Let’s talk about a moment that strikes fear into the hearts of even the most seasoned fundraisers: the ask itself.

Not the stewardship. Not the cultivation. Not the coffee chat or the tour.

The moment when it’s time to name a number and ask a question.

I’ve trained hundreds of folks, from student callers to major gift officers and presidents, and this is where so many otherwise capable fundraisers freeze. They hedge. They mumble. They talk around the gift instead of actually asking for it.

That hesitation is what sinks so many proposals—because if you don’t ask clearly, the donor doesn’t know how to answer. Or worse, they walk away unclear on what you needed from them at all.

The good news? Asking well isn’t about being fearless or charismatic.

It’s about structure. It’s about using a reliable, repeatable framework that gives you confidence and helps the donor have clarity.

​Here’s what I call my Magic Formula for Making the Ask—and it works whether you’re asking for $100 or $1,000,000.

Questioning Opener + Mission Moment + Dollar Amount + Silence
​
Let’s break each part down so you can feel grounded the next time you find yourself sitting across from a donor (or dialing the phone or typing an email, for that matter).

This is one of the biggest giveaways that a fundraiser isn’t comfortable asking: they frame their “ask” as a statement instead of a question.

❌ “We’d love it if you’d help out with a gift this year.”
❌ “It would be wonderful if you supported us again.”
❌ “We’re hoping you’ll get involved this year.”

None of these are technically wrong, but they leave the donor hanging. They don’t invite a response. And they definitely don’t feel like the moment of decision that a real ask should be.

Compare that to:

✅ “Would you be willing to make a gift of $5,000 to support undergraduate research?”
✅ “Can we count on you for support at the $25,000 level this year?”
✅ “Will you help our students with a $1,000 gift to the Dean’s Fund?”

These are direct. Respectful. And clear.
​
By ending your ask with a question, you’re signaling that it’s now the donor’s turn to speak. That subtle shift sets up a healthy, balanced fundraising conversation.

This is where you tie the ask to purpose. Don’t just ask for money—anchor the ask in something that matters.

This is what moves the donor from “How much?” to “What for?”

Instead of:
❌ “Would you consider a gift this year?”
Try:
✅ “To help provide book scholarships for every student in the program, would you make a gift of $10,000?”

Instead of:
❌ “We’d love your support.”
Try:
✅ “To allow faculty to attend national research conferences this year, would you be willing to give $2,500?”

You are the bridge between the mission and the donor’s capacity to make something good happen. That’s your role. You’re not begging. You’re inviting them into something meaningful—with clarity.

And don’t shy away from being specific.

A donor can always say no to a number. That’s okay. But if you ask, “Would you consider helping us out?” and they say “No,” you’ve left yourself no room to move.
 
When you name a number, you create the chance for a real conversation. They might say, “That’s higher than I was thinking,” and now you can respond: “What would feel more comfortable for you?” or “Would you like to stretch that over a multi-year pledge?”

​Specificity unlocks possibilities. Vagueness shuts them down.

This is the part that makes or breaks it.

Once you’ve made the ask—STOP TALKING.

I know. It’s awkward. It feels like an eternity. But it’s crucial.

The silence after the ask gives your donor time to process. It allows them to think. It gives them space to share what’s really on their mind.

And what you learn in that silence? That’s gold.

Maybe the timing’s off: “I just paid my kid’s tuition bill.”

Maybe they need buy-in: “I’d have to talk it over with my spouse.”

Maybe they’re passionate—but about something else: “I’d rather support the scholarships instead of the building fund.”

If you rush in to fill the silence, you will miss all of that.

You’ll speak from your own nervousness instead of their reality—and you’ll never know what part of the ask didn’t work for them.

Practice the pause. Get comfortable sitting in it. It’s where the most honest parts of the conversation live.

Bringing It All Together:

Here’s a strong ask, built using the Magic Formula:

“To help us provide every student in our department with book scholarships, would you be willing to make a pledge of $25,000—$5,000 a year for five years?”

[PAUSE]

If they say yes—celebrate and affirm it. Then let them know next steps to document and facilitate the gift payment.

If they say no—that’s your cue to start the conversation. “Would it help to spread the gift out?” or “Is there a specific area you’d like to support instead?”

​But don’t jump ahead. Let them answer first.

I’ve got a whole system for deciding how much to ask for—based on donor history, capacity, engagement, and more.

If you'd like me to write about that next, leave a comment or shoot me a message. I'm happy to dig into that in a future post.

​Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this… 

• Why Most Fundraising Plans Fail
• 4 Powerful Discovery Questions
• Discovery Visits Demystified
• What to Say to Donors in Uncertain Times
• Questioning our Fundraising Axioms

Let’s bust a myth right now: “Our board won’t help with fundraising.”
That’s almost never the full truth.
Most board members want to help. They believe in your mission. They want your organization to succeed. What they don’t have is clarity or support.
They don’t know what to do, where to start, or how to help in a way that feels comfortable and meaningful.
​In other words: this is usually a training problem, not a motivation problem.

That’s why I created a “Board Fundraising Menu” – an easy, low-pressure way to show board members that fundraising is more than just asking for money. (Full transparency: this is an idea inspired by Andy Robinson, who has great books about how to train your board to raise money.) It’s about helping create the conditions where giving is more likely.

I used this with a higher education Board of Trustees and told them it was an “All You Can Eat” menu but they had to pick at least one from each category: Appetizers, Entrees, and Desserts. I walked them through filling it out in the meeting and left with a list of folks who could write notes, open doors, make calls, and host events!

​Here are 3 specific actions your board members could take today:

If picking up the phone makes them queasy, that’s fine. Start here.

A short handwritten note or a personally signed appeal letter makes a huge difference – and helps board members feel included without the pressure of a direct ask.

This one’s for your connectors.
​
Board members don’t have to ask for money – they just need to open the door. Hosting a gathering where staff shares impact stories or tours a program site is a powerful way to build trust and widen your prospect funnel.

No one is ever mad about a thank-you call.
​
And hearing directly from a board member? That’s memorable. It boosts donor retention (especially for first time donors) and builds board confidence in your development process.

Okay, okay – you’re busy. I know. You’re running events, managing emails, answering the auditor’s questions, and cleaning up after the copier jammed again.

But they’re busy too. They’re volunteers. They have full-time jobs, families, responsibilities – and most of them have never done this before. Anyone would feel unsure operating outside their expertise.

So when a board member says, “I’ll introduce you to my friend,” the best thing you can do is write a draft email for them to send.

Not because they can’t write one, but because it saves them time and anxiety. It gives them something to react to. They can edit it to sound like themselves – but only they can send it.

If they offer to make calls, set them up for success with a guide that explains the data set, answers frequently asked questions, and provides scripts and samples. And don’t forget to give them a seamless way to get all that feedback to you so it can be recorded in your database too!

Your role? Be their concierge. Their guide. Their teacher.
​
When you hold their hand through these steps, you're not just getting results today – you’re building better, more confident board members for the future.

If this kind of clarity and confidence sounds like something your board needs, I’ve built something for you. Tired of chasing your board or getting ghosted after a meeting? Inside the Smart Start Fundraising System, you’ll get a plug-and-play plan to turn passive board members into proactive partners.
​
Because fundraising isn’t a solo sport. It’s a team effort. And your board? They're not just fiduciaries – they’re your fundraising partners. But they need the tools, training, and support to step into that role effectively.

It’s included in the Smart Start Fundraising System – along with a plan to actually activate it.

💡 You’ll learn how to:

• Train your board without making them panic
• Assign roles that align with their personalities and strengths
• Make board fundraising support sustainable, not sporadic

🎯 Enrollment is open now.
Click below to get started and download the full board fundraising menu inside:

👉 [Click here to enroll now]

Because “they won’t help” can become “they’re amazing ambassadors” – with the right structure in place.

Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this…

• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• How to Build a Philanthropy Calendar That Drives Digital Donations
• Why Nonprofits Can’t Afford to Sleep on IRA Rollovers
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• Culture of Philanthropy Check-Up

I get it – events feel like momentum. They’re visible. They’re exciting. And if your board or staff is worried about revenue, the first suggestion is often:

 “What if we did another fundraiser?”

But here’s the thing I wish more nonprofits understood:

​More events aren’t always the solution. Sometimes, they’re the problem.

Sure, your spring gala might net $12,000 after expenses. But how many staff hours did it take to plan? How many other fundraising activities were delayed or abandoned in the lead-up?

Did it bring in new major donors or long-term monthly supporters? Or was it mostly your usual crowd eating chicken and bidding on a silent auction basket?
​
I’m not saying you should never do events. But I am saying you need to know what each one is actually doing for your mission – and at what cost.

Because they trick you into thinking you’re fundraising, when what you’re really doing is facilitating a transaction.

Participants are there to run, or to play golf. They’re not connecting to your mission. They're not hearing stories of impact or seeing their role in your work. They’re getting a t-shirt and a swag bag – and then they’re gone.
​
You might as well be selling donuts on the street corner.

Ask yourself:

1. What’s the ROI?
   What are you really raising after you subtract hard costs and staff time? If it’s costing $0.85 to raise a dollar, that’s not a fundraiser – it’s a stress-inducer. And occasionally events can flip and end up being over a dollar to raise a dollar – in other words, losing money.
2. What’s the point?
   Are you trying to raise money? Attract new donors? Steward existing ones? Events with no strategic purpose are a time-sink. Be honest about your goals.
3. Who is coming – and are they giving again?
   If most attendees are one-time supporters who disappear after dessert, the event might be more flash than follow-through.

​Now, if you’ve got an event that’s locked in – maybe it’s tradition, or there’s a sponsor you don’t want to lose – make it count. Infuse as much mission into that event as you possibly can. Don’t just entertain – connect. I once went to a Broadway revue fundraiser for a group supporting teens in foster care, and in between each number, they played short audio clips of the teens sharing their stories. It was powerful. I still remember those voices. That’s what sticks. And that kind of emotional resonance is what opens the door for deeper engagement. Pair that with a strong follow-up plan – something that nurtures those attendees beyond their ticket or entry fee – and you can turn one-time guests into long-term donors who truly understand and care about your work.

​Every event on your calendar takes time – time your team could be spending building real relationships with major donors, deepening stewardship, or crafting a compelling campaign that brings in five- or six-figure gifts. That’s the real opportunity cost. It’s not just the hours spent on centerpieces or silent auction items – it’s the connections you didn’t make, the asks you didn’t have time to prep, the impact that got delayed because your best energy was tied up elsewhere. If you want transformational gifts, you need the bandwidth to pursue them. Events rarely give you that. A smart plan does.

In my Smart Start Fundraising System, we assess your fundraising “vehicles” – the methods you use to reach donors. Events are just one of many vehicles. And often, there are smarter, leaner options with better ROI.

But the real magic happens when you zoom out and create a Plan – one that aligns your fundraising activities with your goals, capacity, and budget. Not every organization needs a gala. Some need a good direct mail strategy. Others need better donor journeys or stronger partner engagement.

When your events support your overall plan instead of driving it, everything clicks.

Before you plan another event…

Ask yourself: Is this the best use of our time, energy, and budget?

And if you’re not sure?

💡 That’s exactly what my course, The Smart Start Fundraising System, helps you figure out.

We walk through your fundraising menu, evaluate the ROI of each activity, and build a plan that plays to your strengths – without burning your team out.

🎯 Enrollment is open now!
You’ll get instant access to the training, tools, templates, and bonuses – plus 5 CFRE credits.

👉 [Click here to enroll today] and start building a smarter, more sustainable fundraising plan.

Because you deserve a fundraising strategy that works as hard as you do.

Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this… 

• Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising
• My Exhaustive Event Planning Checklist
• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors

Of all my blog posts and TikTok videos, some of the most popular have been when I’ve talked about becoming a Certified Fundraising Executive (CFRE). Every time I share about it, I get a flood of DMs and emails with questions like:

• “How do I apply?”
• “What’s the exam really like?”
• “Is it actually worth the effort and cost?”

​
So I decided it was time to pull everything together – my real-world experience applying, what I learned the hard way when I took the exam (spoiler: I failed the first time), and why I still believe the CFRE is one of the most valuable credentials in our profession.
​
Here’s what I got right, what I got wrong, and why I’m so glad I did it.

Here’s the good news: applying for the CFRE is easier than you think. You just go to www.cfre.org, create a login, and begin your application. Even if you don’t plan to apply right away, you can start tracking your experience and education in the system. It’s like a running professional development journal.

Pro tip: You don’t need those little CFRE credit certificates from every session. If the program was hosted by a reputable organization (AFP, CASE, Academic Impressions, etc.), just record the title, sponsor, and date. Bonus – recent changes mean that all your volunteer and service work now counts under “Education.”

You’ll also track:

• Professional practice (your years in the field)
• Professional performance (funds raised, management projects, communications efforts)

​For example, I received credit for a building campaign I directed – even though I didn’t personally ask every donor – because I managed the campaign from the ground up. For my management project, I submitted a policy document I drafted that improved how naming opportunities were documented and proposals were generated. It counted.

Once you’ve entered enough qualifying experience, the system will literally give you a green light in each section. That’s when you can pay the exam fee and move forward.

Here’s where I blew it.

I decided to take the CFRE exam cold. No prep. No studying. And even though I had 10+ years of experience… I failed by just a few points.

The CFRE exam isn’t just a knowledge test – it’s a judgment test.

It won’t ask: “Why should you start a donor relations program?”
It’ll ask: “What is the first step you should take to build a donor relations program?”

And several answers will be technically correct. You have to pick the best one, in the right sequence, based on what a seasoned, ethical professional should do.

After my initial disappointment (and, okay, a little self-pity), I registered again for the next testing window. I bought the AFP CFRE Review Guide (worth every penny), and I practiced with sample questions to get a feel for the exam’s structure.

If you’re preparing, my advice is this:

• Start 4-6 weeks before your exam date
• Focus on question style and scenario logic
• Don’t try to memorize everything – aim for comprehension across broad areas

Earning my CFRE made me a better advancement professional. Period.

But it also gave me something more – credibility, confidence, and clarity about what kind of fundraiser I want to be.

Here’s why I believe the CFRE is a valuable credential:

1. It signals real expertise.
Fundraising isn’t (yet) an academic discipline. The CFRE is shorthand that you know your stuff. It’s like a degree that speaks directly to your skillset and experience.

2. It shows your commitment to ethics.
The CFRE requires – and enforces – a high standard of fundraising ethics. That matters. It matters to your employer, to your donors, and to the reputation of the entire nonprofit sector.

3. It demonstrates your dedication to continual growth.
In a field that’s always evolving, this credential shows you’re serious about your craft. That you’re not just working hard – you’re working smart and staying sharp.

My new course, The Smart Start Fundraising System, offers 5 CFRE continuing education credits and gives you a complete, strategic system to build your annual fundraising plan.
​
Whether you’re already certified and need credits, or you’re planning to apply soon, this course is a great way to invest in your professional development and build a plan you’ll actually follow.

And if you have questions about the CFRE process or exam – hit reply or leave a comment. I’d love to hear your story. Are you thinking about applying? What’s holding you back?

Let’s talk about it. 💬
​
Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this…

• Why Most Fundraising Plans Fail
• Applying to be a CFRE
• The CFRE Exam
• Culture of Philanthropy Check-Up
• Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less

Let’s be honest: a lot of “fundraising plans” aren’t really plans.

They’re a collection of ideas scribbled in the margins of a notebook. A to-do list that gets buried under meeting notes. Or a spreadsheet no one has opened since last fiscal year.

And when things feel uncertain or urgent, even the most well-intentioned plan gets abandoned.
​
So why do most fundraising plans fail? After 20+ years of working in and coaching nonprofit teams, here’s what I’ve seen over and over again:

Too many plans are built for imaginary versions of our organizations. You know the ones: the org with unlimited time, a full development team, and a budget for days. In real life, you’ve got a stretched-thin staff, a volunteer board, and one printer that jams every third sheet.

The best fundraising plans start where you are. They work with your current capacity – not against it. They help you make choices, not just lists.

Staff turnover is one of the biggest challenges that can set you back in fundraising and burnout is often the cause. If you build your plan around the staff you have and use technology to leverage that plan, you can mitigate burnout and turnover.

If your plan doesn’t tell you how much money you can expect to raise – and from which methods – it’s not a plan. It’s a wish list.

A strong fundraising plan includes projections based on past data, average gift sizes, and realistic conversion rates. This lets you set expectations, allocate resources wisely, and make the case for investments when needed. I did an entire blog post showing you how to build those projections so you know what you are able to raise, not just what you wish you would raise.

No more spaghetti-on-the-wall fundraising. Just clear goals with measurable outcomes.

​Even when a plan exists, it often fails at the handoff: no one knows who’s doing what – or worse, everyone thinks someone else is handling it.

That’s why the final step of a good plan is assigning each task to a specific person. And then assigning a backup person to be cross-trained. This keeps your plan running when life happens – vacations, sick days, job changes – and builds resilience into your team. That’s why I wrote about building a responsibility calendar to protect your plan and ensure it becomes real.

No more scrambling. Everyone knows their role, and the show goes on.

It’s clear. It’s doable. And it starts with what I call the MVPPP Framework, which is part of my Smart Start Fundraising System course:

• Message – Your compelling case for support
• Vehicles – The channels you’ll use to reach donors
• Prospects – Who you’re asking
• Partners – Who’s helping you ask
• Plan – Bringing it all together with structure and accountability

This framework works whether you’re a one-person shop or leading a full advancement team. It’s not about doing everything. It’s about doing the right things on purpose.

My new course, The Smart Start Fundraising System, is officially here! It’s designed for nonprofit leaders who are tired of spinning their wheels and ready to raise more  –  strategically, confidently, and without burnout.

🎯 Inside, you'll learn how to craft a compelling message, choose the right methods, identify and engage donors, mobilize your board, and build a plan you can actually execute  –  all using my proven MVPPP framework.

✅ 5 Pre-approved CFRE credit hours available
✅ Four high-impact bonus trainings included
✅ A 21 page workbook plus tools, templates, and spreadsheets you can plug and play
💻 Enrollment is open now! Price is $549

Take a look, see what’s inside, and get started at your own pace:
👉 Take a closer look here.
Because passion doesn’t build a fundraising plan. But clarity? That’ll take you the distance.
​
Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!