Holding Courageous

Custom In-House workshop

Learn the skills needed to deliver and participate in uncomfortable conversations.

about this workshop

Leaders need to deliver tough conversations from time to time – conversations that can be uncomfortable and require courage. These conversations are necessary in daily life and part of being an effective communicator and leader.

This course focuses on techniques and tools to confidently and successfully address a wide range of difficult issues. Participants will leave this course with the confidence to have courageous conversations with their team members, peers, customers, and their boss.


Who Should Attend?

Entry and mid-level operational, support, and HR leaders who are responsible for developing employees and/or leading teams. 


3.5 hours – delivered virtually or on-site


4 PDC credits provided to SHRM certified professionals

Course Benefits


In-Depth Knowledge

Identify how skilled leaders prepare and deliver challenging messages.


Hands-on Practice

Practice and hone skills in a safe, supportive environment.


peer learning

Learn from peers and develop your network.


expert facilitation

Learn the best approaches to show managerial courage from a skilled facilitator.


continuing support

 45 minute 1-1 coaching follow up with the course facilitator to support development and application of the material.


Practical Tools

Learn our Two-Step Feedback Model and leave with a clear action plan for handling difficult conversations.

Holding courageous  conversations course outline

This course will cover these topics in an interactive and highly engaging way. To ensure maximum collaboration, learning, and individualized attention, the class size is kept small and participants make progress on real-world challenges while in class. 


  • Identify common underlying issues, concerns, and assumptions behind courageous conversations
  • Examine the categories of courageous conversations and learn how to adjust your approach for each situation.
  • Identify ways to be authentic and direct in showing respect to the other person to increase understanding and agreement.
  • Review and practice a Two-Step Feedback Model to start courageous and establish understanding.
  • Discuss ways to effectively respond to questions during tough conversations while managing your own emotional response.
  • Create a clear action plan for implementing ways to strengthen your ability to have candid conversations in the future.
“Stewart Leadership brings a dynamic–yet simple to apply–leadership development process that energized and aligned my executive team! ”

Cory Mahaffey – Managing Partner

Northwestern Mutual