Part 1 of 3: Ask Better, Raise More: 14 Proven Fundraising Ask Tactics
- May 10
- 10 min read
Part 1 of 3: Ask Better, Raise More: 14 Proven Fundraising Ask Tactics
Most fundraisers spend far too much time worrying about the “perfect ask,” as if somewhere out there is one magical sentence that makes every donor instantly reach for a checkbook. There isn’t. Fundraising is not a Jedi mind trick, and donors are not slot machines you jiggle until money falls out.
The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment.
That’s why experienced fundraisers don’t fall in love with just one asking style. They build a toolkit. They know when to keep it simple, when to make it visual, when to create momentum, when to lean into competition, and when to invite support without asking for money at all.
In other words, they don’t walk into every donor meeting swinging the same hammer and hoping everything turns into a nail. They use judgment, timing, and a little creativity—which, frankly, beats awkward begging every time.
This three-part series breaks down 14 proven types of fundraising asks you can use to raise more money more effectively. In this first installment, we’ll cover five foundational ask types that every fundraiser should have ready at all times.
Ask Types and Forms
1. Non-monetary ask
Clever fundraisers know one of the most effective types of asks you can make is one that requests a non-monetary gift. The purpose is to ask people to support your mission with whatever time, skills, expertise, favors, and influence they have to offer.
This is an effective tactic because it feels “low risk” to donors, and once they get connected and involved in the work you do, it is much more likely they will support you financially when the time comes.
This approach also works because it lowers the emotional and financial barrier to entry. Many donors are happy to help, but they are not always ready to write a check the first time you meet with them. Asking for advice, influence, introductions, technical expertise, or volunteer help is often the perfect on-ramp. It invites people into the mission without immediately forcing them into a financial decision. And once people start investing themselves, they often become far more open to investing their money.
“Teri, I understand your CPA firm has a nonprofit accounting division. Would you be willing to ask a few of your team members if they would review our IRS 990 before we submit it?”
“Aaron, we are having difficulty getting our sales permit approved by the city for the “Concert in the Park” event we’re hosting. As the former mayor, would you be willing to make a call to a friend or two at City Hall to see what can be done to move the approval process along?”
“Susan, we need a decorator’s touch. Would you be willing to stop by the new gym and give us some advice on how to make it look ‘cool’ and inviting for the kids?”
The beauty of the non-monetary ask is that it helps donors feel useful before they feel solicited. And useful people tend to become invested people.
2. Simple ask
A simple ask is nothing more than a basic question you use to ask a donor for money. It’s the essence of most ask types and it’s made up of three components: an appeal, an amount, and a stated purpose for the funds. That’s it.
It sounds obvious, but many fundraisers skip one of those three pieces. They make an emotional appeal but never state an amount. Or they ask for an amount but fail to connect it to a clear purpose. Or they wander around the point for so long that the donor needs a snack and a nap before the actual ask shows up. A simple ask works because it is clear, direct, and respectful.
“Jen, would you be willing [appeal] to make a $2,000 gift [amount] to support the children’s choir program [purpose]?”
“Holly, would you join me in supporting the new rehabilitation wing with a lead gift of $40,000?”
“Fred, would you be willing to sponsor four kids for a year’s worth of literacy coaching for $2,000?”
Never underestimate the power of clarity. Donors are often relieved when you simply say what you mean. It saves everyone from that weird conversational traffic jam where both parties know an ask is coming, but nobody wants to be the first one to admit it.
3. Challenge ask
A challenge ask creates a competitive environment that encourages donors at all levels to give money to reach a funding goal. The best-known visual representation of a challenge prop is a thermometer. The more donors give, the higher the indicator moves up the thermometer.
Many fundraisers use props like thermometers because they provide visual tools that encourage new giving, increase current giving, and track total giving. You can design them to work with almost any giving campaign: board giving, annual giving, program expansion, new facility construction, or during the open auction portion of a fundraising event.
Challenge asks are effective because they have a self-fulfilling element. The closer you are to achieving a challenge goal, the easier it can be to fulfill it (which can boost your confidence as well). Why? People like to win, achieve goals, and be part of a team that wins by achieving its goals by specific deadlines.
This is why it’s important to create some type of prop to visually represent the progress of your challenge ask campaign—people want to see how close they are to reaching the goal and winning!
You don’t need to use a thermometer as your prop, but whatever you choose, it should be creative, ignite a competitive spirit, and be prominently displayed, even publicly if possible. You should also put a graphics version of the prop on your website.
“John, with two weeks left in our annual ‘Plant More Trees’ campaign, we’ve raised $75,000 of the $100,000 goal, as you can see by our redwood tree graphic here [show graphic prop]. Would you be willing to buy a ‘Branch’ for $5,000 in an effort to help us fill out the entire tree with branches by the two-week deadline?”
“Peggy, I want to thank you for visiting the soup kitchen today. You now see why it’s important we expand the warehouse if we’re going to feed more children. The Madisons and Crafts made $1,000 gifts last week. Would you be willing to match their gifts and make a $1,000 gift so we can fill the breakfast bowl [show graphic prop] and reach the $30,000 expansion goal by June 1?”
Challenge asks tap into something very human: people like momentum. They like progress. They like seeing a goal get closer. And apparently, they like giant thermometers more than any of us would have guessed.
4. Matching ask
A matching ask is a form of a competitive ask where you tell a donor that if they are willing to make a gift, you’re confident you can find one or more donors who would be willing to “match” their gift.
Experienced fundraising love using matching asks because they know donors become very motivated to give once they realize they’re in a competitive environment (especially with friends and peers), where they can be part of a collective effort to achieve a financial goal to support a worthy mission by matching the gifts of others. In fact, a matching ask campaign can increase overall giving by 30 percent.
Matching asks are also versatile. You can include a matching ask tactic with almost any ask type. Once you have one donor committed to a gift you can go to other donors and try to find matching gifts, no matter what ask tactic you’re using. Or, if you have multiple donors committed to making gifts, you can go to one donor and ask them to match the collective gifts of others.
There are many ways to craft and use matching asks and props. They are very effective fundraising tactics so whenever possible, think of ways you can frame an ask in the form of a match, or use it to augment other types of asks.
“Adam, if you’re willing to make a $10,000 gift, I’m confident I can find two more donors who would be willing to match your gift.”
“Sherry, we have seven people committed to giving $2,500 to support our new program. Would you be willing to match their gifts with a gift of $2,500? If you do, we’ll reach this month’s goal of $50,000.”
“Wiley, the Jenz Foundation is willing to make a lead gift of $1.2 million if we can raise $500,000 in next 60 days. The Spaulding’s are committed to $100,000. Would you be willing to match this gift if I can get three more people to match yours?”
Make matching gifts a regular feature—not a seasonal gimmick. Matching asks work because they amplify a donor’s gift, instantly doubling or tripling its impact and turning generosity into a friendly arms race. And once people hear the word “match,” their brains light up like they just found a coupon for philanthropy.
5. Pyramid ask
Gift pyramids provide donors with giving alternatives in an easy-to-understand visual format. At a glance, donors can see all the available choices and decide which level or block they want to fund or sponsor. The higher up the pyramid, the more expensive the block.
Fundraisers like pyramid props because they provide elements of a competitive ask and a matching ask. You can ask donors to “buy” squares to complete a level or achieve a fundraising goal. You can incite donors to give at higher levels than they did the year before, and you can ask donors to match giving levels of other donors.
In most cases, each pyramid block not only represents a dollar figure for how much you want to raise, but how many people you want to give at that amount. For example, at Level 2 in your pyramid, you may be looking to raise three gifts at $5,000, at Level 4 you may be looking to raise two gifts at $10,000, and at Level 5, the top of the pyramid, you may be looking for just one gift of $25,000.
Once a donor buys a block, ask if you can put their name on the block they bought. This can stir the competitive spirit of other donors you’re asking and it generally increases the total amount of money you raise.
“Peggy, you’ve been one of our most generous donors. Without you, we wouldn’t even have a program for children. I asked you to see our soup kitchen today because I wanted you to see the impact we’re having on kids and why it’s important for us to double our capacity in the next two years. To do this, the kids need your help. I have a sponsorship pyramid here and I want to know if you’d be willing to take a $2,500 square?” [point to a $2,500 square in the giving pyramid that’s in the shape of a dinner table]
Or, “I’m hoping you’d like to sit at the table [point to the picture of the $2,500 square]. This is where I would like you to consider giving. What do you think?”
Or, “Here’s the size of gift I made [point to a $2,500 square in the pyramid]. I hope you’ll match me and five other donors who bought $2,500 squares. Will you join us?”
Or, “You probably recognize many of the names at the $2,500 level on this pyramid [point to all the names at the $2,500 level]. One more name here fills the entire row. Would you be willing to join these folks with a $2,500 gift and help us fill the $20,000 row?”
Pyramid asks work because they make giving visible, social, and specific. It is one thing to ask for support in the abstract. It is another to point at a place on the board and say, “This is where you fit.” People like seeing where they belong. Also, for reasons no psychologist has fully explained, putting names in boxes makes adults wildly motivated.
Summary: The Foundation of Smart Asking
If you get nothing else from this first section, get this: great fundraising isn’t about saying something clever—it’s about choosing the right approach.
The five ask types you’ve just seen—non-monetary, simple, challenge, matching, and pyramid—form the backbone of effective fundraising. They help you lower barriers, create clarity, build momentum, and give donors a clear place to engage.
Master these, and you’ll immediately become more confident and more effective in donor conversations. You’ll stop circling the ask and start making it—clearly, strategically, and with purpose.
But this is just the beginning.
What’s Coming Next
In Part 2, we’ll shift from structure to sustainability and scale. You’ll learn how to:
· Turn one-time donors into predictable, recurring revenue
· Use lead gifts to unlock major campaigns
· Build giving clubs and sponsorships that increase loyalty and identity
· Leverage wish lists and gift tables to make giving tangible and strategic
Then in Part 3, we go big—long-term strategy and legacy:
· How to secure multi-year commitments that stabilize your organization
· How to approach endowment conversations with confidence
· And how to introduce estate gifts in a way that feels natural—not awkward or intimidating
By the end of this series, you won’t just have more ways to ask—you’ll have a complete system for matching the right ask to the right donor at the right time.
And that’s when fundraising starts to feel a lot less painful… and a lot more productive.
Tom Iselin
Rated One of America’s Best Board Retreat
and Strategic Planning Facilitators
About the Author
Tom Iselin is recognized as one of America’s leading authorities on high-performance nonprofits. He has built nine sector-leading nonprofits and two software companies, written six books, sits on multiple boards, and has been rated one of America’s Best Board Retreat and Strategic Planning Facilitators. His work on nonprofit strategy, board leadership, and culture has been featured on CNN, Nightline, and in Newsweek.
Tom is the president of First Things First, a firm specializing in board retreats, strategic planning services, fundraising strategy, and executive coaching for nonprofit CEOs.
Board Retreats & Strategic Planning
If you’re looking for a board retreat facilitator or strategic planning facilitator who has been in the trenches and understands real-world nonprofit challenges, Tom can help your board gain clarity, build alignment, and create an actionable plan that improves performance and impact. His sessions propel organizations to the next level of performance and impact . . . and they're fun!
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