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Preparing Your CEO for “The Ask”

As a philanthropy gift officer and team, you have put in hours of engagement and cultivation to create lasting and authentic relationships with donors and prospects. You have uncovered their passions and philanthropic goals and have aligned those with the organization’s strategic priorities. You are ready to involve your CEO as you engage donors in “the ask”—asking for an investment in the future of health care in your community. How can you create confidence and knowledge with your CEO to ensure the meetings are successful for all involved? Consider these steps:

  1. Set her up for success: Preparation with advanced notice is the key to ensuring your CEO is comfortable with the solicitation process. For CEOs new to the process, select a prospective donor you believe is ready to make a commitment and who will be an active participant in the meeting.

  2. Engage with high value prospective donors: Time is the most precious asset for your CEO. Engaging her with the highest-value prospective donors signals to your CEO that you are a strategic leader who understands the important role she plays in advancing philanthropy.

  3. Prepare the solicitation brief: Providing essential information on the prospective donor helps to inform your CEO on the prospect’s philanthropic, business and personal interests. Additionally, preparing a detailed agenda with talking points provides clarity as to each attendee’s role in the meeting.

  4. Prepare through role play: Take the time to walk through the solicitation brief and agenda with your CEO while explaining the rationale for the flow of the meeting. Not only does this educate your CEO on the philanthropic “ask” but also allows you to assess your CEO’s comfort level on the upcoming meeting.

  5. Share the vision: The CEO can best share the vision of the organization with the prospective donor. It is the vision that the donor is investing in, and the CEO is the individual with the greatest influence in successfully implementing the vision. Hearing firsthand from the CEO brings credibility and enthusiasm.

  6. Listen: Help your CEO feel comfortable with silence. It can be incredibly difficult to remain silent once the “ask” is made of the donor. Coaching your CEO to allow for silence is critical in this process. Explaining that giving prospects the courtesy they deserve to think over the request helps her to understand that this strategy is about respect for the donors and makes your request that much more meaningful.

  7. Keep sights high: After thoughtful research and alignment, it’s important to remember that you are inviting people to be part of your vision. You are asking for an aspirational gift that will transform health care for your community. Most individuals are humbled by a thoughtful but substantial ask.

  8. Manage objections: Explain to your CEO that objections are part of the natural solicitation process. When a donor raises an objection, it is an opportunity to further explain impact and initiative, as well as show different avenues and levels available to make a gift possible.

  9. Make the experience enjoyable for all.

There is no substitute for preparation. Educating and engaging your CEO before prospective donor meetings will further cultivate relationships while moving one step closer to your philanthropic goals. It will also make the experience that much more enjoyable. Help your CEO to see all that is possible with philanthropy and how she can help make wonderful transformational gifts happen.

Accordant Checklist_Preparing CEO for The Ask
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About the Authors:

John Donovan is a Principal Consultant with Accordant. You can reach him at or connect with him through LinkedIn.

Lori Counts is a Principal Consultant and Certified Executive Coach with Accordant. You can reach her at or connect with her through LinkedIn.


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The Accordant Team has published a number of books to advance the efforts of health care philanthropy and help development leaders everywhere. 

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Accordant is honored to collaborate with American Hospital Association Trustee Services to provide issue papers, templates and webinars to support the involvement of healthcare trustees and foundation board members in advancing philanthropy. These resources can also be found on the AHA Trustee website.

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