101 Clever Questions that Unlock Planned Gifts

Inspire donors, supercharge their stories, and close the deal.

Knowing how to ask the right questions is an essential skill – one that can translate to success in all areas of your career and life. Good questions are the key to getting the kind of quality information you need, whether it’s to write engaging, inspiring donor stories, or understand your prospect better so that you can prime them for the ask.

“Last minute checklist” included.

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Clever Questions Book
This item: 101 Clever Questions that Unlock Planned Gifts

In Stock for Clients Only

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Three Planned Giving Pocket Guides
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Original price was: $90.00.Current price is: $70.00.
Planned Giving Pocket Guide for Professional Gift Planners
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For Board, MGOs and Planned Giving Officers

When it comes time to meet with donors and prospects, small talk will take you only so far. While it might get your foot in the door, it won’t seal the deal or help you build a relationship.

To truly find out what makes people tick (and make a gift), you need to ask the right questions — questions that are engaging, revealing, and thought-provoking.

If you struggle to get the conversation started, generate exceptional questions for donor interviews, or even “make the ask,” this booklet is for you. And the best part is, whether it’s an interview for a donor story, annual report, board report, newsletter story — even a job or candidate interview — all of these skills will translate.

Ask a quality question, get a quality answer!

Over 101 Questions

Sometimes it can be a real struggle to generate a list of quality questions. How do you get the donor to open up about their life, their gift, their passion for your mission?

  • What do you ask?
  • Which questions are relevant?
  • Which questions are appropriate?
  • Which questions cross the line?
  • What do you do if a subject isn’t talkative?

This booklet shows you a guaranteed process that will help you produce thought-provoking questions that generate quality, comprehensive answers.

Author: Patrick O'Donnell

From politicians and police officers to celebrities, crooks, and CEOs, our senior editor Patrick O’Donnell has asked his fair share of questions — and now you can benefit from his experience. Patrick spent more than 20 years in journalism as both a writer and an editor. That means he’s done a lot of interviews, and not all of them with friendly interviewees. He’ll show you how to ask tough questions, navigate prickly subjects, and get the answers you need — without offending your prospect and donor.


Wayne Olson, JD, National Director of Planned Giving, Shriner’s Children’s Hospital
Russell James III, Ph.D., J.D., CFP®, Professor, Charitable Giving Program Director, Texas Tech
Scott Janney, Ed.D., Director of Gift Planning at Eastern USA Territory of The Salvation Army
Jeff Comfort, VP, Principal Gifts and Gift Planning, Oregon State University
Viken Mikaelian, CEO, PlannedGiving.com
Jonathan Gudema, JD, Senior Planned Giving Counsel, PlannedGiving.com
Karen Martin, Editor, Giving Tomorrow Magazine
Gordon L. Nelson, CPA, CFP®, Birch Creek Gift Planning

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This is a powerful and practical tool.  It’s going to make a real difference for the fundraisers who use it!
Russell N. James III, J.D., Ph.D., CFP®, Director of Graduate Studies in Charitable Planning, Texas Tech University, Lubbock, TX 

This is outstanding.  These questions keep the focus on the donor, give you critical information about the donor and their goals, and build trust.  It is the trust that opens the relationship door and allows you to help them build a gift that reflects their goals. Congrats!
Kathryn Miree, Miree & Associates, Birmingham, AL

What a great resource. That’s why I contributed to it!
Wayne Olson, Esq., Senior Director of Planned Giving for Shriners Children’s, Tampa, FL

Patrick O’Donnell’s, “101 Clever Questions That Unlock Planned Gifts,” is a must for all fundraisers.  This is a rare resource that should be kept close at-hand and reviewed before every cultivation opportunity.  Building relationships is about having conversations and the questions provided in this booklet give you a myriad of questions to deepen your relationships and ultimately move your prospects to ask readiness.  I applaud Mr. O’Donnell for offering this comprehensive tool that will not only better our missions, but will help our donors make meaningful philanthropic decisions.
Kim Rhinehelder, CFRE, Director of Development & Capital Campaign, Navy SEAL Museum San Diego

What a great resource! I am asking PlannedGiving.com to brand this booklet for our 12 hospitals. I know our gift officers will find it incredibly valuable as they frame their donor conversations.
Greg Ellmer, Vice President of Gift Planning, RWJBaranabas Health, Orange, NJ

This publication puts the focus where philanthropic advisers can have the greatest impact for good. I’m proud to be part of it.
Dr. Scott Janney, Director of Gift Planning at Eastern USA Territory of The Salvation Army, West Nyack, NY

Wow. Another home run from our friends at PlannedGiving.com
Paul “Chip” Hurd, Chief Philanthropy Officer at United Way of the Greater Lehigh Valley 

This is powerful — all the questions you’d ever need. I plan to share it widely.
Brian Saber, CEO, Asking Matters

Don’t leave the office without it! It’s the best tool there is to make a match between the values your organization enacts and the values your donor and you share. Learn the underrated art of asking generative questions.
Claire Axelrad, J.D., CFRE, Founder and Principal of Clairification. 

A jewel of a booklet… it along with their Planned Giving Guide is all you need to succeed. Read it and make it part of your fundraising DNA!
Gary Bukowski, VP for Advancement, Sarah A Reed Children’s Center


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