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#216 Four Lessons Learned From a Bad Ask

Sep 3, 2025
This week, the host recounts a cringe-worthy fundraising pitch that interrupted a Catholic Mass. He shares four crucial lessons learned from this experience. First, he stresses the importance of honesty in fundraising intentions. Next, he advises focusing on one ask at a time for clarity. Context matters, too—some settings are just wrong for requests. Finally, he encourages fundraisers to ask with confidence, highlighting the impact of a respectful approach. A contrasting, successful homily illustrates these points perfectly.
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ANECDOTE

Homily Turned Surprise Fundraising Pitch

  • Kevin Fitzpatrick describes attending Mass where a visiting priest turned a homily into a surprise fundraising pitch.
  • The priest built up a story about serving the poor and then abruptly asked the congregation for money, creating an ambush.
ADVICE

Always Reveal Your Intent Up Front

  • Avoid ambushing donors by hiding fundraising intent until the last moment.
  • Kevin advises to tell people upfront if you will ask for money instead of misleading them.
ADVICE

Ask For One Thing At A Time

  • Do one thing at a time when making asks so the main request doesn't get lost.
  • Kevin warns against piling requests like gifts, committees, and events into a single conversation.
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