This blog post originally appeared as a guest blog post for Guidestar. Woman who suffers from anxiety

I sat down for lunch with a generous donor.

Two years earlier over lunch she and her husband asked me every fundraisers dream question:  “Where do you need help the most?”  I had to think fast on my feet.  My mind scanned their giving history.  Their interests.  I thought of a stretch amount for a project in their sweet spot.  I asked for a six figure gift to build a computer lab.  They wrote me a check on the spot.  Fast forward to today.   They’re divorced.  She got a huge settlement.  She’s starting a foundation.  We nosh on our salads.  The mood is relaxed.  That is, until I dive in and ask her to consider a gift 5 times bigger than her last to create a technology center for girls.

Her face turned as white as a sheet.

She peppered me with questions.  Who else had come in at the level?  Who was on our campaign cabinet?  Who was the chair?  Where were the other lead gifts from?  All excellent questions.  Only I didn’t have the answers.

I asked too early for too much without the proper cultivation.  I confused capacity with interest.  I didn’t take the time to prepare her.  I could have shown her the technology lab with students crammed two to a chair.  The waiting lists of students who couldn’t get a spot.  I could have taken her on a tour of new spaces.  Let her talk to parents on the waiting list or chat with graduates.

I lost that gift but it’s still my favorite mistake.  Why?  It forever changed me as a fundraiser.  It taught me how to cultivate donors and secure major gifts.

Last month I shared 21 of the best discovery questions you can ask a donor.  (hyperlink: My advice?  Use them!  But not all at once.  This is a relationship, not the Spanish inquisition.  When a new neighbor moves in next door you don’t ask them to go on vacation with you for a week.  You invite them to dinner.  Building relationships is a healthy give and take of disclosure.  Remember that donor’s give through us, not to us.  They are supporting the cause.  We help them reach it.  How rewarded do you make your donors feel for supporting it?