• Jim Canfield

One-on-One Meetings with Direct Reports





After two years of remote and hybrid working, reconnecting with your direct reports has become more important than ever. One-on-one meetings with direct reports are a simple, vital way of achieving this. Channeling Robert Greenleaf's "servant leadership" approach, they turn the power pyramid upside down, positioning the leader to exist in service to workers. Here's how to make one-on-one meetings work for you - and your employees.


Why One-on-Ones Matter

The essence of servant leadership is empathic listening, responsiveness, and building a community focused on growing people. A 30-minute one-on-one weekly meeting promotes all of these traits and offers the following benefits:

  • Facilitates communication, allowing you to address issues, answer questions, ensure alignment, or course correct

  • Builds trust and rapport, showing that you're available and willing to listen and show up for your team

Like anything, follow-through matters - don't fall into the trap of prioritizing other things ahead of these meetings, or they'll always end up falling off your calendar. Schedule the time into your planner and protect it like you would if the meeting were with your largest customer. After all, your team members are customers - they're just internal ones.


Running Your One-on-One

It's important to remember that these meetings are an opportunity to air issues and concerns and build trust - they're not accountability sessions.

Start by asking the employee, “How’s it going?” and let them lead the conversation from there. If they bring up an issue, ask, “How can I help?”


Aim to listen more than you speak, and establish a relaxed, non-judgmental atmosphere that makes the employee feel safe asking for help or expressing concerns. Your job is to offer support or allocate resources to help your employees achieve their goals. Be an ally and peer, not a "boss."


If possible, spend most of the meeting time discussing non-business matters, but keep your discussion pleasant and respectful. You want to form deeper relationships, but you don't want to pry into people's personal lives.


While the meeting is ongoing, make sure no interruptions are permitted - that means turning off your phone and setting your OOO if needed. You want your employee to see that you're there for them and are wholly in the moment.


Continue the one-on-one weekly meetings weekly for five or six weeks, then space them out depending on the team member's needs, making sure to check in at least once a month. Make it clear to your employee that you're there for them if they need to arrange an interim meeting as well.


Lead the Way with CEO Tools

Regular check-ins are just one of the ways that you can elevate your leadership efforts and galvanize your organization. Take your company forward with the new CEO Tools Learning Modules, a series of 8 convenient modules designed for busy leaders. Proven, relevant, and easy to implement, they'll help you become the leader you've always wanted to be.


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