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September 23, 2025 43 mins

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.

As the fundraising engine of choice for over 80,000 organizations in 90+ countries, Donorbox’s easy-to-use fundraising tools help you raise more money in more ways. Seamlessly embed a customizable donation form into your website that reduces donor drop-off with a 4x faster checkout, launch a crowdfunding or peer-to-peer campaign, sell event tickets, raise funds on the go with Donorbox Live™ Kiosk, and much more. Learn more at donorbox.org

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

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