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12 Sure-Fire Discovery Questions to Jump-Start Prospect Relationships

Jenny Love
Published:  02/15/2022

meeting over coffee

A couple of years ago, Lauren Wise was working her way through a long list of discovery calls when the person on the other end of the line unexpectedly told her he’d been meaning to talk to someone at her organization about leaving them his 401(K). 

As a philanthropic advisor and director of development at the University of Colorado Anschutz Medical Campus, Lauren knows that for every conversation like this, she reaches out to 80 people who never even answer the phone. Still, she keeps this experience in her mind every time she dials a new number: with the right questions on hand, and some patience and determination, she’ll keep uncovering diamonds in the rough. 


Gain Confidence Through Preparation

If you’re just starting out in healthcare philanthropy, acquiring Lauren’s confidence can seem like an impossible feat. It can be deflating and frustrating to hear “no” so often, especially with metrics and targets looming. Lauren counsels not to give in to such worries. 

“If you're overwhelmed, or you just don't know where to start, I would encourage you to remember that this is a numbers game,” she said. “The good work and the seeds that we're planting today will really pay off in the long run. Trust the process.” 

Trust the process—and be prepared.  

“When I was first starting out, I absolutely had a script,” she said.  

As Lauren became more comfortable in the process, the script faded away, but she still has a go-to list of open-ended questions that she looks at before making a call or meeting a prospect for coffee. The questions are designed to give clues about prospects’ capacity, inclination, affinity, and philanthropic nature.  

These questions help her determine which of the many people on her initial list are worth following up on, and they can help you too. 


Initial Questions 

The questions Lauren asks in her first conversations with prospects are meant to understand their gratitude, affinity, and inclination. These questions assume that the prospect already gave a gift to your organization, but Lauren has found that starting with a warmer list sets you up for the most success in uncovering major gifts. At UC Anschutz, almost three quarters of donors of more than $100,000 started out with a gift of less than $1,000, and it takes an average of nine gifts before a donor exceeds the $10,000 mark. Starting your efforts with recent donors is a good investment in your pipeline. 

  1. What inspired your gift to our organization?
  2. What has your experience been like with our organization?
  3. What impact has our organization had on your life?
  4. How did you first get connected to our organization? 

Capacity Questions 

The types of hobbies and activities a person engages in can give an indication of their capacity. For example, if a prospect mentions they own a second home or have just treated their children and grandchildren to a month-long vacation, it suggests that the person has significant resources.

  1. What do you like to do for fun?
  2. What are you passionate about? 

Questions for More Established Relationships 

Lauren saves the following questions for when she has had the opportunity to build some trust and rapport. Questions like these allow you to further qualify—or disqualify—prospects on their philanthropic nature and their values. 

  1. What other organizations do you like to support with your time and money?
  2. What has been your most meaningful gift?
  3. How did you learn to be philanthropic?
  4. How do you feel about your current level of involvement with our organization?
  5. What gets you up in the morning? What brings you joy?
  6. What is one of your most proud personal or professional moments? 

Starting Point, Not Silver Bullet

None of these questions alone is a silver bullet to qualification. Instead, taken together they will give you subtle indications to determine whether to continue to spend time with a person. For example, when Lauren asked someone how they learned to be philanthropic, they told her that their family taught that you should put your money toward things that are important to you. 

“That taught me that this person understands philanthropy and is philanthropic, and I should continue spending time with them,” she said. 

In an age where data analysis claims to take the guesswork out of prospect identification, Lauren counsels that there is still a place for conversation and intuition. 

“My approach is not as scientific,” she said. “It's mostly just try and get in front of them in a number of different ways and see what works. These efforts are rooted in gratitude, authentic curiosity and inquiry, open-ended questions, natural and authentic follow-up, and the openness to uncertainty.” 

To hear more of Lauren’s advice on starting discovery conversations, identifying potentially fruitful prospects, and growing relationships over time, AHP members can watch her full session, Back to Basics: Discovery Work 101, on demand. 


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Meet The Author

Jenny Love
Chief Content Officer
Association for Healthcare Philanthropy

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