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“Leading with Kindness Amidst Crisis, Chaos, and Change” with Jeff Jacobson


This week on the UpLevel Podcast, join us for a great conversation about the transformative power of leading with kindness through crisis, chaos, and change. Our guest is Jeff Jacobson, a professional coach and facilitator with over three decades of experience. Known for his fierce yet loving approach to coaching, Jeff shares his insights into what true kindness entails and provides actionable components that listeners can integrate into their leadership styles and personal growth.

This episode is about walking the walk toward being an embodiment of kindness — something we desperately need in today's world. Tune in now.

In this Episode:

  • Christie reflects on how Jeff helped her have a significant impact on her life by challenging her to take responsibility during a pivotal moment.

  • Jeff explores the true meaning of kindness beyond common misconceptions such as being a doormat or engaging in toxic positivity. 

  • Jeff introduces the five buckets of kindness: Clarity, Honesty, Sweetness (compassion), Play/Creativity, and Vulnerability.

  • Christie and Jeff emphasize the importance of holding multiple perspectives and managing emotions constructively amidst disagreement or conflict.

  • The conversation highlights seeking professional guidance or community support when dealing with strong reactions or changes is crucial for effective leadership.

  • Personal stories from both Christie and Jeff, such as embracing awkward moments for humor's sake or acknowledging shared humanity within professional settings.

Order of Topics:

  • Jeff’s Profound Impact

  • Defining Kindness

  • The Five Buckets of Kindness

  • Vulnerability in Leadership

  • Playfulness as Growth

  • Sweetness Reclaimed

  • Holding Multiple Perspectives

  • The Role of Honesty and Clarity

  • Personal Anecdotes and Humor

Action Items:

  • Embrace Vulnerability

  • Foster Playfulness and Creativity

  • Practice Sweetness (Compassion)

  • Be Honestly Kind

  • Communicate with Clarity

  • Balance Feedback

  • Set Clear Boundaries

  • Cultivate a Culture of Kind Feedback

  • Practice Self-Kindness

About Jeff:

Jeffrey A. Jacobson, CPCC, PCC, is a professional coach and facilitator with 30+ years of experience in the coaching world. He works with clients to manage change, enhance performance, discover cutting-edge solutions, and create sustainable working environments.

Prior to coaching and training, Jeff studied Asian culture and language for years throughout East and Southeast Asia and went on to teach Mandarin Chinese to business leaders from Ford, Motorola, and Texas Instruments.

Jeff is on faculty at both the Co-Active Training Institute (CTI), and the Trium Group, where he develops and delivers curriculum to coaches, managers, and leaders. He is a board member for Coaching for Everyone, an organization that brings coaching to BIPOC leaders in North America and beyond.

He lives with his partner and their cat in Portland, OR, and is the author of the novel “The Boy Who Couldn’t Fly Straight,” the first in his Young Adult queer paranormal adventure series (he likes adjectives!).

About UpLevel Productions: Founded by Christie Mann, MA, CPCC, PCC, and Rachel Baldi, CPCC, PCC, UpLevel creates, produces, and delivers Transformative Experiences, Workshops, Training, Events + Media that develop leaders who make our world a healthier, more alive, and connected place to be. As Associate CTI Faculty Partners, UpLevel is licensed to sell, produce, and deliver Co-Active coach training and leadership development programs around the world to support the transformational growth of individuals and culture inside the workplace and organization. Instagram @uplevelproductions Facebook & LinkedIn @uplevelproductionscompany


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