February 18, 2025
Episode 126: How to Overcome Your Team’s Biggest Challenges with Jonathan Bennett
In this episode of The Future of Teamwork, Dane Groeneveld chats with Jonathan Bennett, a strategic advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. Jonathan shares his career path from poet to strategic advisor, and how his experiences taught him to coach from a place of deep listening and empathy. Dane and Jonathan discuss the value of emotional intelligence, communication skills, and social capital in leadership. Jonathan explains why you need deep engagement strategies for people outside the team early on, and how to start. They also talk about the impact of therapy on leadership and workplace dynamics, how younger generations are leading differently from their Gen X counterparts, and how self expression is changing in today’s workforce. If you’re looking for ways to improve how your team works together, this episode is worth your time.
How to Overcome Your Team’s Biggest Challenges with Jonathan Bennett
Guest Bio
Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies.
Key Takeaways
00:00 Introduction to the Future of Teamwork Podcast
01:36 Dane Groenveld Welcomes Jonathan Bennett
03:00 Jonathan’s Journey: From Literature to Leadership
03:30 Lessons from Building a New Hospital
08:05 The Role of Social Capital in Leadership
17:33 The New Generation’s Approach to Work
24:57 Dealing with Anxiety in the Young Generation
26:23 Intergenerational Team Dynamics
28:06 Coaching Executives for Modern Leadership
29:54 Role-Playing and Scenario Training
31:24 Indigenous Approaches to Trust and Decision Making
36:29 The Importance of Onboarding and Early Agreements
43:06 Navigating Self-Expression and DEI Challenges
47:24 Concluding Thoughts and Contact Information
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