When Bold Conversations Change Systems

 In this episode, I’m bringing you a story that perfectly captures why courage is one of the most important skills you can build as a fundraiser — and how it can completely change your results. You’ll hear about my client Laura, a high-performing fundraiser who pushed herself to take a huge risk. First, she asked a donor for a $250,000 gift and heard “no.” But she didn’t let that stop her. She kept strengthening her “ask” muscle and later made a $1.5 million ask — which led to an incredible $810,000 gift that helped her team close out their fiscal year strong.

And here’s the thing — this transformation wasn’t about tactics or scripts (though we worked on those too). It was about how Laura saw herself, how she built her courage, and how she led by example for her team. Whether you’re trying to hit a big revenue goal or just want to feel more confident going after major gifts, there’s so much in this story for you.

Here’s what you will learn:

• Why taking bigger swings with loyal donors is key to reaching your next fundraising level
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• How to strengthen your “ask muscle” and get comfortable with hearing “no”
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• Why the way you see yourself as a fundraiser impacts the size of the gifts you ask for
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• How emotional intelligence helps you identify which donors are ready for a bigger ask
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• The behind-the-scenes story of how one bold ask turned into an $810,000 gift
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• How to model courage as a leader so your entire team rises with you
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• Why generosity is contagious — and how your boldness can ripple through donor networks
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Thanks so much for tuning in today. I hope Laura’s story inspires you to take more courageous swings in your own fundraising work. It’s not always easy to push past fear or to risk hearing “no” — but when you do, the doors it can open are incredible. Remember, your donors want to give. Your mission deserves big gifts. And YOU are capable of asking for them.

If this episode resonated with you, I’d love it if you’d share it with someone else who’s on this fundraising journey too. The more we encourage each other to lead with courage, the more impact we can all create. See you next time!

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