Mastering the In-Person Fundraising Ask

Inside Look – this blog will cover the following topics:

01 | It Starts With You

02 | Keys to a Successful In-Person Fundraising Ask

03 | When Fundraisers Are Afraid to Ask for Funds

04 | The Actual Meeting: Tips and Structure

05 | When to be Quiet

06 | 5 Sure-Fire Ways to Blow a Face-to-Face Fundraising Ask

07 | The Problem with Leadership

08 | Your Asking Style

09 | A Step-by-Step Plan for Nailing the In-Person Fundraising Ask

10 | More About the Follow-Up

11 | What if the Answer is No?

Before we really get going, here are the 6 most important rules for mastering the In-Person Fundraising Ask

Nonprofit Tip 1-png-1 Relationships

Nonprofit Tip 2-png Relationships

Nonprofit Tip 3-png Relationships

Nonprofit Tip 4-png Preparation

Nonprofit Tip 5-png Preparation

Nonprofit Tip 6-png Preparation

Do you have a Jimmy in your life? Jimmy is that nephew who you only hear from when he shows up for a visit once a year. On his birthday.

Sure, you and Jimmy hung out when he was a cute little kid. But now he’s 18, not as cute, and you both know he’s only there for one thing: the birthday cash. The conversation is awkward. He talks. You talk. There’s no flow, no real connection. Jimmy has a hard time making eye contact. He fidgets. He asks about your cat, Murphy… who died nine months ago. He tells you about his winning touchdown in Friday’s game…but when did he give up soccer and take up football? And is he still dating Erin? Or was it Evie?

Whether you go on with the charade and send Jimmy on his way with your usual $20 birthday gift, or you finally shut it down… it doesn’t feel good. It’s not something that leaves you happy and proud to be Jimmy’s auntie. It just leaves you feeling used.

That’s how your donors feel when all you ever do is ask. And when you’re talking about the upper echelon of giving – major gifts – the stakes increase exponentially. By the time you’re sitting face to face with a potential major donor, the time for Jimmy-level connections is long past.

Any fundraiser, development officer, major gifts officer needs to know this. The “ask” is the apex of a long mating ritual, of sorts, that unfolds and deepens over the course of months or even years. It’s not a one-and-done deal. Treat it as such and the “deal” will indeed be done – but not in the way you had hoped.


There is a science to making an in-person fundraising ask. There’s a structure to how you spend your time when you’re sitting with a major donor. But the heart of the in-person ask is more of an art. It’s beautifully layered. It’s genuine. It’s human. It’s complex and colorful, and it leaves both parties feeling like they are part of something special. Because they are.

“The role of the person making the ask is to get closure on a conversation that has been occurring over many months, if not years,” says Jeff Jowdy, founder and president of Lighthouse Counsel, a Nashville-based fundraising consultancy. “People perceive that the ask is important, and it is. But the important thing is that the ask be natural – the next step in an increasingly meaningful, usually longer-term relationship where there has been an ongoing conversation about what your goals are and how important they are, and what role the donor can play in them, and what the donor’s goals are and what role the organization can play in them.”

Jeff Schreifels, the senior partner at a Pennsylvania-based fundraising consultancy Veritus Group, defines the role of a major gift fundraiser as “the bridge between the donor and their desire to change the world and the programs and projects you have that do that."


01 | It Starts With You

In a blog post for 101fundraising, Karen Osborne, senior strategist at New
York-based management and consulting firm The Osborne Group, outlines certain traits and talents that major gifts fundraisers must bring to the table to ensure a successful in-person fundraising ask. As Jeff Jowdy says, those traits kick in long before the face-to-face meeting. They include:

  • Strategic agility, “the ability to create a strategic donor plan over six to 18 months that builds a long-term, productive and meaningful relationship,” and visit strategy (“concrete outcome goals, identified strategic questions and key points to make”). The MGO should be able to “then pivot with poise when circumstances change,” Osborne writes.
  • Empathy, “the ability to understand another person without the donor
    explicitly explaining all of her motives and feelings.” “Certainly, you should ask about philanthropic values and motivation,” Osborne advises, “but also sense what she didn’t say.”
  • Professional will, the ability and willingness to ask strategic questions such as, "Would you consider an investment of..." "When you couple empathy with what Jim Collins calls 'professional will' in "Good to Great for the Social Sector," you have a winning duo," she writes. "Will to succeed, grit, tenacity in the face of steep odds."
  • Humility, which keeps your ego in check and keeps you constantly learning. "Arrogance, no matter how successful, you've been will trip you up." Osborne warns.
  • Integrity, meaning you are ethical, honest and transparent, coupled with trustworthiness. "Being trustworthy," she writes, "is not enough. Others must also trust you."
  • Intellectual and social curiosity, which requires strong questioning and listening skills.
  • The ability to deal with ambiguity, since "major gift work is a journey and relationship building is not linear." "Donors don't always know what they want or what they mean," Osborne writes. "Where the gift is headed is not always clear."
  • Good judgment, meaning you can "analyze, assess and make wise and timely decisions both on the spot and after consideration."
  • The ability to organize and set clear priorities.
  • The ability to say no - and the wisdom to know when to. "You have to know how and when to say no to some tasks and some people if you want to hear a joyful, generous yes to your major gift request," Osborne advises. "This can be the hardest of all the competencies since most of us are pleasers with a can-do attitude. The ability to say no, however, politely and firmly gives you the ability to say yes to what is truly important."

To learn more about your 'asking style', attend this free webinar regarding Boards & Asking Styles: A Roadmap to Success by Brian Saber.

"You have to know how and when to say no to some tasks and some people if you want to hear a joyful, generous yes to your major gift request." - Karen Osborne


02 | Keys to a Successful In-Person Fundraising Ask

It all comes down to relationships – pretty much no matter who you ask. Like any good relationship, the major gift officer/major donor relationship needs to be built over time. You must allow the donor to fully understand and embrace the work that your organization does. While the relationship might start with a mild interest or curiosity, time will allow that interest to deepen. Open, honest, consistent, regular, and respectful communication is crucial.

Proper stewardship of your donor relationships is the first step in preparing for an in-person fundraising ask and can cut down on any last-minute scrambling prior to the interview.

“Be prepared,” Jowdy says. “Do your homework. Early on, discern what interests your donor. Not just your organization, but what specifically about the work you do. In an institution of higher education, for example, there is a whole broad menu of opportunities where a donor might have interests.

“Keep records of all your conversations and review them,” he adds. “Learn about them through their experiences. Invite them to get involved in your work. Invite
them to be part of a committee or part of the planning process.” Beyond donors’ interest in your work, Jowdy emphasizes the importance of knowing as much as possible about their lives and businesses as well. Find out things like:

  • What motivates them
  • What other organizations they give to
  • What types of causes are they NOT interested in supporting
  • What gifts they’ve given to your organization in the past
  • How and where they entered the donor funnel
  • How they were introduced to your organization and invited to donate
  • Who on your staff or board they know
  • Their net worth and income (or a best estimate)
  • Major events, milestones in their lives
  • Events that might mean it’s NOT a good time to approach them

“Before you approach them, know what’s happening with their families, their business, their health… as much as you can,” Jowdy says. “You have to build a rapport with them to be let into their lives. I had a board member of a client who was fighting prostate cancer and that’s why he hadn’t responded to a request for a meeting. He shared that with me and asked me to share it with the CEO and incoming CEO. He trusted me with that and to share it with them.”

A critical part of preparing for the meeting is not only being knowledgeable and comfortable with information about the donor, but ensuring that donor is equally knowledgeable and comfortable with information about your organization, the project or campaign, the fact that you are indeed coming into the meeting to make an ask, and even an idea of what the ask amount will be.

“When making a visit to ask for a major gift, if you have to go into any kind of detail at all about your organization or the project, then you weren’t prepared,” Jowdy says. “They should have already asked their questions, already asked for more information and you already should know that they are ready, and you should be confident that everything is all aligned.”

Schreifels agrees: “A face-to-face ask should never be a surprise to a donor,” he says. “If you are cultivating that donor properly and you really know them, the ask should come naturally.

"A face-to-face ask should never be a surprise to a donor." - Jeff Jowdy


03 | When Fundraisers Are Afraid to Ask for Funds

It’s surprising and a bit sad when you hear fundraisers talking about being afraid to make the ask. You hear it in session rooms at conferences, and not just in the U.S. You hear it in webinars. Wherever fundraising and development officers gather, you’re bound to hear someone talking about – or maybe trying not to talk about – the reluctance of fundraisers and development officers to sit down, face to face, with major donors and make the ask.

“Most people have been conditioned growing up not to talk to others about money,” Schreifels said. “For many fundraisers it’s uncomfortable, and they devise ways to do everything but talk to a donor face-to-face.

“The other reason they are afraid is that they 1) don’t really know the donor well and 2) they don’t know the program or project that needs funding,” he says. “This creates anxiety.”

Schreifels offers the following tips for overcoming the fear of asking:

“Have a deep underlying understanding that you are actually helping the
donor find joy in their life and by not asking you’re doing your donor a
disservice and denying them joy in their life,” Schreifels says.

  1. “Know your donor so well, it’s easier to ask them to support your cause,” he adds.
  2. “Just do it and ask,” he says. “I find that MGOs create a story in their head that they will be rejected, so they never ask. But what I found is that once an MGO or ED actually makes the ask, the donor says yes, and then the MGO or ED becomes an asking machine. ‘Hey, that was actually fun’ is a quote I often hear.”

Schreifels and his partner in Veritus, Richard Perry, expand on those tips in
their blog post, “How to Overcome the Fear of Asking.”

“You would not believe how many MGOs are out there in the field right now who have hardly ever asked for a gift,” they write. “They are out there writing notes and e-mails, sending gifts, but they are not asking.

“If you are a manager who needs to hire an MGO, it would be good for you to ask the candidate about several instances where they sat in front of a donor and they solicited a gift. At least three or four instances,” they write. “Why? Because too many MGOs are fleeing one nonprofit to another before they have to actually solicit a donor for a gift… and they keep getting hired!”

MGOs who are afraid to ask often send out signals. For example, they may spend all of their time planning to make the ask. Or make excuses like they missed the window of opportunity to meet with a donor, the donor doesn’t want to meet in person, or they simply can’t connect with the donor.

Suggestions from the post:
Get your head and heart right. “One of the greatest barriers to asking is YOU,” Schreifels and Perry write. “You haven’t settled this whole fundraising thing in your heart and soul yet. You haven’t figured out that donors want to be asked, that they need to give, and that you are actually bringing the donor joy and fulfillment when you ask them to part with their money.”

Get educated. “One reason I find that MGOs are reluctant to solicit donors about a certain project is that they feel they don’t know enough about it, and they are afraid of looking stupid in front of a donor,” they write. “I’m not saying you will become an expert, but you will know how to talk about the programs with ease.”

Know the donor. “This almost goes without saying. But you have to know who the donor is, what their passions are, and what they love, in order for you to make sure what you’re presenting matches those interests,” they write. “Amazing things happen when you are aligned with your donor.”

Practice, practice, practice. Schreifels and Perry write that “solicitations can go terribly wrong if you don’t practice what you are going to say and handle any potential objections or curveballs the donor may throw at you. If you are prepared, you will be less nervous and more confident.”

Plan for the unexpected. “In your practice,” they write, “you should be preparing for objections and anything that might throw you off.”

Jowdy suggests that a major gifts officer take a board member, the CEO or the executive director on the visit to share their passions with the donor. But those non-development professionals needn’t be asked to make the ask.

“If they’re afraid to make the ask, don’t make them make it,” he says. “Don’t worry about it. I used to think everybody has to make an ask. But I can learn in my old age… volunteers and the organization leadership can be a part of the visit to share about their gifts and about the campaign and project plans. But if they don’t feel comfortable with asking, they don’t have to ask. The professionals can handle that part.”

Schreifels reminds fundraisers and major gifts officer who are wary of soliciting gifts that donors really do want to give and that you are actually doing your donor a favor by asking.

“People who give are healthier, wealthier, and happier than people who don’t give,” he says. “And the more they give, the wealthier a donor becomes. So, you see how you are doing your donor a favor. Ask, and ask often!

“Don’t let fear take over,” Schreifels says. You will never succeed as MGO. You will never hold a job longer than a year. You’ll bounce around and around until they find you out. Remember, donors want to be asked. It makes them feel good to give. Now, go out and be what I call a ‘broker of love” and bring that donor some happiness.”

Be prepared with your story by attending Ethical Storytelling for Fundraising Communications by Caliopy Glaros to further nail your approach should you feel you need the help.

"People who give are healthier, wealthier and happier than people who don't give." - Jeff Schreifels


04 | The Actual Meeting: Tips and Structure

Even with due diligence and all your ducks in a row, you still need to know the basic structure of a successful in-person fundraising ask.

In his “The Awesome Ask: How to Approach Your Donors for Gifts in a Way That’s Comfortable and Effective!” webinar for CharityHowTo, Brian Saber, fundraising consultant and president of NYC-based Asking Matters, outlines what an “intentional conversation” looks like. He shares his Intentional Conversation Worksheet, which is built around the Arc of the Ask.

“Every solicitation meeting must cover the six segments depicted in the Arc of the Ask,” Saber explains. “But conversations have a natural flow, and the time devoted to each of the six may vary. You might even find that one or two of the segments unfold in a different order.”

He recommends spending the bulk of the time in exploration… “listening to and learning from your prospect.”

From Saber’s presentation:
Settle: In the first few minutes, conduct light conversation until the participants have a chance to fully focus on the meeting. A great opportunity to ask friendly “what” and “how” questions: “How is the family?” “How’s work?” “What did you do last weekend?”

Confirm: Take just a minute or two to confirm the goal of the meeting and the amount of time available. Reiterate that this is a solicitation meeting: “Thank you again for agreeing to meet with me to talk about a gift to the South Fork Senior Center. Does it still work for us to spend an hour together?”

Explore: Before making your case for support and asking for the gift, explore the prospect’s interest in your organization and views on philanthropy: “What interests you most about South Fork Senior Center?” “How did you first become interested in senior issues?” “How do you decide which organizations to support?”

Ask: Take no more than three minutes to present your case, concluding this segment with a specific request. Remember to focus on benefits and the impacts of those benefits rather than on features. “Our goal is to…” “We make an impact by…” “Would you consider a gift of $5,000 to South Fork Senior Center?” Note: It’s been proven that “Would you consider a gift…” is the ideal way to ask. You can say it this way every time.

Explore: Engage in a robust discussion to determine the gift or next steps that are right for your prospect. “What else would you like to know?” “What would help you make your decision?” “What interests you most about our request?”

Confirm: Review the meeting and agree to the next steps. “Thank you so much…I can’t wait to share the news with Joan, and we’ll be certain to get a confirmation in writing to you by the end of the week.” “I will speak to Robert and forward to you the impact study we commissioned last year. Then I’ll follow up in two weeks to see if you have any questions.” “Thank you for meeting with me. I will circle back earlier next year in the hope that you’ll be able to make a gift then.”

Jowdy says that, in general, you should aim to mirror the donor’s demeanor – if they’re reserved and composed, you should be as well. For a more demonstrative donor, feel free to match his or her enthusiasm. But be sure to avoid being disingenuous. Donors can spot a phony from a mile away. And even if they couldn’t, you should respect them enough to be genuine at all costs.

And definitely avoid “marketing speak.”

“A lot of people are offended by a sales-y personality that comes off like a lot of wheeling and dealing,” Jowdy cautions. “I know of a major gifts officer who always came off as disingenuous because people couldn’t relate to her. She was too concerned with using a precise language that came across as phony.”

Jowdy also offers the following tips for a successful in-person fundraising ask:

  • Script every visit and stick to the basic principles for every campaign.
  • Prepare responses in advance to every possible question or comment you can imagine.
  • Provide coaching and a run-through.
  • Prepare those on the visit to share about their own giving.
  • Have all available information at the ready concerning the organization, the campaign, and goals.
  • Be able to put the donor’s gift in perspective, what role it will play, outcomes,
    what kind of difference they’ll be making.
  • Unless you’re told otherwise, assume that a donor’s spouse or partner will be part of the decision. Be sure to include him or her in the meeting.
  • Make the ask… and then just be quiet.


05 | When to be Quiet

A while ago I was hosting a webinar about major giving, and the panel was a somewhat raucous group of fundraisers who were having a grand old time in the freestyle roundtable format. We were talking about “making the ask” when Marc Pitman, a fundraising coach, and consultant, advised that once you put it out there, the best thing to do is, “Just shut up.”

The panel got a great chuckle out of that, but then they all agreed it was a good idea.

Marc explained that too many major gift fundraisers “talk themselves out of a gift” because in the moments after asking for, say, $25,000, the fundraiser thinks he or she has scared off the donor with too large an ask. So, they immediately will say something like, “If $25,000 is too much, would you consider $10,000?”

“Sometimes when I’m speaking in a session (at a conference), I’ll make a point and then be quiet,” Jowdy shares. “Within 10 seconds, people in the room are squirming. So many have personalities where if there’s quiet, they’re tortured. But if you ask me something important, it may take me a minute or two to respond.”

It just makes sense. Think about it… you’ve just asked someone for a very substantial amount of money.

“They already had an idea of what you were going to ask for, or should have,” Jeff says. ““Don’t automatically assume you’ve asked for too much. Don’t presume at all… you’re probably wrong anyway. They might be thinking about giving more. You just don’t know.

“So let them process,” he adds. “Give them that respect.”

"Sometimes when I'm speaking in a session (at a conference), I'll make a point and then be quiet... Within 10-seconds, people in the room are squirming." - Jeff Howdy


06 | 5 Sure-Fire Ways to Blow a Face-to-Face Fundraising Ask

Nonprofit Tip 1-png-1 Talk more than listen.

Nonprofit Tip 2-png Don't listen at all.

Nonprofit Tip 3-png Go in for the ask without having cultivated a genuine relationship.

Nonprofit Tip 4-png Make the meeting more about you, and not about representing and honoring

     your institution. Let your ego take over.

Nonprofit Tip 5-png Poor timing.

Jowdy shares an example where the president of an institution that was embarking on a major campaign had not spoken to the institution’s largest donor in over a year.

“They were pressing to ask that person for a gift. If we hadn’t done the research and cautioned against it, they would have blown that relationship forever,” he says. “And last week I was talking with an advisory board member who was one of the top five donors to every one of an organization’s annual campaigns.


07 | The Problem with Leadership

Jowdy echoes a lot of the sentiment you often hear at conferences and other gatherings of development and major gifts officers. In-person fundraising asks often go wrong because not enough time was devoted beforehand to cultivating the relationship or really getting to know and understand the donor’s needs and desires or the circumstances of their lives that could affect their decisions.

“I see it so often when the CEO or the board leadership push and rush the development officers,” he says. “And the development officers don’t have the experience or leadership to say, ‘No, the timing isn’t right.’ So, the ask is sloppy and premature, and the answer is no.”

"I see it so often when the CEO or the board leadership push and rush the development officers...So, the ask is sloppy and premature, and the answer is no." - Jeff Jowdy


08 | Your Asking Style

In his webinar for CharityHowTo, Saber explains the idea of individual Asking Styles and shares his strategy for determining them. Most people have a Primary Asking Style and a Secondary Asking Style, Saber explains. Once you know yours, you can use it to make the most out of in-person ask meetings.

Brian and his colleague Andrea Kihlstedt, president of Capital Campaign Masters in New York, coined the term “asking styles” and determined these four dominant styles:

Rainmakers: “Are you comfortable talking to anyone? Do you need a wealth of information at your fingertips? Then you might be a Rainmaker! Rainmakers are analytic extroverts. The information they gather and analyze informs their decisions. Rainmakers are energized by interactions with others and view developing relationships as a rich, vibrant, and important process. Driven and competitive, they enjoy the prospect of succeeding in a field so full of resistance.”

Go-Getters: “Do you thrive on being with other people? Do you bring passion to the cause? You might be a Go-Getter! Go-Getters are intuitive extroverts who act on instinct and connect to donors through their energy and friendliness. They often base decisions on intuition rather than on analysis. This results in the ability to think quickly and fluidly, which enables them to relate well to donors. Go-Getters are extroverts with a natural enthusiasm and energy that draws people to them.”

Kindred Spirits: “Are you private and quietly thoughtful? Do you decide based on instinct? You might be a Kindred Spirit! Kindred Spirits are intuitive introverts who bring passion to the cause and connect to donors through their deep commitment. Kindred Spirits base decisions on intuition, and those decisions come from deep wells of emotion. They are introverted, drawing energy from internal experiences, and more likely to enjoy one-on-one situations. They have a strong desire to selflessly help those in need and want others to do the same.

Mission Controllers: “Do you decide objectively? Do you connect by laying out a thorough presentation? You might be a Mission Controller! Mission Controllers are analytic introverts who are quietly thoughtful and always have a wealth of information at the ready. Mission Controllers are great listeners and observers, which makes them effective solicitors. They place value on gathering and analyzing information, and approach their work systematically, making sure to dot their i’s and cross their t’s.”

You can take the assessment yourself here and find out your own Asking Style
in less than three minutes:


09 | A Step-by-Step Plan for Nailing the In-Person Fundraising Ask

In his CharityHowTo webinar, Brian also shares his Step-by-Step Asking Plan

“Asking is a multi-step process that starts with choosing the right prospects and continues through ongoing cultivation,” he explains.

Below is an abbreviated outline of the process and some actions steps to take along the way.


“Begin by making a list of four people you would like to ask in person,” Saber suggests. “All prospects should have the ability to give a significant gift (as your organization defines it), a belief in your mission, and contact with someone in your organization. Only list prospects who get three checks.”


“Before you contact a prospect to schedule a meeting, be sure you review your own reasons for being committed to the organization,” he advises. “You should also decide how much you will ask each prospect for before you contact them. The amount you ask for should be determined by their giving history, their capacity, and how it relates to your fundraising goal, among other things.”


“Setting up the meeting is often the most difficult part of the process,” Saber said. “Once you’ve got a face-to-face meeting, you are quite likely to get a gift. Depending on your Asking Style, you may be comfortable just picking up the telephone. Or, you may prefer to write first – by mail or by email.” Then write a short script to help you navigate a telephone call with your prospects.


Questions to Get the Donor Talking: “Effective solicitations include a discussion with donors about their interest in the project or organization,” Saber says. “List three questions you will have ready to encourage the donor to share their thoughts. The best open-ended questions begin with the words “How” or “What.” Your Presentation (no more than 3 minutes!)

Outline your presentation first. “Be sure to focus on the benefits of your program and the impact of those benefits,” he advises. “You want to be sure that you are clear on what the prospects’ investment will accomplish.

“There is no one correct way to make your case. Your presentation is YOUR story and will vary according to your Asking Style,” Saber says. “Be sure to practice – with someone else or in the mirror. Remember that if no one in the room is talking but you, you are not on the right track. Simply stop and ask your prospects what they think. You might be surprised.


“Immediately after your meeting, notify all appropriate staff and volunteers so that everyone knows what transpired,” he says. “Send a personal thank you however it suits you best – email, letter, phone, text – but make sure to do it that day. And most important, decide what the next steps will be. Will you invite the donor to an event? Will you ask the donor to volunteer? Will you send material in the mail four weeks from now? You must always have a next step.”


10 | More About the Follow-Up

Once your donor has said yes… get it in writing. Have them sign the letter of intent or a pledge card. But, Jowdy says, not until the yes is achieved. Don’t leave the letter or pledge card with them to sign later.

Reiterate to them how much of an impact their gift will make for years to come and leave them feeling happy and excited. This is also a good time to get them to expand their involvement and help you grow your family of donors.

“Ask them for referrals,” Jowdy advises. “Ask if they have friends or associates who might want to come to an event or be interested in donating. They’re so excited at this point; give them the opportunity to share their excitement with others.”


11 | What if the Answer is No?

Most major donor candidates won’t agree to a meeting just to say no. But it can happen. When it does, find out why. Most will explain it. Maybe the timing isn’t right, or the campaign isn’t right, or the amount isn’t right. Whatever the reason, keep the conversation going.

“Find out if it would be helpful if they could spread out the giving over a period of time, or if they could wait a year to start the gift,” Jowdy says. “There may be some negotiation that can take place. Things aren’t always what they seem.”

And if the answer really is a hard no at the moment?

“Don’t take rejection personally,” Schreifels says. “It’s not about you. And, if they say no, that is just a gateway to an eventual yes.”


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Topics: Fundraising, asking, nonprofit fundraising, psychology of fundraising, fundraising for nonprofits