Editors’ note: This article, first published in print during May/June 2012, has been republished for Nonprofit Quarterly with minor updates.

Asking for money face-to-face or over the phone can be one of the most nerve-wracking activities in fundraising—but it’s also one of the most effective. If you are looking for a major gift, it’s really the only way.

Get your team ready with some simple role-play exercises. Not only does practice make people feel more comfortable, it also gives them a chance to confront fears and address challenges in a safe space.

Trainings on this topic can run for several hours, but we are sharing a shortened version that you can incorporate into a team meeting.

  • Goal: To help your team build a relationship with major donors and make them feel more comfortable about asking for a large gift.
  • Participants: Anyone likely to be asking for major gifts—board, staff, and volunteers—on behalf of the organization. The exercise is easiest when facilitated for 8 to 20 participants.
  • Time: Approximately 40 to 60 minutes.
  • Preparation: Choose a facilitator for the exercise. Provide participants with a fact sheet or overview of the major donor campaign. See “Creating an Effective Volunteer Fundraising Team” (Journal, January/February 2012) for helpful tips.
  • Materials: Informational handouts on the campaign and a flipchart or board for writing instructions.
  • Background: The exercise assumes that you have already shared a significant amount of campaign background, including how much money you are trying to raise, an overview of the “pitch,” and a gift range chart. Participants should be informed about: (a) who the donors are; (b) the extent and nature of their relationship to the organization; (c) the length of their association as donors; and (d) any information they may have already received about the campaign. Team members should also be clearly briefed about their responsibilities and the extent of the organizational support.


  1. Review the campaign goal, pitch, and process.
  2. Have participants list the questions they anticipate from donors. Choose two or three questions that seem the most likely and the most difficult and briefly brainstorm as a group on how to address them. If you are constrained for time, omit the group brainstorming. Instead, have the facilitator choose one difficult question and say, “Here’s how I recommend responding to this.”
  3. Describe the following scenario—or one customized to your organization—for the role-play: There is a donor who has given $100 each year for the past two years. She was sent a letter requesting her to increase her next donation to $250, which is the minimum amount to be considered a “major donor” at your organization. The letter also said that you would be following up to schedule a time to discuss the request. You have since set up the time for the call over email. Your goal is to use the phone conversation to strengthen the organization’s relationship to her and persuade her to become a major donor.
  4. Provide clear step-by-step instructions, customized to your organization: You have 10 minutes. (1) Open the conversation. (2) Ask the donor a key question that will help strengthen your relationship, such as inquiring after one of her special interests or her opinion on an action/program launched by the organization. (3) Make the pitch, outlining why you need a larger gift and how it will be used. (4) Ask for the gift and listen to the answer. (6) Respond appropriately. (7) Close by outlining clear next steps and expressing your appreciation.
  5. Divide the group into pairs and have them self-select who will play the donor and who will play the asker. Start the role-play. Issue a one-minute warning at the end of nine minutes. Stop the role-play at the end of 10 minutes. Have a one minute debriefing period during which the “donor” can provide constructive feedback to the “asker” about what they did well and what needs improvement.
  6. If you have the time, let the pairs reverse roles and repeat the exercise.
  7. Debrief as a group, going over what participants found most effective and/or challenging in making the ask.