“Fundraising is hard work, but I also believe it is sacred work. It offers a powerful and privileged opportunity to be in intimate conversation with another person about the nature of his or her highest commitments and values.” – Lynne Twist; The Soul of Money

Born to Ask

I have never been afraid of asking.

Questions have always come to me naturally - as if among the many things I was born to do, I was put here for some reason or another, to query, probe, and inquire.

As a teen, I would tenaciously ask my junior high Math teacher questions like, so, why does x+y have to = z?

I would push my high school English teacher to answer unconquerable questions like why “beat poetry” wasn’t regarded as part of “the literary canon.” 

And, I would actively quiz my college advisor up through my junior year, about why I really needed to choose a major.

I suppose it wasn’t always easy to be around such an incessantly quizzical person – and yet, still, this character trait of mine never lessened through graduate school or well into the early days of my career. 

I suppose, and, if I am going to be honest, that it’s still going strong today. 

As far back as I can remember, I have always fired off a “why-gun” and even my mom would say things, like, “Jennifer…it can appear as if you never believe what anyone says, he is a doctor you know…he is an expert.” 

The truth is, questioning for me is and never has been about harm. Or defiance. Or disrespect. 

The process of asking questions was simply how I connected, synthesized and stored information. It was how arrived at conclusions, solutions, and truth.

It was a journey. It is a journey.

Employed to Ask

As I grew professionally, in a field fortuitously known for “asking” –the fundraising profession—I found myself oddly resisting this idea of “the ask.” 

A bit ironic, I know. 

In the nonprofit sector, “asking” is not simply a preferred skill for someone tasked with writing proposals, soliciting funds, or closing major gifts – it is essential.

It is the cornerstone of the organization; it’s the pathway to giving. 

Mr. Deepak Chopra himself says in The Giving Way to Happiness, “The more you give, the more you will receive, because you will keep the abundance of the universe circulating in your life. In fact anything that is of value in life only multiplies when it is given.”

The truth is, this concept of “multiplication” is a core fundraising strategy inside any organization that aims to attract private philanthropy or “gifts. “ (Think: annual giving, match giving, crowdfunding and peer-to-peer fundraising).

Multiply. Ripple. Repeat.

This is the ripple effect as the Dalai Lama describes it,  “Just as ripples spread out when a single pebble is dropped into water, the actions of individuals can have far reaching effects.””

Or Mother Teresa who says, “I alone cannot change the world, but I can cast a stone across the waters to create many ripples.”

In many ways, I believe a fundraiser’s job is simply to incite ripples, to inspire giving and well, to make many, many “asks.” 

I love this reframe and yet for some reason, for a woman primed her whole life with this skill and ability, I have found it rather difficult to fully embrace the precise use of the phrase “make the ask.” Something continues to tug at me. 

And so I have been fighting it – I fight my “fundraiser” title – and I fight my calling.

When I lay out a sequence like this: “ask and you shall receive, receive and you can develop programs, and develop programs and you can change the world,” I often find it easy to champion this responsibility. 

I mean, to say that one’s job is to ask for things that can change the world – that’s an honor, right! 

Nevertheless, this sequence however logical like the x+y math equation above is not always the strategic framework that guides large fundraising offices or development education, in my experience.

In my experiences (as I am mindful not to over generalize), I would often receive source material, like the “three minute guide to fundraising asks” or was encouraged to role play “the making of an ask” – and like this, I would feel this immediate discomfort in my bones, something unlike the thrill I would experience when I piped at my teachers as a teen. Something so not world-changing. Something forced. 

Something was clearly missing. 

Learning to “make the ask” in this way never felt organic, or authentic, or connected to a broader sense of meaning or purpose. It felt transactional. Like a means to end. Not the beginning of journey.

And as I continue to see this for nearing 15 years in my industry, I have found myself also fighting my own identity as a fundraiser.

Something about the label combined with a rampant sales-like approach to “asking” has felt icky.  So over the years, I have taken up euphemisms like, “I am a development professional,” or “I work in advancement,” or I “facilitate giving” – when the truth is, I AM A FUNDRAISER.

This reminds of a quick storyWhen I was fundraising for an internationally renowned scientist, I asked him once, “Do your young investigators ever lose sight of the fact that the cells in those petri dishes actually belong to a human or an animal?” I was aiming to humanize the scientific process so I could better sell it to philanthropists who wanted to invest in curing disease. Thankfully and resonantly, he said “no.”

When I reflect on this line of questioning, I realized that much like I was concerned about the siloing of science from humanity – I too have grown equally concerned about the siloing of “the business of philanthropy” from its roots that truly are by, for, and about humanity.

“Giving is what liberates the soul,” Jenny Santi writes, “What brings families closer together. What combats the blues. What fills the gap. What provides a feeling of security. What provides a sense of empowerment and accomplishment. What can heal. What allows us to experience a deep connection with others. What gives inner peace. What brings great meaning, and fulfillment, and happiness.”

“The answer lies in giving,” she says.

So this then leads me to ASK yet another question. Go figure

What am I really fighting? 

The perception of beggary around the ask? The lack of historical context? The missing linkages to philanthropic tradition?  

Robert L. Payton and Michael P. Moody, in their book Understanding Philanthropy: It’s Meaning and Mission, talk about how philanthropy appears in some form in all cultures and civilizations through all recorded history. They uncover that very human thing that calls philanthropy into being; that thing that I also believe calls people like me – like US to the work, that thing that calls the donor into a mutually beneficial  conversation – the thing, the instinct we all share to make the world a better place. 

And just like that, I ask further: What does it really means to do this work? Why are we doing it? How do we release stigma around this idea of the ask? What needs to happen to shift perception? Why does it matter?

So my answer in no simple summation: I am calling for a reframe. For a language check. For an assessment of not simply what we do, but why we do it. I am calling for authenticity, connection, and clarification. I am calling for a revival of philanthropic tradition, a celebration of what is human about the work, a new lexicon that binds us all in its essence, and a look ahead at what it will take to create bountiful future. I am calling for it. Inviting it in. And I am asking that you join me.

Called to Ask

A moment of truth. I started this piece to intentionally reconcile the tension I feel between my profession and my calling, and specifically the discomfort I feel when employing “fundraising language” to describe what I do for a living.  Words like “asking,” “moves management” and “soliciting” still make me cringe - and yet- as a professional and an advisor, I know these terms hold fundraising teams accountable and encourage an outcome-oriented mindset. So begrudgingly, I use them. 

Given this, I am called to ask an even deeper question: What do I do with the tension? Where do I put it? Where do I begin? Where do we begin? 

Now, I realize I can’t possibly take on an industry that has evolved and modernized since the 17th Century. Or earlier.  

And so I decided to begin at a place I know well, that place I called upon in at the start of this piece, that place inside myself, that part of me that found the act of “asking” as a meaningful journey to purpose and truth. That place that props up purpose and truth as the key to happiness. And happiness as the source of abundance. 

So I confess. It is my purpose, no matter how much I try to deny it, to ask.

It is sacred, powerful, and privileged work. It spans my personal and professional life. It’s a calling that I believe exists in all of us. 

Mark Twain said, “The two most important days in your life are the day you are born and the day you found out why.”  “Why” for me, is the question and the answer.

In an effort to change the existing storyline around professional fundraising and to perpetuate a new approach, I am beginning with this idea of “why” and I am coining, “the authentic ask.” And I invite the following tips for fundraisers, volunteers, and humanists of all kind. 

Awakening the Authentic Ask

1.    Go Inward + Connect: Why are you here? Connect your story to the prospective donor story to the story of the ask; you have likely done your research; connecting the dots this way goes a long way.
2.    Know + Share Your Why: Simon Sinek says, “People don’t buy what you do, they buy why you do it;”  knowing and sharing your purpose, cause, and belief, invites connection, comfort, and communication, share this with your donor in print and in person; you might be surprised to find you have just given them permission to share their own.
3.    Be Present + Listen:  To have an intimate conversation about philanthropy requires trust, and trust is born out of listening, clarifying, and being. We can “do” a lot of things for a prospective donor, and yet being sometimes transcends the doing. A mentor of mine once said, “Do more listening.” This is a way of doing and being simultaneously! ☺
4.    Clarify Interest + Passion: Being able to say, “I am hearing you are passionate about health care…” goes along way. Line up these interests, commitments and values with your own, and with the organization, keep going inward and connecting!
5.    Fortify the Case for Philanthropy: Your prospect knows you are meeting to talk shop; set the stage in way that meaningfully connects the philanthropic story or the “case” to his or her personal story; inspire the prospective donor to ask “how can I help?”
6.    Talk About Money Confidently, Transparently + Soulfully: Yes, I said soulfully. It costs money to lead social change. And nonprofits seek partners and friends who believe in the work and see their investment as one that is dynamic, that can change an organization, a person, and the world. Donor meetings are not “The Shark Tank.” You can talk about feelings. About impact. About healing. About love. It’s all part of the ROPI (return on philanthropic investment) – an investment in humanity.
7.    Use Your Gut + Authentically Ask: Don’t push an ask – I have seen fundraisers do it, and it’s painful. Read the narrative of your meeting, take a breath, get up if you have to. A closing action step I find works well is to authentically ask them “how do you feel about what we have talked about, is there anything more I can provide for you…and alas…would you be interested in seeing a menu of opportunities to get involved further?” 
8.    Express Gratitude + Follow Up with Some More Gratitude: Remember this is sacred work, let them know you know that in person and via email/thank you note. Remind them that the reason WHY you are “asking” is much bigger than you.  

By awakening to the authentic ask, I do believe you will achieve abundance in your life and in your business, the kind of wealth  that serves personal growth and healing, develops organizations and businesses, and preserves communities and histories. 

To learn more about my work or to help “awaken” your team, check out: