Major Gift Asks: How to Turn a No into a Maybe and a Maybe into a Yes

Mar 31, 2023
Donor Cultivation at Coffee Shop



All solicitors get nervous during major gift asks because it puts you in a vulnerable place. What if the prospect says no? What do I do then? Well, today, I’m going to teach you a trick that has boosted my confidence in major gift solicitations and helped me close millions of dollars of gifts. I promise this will be a game changer.

In the early 2000s, I was just cutting my teeth with cultivation and major gift asks. My first solicitation out on my own was a disaster – I’m pretty sure I skipped words in the ask. I think back to that meeting and cringe. I needed some tools so I was reading and learning everything I could get my hands on about development and major gifts.  I ran across a book that was revolutionary. I don’t know how it made its way into my life – maybe divine intervention. It’s a tiny book at about 100 pages but it forever changed how I thought about major gift asks, how I solicited funds, and how I engaged board members.

Since discovering that first book, I have read every single book this author has written and I’m a better fundraiser for it. His name is Jerry Panas, and the book that had this profound influence on my career was called Asking: A 59-minute Guide to Everything Board Members, Volunteers, and Staff Must Know to Secure the Gift.  It was this book that taught me how to turn a no into a maybe and a maybe into a yes.

The book is power-packed with tons of helpful advice, but one strategy in particular has been my saving grace during solicitations. When you sit down to ask for a gift, there’s a possibility that someone will teeter with their decision. We all know that after you make your ask, you want to leave space for the prospect to answer. The prospect should be the next one to speak after you’ve made your ask. That moment or two can be tough to get through because we all want to jump in and fill the silence. When the prospect does answer, hopefully you get a yes! But, you might get some hesitation from the donor – and you need to know how to gracefully handle a maybe or a no. 

There are three questions that you need to keep in your back pocket in case your prospect is noncommittal to making a major gift. When I say noncommittal, I mean the prospect says I’m not sure or I need to think about this or I’ve got a lot going on. You probably won’t ask all three of these questions because you’ll want to select one or two that are appropriate. These questions will get the prospect talking about what their hesitancy is. The answers to these questions are going to help you understand what is getting in the way of this prospect giving you a yes.  Once you understand the reasoning behind the hesitation, you can respond to it.

Handling Objections During Major Gift Asks

So, you’ve made your ask: “Vince and Stacey, would you consider a gift of $100,000 to support the capital campaign for the Food Bank?” At this point, you remain silent until the prospect responds. If you get a yes, high five! If you get anything other than a yes, here are the three questions you can draw upon:

  1. Is it the program/project/campaign? But you don’t want to say “is it the program/project/campaign.” You’ll want to finesse it for the donor. You would want to say something like: “It’s completely understandable that you want to think this over. It would be helpful to know what’s on your mind. Over the last few months, you have shared with me that mitigating food insecurity is one of your top philanthropic priorities. Is this still the case?” This question is about making sure that you have presented the right opportunity for them. If they aren’t into capital funding you can say: “Although I’ve presented an opportunity for supporting the capital campaign, would you be more interested in supporting our day-to-day operations?”


  1. Is it the amount? Most likely you’ve done your homework and have a good idea of an appropriate gift amount. But sometimes, it’s difficult to know how much to ask for. So, this question is about testing the amount and finding the difference between where you are and where they see themselves. You might say, “Stacey and Vince, I know how important the Food Bank is to your family. You’ve supported us for many years and made a lasting impact on our community. When we thought about asking you to come in at a leadership level, we thought that $100,000 would be within the realm of possibility. Did we get that right?” This helps you understand if you are in the right ask range or if the prospect sees themselves somewhere else. 


  1. Is it the timing? Our donors have a lot going on in their lives. Their children or grandchildren are in college or getting married. They might be getting ready to take a six-month cruise around the world. Timing is really important. If your prospect says “I don’t know, my daughter is getting married in six months and that’s a lot for us right now.” You can respond with something like this. “First of all congrats on the wedding! I understand weddings are a lot, and I want you to be able to make the gift you’d like to make. Let’s see if we can time this in a way that works for you. Would it be helpful to pledge the gift and make your first payment a few months after the event or spread the gift out over the next 3 years?” This presents options to your prospect that they might not have considered. 


Now that you have these three questions in your back pocket, you can handle any hesitancy that comes up during solicitation. You can handle a maybe. You can handle a no. This should take all the fear of making the ask away. The answers to these questions will help you understand and respond appropriately to your prospect’s concerns.

About Mary Hackett

Mary Hackett is a vibrant and engaging powerhouse in the world of major gift expertise, with a sparkling career steeped in the intricacies of fundraising operations. Residing in the picturesque town of Bend, Oregon, Mary's professional journey is as lively and inspiring as her scenic surroundings. Her extensive experience in fundraising is marked by a unique blend of strategic insight and a contagious enthusiasm that has consistently propelled organizations to new heights of success. With a knack for connecting with people and a deep understanding of the nuances of philanthropy, Mary has become a sought-after expert in her field. Her approach to fundraising is not just about meeting targets; it's about building relationships, weaving stories, and creating impactful experiences that resonate with donors and communities alike. In Mary's world, every fundraising campaign is an adventure, filled with opportunities to make a meaningful difference while having a whole lot of fun along the way. Want to work with Mary? 

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Learn more at www.maryhackett.co