A Beautiful Invitation


I live with a pre-schooler. He asks for things all the time (if you are a parent of a young child, you know the endless asking)—for candy in the check-out line, for dessert before dinner, for help to put on his shoes, for 5 more minutes in the bathtub, for another book before bed, for more peas (only kidding) . . . the asking goes on and on and on. And this doesn’t even begin to account for all the questions that start with “Why?”

Even if you aren’t a parent, you’re not immune from having things requested of you—at the office, at home, from a friend, from a spouse, from a pet staring up from an empty food bowl.

We also ask things of others. Think about it for a moment. How long has it been since you asked someone for something? Maybe you asked your partner to drop the kids off at school, your cubicle mate if he had a stapler you could borrow, or the restaurant hostess if she could seat you on the patio for lunch.

My point is: asking is something we do all the time—sometimes with great contemplation and sometimes totally impulsively. Most asking we do is not nagging, or pleading, or imploring—it’s simply part of everyday interaction. It’s a conversation starter, a way to learn more, a way to put off the answer you don’t want to hear, a way to connect.

Yet, as soon as money enters the equation, the vast majority of us—even fundraisers—hesitate, feel uneasy, or totally push a panic button. We worry that our asking suddenly comes with an expectation attached (as if the other times didn’t). We worry that asking will leave us feeling exposed and vulnerable—to rejection, to fear, to unworthiness, and to all of those raw, emotional insecurities.

Yet, vulnerability—a key component of asking—is also a key component of building connection. Asking and connection are poured from the same vessel. You simply can’t have one without dipping into the other.

Asking Truth #1:

We are almost always vulnerable when we ask. Sometimes asks represent great risks, and other times the risk is minimal. For instance, you might feel substantial risk when asking for a raise or asking for forgiveness, and considerably less risk when asking for assistance loading a heavy piece of furniture into your car. Regardless, your query puts you at the mercy of another. Yet, through your ask, you create something bigger: confidence, honesty, a helping hand, an opportunity for someone to give back. You build real, authentic connection with another.

The same goes for asking someone to invest in your nonprofit’s vision. Let’s assume you’ve done your research, and more than likely you know your potential donor well. While there will always be a certain amount of risk, of uncertainty, and of emotional exposure, showing up and being your natural, authentic self actually makes your ask more attractive. Humans love authenticity. If you are real and vulnerable when you ask—even if it’s not “perfect”—you create a space that allows your donor to be comfortable, real, and authentic with you. And, most importantly, you offer them a legitimate way to give back and make a connection with their community.

Asking Truth #2:

Asking authentically is an integral part of beautifully designed fundraising—from the tone, to the phrasing, and down to the design of the question itself. As in more traditionally defined “design” where the goal is to create connection and interaction with an end product, the goal of a fundraising ask is also to create connection and interaction with the broader community through a financial investment. So, with that in mind, spend some time designing your ask. If it is authentic, strategic, simple, inviting of connection and interaction, and creative of community—you’re probably headed down the right track. Not sure if you are applying good design practices to your ask? Check out my previous post on designing donor experiences, as well as my favorite 10 tips for thinking like a designer.

Asking Truth #3

Asking can joyful. If asking is about creating connection, and moments of deep connectivity are a way to create joy—then, yes, asking can be joyful. Conversely, it can be fraught with fear. But, just like vulnerability and asking are poured from the same vessel, joy and fear are also kindred spirits. How often has your excitement turned to fear. (“Oh my goodness, I’m so excited about my promotion! What if I hate it?”) Be courageous in your ask. Be bold. Yes, you may be terrified for a moment, but the joy of a “yes” will far outweigh and outlive that short moment of fear.

Asking Truth #4

See above. We all get nervous to ask. Being vulnerable and courageous is not for the faint-hearted. My advice: focus on the connection. Engage, listen, be interested, be interesting. Extend an invitation to be a part of something. To invest. To make a difference. To connect. Everyone loves to be invited to the party. And, you might be surprised, vulnerability—and its benefits—can be contagious.

Final thoughts: Asking does make you vulnerable. There is no doubt about it. But, without asking, we lose connection—the biggest gift of all.

Still not convinced? Check out a TED talk I think every fundraiser should watch—Amanda Palmer’s TED talk on the Art of Asking.



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