Good salespeople and good fundraisers recognize their role is to help people do what they are already inclined to do. Unfortunately, most people hesitate to ask tough questions that challenge a prospect to think critically and differently about their situation.

Questions can help a prospect visualize a better outcome or a surer path to their end goal. Salespeople are adept at asking classic, albeit boring, qualifying questions:

Who are you currently with?

How much do you currently pay?

How has your experience been with your current company?

What would we need to do to earn your business?

1. “What is your proudest moment in  business (charitable giving sponsorship)?”
2. “What values do you hold most dear?”
3. “What has been the biggest challenge/obstacle you have overcome?”
4. “From your perspective, what are the most important issues in your industry/of the day?”
5. “What do you see as our company’s/nonprofit’s obligations in addressing them?”

These questions are designed to make your prospect or customer stop and think about their personal experiences. The conversation will move from being transactional to being relational. When you are qualifying and discovering details with a prospect, use thoughtful open-ended questions to engage in a useful conversation that gets you the details you need. From the prospect’s point of view, they will feel that they are having a conversation with someone who understands their values.