By Jiji Lee

Nervous About One-on-One Meetings? Here’s How to Prepare.


This meeting is important for everyone - make it count.

When I had to attend my first one-on-one meeting with a senior-level Director, I was filled with anxiety and nerves. 

How should I prepare? What should I say? I even asked other colleagues for advice on how to prepare for this meeting, but they didn’t seem to know the purpose of one-on-one meetings either. Later, when the Director ended up having to cancel the meeting, I felt a wave of relief. 

Whether you’re a manager or a direct report, you might have had a similar experience with a one-on-one meeting. You’re either relieved that it’s postponed or you’re really excited for it, only to have it later cancelled by the manager. But if we want to improve workplace culture and enhance the well-being of our employees, we need to make more of an effort to establish better one-on-one meetings. 

One-on-one meetings are a crucial element in building strong, positive workplaces. 

It’s not enough to just hold regular team meetings and town halls. You need direct channels of communication in order to build trust, empower employees, and improve productivity. By having regular check-ins with employees, you can bring about positive changes within your team. And from the employee standpoint, you’re more likely to feel valued and heard when you get to have one-on-one interactions with your manager. 

With just a little organization and prep work, you can have a really positive one-on-one meeting. Below are some tips and tricks that both parties can use to get the most out of these one-on-one meetings. 

How often should you meet?

The frequency of your one-on-one meetings can depend on the size of your team and company, as well as the relationship you have with your manager or direct report. You can try meeting once a week for 30 minutes or meet bi-weekly for 45 minutes to an hour. It should happen more than once a month.

The most important thing is that you should meet on a regular, reliable basis. Even if you regularly “see” your team members around the office or in meetings, make sure to carve out time for face-to-face check-ins that are just about connecting one-on-one.

According to this Harvard Business Review article, these meetings are critical in building rapport:”...they are how you show employees that you value them and care about them.”

Agenda for a one-on-one meeting

A simple way to ensure a successful one-on-one is to establish the meeting agenda beforehand. This way, you don’t have to feel the dreaded “what are we going to talk about?” and can go in feeling prepared.

To help you organize your meeting, you can use the Ink+Volt 1:1 meeting notepad, a productivity tool designed to add more structure and organization to your meetings. 

First, set meeting topics and expectations beforehand. If you need help focusing on what area to discuss, take a cue from former Google CEO Eric Schmidt and have each person make their own list of topics. If you see the same topics on both lists, then make sure to prioritize them during your meeting.

Here are some possible topics of discussion:

  • Follow-ups
  • Progress
  • Goals
  • Obstacles
  • Questions

You can also approach your conversation by thematic area. For example:

  • Career development and training
  • Budget and operational issues
  • Meetings and travel
  • Workplace layout and well-being

This is an important opportunity to have a deeper conversation on a work issue. If it’s a conversation that you could easily exchange over email or Slack, then you’ll probably want to save it for a different time.

The topics don’t have to be the same every time. Some weeks might be more about personal development, whereas others are more strategic or project-focused.

As an employee, think about the critical issues that you’d like to discuss with your manager and get their insight on. If you don’t feel comfortable bringing up certain subjects at a team meeting or town hall, then maybe you can use the one-on-one as an opportunity. 

Maybe you’d like guidance on how to resolve challenges on a work project or interpersonal issues with a colleague. Or maybe you’d like advice on how to meet your career goals. Or maybe you’ve been struggling with your workload. These are all valuable topics you could raise during a one-on-one -- and because you know the meeting is coming, you can prepare your thoughts and even practice what you want to say. 

Conversely, if you’re a manager, think about how you can empower your employee during this meeting and beyond. What kinds of topics can you discuss that will invite meaningful, productive conversation? How can you make them feel comfortable sharing and being listened to?

When you identify discussion topics prior to the meeting, you will have much more confidence going into the meeting. As an employee, you can do your due-diligence and brush up on what you need to discuss. As a manager, you can figure out what you can support your employee ahead of time. This way your meeting can feel like it's flowing productively.

How to have an open and meaningful conversation

One of the most positive impacts of a one-on-one meeting is that it can help build trust and connection in the workplace. Therefore, as a manager, it’s essential that you help your employee feel supported and heard during this conversation.

Maybe at the top of the meeting you can ask how their family is doing or ask them about their weekend. This is a small but meaningful way to start the meeting off on a personal note and build rapport.

Another way to create an open and supportive discussion is to ask your employee for their feedback on something work-related. Asking someone for their opinion is an amazingly effective way to build trust -- it shows you take their thoughts seriously.

Encourage your employees to share their opinions on a work project or a recent change in the workplace. Ask them what they think or how they would do things differently. If they are a new employee, ask them how they conducted things in their previous workplace and if they think those procedures should be implemented here. These simple questions can go a long way in creating a collaborative discussion.

You can use the topics you both brought to the meetings to steer the agenda, but also feel free to just use them as a jumping off point. 

For instance, If you start a discussion on a work project, but then the employee mentions an interest in attending a specific conference, take that opportunity to discuss their interest and see if there’s anything else you can do to support them. Maybe this could segue into a discussion on additional training or allowing them to try on different roles to develop their skills. By being open and flexible during the discussion, you could make a positive contribution to your employee’s career.

Throughout the discussion, make sure to frame your conversations in a positive way and tell your employee that they’re doing a great job and that you value their feedback. Make sure to affirm them and ask your employee what kind of support and tools do they need to ensure their success.

Remember: it’s not always easy for employees to open up and discuss work challenges or career goals with a colleague, especially their boss. Make sure to be fully present and engaged during these meetings. 

Put your phone on silent. Step away from the computer monitor. Don’t let others interrupt the meeting. Physical cues are so much stronger than verbal ones. Remember to listen and remain fully engaged during this discussion. 

Action items

Not only are one-on-one meetings beneficial in building rapport and trust, but they’re also effective in improving productivity. 

After going over a discussion on project details, you can jot down action steps to be taken on the notepad. This way, you’re both committed to taking these steps to move forward. You can also email this list of action steps to each other and ensure you’re both on the same page.

Afterwards, you can enter these items into your Google calendar or Ink+Volt planner to keep track of deadlines and ensure that you’re meeting these milestones and keeping yourself accountable.

With a little preparation, you can start having powerful and effective one-on-one meetings. In this age when so much of our work is conducted online, it’s so crucial to have channels like one-on-one meetings as a way to touch base with our colleagues and forge a more meaningful connection. 

If you’d like more tips on how to have better one-on-one meetings, be sure to check out all the tips here