The Art of the Ask.
Adapted from the Chicago Latino Arts & Culture Summit 2026 donor engagement workshop, presented in partnership with the National Museum of Mexican Art + Conlon Public Strategies. The framework that turns one conversation into a multi-year relationship — and a multi-year ask.
The 4-step Ask Framework
Use this sequence in every major-gift conversation, board ask, and stewardship meeting.
Get permission. Create context. Acknowledge the donor's time. "Thank you for being here — I want to share something important with you today." Build the container before the ask.
Tie the request to the donor's mission, values, and identity. Name what THEY have told you matters to them. The ask is not about your need — it is about their meaning.
Tell stories demonstrating measurable outcomes and community transformation. One concrete person. One concrete number. One concrete outcome. Stories first, statistics second.
Be explicit and confident in the funding request. "Will you consider a gift of $25,000 this year?" Silence is your friend after the ask. Do not fill it. Let them respond.
Donor discovery questions
For first conversations + cultivation meetings. Ask, then listen. Do not pitch.
Stewardship questions for existing donors
For renewal conversations, upgrade asks, and legacy-giving openings.
Monthly. 5-min read. One impact story, one ask, one event.
A library of 12-15 short stories per program. Reuse in every grant + every solicitation.
Visual. 8-12 pages. Numbers + one full-page transformation story. Mailed to top 100 donors.
Quarterly. Photos + specifics. "This quarter we served 240 families with…"
Year-end giving (Nov-Dec), Giving Tuesday, anniversary. 3-5 touches per campaign.
Inside 48 hours. Hand-written for gifts over $500. Phone call for over $5K.
