Unlocking the Power of One-on-One Meetings

A Guide Based on Enneagram Type

"What is your inner critic telling you?" my boss asked. I was two weeks into the job, and while I wasn't new to one-on-one meetings this question caught me off guard.  It felt strange to trust someone I just started working for with the messages I was constantly hearing from my inner critic.  

How honest or vulnerable do I need to be here? 

What if he agrees with my inner critic? 

What if he gets a peek behind the curtain of my mind and realizes I’m actually crazy?

Am I crazy?  Focus, Kelsey.  He just asked you a question! 

I pushed past my fears and answered the question. 

"My inner critic is telling me that you never should have hired me.  I'm not learning fast enough. I'm a burden to the people who are training me, and I don't deserve this job." 

I exhaled and waited for his response. 

"Well, all of that is trash." 

At that moment, his affirmation washed over me like sweet tea on a hot day.  Not only was it refreshing, it also gave me fuel to push through the frustrations that come with learning a new role.  

And that, my friend, is the power behind leading effective one-on-one meetings.  If you aren't doing one-on-one meetings with the people you lead, you're missing opportunities to provide encouragement, coaching, or essential feedback. 

So, what exactly is a one-on-one meeting?

A one-on-one meeting is a meeting between a supervisor and a team member. These meetings can take place in person, over the phone, or through video conferencing. The purpose of a one-on-one meeting is typically to discuss work-related topics, provide feedback and coaching, and build a stronger working relationship. 

One-on-one meetings can be structured or unstructured, and they may occur on a regular basis (such as weekly or bi-weekly) or as needed. The goal of a one-on-one meeting is to create a safe space for open and honest communication, where both parties can share their thoughts, concerns, and ideas in a supportive environment. 

Coach Kelsey here - I would HIGHLY recommend in person one-on-one meetings if you can swing it. Video conferencing is a good alternative. Also if you have the ability to meet weekly or bi-weeily do it. I wouldn’t recommend going more than 2 weeks without touching base with your team members. Keep in mind, these meetings don’t have to be long. Keep them between 15-30 minutes. 

What happens in one-on-one meetings?

One-on-one meetings provide a space for open communication between managers and team members. They create an opportunity for managers to share their expectations, provide feedback, and offer guidance. Additionally, one-on-one meetings allow team members to ask questions, share concerns, and provide feedback to their managers.

Regular one-on-one meetings can also help build trust and foster a positive relationship between managers and team members. By providing a dedicated time to discuss performance and goals, team members feel supported and valued, which increases job satisfaction and engagement.

6 Characteristics for an effective one-on-one meeting

  1. Clear agenda: An effective one-on-one meeting should have a clear agenda that outlines the topics that will be discussed. This ensures that the meeting stays focused and productive.
  2. Open communication: Both parties should be encouraged to speak openly and honestly during the meeting. The supervisor should actively listen to the team member and ask questions to gain a deeper understanding of their perspective.
  3.  Feedback and coaching: The supervisor should provide constructive feedback and coaching during the meeting. This can help the team member improve their skills and enhance their overall performance.
  4. Goal-Check In: The meeting should include a discussion about goals and progress towards achieving them. The supervisor should work with the team member to set achievable goals and create an action plan to achieve them.
  5. Problem-solving: The meeting should provide an opportunity to discuss any issues or concerns that may be impacting the team member's work. The supervisor and team member can work together to identify solutions and develop a plan to address these issues.
  6. Follow-up: An effective one-on-one meeting should end with a plan for follow-up. The supervisor should summarize the key points discussed during the meeting and outline the next steps. This ensures that both parties are clear on what needs to be done and helps to hold everyone accountable.

What if I don’t have time?

Coach Kelsey here:  Make time. Not in the literal sense, although if you do figure how to literally make time, would you do me a solid and let me in on that?  In all seriousness,  you must make time for these meetings. The benefit far outweighs the inconvenience.  That being said, I know you’re busy and stretched for time… so here are a few tips to implement these meetings with efficiency and ease:

  • Schedule the meetings in advance: By scheduling the meetings in advance, you can ensure that both you and your team member are prepared and have the time blocked off on your calendars.
  • Make the meetings short: One-on-one meetings don't have to be long to be effective. Aim for a 15-30 minute meeting that is focused on a few key topics.
  • Prioritize the most important topics: If you're short on time, prioritize the most important topics for the meeting. This can help you stay focused and ensure that you're making the most of the limited time you have.
  • Be flexible: If something comes up and you have to cancel or reschedule a meeting, be flexible and work with your team member to find a new time that works for both of you.

Remember, the goal of a one-on-one meeting is to create a safe space for open and honest communication where both parties can share their thoughts, concerns, and ideas in a supportive environment. By following these suggestions, you can still make the most of your limited time and create a positive and supportive environment for your team members.

5 consequences of not doing one-on-one meetings

If you, as a manager, never participate in one-on-one meetings with your team members, several negative consequences could arise, including:

  • Avoidable misunderstandings: Without regular one-on-one meetings, communication between you and your team members may be limited or nonexistent. This can lead to misunderstandings, conflicts, resentment,  and a lack of trust.
  • Decreased productivity: Without regular check-ins, team members may not be clear on their goals, priorities, or expectations. This can lead to a decrease in productivity and a lack of progress towards achieving objectives.
  • Missed opportunities for feedback and coaching: One-on-one meetings provide an opportunity for you to provide feedback and coaching to your team members. Without this feedback, team members may not be aware of areas where they need to improve, which can impact their performance.
  • Reduced engagement and job satisfaction: When team members feel disconnected from their manager, they may become disengaged and dissatisfied with their work. This can lead to turnover and difficulty retaining top talent.
  • Lack of accountability: One-on-one meetings provide an opportunity to hold team members accountable for their work and progress towards goals. Without regular check-ins, team members may not feel accountable, which can impact their motivation and performance.


To retain your administrative assistants, you should understand what motivates them and  focus on providing a positive work environment, opportunities for growth and development, and a supportive workplace culture.

Can you give me ideas on how to approach one-on-one meetings based on Enneagram Type?

The Enneagram is a powerful tool for understanding individual personalities and how people interact with the world around them.  Here's how to tailor your approach to one-on-one meetings based on Enneagram Type:

Type 1 - The Perfectionist

Type 1s are driven by a desire to do things the right way and achieve perfection. They can be hard on themselves and others, and may struggle with criticism or feedback. 

When approaching one-on-one meetings with Type 1s, it's important to focus on setting clear expectations and providing constructive feedback. Be specific and avoid generalizations or broad statements. Encourage them to share their concerns and ideas, and provide specific examples of where they can improve.

Type 2 - The Helper

Type 2s are driven by a desire to connect with others and be of service. They may struggle with setting boundaries and may prioritize the needs of others over their own needs. 

When approaching one-on-one meetings with Type 2s, create a warm and supportive environment. Listen actively and ask questions to show your interest in their personal and professional lives. Provide opportunities for them to share their accomplishments and successes, and offer support and guidance when necessary.

Type 3 - The Achiever

Type 3s are driven and goal-oriented. They thrive on accomplishment and recognition, and may struggle with failure or setbacks. 

When approaching one-on-one meetings with Type 3s, focus on setting challenging but achievable goals. Encourage them to think creatively and to pursue projects that align with their values and passions. Provide recognition and praise for their accomplishments, and offer feedback and guidance to help them continue to grow and develop.

Type 4 - The Individualist

Type 4s are driven by a desire for self-expression and authenticity. They value creativity and may struggle with feeling misunderstood or unappreciated. 

When approaching one-on-one meetings with Type 4s, provide opportunities for creativity and self-expression. Encourage them to share their unique perspectives and ideas, and to pursue projects that align with their personal values and interests. Offer support and guidance to help them channel their creativity in a productive and meaningful way.

Type 5 - The Investigator

Type 5s value knowledge and expertise. They are analytical and may struggle with emotional expression or connection. 

When approaching one-on-one meetings with Type 5s, provide opportunities for learning and growth. Encourage them to pursue new skills and interests, and to share their knowledge and insights with others. Offer support and guidance to help them connect with others and develop their emotional intelligence.

Type 6 - The Loyalist

Type 6s are driven by a desire for security and stability. They may struggle with anxiety and worry, and may seek reassurance from others

When approaching one-on-one meetings with Type 6s, create a supportive and reassuring environment. Be patient and understanding, and provide opportunities for them to voice their concerns and fears. Offer guidance and support to help them build their confidence and overcome their anxiety.

Type 7 - The Enthusiast

Type 7s are driven by a desire for adventure and new experiences. They may struggle with boredom or feeling constrained. 

When approaching one-on-one meetings with Type 7s, provide opportunities for innovation and creativity. Encourage them to think outside the box and pursue new and exciting projects. Offer guidance and support to help them channel their enthusiasm in a productive and meaningful way.

Type 8 - The Challenger

Type 8s are driven by a desire for power and control. They may struggle with vulnerability or being perceived as weak. 

When approaching one-on-one meetings with Type 8s, be direct and assertive. Provide clear expectations and feedback, and avoid vague or ambiguous statements. Offer opportunities for them to demonstrate their strength and leadership skills, and offer support and guidance to help them develop their emotional intelligence and vulnerability.

Type 9 - The Peacemaker

Type 9s are driven by a desire for harmony and peace. They may struggle with assertiveness or setting boundaries. 

When approaching one-on-one meetings with Type 9s, create a calm and supportive environment. Encourage them to share their perspectives and ideas, and provide opportunities for collaboration and teamwork. Offer guidance and support to help them assert themselves and set clear boundaries when necessary.

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