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 or Taste of Transformational Coaching.

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 courses modules) will meet this requirement.


This learning experience takes place over the course two 2-hour learning blocks with a short brain break in between. All times are Pacific:

  • 8:30am – 10:00am PT
  • 10:30am – 12:00pm PT

What people say

“I’ve been trained in other coaching methods, but this workshop totally blew me away in the clarity and precision with which it was delivered. Thank you, Elena! You are an incredible teacher and facilitator.”

Miho, non-profit leader, Pasadena