Overcoming Personal Money Beliefs to Ask Directly

 In this episode, I’m digging into the real shifts that happen when leaders stop performing, stop softening themselves, and start showing up with clarity, honesty, and real authority — especially in major gifts work. Regina, an Executive Director in Courage Lab, shares her experience of shedding the “always upbeat, always polished” persona and stepping fully into her CEO energy. She talks about what changed when she stopped trying to be overly cheerful for donors who didn’t need or value that, how being direct actually accelerated trust, and what she’s learning as she leads a new development director through this work. Together, we explore what authentic leadership looks like, why relationships deepen faster when you tell the truth, and how taking courageous action creates real momentum inside an organization.

WHAT YOU WILL LEARN IN THIS EPISODE

• Why donors don’t need (or want) a polished persona — they want clarity, vision, and real talk

• How Regina realized she was draining energy by trying to sound upbeat instead of operating as a CEO

• The difference between relationship building and performing happiness

• How direct, honest communication fast-tracks donor trust

• Why showing donors the real challenges — not just the “shiny penny” — actually strengthens the partnership

• How her development director stepped into courage early, even while still learning the organization

• The mindset shift that helped her team make direct asks confidently, even without long-term relationships

• What happened when donors began engaging more deeply, referring others, and leaning into honest conversations

• How consistency, authenticity, and direct asks created organizational momentum

• Why Regina invested in Courage Lab, what stood out to her, and why the accountability model made all the difference

• What changed for their board, their fundraising approach, and their long-term strategy

• The transformation she’s already seeing just one month into the program — and what she hopes others take away from this work

This conversation is such a powerful reminder that major gifts aren’t built on performance — they’re built on leadership. When you stop worrying about being overly positive, deferential, or “pleasant” and instead tell the truth about what’s needed, donors rise to the occasion. Regina’s story shows what’s possible when an Executive Director claims her authority, leads authentically, and commits to courageous action even before everything feels perfect. It also shows how quickly things can shift when a team has the right structure, accountability, and support. If you want to hear what this kind of transformation looks like behind the scenes — and you’re curious about what Courage Lab can unlock for you — this episode is absolutely worth a listen.

Want 15 leads in 5 minutes? DM me "Breakfast burrito" on LinkedIn and I'll send you a pdf and 6-minute training to help you generate 15 leads for your nonprofit in minutes. It's totally free. All you need is an email to sign up. DM me "Breakfast burrito" - I'm from Texas, what can I say? - to get your pdf and mini training. 

If you're an org with at least $800k annual budget and major gifts is your top priority, but you need a better strategy and approach, get on the waitlist for the next CourageLab cohort here: https://julieordonez.kit.com/couragelab2