Question #3: How do I know someone is ready to make or increase a gift?

By Rachel Cyrulnik

[Eight Burning Fundraising Questions for Eight Nights of Hanukah continues.]

This is where the art of fundraising comes into play. But if you don’t just have that amorphous “feeling” that it’s the right time, here are a few pointers:

  1. Look for Patterns – if it is a repeat gift, look at when the gift was given in the past – if the donor usually gives in December, you’ll want to make sure you reach out before year’s end. Review giving history. If the gift has remained flat for several years, consider asking for an increase. If the donor has increased on her own in the past, she has demonstrated their proclivity to increasing her gift.
  2. Engage – for both prospective and existing donors whose gifts you wish to increase, present opportunities that strengthen ties to your cause and deepen relationships with your organization’s representatives. I often encounter organizations that expend significant time and energy on identifying and researching prospects, but when they want to ask for a gift, they review their cultivation efforts and come up short. Your donors should have 3-4 positive interactions with the cause before you ask for a gift.
  3. Listen! You can learn a great deal about how ready your donors feel regarding making a gift by asking open-ended questions about their attitudes toward and impressions of your cause at face-to-face meetings.
  4. Leverage Events and Milestones – If you’re not sure when to pop the question, events and milestones can be a useful tool and provide a reason for why you’re asking now.

Rachel Cyrulnik is founder and principal of RAISE Nonprofit Advisors (, a strategic development firm servicing nonprofits. Contact Rachel at