I often see in and out of nonprofits that many of us don't ask a question (or questions) that we think we know the answer(s) to.
We know that it is with too little notice for someone to go out for a meal.
We know that going to see that movie won't be of interest to a friend.
She won't be able to support my nonprofit with a gift at that level.
He doesn't have the time to make follow-up phone calls.
And the list can go on.
As a coach, I work to ask the question. I work hard to make sure I haven't answered in my head a question that I haven't even asked. I make sure that I am asking so that the person can set the direction for the conversation. I am following the lead, not leading. I know where I want to go, but I don't need to know how we are going to get there.
In Nonprofit Development, especially with staff inexperienced with direct asks and volunteers who are reluctant to ask, we often hear that Ms. Smith won't/can't give that much. I will ask, how do we know if we don't ask. If you don't ask, you are correct, she won't give that much.
I encourage you to be conscious that we don't know the answer without asking the question. I think you will be pleased with the results. Your donors will appreciate that you asked!