The best advice I ever received was this: Listen first. Always.

Always ask questions.

Always be learning.

Always, always listen.

I know how daunting the fundraising world is these days. There is so much competition. So much uncertainty. So much pressure. And so many things changing. 

It can make the task at hand overwhelming when you're pulled in so many directions. And one of the first things that tends to go under these conditions is the time to invest in understanding your donors more and more.

We get so focused on doing that we stop making time to listen

I'm going to show you a strategy I use on every project I work on.

It is so simple, yet most likely provides more valuable insights than anything else you can do. And it's one of those things you can setup once and then let it run forever. 

This one little question will give you a real-time pulse on your donors, feedback that will improve your entire fundraising program, and creates an experience capable of boosting your donor retention. 

Here's how to do it...


One of the most common things that happens when organizations want to make a concerted effort to better understand their supporters is that they create a survey. And almost always that survey is long, tedious, and boring

Your donor's experience should be memorably good, not bad.

On the organizational side, you’re left with a montage of random data points but without much more insight into who your donors actually are and what they care about. 

This is a big problem. 

And it’s one that we can solve by using curiosity and humility. And one little question. 

"Ask every one of your supporters why they signed up."


You might remember receiving an email from me that looked this:

Fundraising Email

In the very first email you send every person who signs up, you want to hear in their own words why they signed up

In a minute, you will see why we use an open-ended question instead of providing a list of checkboxes. First I want you to understand why this question is such a powerful tool for your fundraising efforts. 

This simple little question has the ability to do two major things:

  1. It provides you with insights you can use to tailor your content for effectively drawing in new supporters. In other words, your supporters will actually tell you how to convert donors better. 
  2. A small ask builds relationships with your audience in a way that creates an ideal initial experience and increases their engagement level with you. These are critical steps for retaining your donors. 

Too often we trick ourselves into believing we have a good enough understanding of our audiences. 

"If you aren’t constantly soliciting feedback, you are overlooking insights that could be bringing in more dollars." 


And using a single open-ended question like this is useful because it elicits insights that you wouldn’t know to ask about otherwise. And, as you’re going to see, insights about why your supporters are drawn to you often also comes with recommendations about how you can capture even more. 

All you have to do is listen. 


If you want to get more of your prospects to give, then it’s best to think of the donor experience as a series of conversion points. 

Each conversion is a step towards getting a person to give to you. 

In order to convert a person — say from a prospect to an active donor — you have to understand what the experience feels like from their perspective

What do they care about?

How do they want to be spoken to?

What are they looking for in supporting you?

Once you know these, you can speak directly to their interests and concerns. Asking each of your new supporters why they support your work gives you these insights in the easiest and most affordable way possible. 

Plus the email with this question can be automatically sent to each person as soon as they sign up. That means you can enjoy one of the main benefits of automation: it saves you a ton of time!

And, amazingly, when you ask people why they are drawn to support you they will also offer you incredibly helpful advice on how you can improve your messaging.

For example, when I learned that people who signed up for my old project Dwilly were more interested in a community of social innovators than the practice of generating new solutions to social problems, I changed the site’s headline from this original one:

Effective copywriting

To this one:

Fundraising messaging

Was it effective? Definitely!

The second version converted people at twice the rate as the original.

And, as you know... 

"More people means more money." 


This feedback loop of soliciting insights and improving your messaging makes you better. In essence, it eliminates the guesswork involved in your work for free.

Here’s how you apply it:

  1. Refine the copy that you use on your website to highlight the aspects your donors have expressed interest in.
  2. Where possible, use the language your donors use.
  3. Use the question as a prompt for a light exchange that comfortably welcomes a new supporter to your organization. 
  4. Track donor insights and follow-up with them about changes you made because of their feedback. 

You don’t have to wait until you can afford a consultant’s overpriced study to gain a better understanding of your supporters. By building this feedback loop into your onboarding process, you will have a steady stream of insights to use to convert more people to support your organization’s work.

We’re now going to look at how this little question of why is so valuable for retaining donors as well.


Donor retention is abysmal. 

Year after year after year. 

Giving to the nonprofit sector tallies over $350+ billion each year and yet the ability of individual organizations to retain the donors and their funds behind the majority of this outpouring is unsustainable, to say the least.

Even worse, it turns out we actually know very little about how to impact donor retention. Sure, we know nonprofits are losing 103 donors for every 100 they retain or gain. And only 43% of donors give to the same organization two years in a row.

The issue of retention is made even more urgent by findings from The Millennial Impact Project showing that young adults tend to get heavily involved in the organizations they engage with once those organizations capture them. As this generation increasingly accounts for a larger percentage of charitable giving, the payoff of keeping donors longer is going to only increase.

As you know, it can be costly to find new donors. That’s because the majority of the cost outlay is upfront. 

"It takes far less money to keep a donor than to find one."


The problem is that most development departments are letting far too many donors slip away and disappear. 

Here’s where our little question of asking new supporters why are you interested in us? comes in. 

There is some really strong data on retention that shows that whether or not you give your audience an ideal initial experience is the strongest predictor of their long-term retention. 

"What do most organizations provide as an initial experience?"


The answer is basically nothing. 

When you sign up for most organization’s newsletters, supporters are met with nothing more than a “Please confirm your email address” message and then they start receiving the monthly communications. 

Fundraising tips

This is almost a non-experience. It is forgettable and pointless from the supporter’s perspective. To say it is far from ideal is an understatement. 

Again, think about the experience from your supporter’s perspective and ask how you can provide something more meaningful than what they are used to and expect. 

By asking them why they are interested in your work, you position them as valuable in a way that asks very little of them.

You are also demonstrating an organizational interest in hearing from them and, hopefully, incorporating those insights into how you engage with your supporters. 

It might seem counterintuitive but donors feel more connected to organizations that they help more. One way this plays out, as demonstrated in new findings, is that larger donations correlate strongly with more volunteer hours

"You need to engage your audience as early as possible." 


By asking them why at the very beginning of their relationship with you, you are simultaneously building a relationship, gaining insights, and increasing their engagement with your organization. 

It might be a small question, but it checks some very important boxes of donor retention. And with how difficult it is for most organizations to keep their donors over time, it might just be the thing you’re missing. 


One of the most tempting things to do in fundraising is ask for a donation too soon. 

When you’re up-against-the-gun and need to produce results, it is easy to start acting out of urgency instead of confidence. 

The best part about using the why question is that it, in some ways, forces you to adopt a long-term mindset. Yes, you need gifts, but you don’t necessarily need this gift. Instead, what you’re doing is recognizing clearly that you will raise more money over time if you focus on learning more right now. 

A light engagement like this — where you’re framing the supporter as the expert and enabling them to feel valued from the very beginning — is perhaps the most valuable way to build your relationship with them.

It moves them closer to being a donor without them realizing that’s what is happening. And that is the secret of all donor behavior.

I’ve found that after you have around 50 of these brief back-and-forth email exchanges with new supporters, something just clicks. You will start to see brand new patterns emerging and a new, clearer understanding of your audience emerge than ever before.

Finding out what a dynamic, fascinating group of individuals are drawn to your organization’s work is a humbling and beautiful exercise.

The value is something simultaneously tangible and intangible.

You will feel your audience’s pulse.

And that pays huge dividends.