Powerful Connections: The Journey from Fear to Bold Asking™ (Part 1)


(Part 1 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 training.) 


Do you believe deeply in your organization’s mission? 

“What?”, you say.  Whether a board member, CEO or development staff, of course, you believe deeply in your organization’s mission.

Now, how do you feel about fundraising for that organization?

I ask this question at the beginning of our  Bold Asking™  workshops.  The answers are enlightening, but rarely surprising! 

Many years ago, when I was just starting out as a development officer, someone innocently asked me, “How do you do what you do? I could never ask anyone for money!”  Over the years, I’ve become accustomed to this question.  I even enjoy it!  But, at the time, I was stunned.  I felt like my chosen profession was, well, rude. 

I was embarrassed and sheepishly replied, “I love what I do.” 

My feelings and gratitude for my profession and for the field of philanthropy have deepened over the years.  I love helping organizations connect with people and their shared visions and passions.  Whether you’re a board member, CEO or development professional, I bet you’ve had the same reaction I first had:  embarrassed and even fearful of asking people to support an organization… even one I believed deeply in!

Feelings and attitudes about money are deep seated.  It’s one thing to consider a company’s balance sheet.  Personal funds are quite a different matter.  In marriages or partnerships, money is oftentimes one of the most difficult subjects.  Most of us (especially my baby boomer generation) were probably taught that talking about and certainly, worse, asking for money is not polite. For some, there may be gender implications.  For many, asking for money is scary.  We may fear rejection or, even worse, damaging a relationship with a close friend or associate. 

In this 8-part series, The Journey from Fear to Bold Asking, we’re going to explore many aspects of philanthropy and fundraising.  Ultimately, in its best form, fundraising is far from asking for, or inviting, a gift. It is about transformation.  Transformation of the donor and the organization.

Whether you’re a board member, CEO or development officer, I hope you and your colleagues will join me in this journey.  My hope for each of you is that by the end of this eight-part series you will have a newfound confidence in your ability to partner together to transform giving for your organization’s noble mission.

So, let’s get started!

Toolkit I: Powerful Connections in the Journey to Bold Asking

Philanthropy, or the love of “brotherhood”, is about transforming our communities and our world.  Still, even in the face of such noble pursuits, attitudes about money influence the way we think about philanthropy and fundraising.

Take just a moment to reflect on your experiences with and attitudes about money.   Below are a few exercises that can help open a productive conversation amongst your board, leaders and/or staff in their attitudes about money.  You may share these at a staff meeting, board retreat or other appropriate setting when you are exploring strategies to develop comfort with fundraising.


1. What are your experiences with money?  Are those experiences painful?  Have they brought you joy?

2. If they have brought you joy, how has money contributed to your joy?  Has it provided opportunities for family, for family experiences or for material acquisitions?

3. Does money reflect your values?  How has money helped you remain true to your values?

4. How has money helped you achieve your goals? 

5. Would you have been able to achieve those goals without financial resources?

Now, keep your answers close by as we move on.  We'll come back to your reflections throughout this series. 

Connection.  It’s a powerful human drive, whether an introvert or an extravert.  The drive to connect with others is deep in our brain’s wiring. [1] Recently, the surgeon general identified the lack of human connection, or isolation, as one of our most pressing health concerns, even as great as heart disease and cancer.

To be clear, I’m not talking about social connections, a “who knows whom” exercise. That has its place, once we venture into tactics.  Rather, I’m talking about meaningful relationships. Each person has a different style or approach to connecting deeply with people.  In today’s high tech, 140- character world and online connections, true engagement can be challenging.

Although there are other places we could start, we’re going to begin our journey to bold asking with the power of human connection.  It is the bedrock of philanthropy.

Giving is personal.  It is emotional.  And, it provides meaning. 

It’s so easy to hide behind facts, figures and charts.  They may even feel safe.  As well intentioned and rehearsed as I’ve witnessed some CEOs be, it was only when deep conversations about shared passions and challenges occurred that truly meaningful philanthropy occurred. At some point, data has their place.  But, to transform your philanthropy program and provide meaning to your partners and your own work, deeply personal human connections must be made.  As in the case of some great wines, these things simply can’t be rushed.  True connections take time.  They require authenticity, open, forthright dialogue, active listening, trust and vulnerability. 

Giving is personal. It is emotional. And, it provides meaning.

Connection is not about the money. And, its not about asking for the gift.  It’s about understanding and respecting the other person’s values, aspirations, hopes and even fears.  With this common understanding, collective solutions can be crafted; solutions that involve an investment by both parties, not just proposals that may be accepted or rejected.

I once interviewed a philanthropist about her experiences with inviting friends to participate philanthropically in projects she cared deeply about.  She told me that philanthropy had taken her to some of the most interesting places and people in her life, where she had made great friends.  “Susan,”, she explained, “Even if they didn’t choose to participate in the project, inevitably I made a great friend.” 

Toolkit I Powerful Connection Tips for Board Members, CEOs and Development Staff

1. First, evaluate how you are connecting with each other:  board member, leader, philanthropy staff.  Clearly, meaningful relationship building and connection must occur outside regularly scheduled board and committee meetings.  Are there ongoing opportunities for individual interactions between board, leaders and staff?  Are they a part of regularly planned activities?  They won’t just happen! In the rush to reach out to new friends and philanthropy partners, don’t forgot the powerful connections that need to be made with those closest to you.

2. Are other family members, spouses or small groups included from time to time in these interactions?  Think carefully about the nature of the interaction.  Is it authentic? What’s the genesis for the dialogue?  This is not about make a case or asking for a gift.  The purpose is to connect and deeply understand the other person, their dreams and aspirations.

3. I’ve seen several leaders successfully establish a regular routine of “Sunday Suppers”.  Intimate-sized gatherings are convened.  There may be a topic for the evening, or it may simply consist of casual conversation. 

4. If a “Sunday Supper” or similar approach is employed, consider intermixing other leaders from the community or other constituents from time to time, or old friends that have fallen out of touch.

5. The CEO and development leaders must be well briefed on their guests but remember, this is a time for dialogue, for story-telling, sharing and connecting, not for making your case.

6. In our haste to promote our organization rather than truly connect, we become so accustomed to talking about the organization that we frequently forget to listen.  Be sure the CEO and staff are coached with “active listening” questions.  (A future topic in this series.) These are open-ended questions that help spark an authentic dialogue about passion and hopes.  I am reminded by the questions my three-year old grandson frequently asks me.  He rarely asks me “what” I am doing, a closed question.  Rather, he asks “why” I am doing something; much more telling!  Out the mouths of babes!

7. Help others connect.  Great development officers know how to connect the dots.  As your circles expand, make sure that you, the CEO, board member or development staff, are helping others connect their shared aspirations and passions.  There’s no telling where this will lead in the quest for deep, personal connection and achieving shared goals!

Now, think for just a minute.  Did your fear of rejection or of talking about money ever come up as you were connecting and truly engaging with new or old friends?

Coming up soon, Part 2:  Passion:  Understanding your own motivations

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 susan@visionphilanthropy.com

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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 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.

Copyright ©2017 Vision Philanthropy Group.  All rights reserved.

[1] Social:  Why Our Brains Are Wired to Connect by Matthew Lieberman.