't just to BS with another person for 30 minutes or whatever but to talk about the factors that are affecting work and that isn't always just things that happen at work. As far as items that do pertain to the job at hand or work relationships we can talk about blockers, employee issues, goals, etc.

An agenda is crucial

Free form 1 on 1 meetings will quickly go off the rails, not add much value and will generally end early. Below is a sample agenda I would use for 1:1s with software engineers. This agenda was a starting point and would be adjusted as needed. Everyone is different so 1:1 meetings will need some tailoring for each person.

• Follow-up (this time is used to make sure the last meeting's action items were handled)
• Accomplishments (what is something you're proud of right now? let's celebrate the great things we do and bonus we keep a running list of accomplishments for end of year reviews)
• Concerns/Help (this is when you identify blockers that need attention)
• Action Items (these will be identified during the meeting)
• Goals (this one is unique to each individual. a manager and an employee can determine goals together, then start plans to meet those goals. new goals are not needed each meeting)

1:1s aren't just for direct reports

Do 1 on 1 meetings with everyone on your immediate team. Just because the designer or analyst doesn't directly report to you doesn't mean that you shouldn't meet with them individually on a regular basis. Your team is your team and to build a high-functioning team everyone needs to be in it together. Take this time to make sure they feel as much a part of the team as everyone else and to help them with their careers. You'd be surprised with what you'll learn just listening to the struggles that someone in another position has with their work. Together those struggles can be turned into strengths or opportunities to make the team better.

Take and share notes

I like to share my screen with a running Google Doc for each person's 1:1 with me. Update the agenda items to include the notes of what we talked about and write the action items. Share this file with the other party so they can review and even add notes outside the normal 1:1 time.

This meeting isn't just work focussed

Use these meetings to get to know your coworkers on a deeper level. Especially in a remote world trust can be hard to build. Being human, empathetic and a friendly with the people you work with can be a big step in that direction. You don't need to be friends with everyone you work with but having a good relationship with others will help in ways that may not be obvious all the time. A close-knit team outputs far better products than a team that acts as individuals and less collaboratively.