Fundraising Q&A: Asking a friend for a major gift: Part two

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A close friend of mine frequently makes significant gifts to her favourite causes. I sit on the board of a charity; how do I get her to support mine?

Last month I began answering our reader's question by addressing steps leading up to the all-important ask. What a cliffhanger that last article was, leaving details for a month before getting to the punch line! I hope you've managed to use this time productively, planning how to cultivate and canvass friends who have the ability and interest to respond.

In terms of time invested, the "ask" is one of the smallest steps in the development continuum and yet without it we make no headway. Not everyone is suited to requesting funds. If you are really uncomfortable please don't opt out entirely. You can still play a vital role in the process. Cultivation and stewardship are both strengthened by board involvement. However, your question indicated you are willing to learn how to ask your friend to support your favourite charity. Refer back to that article to help reset the stage. We were on "second base" thanks to your mutual friendship and her already-established track record of philanthropy.

To get to home base you must first hit the ball. You can't expect a donation without asking for a gift. Occasionally manna from heaven occurs but is definitely not the norm (and usually indicates potential for greater investment if the charity researches the source and introduces themselves properly).

Don't make assumptions

Despite any discomfort you may feel toward actually asking for a donation, I would encourage you to set aside preconceptions. Philanthropic people WANT to make a difference and they'd rather give some of their disposable income away to a friend's cause than to charities they know nothing about.

Consider all your contacts (Linkage) — who have a track record of support (Ability) — who might share your passion for a mission in which you believe deeply (Interest). That's the difference between a "prospect" and a "suspect" and increases that chances of success. Remember — Rule number one — people give to those they know and trust. While the charities' cause is an important one you, the canvasser, serve as the impetus for a gift. You are the catalyst.

Rule number two — people give to those who ask. Don't shy away from the need to make a request. The best fundraising occurs amongst friends, family, colleagues and acquaintances. Don't lose that important opportunity just because you feel like you're "begging" or you fear their rejection; that is your ego getting in the way. This request is not about's about a charity that is doing great things. The fact that you are integral to the organization's success helps motivate your friends to invest!

The six (not so big) secrets of major gifts

The right volunteer asks the right donor for the right amount at the right time to support the right projects with the right approach.

Right! Easier said than done but something that successful fundraising teams rely upon (and Ken Wyman wrote a whole book on that is linked below).

Lead by example

Your charity has identified a strategic priority that everyone believes would interest your friend, based on her values, beliefs and her donations elsewhere. Have you made your gift prior to asking others? I am not discounting your significant investment of time that you give as a board member but major gift donors know the fundraising game. They usually sit on charity boards themselves or have done so in the past. They know the role of board members as champions and look for evidence of their leadership.

One philanthropist who has given away millions in his lifetime and chaired countless boards intentionally studies the donor list of charities who request his support. If he can't see proof of 100% commitment from the board of directors, he doesn't make a gift. "After all, why should I invest in an organization when its leaders don't even make their annual donations?"

You'll never walk alone

Remember — success is a team effort! Volunteers bring contacts, credibility and commitment while staff members implement.

It's most beneficial to bring your chief executive or another staff person who understands the project and can answer administrative or technical questions. Your role is to share your passion of why you volunteer and believe this opportunity is a good one. Be sure to identify which of you will make the actual request and practice role playing. Depending on how your friend makes her philanthropic decisions she may invite her spouse to attend. The location will also be based on her preference, usually in her home or office. You have already told her you are coming to discuss a project she might like to support and she will expect you to cut to the chase!

After all your preparation the meeting will only take 30 - 45 minutes. Once you and the staff member have described the project, outlined the financial sustainability, identified other investors and explained the role your friend could play in this initiative, the actual ask is as simple as, ?We would like you to consider making an investment of $(amount).?


Despite all our research, sometimes we don't know how much to ask for. A longtime capital campaign trick has been, "Mr. Smith, we would like your company to invest $25,000," then watch! If Mr. Smith gasps at the amount, you add "over a five year period" or if he remains engaged you can close the request by saying "a year for five years". This humorous example of the "flinch test" is one that really works. Twenty years ago I witnessed a seasoned volunteer double the planned request to his friend when he saw the interest in our proposal. At the end of the meeting I returned to the office and changed our appeal from $50,000 to $100,000 and the charity got the gift...what a thrill.


We have two ears and one mouth for a reason. Ideally we should listen twice as much as talk. Once you have made your request — bite your tongue! Resist the temptation to fill the silent gap. Let your prospective donor be the first to speak. The team can then answer any questions she or her spouse may have.


Chances are excellent that all your preparation has paid off and your friend makes a commitment to your charity. Be sure the organization thanks her promptly and keeps her informed of how her gift makes a difference.

Additional Resources:

Face to Face: How to Get Bigger Donations from Very Generous People (1993 Canadian publication and still very useful!)

Excellent one hour presentation by Karen Osborne

How NOT to Ask for Money: The Most Common Mistakes

Cynthia Armour is a freelance specialist in fundraising and governance. A Certified FundRaising Executive (CFRE) since 1995, she volunteers as a subject matter expert with CFRE International. She works with boards and senior staff to ensure that strong leadership will enhance organizational capacity to govern and fundraise effectively. Contact Cynthia directly at 705-799-0636, e-mail, follow her on Twitter at @CynthiaJArmour, or visit for more information about her services.

To submit a question for a future column, or to comment on a previous one, please contact No identifying information will appear in this column.

Disclaimer: Advice and recommendations are based on limited information provided and should be used as a guideline only. Neither the author nor make any warranty, express or implied, or assume any legal liability for accuracy, completeness, or usefulness of any information provided in whole or in part within this article.

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