Never a Good Time to Ask

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Never a Good Time to Ask

“Just as we develop our physical muscles through overcoming opposition, such as lifting weights, we develop our character muscles by overcoming challenges and adversity.”


You’ve heard it said before that “you don’t know what you don’t know,” and that’s what can get you in trouble.  Most of us know what we don’t know.  I’ve found that most people who have not asked for a major gift don’t know the process or even how to ask.  Some assume it’s easy, but how many times have you asked someone for a significant six or seven-figure gift without being prepared?

This idea is also true for knowing when not to ask for a gift.  I still enjoy going on donor calls as it keeps me current with the donor mindset. Things have changed over the last 30 years, but human nature with respect to giving remains the same.  The other day I went to meet a new prospective donor on behalf of a client.  I couldn’t find much, and there was little information, but I was told that they were married to a hedge fund manager.  Within the first 10 minutes of the conversation, I learned about the pending divorce, health issues, and the loss of a job.  Not a good time to ask but a great time to listen, be empathetic and thank them for what they did in the past.  I didn’t ask but a few hours later I received a text asking if they could send $5,000 for the initiative I discussed.

I remember one of my first calls for the university I worked for, and my boss (the V.P. of Development) told me to watch and learn.  We met with the donor who had made several major gifts, and he proceeded to share with us that his partner embezzled money from the company, and his wife was in ill health.  I was ready to leave and felt terrible for him, but my boss plowed ahead and asked for $50,000.  I thought the donor’s eyes would pop out of his head, asking my boss if he heard what he just said.  I guess you can figure that he was good at delegating but not good in the field.  It took me two years to repair that relationship, and eventually, life settled down again for this donor, and I did get a significant gift.  Often in the work we do, “no” means “not now.”

My point is to be a good listener and find out what is going on in the person’s life before jumping into the pitch and the ask.  If you have good research, you would know not to ask for money from donors dealing with health issues, divorce, financial challenges, or family challenges.  Stay in touch because life changes, but don’t ask for a gift as the answer is predictable.

Fundraising is a relationship-based business.  Do you know what’s going on in the lives of your major donors?  Can you be empathetic for a time?  Do you know when to ask and when not to ask?  Do you know what you don’t know and are willing to find the answers?


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