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When Asking Goes Wrong: A Case Study in Communication Failure

When Asking Goes Wrong: A Case Study in Communication FailureCommunicating by email and text can be tricky. You don’t have the advantage of vocal inflection as you do on the phone, or visual cues as you do in person.

Not to mention potential grammatical errors—which can sabotage the best of intentions.

For example, “Let’s eat, grandpa,” versus “Let’s eat grandpa.”

When Asking Goes Wrong—A Personal Story

A few days ago, I received an email from “Fred” asking if I could provide a discount for my online course, Mastering Major Gifts. Now, I realize this isn’t quite the same thing as asking for a gift—but the point to this story still applies, so bear with me.

As a fundraiser, I truly believe you should ask for what you want and need. It’s the best way to get what you require to run your organization and programs effectively.

Therefore, in retrospect, I shouldn’t have been surprised by this request. In fact, assuming Fred is a fan of my blog, he may have learned to ask for what he wants from me!

But, as they say, hindsight is 20/20.

Each Party Is Coming from a Different Place

Communication is a two-way street. Each party must take into account the current emotional state of the other, which is nearly impossible to glean via text and email.

So with that, know that I get similar requests (for free and discounted services) on a regular basis.

You may not realize, but I put my heart and soul into creating Mastering Major Gifts. It’s 10 years of hard work rolled into one groundbreaking course. I truly believe it’s an incredible value with a fantastic ROI. Therefore, the constant requests for discounts can start to grate.

My Response to the Ask

My response to appeals for freebies or discounts generally goes something like this:

The Early Bird price is the lowest discount I can afford to offer for Mastering Major Gifts.

Sometimes I mention that I give several full scholarships per year … sometimes I don’t.

I continue by suggesting that if Mastering Major Gifts is outside the scope of their budget, that’s an indicator that their organization may not be ready for the content yet. In that case, they can start with some of my more lower-priced products and services—I mention my books and my blog (free).

I never want to pressure anyone into taking the course until they are ready. So that’s what I thought I was doing when this request came across my desk.

Here’s what I wrote, specifically:

The Early Bird price is the lowest discount I can afford to offer for Mastering Major Gifts. If you can’t afford it, you’re probably not ready for the course yet, as you do need some existing donors for the course to be effective.

I suggest starting with my books on Amazon. Try Major Gift Fundraising for Small Shops. I also offer regular free fundraising advice through my blog. You can subscribe at

Understanding My Personal Point of View

Whenever any organization can’t afford my services, I’m happy to provide tons of free fundraising content (via my blog, videos, webinars, and the Major Gifts Challenge). That’s how I give back to the sector. (Not to mention serving on boards, volunteering my time, and donating money.)

My courses, along with my speaking and training, on the other hand (which provide tons of value and years of expertise), is how I make a living to support my family.

His Response to My Response

I received an almost immediate response from Fred. He called me “arrogant and rude.”


I’ve been called a lot of things in my life, but arrogant and rude have not been among them.

The idea that my email was perceived as anything but genuine was shocking to me!

Although I was taken aback, I took a deep breath and drafted a measured response. And I’m happy to report, after four emails back and forth, we got to the root of the confusion:

I made an incorrect assumption.

I apologized for making an assumption that Fred could not afford the course and wasn’t ready for the content. He appreciated my apology.

Of course, Fred was just being a cautious nonprofit executive, negotiating for the best price he could get. I can see that now.

I misinterpreted his request for a discount to mean he didn’t have the budget for training.

Communication Is Nuanced

Words matter. Tone matters. How you speak and write to donors matters.

Often it’s about HOW you ask. Remember—everyone is coming from a different place. We all make assumptions about where the other party is coming from … and that can be dangerous—especially when communicating by text or email.

Citing my example above, dozens of people who are eager to take Mastering Major Gifts have reached out to ask for an extension on the Early Bird price. When someone says, “I’m ready to sign up, and was wondering if you could give me the Early Bird price?” I almost always say, “Yes!”

But my response is often predicated on assumptions. Just as your donors’ responses are always based on their assumptions when you’re asking them for a gift. They make assumptions about how the money will be used, how much you really need, and so forth, which is why it’s so important to be clear and informative.

It’s up to you to ensure your donors’ assumptions are accurate and correct. This is why face-to-face meetings are so important, especially when it comes to asking for a major gift.

We’re All Imperfect, with Imperfect Communication

No one’s perfect. Not me. Not you.

And some days are better than others. We’re all doing the best we can on any given day.

Our imperfections are what cause miscommunications. So often conflict can be avoided when we simply take the time to understand where others are coming from. (This is doubly important when asking your donors for a gift.)

I can admit that I made a mistake, and I’m committed to learning from my mistake.

I’ve learned a ton from this communication failure. I thought I was doing the right thing by not pressuring people to pay for a course they may not be ready for, but it turns out I was unknowingly being condescending.

I won’t be making that mistake again. Onward and upward. Tomorrow there are new mistakes to make. 

Have you ever miscommunicated via text or email?

How about you? Have you ever miscommunicated with a donor, boss or colleague through email or texting? Tell me all about it in the comments.

This post is reprinted from Amy Eisensteins blog.

When Asking Goes Wrong: A Case Study in Communication FailureAuthor, speaker, and trainer Amy Eisenstein, ACFRE, is one of the country's leading fundraising consultants. She's raised millions of dollars for dozens of nonprofits through event planning, grant writing, capital campaigns, and major gift solicitations. Check out her blog and video posts at for free fundraising tips and best practices.

Topics: Donor Communications