The Paradox of Asking

So what is an advancement officer to do? I have demonstrated this paradox to leadership volunteers during many board trainings I have conducted. The exercise goes like this. Volunteers are asked to rate their feelings in different fundraising situations using an entertaining scale of emotion icons. They are first questioned about their comfort in asking for a gift. Inevitably, most volunteers feel more comfortable asking a relative stranger for a gift than someone they know well. Then volunteers are asked to rate their feelings about being asked for a gift themselves. Most rate having the greatest comfort when being asked by a close friend.