MatchOne of the best interview questions I’ve ever heard is: “What kind of manager do you not like to work for?”

My business provides staff for events and hires event managers, so I have to conduct a lot of interviews. This question is one of my regulars, because it allows me to weed out the difficult staffers and uncover a candidate’s leadership abilities. The best candidates don’t just talk about bad managers; they also highlight their own best management qualities and how these distinguish them.

Odd queries do more than put potential hires in various “what if” scenarios. The strongest candidates can take these questions and apply them to real-world scenarios. I love when people take what looks like a completely random scenario, ground it in reality, and provide a quality solution that displays their ability to react in a professional and appropriate manner.

An employer can gather a lot of great information about candidates by going off the beaten path with their interview questions. Here are four off-the-wall prompts I use to dig deep during interviews:

1. “Your grandmother died yesterday. You were very close, and the funeral is tomorrow. You have work to get done today. What do you do?”

In my industry, accountability and responsibility trump everything. Some people will answer this question with a simple “Of course I would get the work done,” but it’s easy to tell who’s genuine and who’s not.

The best answers so far have come from people who could relate to that scenario. Those candidates mentioned how they pulled themselves together, worked for six hours, and then cried all night in the car after the event.

It may sound cold and insensitive, but I want to know whether somebody will show up no matter what. A candidate who proves they will still get their work done in the face of personal tragedy will move straight to the top of my list.

2. “What is the biggest mistake you’ve ever made?”

GlassesI don’t elaborate. I leave this question at that and rely on the candidate to provide details. Doing so not only allows people to be honest, but it also gives them the opportunity to tell me how they turned a negative into a positive or an error into a lesson.

This question throws some candidates for a loop. Some offer soft responses, but the best of them revisit the question later in the interview and provide more depth. I can’t stand the ones who can’t think of a misstep: We all make mistakes, and we all have to learn from them.

3. “If you had the opportunity to make $1 million ethically or $100 million unethically, which would you choose?”

Most people pick the $1 million option because it’s the “right thing to do,” but the key to this question is the follow-up: “Why?”

I don’t like interviewees who say $1 million is plenty and that they’d rather be decent. I’m more interested in a candidate who explains how he would parlay that $1 million into other ventures.

There’s also something gutsy in this blunt $100 million answer: “It depends who I’m screwing over.” I remember one candidate asking, “Can I be ethically unethical?” I called him Robin Hood.

4. “Give me your obituary if you died 10 years from now.”

This question tells me about a candidate’s goals and vision. It gives me a look into how they live their life. A lack of balance between personal life and work in the response is always a red flag.

Finding the right employee is a matter of finding the right question to ask. When every candidate looks the same on paper, it’s the off-the-wall question that will differentiate the best from the rest.

Grain stalkTo me, cookie-cutter answers to complex questions are a huge turnoff. I’d rather a candidate talk through an answer because the journey there can often be more important in defining character than that final response.

Perhaps I’m in the minority here, but I take notice when somebody responds to an open-ended question by admitting they don’t have all the answers. The ability to own their imperfection puts a candidate head-and-shoulders above the competition in my book.


A version of this article originally appeared on BusinessCollective.

Anthony Russo has been a self-employed business owner for more than five years, and his seven-figure agency, Identity Marketing, is recognized among the top companies in the field of experiential promotional marketing. Russo is also a professional speaker and an emcee for large national events.

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