The Art of Coaching When You’re the Boss

How to incorporate coaching strategies into your leadership practice


For years, you’ve asked, “I’m a principal/manager/director/etc. How can I be a coach? The lines are blurry!” And I’m ready to answer and guide you through the complicated waters of straddling the roles of supervisor and coach, and of using coaching strategies to transform your organizations. Space is limited, so don’t wait to sign up.

You are not “a coach,” but you want to learn how to integrate coaching strategies into your leadership toolkit. You know there are times when you need to be “the boss,” and you know there are times when it would be helpful to take a coaching stance. But you’re not sure how to determine when those times are, or what exactly “taking a coaching stance” would look like in action. This workshop will help you explore the distinction between the roles you need to play, even when your official title is boss (or supervisor, principal, manager, etc.), if you want to maximize opportunities to guide someone’s reflection and growth. You’ll practice using a few core coaching strategies that will allow you to see immediate impact in your ability to connect with those you directly supervise, develop their abilities, and be the leader you want to be.


Participants will:

  • Understand the different hats they wear as leaders and the purposes and requirements for wearing each of those hats
  • Recognize the opportunities in putting on a coaching hat, and the power in using Transformational Coaching strategies
  • Observe the impact and potential for change from using Transformational Coaching strategies
  • Practice using three Transformational Coaching strategies

Activities include

  • Observing a coaching conversation in which Transformational Coaching strategies are used
  • Small group discussions
  • Role play practice
  • Question and answer

Who should attend

Anyone who holds a supervisor role: principals, assistant principals, managers, superintendents, CEOs, etc.


Participants in this learning experience must have attended one of our foundational learning experiences: The Art of Coaching 101.

If you are not able to complete a full prerequisite workshop in advance, completing the self-paced portion of The Art of Coaching 101 workshop (6-8 hours of online course modules) will meet this requirement.


This learning experience takes place over the course of two 2-hour learning blocks with a short brain break in between.

The virtual-live session will be recorded (except for breakouts) in the event you cannot make a session or if you would like to rewatch at a later time. Participants have access to content for 30 days after the learning experience.

What people say

This workshop has given me the tools to support the growth in my staff as a high school vice-principal. The importance of being in a coaching stance and the tools to support this will stay with me throughout the rest of my career. The workshop had a strong balance between theory and practice, with valuable opportunities to interact with others. I highly recommend this class for all school leaders.

Andrea (Bright Morning member)

This workshop articulated skills that I needed support in, without even realizing it yet! I am motivated to continue working on my Transformational Coaching skills as a year-long goal and feel very set up for a successful trajectory thanks to this workshop. Being both a supervisor and a coach is challenging. Having a workshop focused on how to navigate both roles was very helpful.

Ginger (Bright Morning Member)

I feel refreshed, rejuvenated, and equipped with a new arsenal of tools after attending this workshop.