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5 Questions to Ask Your Next Development Director

This article was written by Ariel Glassman. She is no longer with Ostara, but we want to preserve this piece so that you can learn from her and from the work she did while part of the Ostara team.


It’s January – the time of year when many fundraisers are burned out from the busy December fundraising sprint. And thus, it’s a time of year when many fundraisers decide to look for new jobs. Your organization may find itself looking for a new development director, come February or March.


Our sector already knows that development staff turnover is costly. The retraining costs for a fundraising role after turnover equal around 25-33% of the salary costs for that role. This doesn’t include the opportunity cost around whatever revenue might have been raised in that time period if the organization had been fully staffed. For so many reasons, it’s imperative to keep effective fundraisers around and satisfied in their work.


Fundraiser retention starts with making the right hire in the first place. That’s a no-brainer, right? But it turns out that hiring for development positions is hard – really hard. And not just because fundraising is hard (which it is). It’s difficult because fundraising is an experiential profession that, by its nature, happens to be full of eloquent communicators. Development pros are great talkers; it’s in our nature. We know how to generate contributions from tough-minded business people and soft-hearted grandmothers alike; we can run circles around standard job interviews.


Often, the key to hiring a great development director is the ability to separate those who can just talk the talk from those who can truly walk the walk. What’s the hitch? Most of the time, that’s not something you can do without having done it yourself. The problem lies with who hires a development director. It is imperative to have people involved in the interviewing process with direct experience and systematic participation in the hard work of fundraising. It’s easy to be swayed by a resume full of results without context, or by a smooth personality. Even the most strategic and hard-working search committees can have a sizeable blind spot around hiring fundraisers.


Ostara has developed five tried-and-true interview questions for development directors to help you sort out the doers from the schmoozers:


1. How would you go about learning more about [insert your organization’s sector or mission space] so you can work more effectively with donors in this mission space?


Why ask? Unless your organization is sitting pretty on a pile of cash, any fundraiser you hire – especially at the leadership level – will need to hit the ground running. But unless they have significant experience in your specific slice of the nonprofit sector, they probably don’t have enough knowledge of your mission and your impact yet to go toe-to-toe with sophisticated major donors. Fundraisers need to know as much about program work as your program staff, and you want to make sure that the person you hire knows how get up to speed quickly so they can dive in. This is one of the upsides to fundraisers that have jumped around a lot, or who have spent time consulting – they have practice getting up to speed quickly.


What to look for in their answer: Some candidates will look to books, magazines, websites, or articles; some will start with speaking to experts or leaders in the field. Others will balance those approaches, or come up with something totally out of left field that you’ve never thought of before. There’s no right answer in general, but one of these styles might be a better fit for your organizational culture or your specific sector. The best way to get up to speed after joining an infectious disease research institute is probably not how you would get up to speed at a performing arts center. Think through what’s best for your organization before you ask this question in the interviews.


2. Tell us about the gift you are most proud of securing. Why are you proud of this gift? How did you structure the giving opportunity, and how did you cultivate and solicit the donor?


Why ask? Asking for a specific anecdote or example of a key fundraising activity will tell you much more than a conceptual conversation about that skill. Lots of fundraisers can tell you what moves management is; far fewer actually do it well. A great director of development or major gifts officer will be able to unpack their process for you in detail. It’s important to understand the level of critical thinking and intentionality they apply to donor relationship development. This question really helps identify those whose experiences have prepared them to lead and beat their goals. And, how fundraisers defines their success, and what they are proud of, is crucial to understanding how they set goals, approach their work and stay motivated.


What to look for in their answer: Many fundraisers will choose the example of the largest gift they have closed. That’s fine – after all, fundraisers need to bring results, and there’s no shame in celebrating big wins. But truly great fundraisers are purposeful and donor-centric. Some of the best fundraisers I’ve hired chose to talk about gifts that were not necessarily their largest, but that allowed their organization to accomplish something long-awaited or important. Others chose gifts that they could tell were the most meaningful to that donor. Either of these types of answers is a good sign that the candidate understands what it means to be donor-centric.


Extra points go to examples that include partnership with their executive director, board members, development committee members, and/or other volunteers in cultivating and soliciting the gift. Though you need them to be effective solicitors themselves, great fundraisers recognize that donor development is often a team sport. They know when to bring volunteers in to help close the gift.


3. Tell us about a mistake you made that impacted a donor or other important organizational relationship, and how you recovered from it or addressed the situation. In retrospect, is there anything you would have done differently?


Why ask? Mistakes happen. Development professionals are human. It’s great to have an example of how someone recognizes and rectifies their own mistakes, and to hear how comfortable they are acknowledging their own imperfection. This question fundamentally acknowledges that no one is perfect, and tells savvy candidates as much about your organization’s culture as it tells you about their self-awareness and humility. It communicates that once on the job, they’ll be allowed to make mistakes and grow from it.


What to look for in their answer: Self-awareness about the gravity of the mistake; the instinct to be honest with other organizational leadership (like the executive director or board member connected to the donor) about the mistake; a collaborative problem-solving style; and a donor-centric approach to mitigating the impact of the mistake.


4. What have you learned from previous supervisors or managers that has informed how you lead and manage a team?


Why ask? Most nonprofit sector employees never receive training and education in how to lead and manage teams, because professional development is costly. As fundraisers advance their careers and grow their skills, they often receive promotions or pursue new positions that put them in a management role at the leadership level without any formal or informal preparation for leading a team. The only example most have is their own former supervisors, who most likely also didn’t have formal training. This phenomenon means nonprofits need to dig deep on management style for leadership-level positions during interviews (and be prepared to offer professional development support for management skills).


What to look for in their answer: Evidence of prior critical thinking about management and leadership; an articulation of what worked and did not work for them; and a clear articulation of their own intended management style. There’s no right answer here, but listen carefully for an orientation towards trust, frequent communication, and a positive rather than punitive approach.


5. What’s your superpower, and what’s your kryptonite? And why?


Why ask? This is another way to ask the standard question about strengths and weaknesses, which any candidates prepare to answer. But the casual and fun verbiage of this question will catch many off guard and produce a more authentic answer – especially if you throw it in between more serious questions.


What to look for in their answer: A “kryptonite” that is actually a weakness or flaw, rather than a way to turn a weakness into a strength. Of course, a good fundraiser can spin their weakness into an upside; a great fundraiser will allow themselves to be vulnerable. If necessary, dig deeper and ask why something has become their superpower or kryptonite. Self-awareness of strengths and weaknesses is important in a field that is based on understanding and connecting with others.


PS: Once you make a hire – there’s no shortage of great advice out there about how to retain your talented fundraisers. 

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