Why Everyone Should Have a Coaching One-on-One - Docket

Why Everyone Should Have a Coaching One-on-One

Coaching one-on-one meetings are considered one of the most effective training methods and establishing a strong team of employees. However, mentoring one-on-one can be daunting, depending on the location or platform of the coaching session. Whether your meeting involves goal setting one-on-one, giving directions, or setting agendas, you need a collaborative meeting platform that ensures your coaching is always useful.

While regular one-on-ones for day-to-day check-ins and project updates are also necessary, a coaching one-on-one agenda differs in that it is a time set aside to discuss the employee’s individual growth goals and how you, as their manager and coach, can aid them in their growth journey.

Benefits of One-On-One Mentoring

How much time do you dedicate to your employees? Think about the number of times you have engaged with your workers this year through one-on-one conversations focusing on their development and performance. Well, mentoring and coaching your employees enhances their skills and makes them more valuable to your organization.

According to the one-on-one coaching meaning or one-on-one mentoring definition, coaching or mentoring provides an opportunity for your employees to share their career advancements, ideas, and frustrations. Here are some benefits of mentoring during the different stages in a one to one coaching process:

Builds Confidence

Some employees are more confident than others because of various reasons. For instance, new employees may not act with the same confidence as those you have worked with for several years. However, you can easily build their confidence through one-on-one meeting sessions.

Center of Attention

1-on-1 mentoring puts the mentee in the center of attention since it’s relatively easy for some mentees to be overlooked during group meetings. Because of its nature, one-on-one sessions provide an excellent opportunity to deliver detailed information to the mentee to realize improved performance. Moreover, the meetings can help you determine the effectiveness of your one-on-one mentoring style.

Creates Better Relationships

Do you have many introverted employees? What is your relationship with them? Sometimes introverted employees behave the way they do because of their work environment. A one on one mentoring session offers an intimate setting where you get to forge better relationships with your mentees, including introverted mentees.


Due to the flexibility of one-on-one mentoring, these meetings can happen quite often. As a mentor, you only need to inform your mentees about a meeting. With this kind of flexibility, it’s easy to tell your employees about changes within your organization.

Psychological Development

One-on-one mentoring creates an environment where the mentor continually challenges his or her mentees. The coaching also encourages employees to take responsibility for their actions, which bring about social and psychological development.

Encourages Innovation

One-on-one coaching encourages innovation because the received knowledge continues to be passed on. After these kinds of meetings, individuals can become innovative and find solutions to various organizational problems.

Coaching One-On-One Questions

Given the above-mentioned one-on-one coaching benefits, which questions should you ask your employees? One-on-one coaching questions are essential because great coaches don’t just provide answers — they ask questions. A simple question from a coach can make all the difference, especially when it comes to team performance.

Effective one-on-one questions allow you to use different one-on-one mentoring models for different trainees to help them solve problems, improve performance, or reach their career goals. The following are a few questions that should be in your one-on-one coaching template:

  1. What are you enjoying most about your current role?
  2. What frustrations have you had recently?
  3. Who in the company would you enjoy working with or shadowing?
  4. Are there other parts of the business you’d like to be more involved in?
  5. Since you have achieved your current goal, what will be your next goal?
  6. What obstacles have you faced so far? How did you overcome them?

To avoid having problems during meetings, employees should also prepare for one-on-one coaching in advance. As an employee, you need to come up with relevant one-on-one meeting questions to ask your manager. Here are a few one-on-one meeting agenda questions to ask your manager:

  1. How did you come up with our organizational targets?
  2. What can I do to improve the performance of department X?
  3. How should I send sensitive information to you in the future?
  4. What achievement do you wish the company to achieve in this financial year?
  5. What do you make of the way I solved problem X? Could I have done it in a better way?

Coaching Session Example

If you want your one-on-one coaching session to be successful and ensure all major issues are covered, you need to create a session plan from scratch or use a most applicable template for your meeting. Here is a one-on-one coaching template example you can use for your coaching.

Mentoring and Coaching One-on-One Agenda

Personal Updates

What’s working

  • What are you enjoying most about your current role?
  • Which projects excite you most?
  • What are you most proud of?


  • What frustrations have you had recently?
  • Is this getting in the way of your professional growth goals?
  • What will your next steps be?

Growth Discussions

  • What skills are you working on?
  • What are you reading?
  • Who in the company would you enjoy working with or shadowing?
  • Are there other parts of the business you’d like to be more involved in?
  • Are there regular meetings you feel you should be a part of that you’re not?

About the Author

Heather Hansson

Heather is VP of Product and Chief of Staff at Docket. She enjoys leading cross-functional teams to work together on vision, strategy, and implementing solutions that help people work and live better. When she isn’t helping rid the world of wasteful meetings with Docket, Heather likes to run, take violin lessons with her son, and spend time with her family.

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