Address Awkwardness Directly to Strengthen Relationships

Hey friend! I’m recording from my new apartment in Chicago, and I’m so excited to bring you Part 3 of my series on end-of-year giving strategies. This episode is a pep talk about the single most important thing I want you to focus on for a successful end of year: asking for more.

I know it sounds simple, but asking for more is the strategy that makes the biggest difference in raising money. I’m talking about asking current donors, loyal supporters, and even monthly donors for more — without overthinking it, without worrying about what’s “too much,” and without trying to budget their philanthropy for them. Your job is to communicate the need, build relationships, and invite generosity. The rest is up to them.

 IN THIS EPISODE:

• Why asking for more is the #1 strategy for end-of-year success
• 
  
• How to stop worrying about what’s “too much” for your donors
• 
  
• Why perfectionism and over-preparing can actually hold you back
• 
  
• How humility can make up for lack of know-how or missteps
• 
  
• Why fundraising is risky — and why that’s okay
• 
  
• How to turn mistakes into stronger donor relationships
• 
  
• Tips for having confident, clear conversations with your supporters
• 
  
• My approach to determining ask amounts and staying decisive
• 
  
• How to navigate awkwardness, conflict, and uncertainty with donors
• 
  

The truth is, most of us overthink asking for more, and that hesitation costs time, energy, and ultimately, donations. I want you to feel set free from the fear of asking for too much or getting it “wrong.” Humility, emotional intelligence, and willingness to risk are your allies — they allow you to make the ask, repair missteps if needed, and build stronger, healthier relationships.

Whether you’re raising major gifts for the first time or trying to hit your end-of-year goals, this episode is packed with practical advice and encouragement to help you lean in, take the risk, and ask for more.

DM me CL to learn about joining Courage Lab, my cohort for leaders who want to raise $100K+ in just 1–2 hours a week.

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