Worst Case Scenarios: Asking For Money

by Joan Garry

Many people say they are “terrified” of fundraising. Even though they are deeply committed to causes, local orgs and candidates. What’s the worst thing that could happen if you ask?

True story.

I’m at a major donor event.  I am a brand new executive director. There are prospects to engage and current donors to appreciate.

I am well prepped by my Development staff. I have an index card folded in my breast pocket. Handwritten notes like “Patrick O’Donnell, lawyer, $2,500 ask” and “Suzie Johnson and Bob Mellman, thank you, major donors for 10 years.”

I find Patrick, like the obedient ED I am. He is lovely and he seems very knowledgeable about the organization. But he is not looking at me. He is staring at my breast pocket.  This goes for on uncomfortably long time. Finally, I can’t take it any longer.

“Are you reading my pocket?” I ask sheepishly.  He smiles. “Sure am.”  I have figured it out without looking. I have folded the card the wrong way. I try to compose myself.  He is still smiling. I ask the obvious question. “So what does my pocket say?”  He reads clearly. “Patrick should be a major donor.”  So what did Patrick say next?

Time for you to guess the answer.

I won’t leave you in suspense. He laughed. Patrick told me he was impressed that I was prepped, well informed, engaging and passionate about the work.  “Patrick should be a major donor, ” he said. And that night he became one.

There it is, my most embarrassing ask.  See how well it turned out?


I get it. Board members find asking for money stressful.  Maybe it feels like there is something inappropriate about talking to people about money? Let’s tease it out.  What could go wrong? Here are five possible scenarios:

1)  You screw up the ask.  (See scenario above)

2) They stop liking you.

3) It impacts your business relationship with them.

4) You are completely unprepared to answer any of their questions and look like a total idiot.

5) They say “no” and you feel really bad.



Let’s take them one by one.

1) Screwing up the ask. Happens all the time.  An executive director shouldn’t do it – that’s bad.  But a board member is a volunteer.  You are only expected to do your best. A flawless ask is rare.

2) They stop liking you. I have seen board members write this  concern on index cards during fundraising trainings.  Why on earth would someone stop liking you for being committed enough to a cause to ask you to participate?  Come on.   Please let me be blunt:  that’s not a worst case scenario.  (NOTE: One exception. If the person is blindsided, and has NO IDEA WHATSOEVER that she is going to be asked, this could be a worst case scenario) (That is the subject for another day and another post).

3) It impacts your business relationship.If asking a colleague for money for an organization you support with time and money has an negative impact on your relationship, it wasn’t a good one to begin with.  In addition, remember: your rolodex is one of the most important assets you bring to an organization as a board member.  If you are going to leave it home, reconsider board service.

4) You’re completely unprepared. Don’t sweat it. Assume you will be.  You’re a volunteer.  In your day job, you are paid to be prepared. As a board member, you don’t know the details.  So try this.  “Great question and to be honest I don’t know (easy to find out though).  But here’s what I do know <insert compelling anecdote, sticky fact that draws the prospect in>.  And don’t prolong the process by volunteering to send more info.  Your story may be all you need.

5) If they say “no,” I’ll feel bad. The easy answer is that as a board member, your job is to ask.  The prospect’s job is to decide.  The victory is in the ask, because that is all you control.  For every 10 asks, you will hear “no” about 7 times.  Get used to it.


Two things to consider.

1) If your boss said it was your turn to run the United Way campaign at your office,  would you say no?  As a Type A person (typical profile of a board member), would you do a poor job?  I think not.  I’m thinking you will do a great job.  Because it’s been assigned to you as a job.

2) If a friend or colleague worked his/her tail off as a board member for an organization, would you be impressed with that person for making that kind of commitment?  Of course you would,  you might even think “Gee, I should get involved in nonprofit work.”


One last comment from atop my bully pulpit (such as it is).  I was delighted that my 17 year old daughter interned in a Development department of a nonprofit organization this summer.  She is a shy person.  Her experience was rewarding.  She became someone I barely recognized – enthusiastic and assertive in engaging people.  I wrote about this a few weeks back.  If  A 17 Year Old Can Fundraise, So Can You!

The bottom line is that fundraising is good for you.  I mean it.

I am a better person because I know how to raise money. I helped elect a president I care about. I have made a difference at the private school my kids attended. I was able to increase the scope and impact a nonprofit organization I cared passionately about. I model behavior for my kids, that I hope they notice. And last but certainly not least, every time a person writes a check for a cause they believe it, they don’t feel robbed. They don’t feel strong-armed.

They feel good.  And they should.

3 thoughts on “Worst Case Scenarios: Asking For Money”

  1. Clearly, my whole afternoon is awash now that I have discovered this website! Thank you!

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