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Knowing When To Make The Ask

How do you, as a development professional or a capable and willing board member, know when it’s the right time to make that ask of someone for a contribution to your organization?

If I’ve heard it once, I’ve heard it a million times: “I don’t know when is the right time to ask someone for a donation.”

Although the turn of phrase, “there’s no time like the present” comes to mind, we philanthropy professionals know so much more goes into soliciting a gift. We are giving donors the opportunity to join us and others in bringing our mission to life for those being served. After all, who among us doesn’t want to do our part in helping others who would benefit from a leg-up on basic needs, a boost to their life skills, or a life-affirming encounter with the arts?

I was enjoying a quick lunch chat with a dear friend this past week while we both were visiting our shared undergraduate alma mater. My friend – an inspiringly thoughtful, successful and wise woman in tech – mentioned that her college’s gift officer is bright, engaging, well-prepared but hasn’t “made the ask” yet, in spite of my friend being more than ready. And that is the gift officer’s job and the reason they were together - to ask for support for the college. 

My friend established both a scholarship and a dedicated fund at the college years ago (thus, she’s already an active donor), is engaged with speaking at the university, on a board at the school, and had not one, not two, but three recent lunches with the gift officer. She is expecting the ask.

And yet, still no ask!

“I’m more than ready,” she said to him at their recent lunch. “Are you going to ask me for a donation sometime soon?” she encouraged him.

What was he waiting for?

Do you find yourself wondering when the time is right to make the ask? Do you ever find yourself second-guessing if now is the right time? Do you ever feel like you “chicken out” in soliciting a gift?

I’d propose the following prompts to guide your own thinking about when to make the ask:

  • If you’re waiting for the perfect moment to make the ask, you might be waiting forever. 

  • Consider asking the donor, “I’d like to ask you for a gift at our lunch today. May I bring with me a few ideas that I think align our needs and your interests?”

  • Good Research: Do you know what area of the organization your donor is most interested in, what their go-to area of curiosity and engagement is? Do you know what dollar amount they give to other organizations? These are helpful tidbits in crafting your own solicitation approach.

  • If you don’t make the ask, there’s a good chance another organization is waiting in the wings. If your mission is vital and meaningful, wouldn’t you prefer their donation to support your important needs?

Oh, and you have to actually solicit the gift. It’s no fair grazing over the solicitation!

A passive solicitation or one without clarity doesn’t count as truly soliciting a gift. Sometimes people feel as though they made the ask, but in all reality it was a surprisingly disguised solicitation such as:

“Would you want to make a donation sometime to our organization?”


“We can count on you to make a donation to our campaign, right?”

That’s avoiding the topic, merely skirting the issue. If we were keeping track of the number of solicitations a staff solicitor was making in their portfolio, those most certainly would not qualify as solicitations!

In 9 out of 10 times, a solicitation must contain these four elements:

  • A specific dollar amount

  • To be used for a specific need

  • To be given (or pledged) by a specific date (i.e., by March 31, or by Memorial Day, or by the final day of the school year)

  • The follow up: within a week, within two weeks, and then by the agreed upon due date

As an example, a solicitation using those three points might sound like:

“Maria, would you support our campaign to expand our ‘Healthy Mothers & Children’ program with a $10,000 donation to be paid by Labor Day this year?”

We encourage you to ensure you’re really making the ask. This honors the power and the immense respect that comes from inviting someone to take the step and become a donor.

Michael Pettry

Cape Fletcher Associates

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