My experiece, and all the training I've ever received, indicates that it's always best to go with another person to the meeting for the Ask. If you're staff, the thinking is that you should go with a volunteer or contact of the prospect. The logic is that:
- One person can be watching the body language while the other speaks
- Two people make for more accurate memory of the meeting and any points raised
- The staff person can handle any "technical" questions, and the volunteer or contact reinforces the personal nature of the relationship
- Since the volunteer or contact has also already made a gift this puts the Ask on a more authorative level (e.g. I've given and I invite you to do so as well)
- Since "like gives to like" the volunteer or contact is assumed to be at the same "level" as the prospect
The most recent issue of Advancing Philanthropy has an article that summarizes several examples where even having a pair of eyes printed on a poster asking for a donation generated higher giving. And another example where the pleasure of giving is measurably higher for the donor when done while being watched.
So next time you're ready to make an Ask, be sure to bring a friend!