(Part 4 in an 8-part series of topics to contemplate in major gift fundraising.  This series of blogs is designed for boards, CEOs and advancement staff.) 


Listening is one of our most important life skills.  It can also be one of the most pleasant:  a baby’s first cry, the finale of Beethoven’s 5th, birds on a quiet walk. Think about it; how often do you truly listen, or just tune out all the background noise? I’ve certainly spent a lot of time walking down the streets of New York, trying to shut out the sounds of sirens. Unfortunately, more oftentimes than not, listening is also one of our most underdeveloped skills.  How much is missed, or is misunderstood, because we fail to truly engage, ask questions and listen!  In philanthropy, this can be the kiss of death to developing authentic relationships and meaningful donor engagement. 

Many of us are prone to interrupt, finish sentences, talk without allowing the other person an opportunity to express themselves or just plain daydream.  Think back to one of your most recent conversations with a colleague, prospective donor or even family member.  Be honest!  How did the conversation go?

According to Stephen Covey, ““Most people do not listen with the intent to understand; they listen with the intent to reply.”  How true! Or worse, we assume we already know the answer to a question.  Assumptions can get us into big trouble and do not deepen the conversation.

“When people talk, listen completely. Most people never listen.”

— Ernest Hemingway

Over the course of my thirty-plus career in philanthropy, I’ve participated in countless numbers of gift strategy meetings.  Time and again well-meaning and sometimes even skilled development officers and executives have discussed the project and amount to be proposed to a prospect.  But, a meaningful discussion, filled with lots of listening, about the project has yet to occur!  Hold the bus!  Let’s start there!

In the world of fund development, we spend a lot of time perfecting the “ask,” planning when and how to make the ask, and determining who should go on the call.  Of course, these are all essential steps in planning a productive meeting with a prospective donor.  But, the time spent thinking about and planning the all-important questions that will enable us to really get to know, understand and genuinely connect with our prospective donor are just as important.

At Vision Philanthropy Group, we advocate that our client-partners prepare an outline before every meeting with a donor and prospect.  It is important that the outline define the roles each person will play who is attending the meeting.  We also stress the importance of practicing before the meeting. It is also critical to make sure you can answer these questions:

  • What are the meeting objective(s)? 
  • What is the critical information that must be shared to achieve those objectives?
  • Who should be included in the meeting and what’s the right size?
  • Is it time to ask for a gift, or simply introduce and explore the subject? 
  • What action do we hope the prospect will take because of the meeting? 
  • What are the next steps that will advance yours and the prospective donor’s objectives? 

We also counsel our client-partners in the importance of active listening.  In fact, in most meetings, we hope there will be far more listening, that is carefully planned in advance. with the hoped for outcomes in mind.

“Wisdom is the reward you get for a lifetime of listening when you would rather have talked.”

— Mark Twain

Transformative giving is created out of shared visions, deep relationships and productive partnerships.  There is so much to learn from and about our prospective donor partners.  We will never understand how together we can achieve our shared objectives if we are not actively asking questions and listening.  It is through asking the right questions and carefully listening that we truly understand our donor partners’ goals, passions and intersections with our organization.  This is about transformation, not about transaction. 

Toolkit IV:  Active Listening – Sample Questions for Board Members, CEOs and Advancement Staff

We have found the following sample questions helpful in guiding and deepening donor and prospect conversations.  Although the point of this exercise is to deepen your understanding of the donor, remember, studies have shown that asking people questions about their intentions, can enhance the likeliness that an action will be performed.[1]

A few sample open-ended questions:

  1. I have enjoyed a long relationship with {your organization}. I’d love to know about your history with us.  Can you tell me about your connection with us and how it began?
  2. What has motivated you to stay involved with us?  Tell me about who you are closest to in our organization.
  3. I’d love to know more about what is most important to you your life and your philanthropy, can you tell me about it?.
  4. You have been very generous to our institution over the years.  I would love to know more about what interests you most in the work we are doing.
  5. We have many plans afoot that we've discussed, perhaps you can share with me what interests you most.
  6. What could we do better together to serve our community?

Bold Asking™ is an innovative training program in high-impact, major gift philanthropy designed for board, CEOs and advancement staff.  In Bold Asking™ we explore this and many other topics essential to creating high performing philanthropy partnerships and programs For more information about Bold Asking™ workshops, please contact



About the author:  Susan Holt is the founder and president of Vision Philanthropy Group, a full-service philanthropy and fundraising communications consulting firm specializing in health care, biomedical sciences and education philanthropy.  Susan has partnered with others in creating gifts ranging from $1M to $250M and has been the architect of multi-million and billion+ campaigns. VPG is based in Nashville, TN.