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  • Writer's pictureDebra A. Gill

Hiring Successful Fundraisers

Experience Matters

There seems to be a lot of employment transition in the philanthropy field right now. More than half of my clients are recruiting for key positions and are steadfastly focused on distinguishing those who have what it takes to succeed in these challenging jobs from those who will be passing through on the way to their next opportunity.


Below are interview questions that I’ve found to be advantageous, developed with colleagues along the way. There are two areas of inquiry worth pursuing.

Performance/Behavioral Questions

  • Describe in detail your work history from your very first job to the most recent. Be specific about likes, dislikes, and reasons for changing positions.

  • How do you measure your success?

  • What motivates you to do a good job?

  • What is the one professional accomplishment of which you are the proudest?

  • Describe a time when your work was below your personal standards and why. What did you do to raise your standards of performance?

  • Describe a situation where others you were working with on a project disagreed with your ideas or technique. What did you do?

  • What do you do for professional development (books/articles read, conferences attended, etc.). What is the most useful piece of new information you have learned lately?

  • How do you determine priorities in scheduling your time? Give specific examples.

  • What really makes you frustrated or upset on a job?

  • Tell of the most difficult “conflict” experience that you have ever had to handle, perhaps an angry colleague or donor. Be specific and tell what you did and what the outcome was.

  • Give an example of a time when you received constructive criticism. How did you react?

  • What kind of leader do you work best for? What did you like best, and least, about your last supervisor?

  • Where do you see yourself professionally in 5 years, 10 years, 15 years?

Philanthropy Questions

  • Tell us about your experience with the following, being as specific as possible (as appropriate):

    • Major Gift Solicitations/Planned Giving/Capital Campaigns/Annual Campaigns/Prospect Research/Data Analytics

  • Describe in detail two successful major gift approaches and two unsuccessful major gift approaches that you have personally conducted.

  • What is your biggest strength in fundraising? Why do you say that?

  • What is your biggest challenge in fundraising? Why do you say that?

  • One of the aspects of this position is to connect with new donors and strengthen our ties to existing supporters. How would you approach this process?

  • Tell us about your experience working with volunteers (i.e., board) and team members to cultivate individual gifts. How would you manage to do that successfully in this role?

  • How many prospects would you see yourself having in a portfolio and how would you manage that group?

  • Describe your approach to moves management and any other techniques you use to facilitate donor relationships.

  • Describe your motivation to apply for this position and how it relates to your career goals.

  • If you are hired for this position, tell us in detail how you would approach each day.

  • What questions do you have for us?

My favorite question from this list is the very first bullet of the philanthropy inquiry. Applicants are very practiced these days. They know the questions and they know their answers. Getting them to relax and talk conversationally about their work history along with sharing their likes, dislikes, and reasons for moving on is an excellent way to discover intel that may otherwise be concealed in practiced responses.


Ask the right questions – I once was interviewing an executive assistant candidate. The skills and abilities required were standard. As the person began describing their work history, I pushed to discover what they didn’t like about each position. As it turned out, it was filing – “I let it get up to here (hand held high) before I take it on.” They didn’t even realize they had said it until the cat was out of the bag. Not a good fit for a job that, back in the day, required extensive filing.


A recruiter friend of mine offered some good advice. No one is going to give you a bad source for a reference. With today’s connectivity, do a little sleuthing of your own to find people who have the real skinny on someone’s capabilities – honoring confidentiality as appropriate of course.

Go beyond the reference list – I failed to do this once and regretted it. A candidate and I shared former colleagues, but I didn’t take the time to reach out for a behind-the-scenes reference. After a failed hire, I mentioned it to the person I should have connected with and was told I could have saved myself some grief as they would have said no way to this hire.


Philanthropy team members must possess diverse skill sets and the best way to assess these is by observation. Integrate virtual interviews into the early selection process. Dine with candidates in a public setting to observe their manners and interaction with servers. Expect a timely thoughtful thank you communication after an interview – a strong indication of how they will treat your donors down the line.


How they interview reflects their performance standards – I scheduled a video interview with a candidate and was quite surprised by not only how casually they dressed but by the background setting of the call. It was honestly so distracting that I wrapped the interview early. Had I been a donor, no gift would have been forthcoming.


Probably the most important aspect of hiring is the team interview. Involving those who will be working with the successful candidate, including donors, if possible, is the best way to make sure the fit is right. Each team member has the questions and a score sheet with the opportunity to document their observations. Inevitably, someone will point out strengths and weaknesses that others overlook, resulting in valuable insights.


The best interview is a team interview – Twenty-five years ago I was interviewed for my first hospital foundation leadership position in a room with a circle of a dozen people. It was intimidating, stimulating, and the best interview I ever experienced. They each introduced themselves, asked a question, and gave me the opportunity to thoughtfully respond while demonstrating my ability to connect with the group. I stayed 17 years.


Hiring is difficult and takes a lot of time, energy, and resources but nothing is worse – or more expensive – than having to restart the process. It behooves us to have a solid recruitment plan, follow best practices, and do everything possible to identify the most effective new team member the first time around.


Alliance Philanthropy’s philosophy is to inspire staff, volunteers, and board members for all types of not-for-profit organizations to raise funds enthusiastically and passionately - at maximum levels - in support of their mission.

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