DiscoverLead with Heart | Philanthropy, Nonprofit Leadership, Nonprofit Management & FundraisingE111: Mastering Difficult Conversations & Building Trust in Nonprofit Leadership with Chris Wong
E111: Mastering Difficult Conversations & Building Trust in Nonprofit Leadership with Chris Wong

E111: Mastering Difficult Conversations & Building Trust in Nonprofit Leadership with Chris Wong

Update: 2025-09-23
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I am so excited to welcome Chris Wong to the Lead with Heart Podcast. Chris is a licensed therapist, executive coach, and host of The Art and Science of Difficult Conversations podcast. With over 15 years of experience in the nonprofit and health sectors, Chris specializes in helping purpose-driven leaders navigate difficult transitions, rebuild trust, and lead culture change that actually lasts.

In this episode, we dive deep into the art of mastering hard conversations, the psychology behind conflict, and how nonprofit leaders can strengthen trust and resilience in their teams. Chris shares practical strategies for bridging generational differences, navigating hybrid workplaces, and leading with clarity when the stakes are high.


In this episode:

  • [05:05 ] Nonprofit leadership challenges: scarcity mindset
  • [07:07 ] Bridging generational differences in nonprofit leadership
  • [09:36 ] Why leaders avoid hard conversations and how to reframe conflict
  • [14:14 ] Building trust in nonprofit teams and organizations
  • [18:12 ] Cultivating relationships in hybrid nonprofit environments
  • [20:58 ] A framework for approaching difficult conversations
  • [27:55 ] Preparing nonprofits for crisis conversations
  • [33:22 ] Addressing gossip during organizational change
  • [34:21 ] Insights from Chris’s own podcast on difficult conversations
  • [36:53 ] Advice for anyone about to have a difficult conversation


RESOURCES

E7: Focusing on Emotional Connection to Boost Performance in Your Organization with Lola Gershfeld


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Send Haley a suggestion or request via text HERE!

My book, Sow, Grow, Lead is live on Amazon! It shares my journey of starting a nonprofit in Malawi and offers practical strategies for nonprofit leaders to create real impact.

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Dr. Lola Gershfeld’s EmC Masterclass helps you boost communication skills to raise more revenue. Trusted by top universities and global organizations. Use code LEADWITHHEART for 10% off.

CONNECT WITH HALEY
Haley is a CFRE, Stress Management Coach, and EmC trainer. Founder of The Savvy Fundraiser, she brings experience in human services, homelessness, and youth nonprofits. She specializes in EmC, leadership, board development, and fundraising, empowering nonprofit leaders to build thriving organizations.
Instagram: @thesavvyfundraiser
LinkedIn: Haley Cooper, CFRE
Website: thesavvyfundraiser.com

Produced by Ideablossoms

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E111: Mastering Difficult Conversations & Building Trust in Nonprofit Leadership with Chris Wong

E111: Mastering Difficult Conversations & Building Trust in Nonprofit Leadership with Chris Wong

Haley Cooper | Certified Fundraising Executive (CFRE), Certified Stress Management Coach, Certified EmC Trainer