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3 enduring ‘making the ask’ lessons learned from a high school candy drive

3 enduring ‘making the ask’ lessons learned from a high school candy drive

March 28, 2024
Alphonce Brown

Asking for money is an essential part of what most nonprofit organizations must do to survive, especially for major gifts as total giving increases from fewer overall donors. Without proper organization and planning, it can be challenging for both new and seasoned professionals.

Almost 50 years ago, I learned the rudiments of making the ask from a project initiated by my high school band director, who proposed the idea of students selling candy to generate funds to support priorities not funded by the school. That was my first fundraising campaign.

Prizes were awarded to the top three winners selling the most candy and raising the most money. (The top prize was a ladies’ watch I had hoped to win for my mother.)  I was competitive – and the first student to contact families in my neighborhood, church members, community leaders and others asking them to purchase the candy. 

While other band students supported the campaign, many were apprehensive because they did not know what to say. 

I gained three important lessons from that initial experience that provided the foundation for my 40-year career in fundraising.

Lesson learned #1

It helps when one can make a case for the program, product or service for which funds are being raised. I outlined and committed to memory a brief message explaining the reasons for the campaign and why it was important for donors to contribute – and I won the top prize. (Little did I know that was the creation of my first case statement.)

The fundraising campaign was so successful the first year that the band director and students agreed to conduct the candy drive a second year. (The top prize that year was a beautiful necklace I had hoped to win for my mother.)  My fellow students realized the speedy approach I deployed paid dividends and began preempting my solicitation efforts by contacting many of the people I had enlisted the previous year (including some members of their own families).

Lesson learned #2

Many of my fellow band members either did not make a timely ask for donors to give – or simply did not ask their family members or friends to participate in the campaign at all! Perhaps, it was the fear of being told “no.” Regardless, I quickly learned one must ask for the gift in order to receive it.

Because the competition intensified exponentially the second year, it was apparent that I needed to develop a plan to expand my pool of potential donors. With the permission of my parents and the band director, I decided to expand my potential donor base outside of my own community and pursue sales in white neighborhoods in the most affluent part of the city. With my talking points at the ready, I proceeded to go door to door asking households to support our band efforts by purchasing multiple boxes of candy. The plan worked and, again, I won the top prize by a landslide. 

Lesson learned #3

One must be willing to qualify, target, approach and ask for money from viable prospects even when the outcome is unknown.

Breaking it down

These three basic lessons learned in high school were important because asking is fundamental to everything we do daily – whether it is asking for a job, a raise, a date … or money for a nonprofit.  

After high school, I further honed my asking skills by selling Bibles door to door during the summer while attending college. This allowed me to refine my ability to ask, resulting in increased interpersonal and communication skills, the construction of better case statements, better use of prospective donors’ and my time and ultimately substantial savings in the bank at the end of my college career. 

There are seven simple steps to consider when seeking to make a successful ask:

  1. Planning and preparation.
  2. Opening the conversation.
  3. Asking questions.
  4. Listening.
  5. Presentation.
  6. Making the ask.
  7. Thanking the prospective donors


People give for many reasons, and having an idea about what motivates a prospective donor to give only enhances your ability to ultimately secure a contribution. It has been often said that 80% of the process of asking for a gift occurs long before asking the donor to give a dollar. Having sufficient background information and determining the audience will dictate the type of ask being made. 

Asking strategies for an annual gift for a nonprofit organization, for example, require very different approaches than asking strategies for a major gift. In the former, the ask could be solicited by using direct or mass mailing, social media or special events and include a range of giving levels.  With the latter, a major gift solicitation must be highly personalized, preferably include face-to-face visits, and is usually specific and for a larger amount. Both major gift and annual fund asks require the creation of compelling case statements

The more background information available about the audience and the prospective donor (e.g., relationship to organization or key organization donors, giving history, giving capacity, philanthropic interests, what his/her gift will mean to the organization, potential ways to recognize the contribution, etc.), the more likely one will be able to secure a gift. 

The planning process should include ways the donor will be recognized and stewarded. Will he/she be recognized in publications, at a major or special event, in collateral materials, on the website? Will there be an incentive offered commensurate with the size of the gift? How will anonymity be handled?

In addition to identifying the proposed ask amount or giving levels during the planning process, there are other factors that should be considered including:

  • Who are the best people to present and make the ask?
  • Where is the best location to meet?
  • When is the timing right to make the ask?

Major gift solicitations require the engagement of the top leaders in the organization, i.e., the president, executive director, board chair or member, current key donor or a V.I.P. The prospective location of the meeting should be one mutually agreed upon that is quiet and ensures the prospective donor feels most comfortable. The timing of the ask could be made to coincide with a special anniversary, retirement, sale of a company, etc. These are all important considerations when preparing to make the ask for a significant contribution.

It is strongly suggested that an annotated outline of the presentation be developed prior to meeting with the prospective major donor. It should detail the specific points to be covered during the presentation and identify who will lead the discussion. Each role and segment in the presentation should be pre-assigned. The outline should be reviewed and the roles fully understood by each presenter prior to meeting with the prospective donor.

At a minimum, the presentation should include a brief description of the organization, a list of the organization’s key successes, the need, the difference or impact his or her gift will make and how the donor will be recognized and further engaged with the organization. Depending on the type of gift, a timeline could be suggested for the fulfillment of the gift. 

Opening the conversation

When face to face with the prospective major donor, the opening of the meeting need not be awkward – especially if there has been sufficient research about them completed ahead of time. Whether this is a first-time visit or one that has been cultivated over time, this is an opportunity to build, or strengthen, the relationship between the organization and the donor. 

Begin by introducing yourself, briefly explaining your connection with the organization and why you feel the project or program is important. This also is the opportunity to introduce other members of the asking team, as well as engage the donor by asking about his or her connection with the organization. Ask why the organization has been important to them if he or she is a current or previous donor. 

The opening dialogue need not be lengthy, nor should it be insincere. Be mindful of the prospective donor’s time, but be direct when explaining the reasons for the visit. They generally will know why you are there.

Asking questions

Questions can provide a roadmap for engaging the donor. Questions not only can permit you to gauge a donor’s interest, but they can allow you to discover information that may have been previously unknown. Always ask open-ended questions rather than “yes/no” questions. The latter is a definite way to end the conversation.

Over time, you will develop the art of knowing what questions to ask a prospective donor and when to ask them. If the replies are consistently negative, it may suggest a lack of current interest or no interest at all. Having this information can save you and the prospective donor valuable time. Remember to use questions throughout the conversation to direct your presentation.


One of the greatest assets of making an ask, especially for a major gift, is knowing when to listen – and is one of the most difficult skills to master. A presenter can be so excited about the project that he/she talks too much and overshadows or ignores the reaction or interests of the prospective donor. There have been instances when the presenters have talked themselves out of a potential gift because they didn’t allow the prospective donor to be engaged. Listen for the clues major gift prospects provide when they are encouraged to talk. 


The presentation should be exciting and clear. It should highlight the primary issues of the project, program, campaign, etc. It should describe who benefits from the gift, anticipated outcome and the impact the gift will make. If you have a longstanding relationship with the major gift prospect, it should highlight their specific overlapping areas of interest. Occasionally, collateral materials in the form of a case statement are sent to the prospective donor in advance. Let the case statement serve as a guide for the conversation. Be prepared to leave a hard copy with the prospective donor at the conclusion of the presentation if they don’t have it.

Making the ask

Always think positively and assume you are going to get the gift or a pledge. Make asking for the gift a part of the presentation. Have the specific amount or range of the gift in mind and know in advance who will actually make the ask. Do not vacillate. Give the donor a choice between “something and something” but never a choice between “yes and no.” Smile … and then, “shut up!” Allow the prospective donor(s) to respond. 

Know in advance that many first-time visits will not result in a gift or pledge. A major gift ask may not be appropriate on the first visit. Anticipate potential objections and think of creative ways to answer them. Don’t let a negative response to your request immobile you. A “no” today does not mean “no” forever. Assess whether additional cultivation is required and determine how it may be creatively presented as a next step in the asking process. 

As an example, if you are seeking an endowed scholarship for talented students, you may consider hosting a brown bag luncheon with the prospective donor and one or two current scholarship recipients who can share what their scholarships have meant to them. Most importantly, don’t forget to showcase benefits that may align with the prospective donors’ interests, e.g., named scholarship in memory or honor of a loved one.

Remember, asking for any gift is predicated on the proper foundation being established between the prospective donor and the institution – and discovering what excites the donor. This is especially true when asking for a major gift. It may take time. Appropriate open-ended questions can always be used to determine where the donor is with regard to his/her deliberation. “What are your thoughts regarding the Named Presidential Scholarship that requires a contribution of $100,000. Would you prefer your gift be paid over three or five years?”

Thanking the prospective donors

Always thank prospective donors whether he or she elects to give or not. A personal note, while not expected, is always appreciated by prospective donors and should be considered a part of the stewarding process. Be presumptive by asking if they would mind you keeping them informed of the progress of the program/project as it moves forward. Find unobtrusive ways to remain connected with them.  This will serve you well the next time you have an opportunity to revisit them and ascertain where they are in the asking process. 

Better over time

Making the ask is an integral part of the cultivation and solicitation process, and it gets better with practice. Making a successful ask requires extensive preparation and planning. The more proficient you become at asking open-ended questions and honing your listening skills, the more confident you will become when making the ask. 

Ultimately, making the ask should become one of the most valued and rewarding experiences during your professional life – especially as prospective donors agree to make the gift. 

Plan, ask often … and have fun when making the ask!


Alphonce Brown

Alphonce J. Brown, Jr. is the principal consultant for Docere Consulting, which he founded in 2003 to help clients achieve sustainability using new technology and proven fundraising methods. Alphonce has worked with large established nonprofits, as well as small grassroots organizations and has consulted with local, state and federal governmental agencies and international NGOs.  He was the director of development for the National Minority AIDS Council in Washington, DC; vice president of university advancement at California State University; president and CEO of the Prairie View A&M University Foundation; assistant dean of external relations at the College and Graduate School of Business, University of Texas at Austin and has held senior positions at a number of other nonprofit organizations.  He is a graduate of The University of Texas at Austin, an Advanced Certified Fundraising Executive and an AFP Master Trainer, as well as a past chair of AFP International.