woman conducting a video meeting

Asking the right questions can make all the difference when hiring a new assistant or associate. While conducting a job interview can be more art than science, some questions are more useful than others in identifying the best person to join your team.

Amy Davies often asks, “When you came to your boss with a new idea, how did they react?” If the response is that their boss hated it, that would be a big red flag, said Davies, founder and president of Toronto-based First30, which specializes in employee onboarding and orientation.

“Everybody loves ideas, right? It could be a sign that person has difficulty working with other people or working with their leader,” Davies said.

If the candidate responds with a detailed story, it gives you a sense of how resourceful they are and the types of ideas they bring to the table, she said.

Having them walk through how they would handle different scenarios can also be telling. Davies likes to avoid general questions like “Tell me about a problem you had in the workplace and how you resolved it.”

“That can be your starting point, but then you’re actually going to want to give them a problem to solve,” she said. “Often, we go to interviews and we have rehearsed answers. Give them an actual example. Say, ‘I would love your ideas around how you would solve this problem or overcome it or engage with the client.’”

Kiljon Shukullari, HR advice manager with Peninsula Canada in Toronto, gets around rehearsed answers by asking questions like “What’s your preferred working environment?” and “What is feedback to you?”

“We’re going to make sure that this is someone who’s going to take feedback and be constructive about it,” he said. “You’re going to have them working with different clients — how do they go about doing that?”

He also likes to ask candidates to describe themselves, but from the perspective of other people: “If I were to ask your manager, friends or previous employer, what three words would they use to describe you?”

Answers that include words like organized, energetic and relatable are the ones he likes to hear for assistants and associates, he said.

Offbeat interview questions can also be useful in gauging how someone thinks and approaches problems. The idea behind these questions, which don’t have one right answer, is to uncover how people approach problem-solving.

For example: How would you move Mount Fuji? That’s the title of a book by William Poundstone examining how Microsoft and other top employers select the most creative workers.

“They’re useful because it gives you a good insight into how the person will approach something that doesn’t have a very concrete answer,” Shukullari said.

Some questions must be avoided for legal and reputational reasons. Asking anything related to religion, family status or disability can land employers in hot water, Davies said.

“Those are illegal questions, and we have to be careful about it,” she said. She has seen people stumble into trouble by asking an innocent question at the start like “Tell me about yourself.” That opens the door to discussing their personal life.

“Instead, frame the question to say ‘Tell me about what made you excited to get into this line of work?’ Or, ‘Tell me a little bit about your career history over the last five years,’” Davies said.