

1889 – Navigating Leadership and Entrepreneurship with Jennifer Wilson
Apr 23, 2024
16:47
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder and Lead Coach of Oak Bay Coaching and Consulting, Jennifer Wilson.
Jennifer Wilson is a leadership coach and the founder of Oak Bay Coaching and Consulting. Transitioning from a ski instructor and midwife to a family business leader and coach, Jennifer brings valuable insights to entrepreneurs and leaders. Her background in guiding skiers and assisting in childbirth has given her a deep understanding of human potential and the nuances of leading individuals through difficult transitions. This wealth of experience has propelled her into leadership coaching.
In discussions, Jennifer describes herself as a "thinking partner" to her clients. She adopts a non-directive role, encouraging clients to explore their solutions through introspective and powerful questions. This method promotes client autonomy and instill a sense of responsibility for their decisions and consequences.
A key focus of the discussion was Kolbe, a tool that Jennifer Wilson uses to assess individual strengths and problem-solving styles. She highlighted the importance of recognizing and utilizing these strengths and acknowledging the diversity within a team. This understanding is essential for entrepreneurs dealing with complex team dynamics.
Key Points from the Episode:
- Jennifer Wilson's journey and transition to becoming a leadership coach
- Her role as a thinking partner and guiding clients to solve their own problems
- Working with clients in family businesses and women in leadership
- Coaching framework as a passenger in the car while clients are in the driver's seat
- The value of Kolbe in understanding problem-solving strengths
- Challenges that entrepreneurs face, including effective delegation
- Addressing burnout and the importance of self-reflection and leveraging strengths
- Resources available on oakbaycoaching.com for new leaders and preserving organizational culture
- Encouragement to join the Thoughtful Entrepreneur community
- Promise to continue bringing positivity and inspiration to listeners' daily lives