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Mastering One-on-One Meetings: A Guide for Managers

One-on-one meetings between managers and their team members are a cornerstone of effective leadership and employee development. These dedicated sessions provide a valuable opportunity to build rapport, offer support, provide feedback, and align goals. However, leading one-on-one meetings effectively requires more than just scheduling a slot on the calendar. It involves thoughtful planning, active listening, and fostering an environment of trust and collaboration. In this guide, we’ll explore strategies for leading impactful one-on-one meetings and provide a list of questions to enhance engagement and support within your team.

We’ll also like to mention a few ways in which you can save time as a manager, and prepare for these meetings and get access to templates that can help you lead meaningful conversations without having to spend too much time preparing.

When to Cancel Your One-on-Ones?

Some managers and project managers tend to schedule one-on-ones to track progress. While this mindset is changing, I encourage you to cancel one-on-ones scheduled for this purpose. Instead, have a check-in(stand-ups) meeting with the whole team where each person shares their objectives for the week and any blockers they’re facing. This will save you hundreds of hours and will bring more transparency between team members because everyone will be informed about progress and each other’s priorities.

Instead, leverage your one-on-ones as an opportunity to support team members, coach them, build rapport, and foster trust and a relationship of admiration in both directions.

Preparing for Success

  • Set Clear Expectations: Define on your invitation what types of conversations and topics team members can bring to their one-on-ones.
  • Create a Comfortable Environment: Choose a conducive setting for the meeting where both parties can speak openly without distractions. Whether it’s a private office space or a virtual meeting room, ensure that the environment encourages open dialogue.
  • Encourage Two-Way Communication: One-on-one meetings shouldn’t be one-sided conversations. Encourage team members to share their thoughts, concerns, and ideas openly. Actively listen to their perspective and provide constructive feedback where necessary.
  • Respect Confidentiality: Build trust by respecting the confidentiality of discussions during one-on-one meetings. Assure team members that their concerns will be handled with discretion and confidentiality.
  • Encourage Team Members to Own the Meeting and Bring Topics: Encourage them to bring topics to the meeting, like personal aspirations, concerns, conflicts, career goals, etc.
  • Prepare for the Meeting: Not everyone is the same! Some team members may start the conversation easily, some team members may default to work topics like projects, and some others may even remain quiet, making you end the meeting earlier. But your role is to adapt to each employee and prepare a few questions and topics in case the employee didn’t bring anything to the meeting so that you can help that employee grow and build a space of trust between you two. Even if at the end of the meeting you don’t end up discussing your topics, you can have that ready for another day. What is key is that you are actively listening and use that time to really connect and support your team.

Preparing for your one-on-ones as a manager.

To prepare for your one-on-ones, think about a topic or the type of questions you want to be asking. Sometimes you can bring a topic when an employee has mentioned that they want to get better at something, for example, “presentations,” or maybe you have noticed that there are things that they could improve. In this case, you can bring anything to the meeting: a tool that they can use as a template, a metaphor so they think about the topic, or you can provide feedback.

In other cases, you may want to learn more about this employee or build rapport. To do that, you will define a list of questions, probably just 3 or 4 questions. To help you out and provide some inspiration, we have created a list of typical questions.

Effective Questioning Techniques:

As a manager, asking the right questions can unlock valuable insights, foster deeper connections, and demonstrate your support for your team members. Here’s a curated list of questions to consider incorporating into your one-on-one meetings:

1. Relationship Building:

  • How are you feeling about your role within the team?
  • Is there anything on your mind that you’d like to discuss?
  • How can I better support you in your current projects?
  • What are your career goals, and how can we work together to achieve them?

2. Progress and Performance:

  • What progress have you made since our last meeting?
  • Are there any challenges or roadblocks hindering your progress?
  • Is there any additional training or resources you need to succeed?
  • What accomplishments are you most proud of since we last spoke?

3. Feedback and Development:

  • How do you feel about the feedback you’ve received recently?
  • Are there any areas where you feel you need additional support or development?
  • What skills or competencies would you like to focus on improving?
  • How can I help you grow professionally within the organization?

4. Goal Alignment:

  • Are your current tasks and projects aligned with your career aspirations?
  • Do you feel motivated by the goals we’ve set together?
  • Are there any adjustments we should make to your objectives or priorities?
  • How can we ensure that your work aligns with the broader goals of the team and organization?

5. Work-Life Balance and Well-being:

  • How are you managing your workload and maintaining work-life balance?
  • Are there any concerns or stressors outside of work that are impacting your performance?
  • What support or accommodations can I provide to help you maintain well-being?
  • Are there any initiatives or resources you’d like to see implemented to support employee wellness?

How to Organize Your One-on-Ones?

Organizing and preparing your one-on-ones, making sure you keep track of your notes and some of the topics mentioned, requires time. For that reason, we are suggesting two methods that can really help.

1-on-1 notes — Nova

The first one is using a whiteboard. It’s a visual way to keep your notes there. It also provides some questions that you can use as inspiration that will be already prepared for you.

If you add your conclusions and notes inside the conclusion section, you will be able to access those from your calendar, creating an overview of all your notes over time. (Nova users only)

Emotional Check-in — Nova
Nova’s Calendar

If you are using a traditional session, then it gives you much more flexibility because you can share it with the employee and they can take notes about next steps and takeaways, and you can see those notes, while you also have your questions and notes in the same session but it keeps it invisible to the employee. So it’s keeping both sides in one place and all organized by dates. Watch this video to understand how it works if you are using Nova.

Effective one-on-one meetings are a testament to strong leadership and a commitment to the growth and well-being of your team members.

By implementing the strategies outlined in this guide and utilizing thoughtful questioning techniques, you can create a supportive environment where team members feel valued, heard, and empowered to excel. Remember, the key to success lies not only in the quality of the questions you ask but also in your genuine interest and investment in the development of your team.

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