The Pretzel Twist

This happens when we bend ourselves into pretzel knots trying to attract supporters. If we just put together a more attractive package of benefits maybe they’ll get on board. What if we ask them to serve on our board? Are they willing to get involved or will it feel like just “one more thing” being added to an already full plate, pushing them out the door never to return? Do you think that this package of benefits will work for our event sponsors?

What if we offer more of that will we be able to get more of them? We head off with our next best idea, assemble the pieces, roll out our new donor attractant, cross our fingers (and toes) and hold our breath. Sound familiar?

The Spaghetti Approach

You’ve probably tried an approach like this before (it’s one of the nonprofit world’s favorites). It’s the spaghetti approach: you throw something at the wall and see what sticks. There’s a flurry of ideas and everyone heads out to try something new.

What if there’s a better, faster, more accurate way to dish up exactly what will attract your best donors? One that saves a lot of time in clean-up – that cold pasta on the floor makes a huge mess!

So how can you hit the bull’s eye every time you set out to attract a new supporter to your cause? How can you know with certainty what you’re offering is just exactly what your prospective supporter will find delicious?

You’ve Heard That Life is Too Short, So Eat Dessert First, Right?

The solution is deceptively simple. You must ask. Yep, you start with dessert! Go straight to the source, cut out the middleman, get it right from the horse’s mouth.

Now usually when I make this recommendation people suddenly stare at me as if I’ve served them a bowl of soup with a fly in. This brief pause is usually followed by a litany of things that have already been tried, packages that have been rolled out, tweaks that might be needed and ideas about what might actually work. After this list is exhausted it’s usually followed by all the reasons why asking these questions just can’t be done.

We’re using our prospects application form – Surely it would be insulting to ask questions when they have a form – with instructions! We don’t want them to think we didn’t read the instructions! (Yes, questions work for grant-makers, too.)

I don’t want to waste their time!  (Would you rather ask someone to endure a fumbled attempt to engage their interest?)

I’m sure they have people vying for their attention all the time. I don’t want to bother them.  (If people are asking them all the time, how will you be any different from the masses when it’s time to ask for their support?)

Being able to crawl inside your prospective supporters’ heads – to understand what will motivate them to get involved with your cause – is so important that we’ve created a module in Ask Masters called “Find the Right Connection” to help you get that strategic insight and connection to your prospects – in such a way that you inspire people to join your effort. It’s all about using the right honey to attract your bees – finding out what carrots you have to offer.

What’s On The Menu?

The secret about asking questions is that if you ask the right ones, people feel good about answering. There’s something powerful about knowing that your insight is important enough to be sought. It matters to others what you think. So how do you unobtrusively find out what interests and attracts your potential supporter? It’s simple really. (I know, you’re thinking nothing is ever simple, right?) In order to keep it easy, here’s a menu of 3 question lines you can use. No matter how you communicate, by letter, face-to-face, by email, by phone, you can mix in one or two of these 3 kinds of questions to gather essential insight into your supporter.


Now this question line happens after you do a little educating. Pick something that piqued your interest. Describe what you learned and wrap up your factoid with a question like “Isn’t that amazing/shocking/interesting?”

Here’s one of my favorite examples of using this question line.

“I was shocked to learn that 1 out of 4 women will experience domestic violence. Did you know that this is more than twice the risk factor for breast cancer? When I think about all the exposure and awareness that’s been built with pink ribbons, I wonder what can be done to increase attention to the much more prevalent impact of domestic violence. Isn’t that crazy? What do you think would help?”

Yep, you guessed it. You can take this conversation line in several directions from introducing what you are doing to asking what they think is important and would support. Keep asking questions to pinpoint your prospective donor’s potential support.


With this line, you actually start with a question. “Isn’t it strange that… (unusual fact your cause addresses)?”

This question offers a world of opportunity to engage in a discussion around something specific or strategic about your cause. Follow up this opening question with open-ended questions like “What do you think?” Or, “Have you ever seen anything like this?”

Follow this line of questioning and you’ll learn what resonates with your donor or prospect. You’ll also be able to gauge the amount of interest in your point.

For extra sugar on top, turn this question around like this… “I’m curious about (point about them or the funding process). In your eyes, what’s most important? Can you explain/help me understand?”

Believe it or not, questions are as incredibly effective when you work with foundations and corporations as they are with individuals. Asking these questions can also be hard to do. Which is why we identify specific exercises to get you fundraising fast in every session of Ask Masters.  Rather than throw big, vague ideas at you, we break them down so you know exactly what next actions to take.


This is one of my favorites. It’s a great way to find out exactly what your prospect will respond to.  Use it liberally. Stack ‘em up. This is the All-You-Can-Eat-Buffet kind of question. You can always go back for more.

“Do you think (point from your cause) is more important than (other point from your cause)?”

“Which do you think people will respond to… this message… or that message?”

“What do you think is more intriguing… this point… or that point?”

“If you were making the decision, which would you recommend we do, A or B?”

These are great questions because you can ask so many pretty quickly. And of course there’s always the follow-up question “Why.” An invaluable tool to draw out your prospect’s thinking and find out more about what resonates with them.

The trick is to build a little mental menu of questions. Keep some handy so you can drop a couple in on an impromptu conversation. Sprinkle your emails with a question or two. Or use them to strategically connect with a supporter. You’ll be surprised how quickly you’ll learn what interests your prospects or donors.

With a little bit of practice, you’ll start to see trends! From there it’s just a hop, skip, and a jump to putting that insight to good use with an invitation to support your cause. One that you already know they will be interested in. After all, they’ve already told you!


Using questions like these is a great way to get comfortable with the process of… asking! Just think how much more relaxed you’ll be when time comes  to ask an important question about a gift. You’ll already know they’re interested! Isn’t it great to head straight for dessert? And there’s a whole lot less mess to clean up. Besides, we don’t really advocate throwing your pasta against the wall.

…we met with a potential funder and asked a question we had developed in Ask Masters. It so happens that Early Childhood Development is exactly the type of project they are passionate about and have agreed to support us for the rest of the year and for future projects in this realm!” ~Shelley Belohrad, Gone Rural boMake


“I’ll do anything to help but fundraise!”

How often do you hear that when asking people to help with your cause? We’ll wrap up the Ask Masters Fundraising Accelerator series with the webinar session “Just Don’t Make Me Fundraise.” You’ll get 3 secrets that will help turn supporters into fundraisers.

If you’re already on the Ask Masters Fundraising Accelerator list, that chapter will be coming to your mailbox in a few days. And if not, why not jump on now? It’s free, and our aim is always to give you information that will help you reach your fundraising goals as quickly (and enjoyably) as possible. Can’t wait to share!

Until next time,

Heidi Hancock


Heidi Hancock, CFRE
Principal of Mosaic Non-Profit Development and creator of Ask Masters Fundraising workshops and webinars

If you found this page but didn’t sign up, why not grab the whole series? Sign up to be sure you get all the parts of the Ask Master’s Fundraising Accelerator!

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