When you’re looking for an employee, it’s not a decision you undertake lightly – especially when it’s someone who will have as much of an effect on your organization as a Major Gift Officer.

The MGO is a big deal because it requires a unique skill set: a love for people and – ideally – an authentic dedication to your cause, a knack for storytelling and listening, and, of course, a flair for fundraising. Most of all, you want to make sure that a potential gift officer is compatible with your vision.

So while your personal preferences may vary, the top qualities of a major gift officer are pretty consistent. They really like people, are dedicated and enthusiastic about your cause, are great storytellers and listeners, have a real gift for raising money (of course!), and possess long-term compatibility with you and your plans.

But not all of these may be immediately on display when you’re interviewing someone – so you have to ask the right questions to find out! Here are the top five questions to ask a prospective major gift officer.

When you’re thinking up questions to ask a prospective MGO, directness, and simplicity is key, says Ayda Sanver, a Maryland-based fundraiser and consultant to nonprofits, with emphasis on smaller and emerging organizations.

The most important question, she says, is the simplest one: 

“Do you like working directly with donors and prospects, and are you comfortable asking for gifts?”

That’s way better than talking around the issue unless you’re just curious and trying to get a feel for who they are as a person. If working directly with people isn’t someone’s cup of tea, then you shouldn’t hire them – at least not for this position.

What kind of experience do you have with large-scale fundraising?”

Of course, experience is important, but how they answer this question is just as important as what they answer with. In fundraising, there’s more than just practicing “the ask.” There’s also enthusiasm – although which to value the most is up to you and the position. Sanver said sometimes you can just go with your gut about a less experienced hire, as long as they’re demonstrating enthusiasm.

“This depends on the level of seniority [and] supervision required in the position,” she said. “For a junior major gift officer, the above characteristics mean the person has a foundation to learn and be molded into a great major gifts officer, given that they are willing to attend training, read books/online articles, and be mentored by someone more senior, or develop their own network of other major gift officers to bounce ideas off of.”

So what if you want to get hired as a major gifts officer, don’t have a lot of experience, but think you’d be really good at fundraising? According to Sanver, one of the best markers of enthusiasm is teaching yourself the ropes: attend training, watch webinars, and read websites. If you’re an employer and have a great feeling about someone with not much experience, ask them what they have done to learn about raising funds for charities.

Why would you like to work here?”

This question isn’t just asking for affirmation. It’s asking whether they did their due diligence about your organization and know what it’s all about, rather than just firing off a one-size-fits-all resume to every opportunity out there. This question can also be answered in a really good cover letter, Sanver said.

“For me, a good cover letter shouldn’t be very long, but demonstrate enthusiasm to be considered for the position, a good understanding of the nature of the nonprofit’s work, and how the applicant would be a good fit for the existing team,” she explained. “In other words, demonstrate you did your homework and actually know what the nonprofit is all about.”

What was the best gift you ever secured for an organization, and how did you get it?”

Why you would ask this question of a potential hire is self-explanatory, because it gives solid insights into their fundraising process, as well as showing you what they’re capable of.

The next question, though, should be equally important, if a little more uncomfortable:

What was your worst fundraising experience, and what did it teach you?

Everybody makes mistakes. How you react to them and how you learn from them is a key part of the experience you gain, not just as an employee, but as a person. How do they answer this question and tell the story about their worst experience? Is it something they can laugh about now, if only ruefully? Do they get frustrated? This question can go a long way in showing you how experienced they are and how they will react when there’s friction on the job.

When you get to the point in your nonprofit’s life that you’re looking into hiring an MGO, it’s not something that should be undertaken lightly. Approach your hire like you might approach any other important interpersonal relationship. If you find someone with the right combination of smarts, curiosity, and friendliness, as well as fundraising drive and verve, you, your new major gift officer, your donors, and your causes will be well on your way to a beautiful friendship.