Ever go into a meeting with a major donor with a plan to ask for a gift, and something throws you off?

You leave the meeting kicking yourself because you didn’t make the ask. You had a purpose for the meeting, but somehow you got off track, and now you feel like you wasted your time with this major donor.

This has happened to me what feels like 10,000 times in my career. And after coaching 651 nonprofit CEOs, development directors, and major gifts fundraisers over the last eight years, I’ve seen the same thing happen again and again.

In this episode, I’m sharing a behind-the-scenes clip from one of my weekly CourageLab coaching calls. We get into the hidden dynamics behind why we back down in major donor meetings, especially with rich, powerful, assertive donors, and what you can actually do about it.

What you'll learn in this episode

How difference and power dynamics can take you off track in a donor meeting
How to relate to rich, powerful people without giving away your own power
Why you must reclaim your power when a conversation gets uncomfortable
The dynamics you need to understand when it feels hardest to hold your ground
What really stops you from making the ask
Why asking donors for advice can be a dumb idea
Where confidence actually comes from, and how to strengthen it in tough circumstances
How to develop a no-pressure fundraising culture
Why great partnerships are built on honesty, not just transparency
Why giving donors more information can actually create more confusion

If you’ve ever felt like your best-laid plans are hard to stick to when you’re sitting across from a powerful, rich, assertive donor, this episode is for you. If I were sitting down with you over coffee and sharing the truths I hope would get into your bones, this is that conversation.

Every nonprofit founder, CEO and fundraiser needs this conversation. share this with a colleague or friend. DM me the letters CL on LinkedIn if you’d like to learn more about CourageLab and raise more unrestricted major gifts.

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 ED or DD of a $1M+ making a difference in your community and you’re ready to make bigger, bolder asks, then DM me “CL” on LinkedIn and I’ll share details.