5 Tough Interview Questions for Hiring Managers to Ask

Hiring new employees is a critical responsibility for leadership. But how do you strike a balance between evaluating candidates carefully and hiring new talent quickly?

Asking tough interview questions is one way to streamline the hiring process.

While it’s good to start an interview with small talk or even funny interview questions, it’s more efficient to transition quickly to hard questions. By digging deeper during the interview, you can unearth more substantial and intrinsic characteristics that help you determine a candidate’s compatibility with your company, its values, and its people.

To be clear, we’re not suggesting you lay traps with “gotcha” types of questions that make them feel uncomfortable or intimidated if they answer “incorrectly.” In fact, tough interview questions don’t even have “right” or “wrong” answers. Instead, they’re intended to assess a candidate’s critical thinking skills, adaptability, and creativity.

Keep reading to learn more about the value of hard interview questions, plus examples of what to ask.

Why Ask Hard Questions?

Asking tough interview questions—and giving candidates plenty of time to answer them thoughtfully—is a critical practice in today’s hiring landscape. After all, a well-prepared candidate knows you’re going to ask questions during the interview, but expected questions often elicit expected answers.

To truly gauge a candidate’s potential, you need to go beyond the prepared spiel and dig into the core of their experiences, their character, and their problem-solving skills. This is where tough interview questions come in.

These questions help hiring teams evaluate a candidate’s personality traits, cognitive abilities, cultural fit, and soft skills that might not be evident in their resume, cover letter, or during early interview sessions.

Here are some reasons to ask tough interview questions of your candidates:

Find out how they think on their feet
Understand their level of self-awareness
Assess their resilience and adaptability
Measure their emotional intelligence
Identify their leadership potential

5 Tough Interview Questions to Ask Candidates

Asking hard questions can deliver excellent insights into candidates and how they will function in your company. Here are five questions to consider asking during your next interview session.

1) Tell me about a time when your project didn’t go as planned.

Purpose: This behavioral interview question assesses a candidate’s ability to handle setbacks and learn from failure, an important quality in a fast-changing work environment.

Skill Assessed: Adaptability, resilience

Why It’s Tough: It pivots the conversation from highlighting successes to discussing failures, which some candidates may find challenging.

2) Have you ever had to work on a large project with a difficult team member? How did you handle it?

Purpose: This question delves into a candidate’s ability to navigate team dynamics and handle challenging situations.

Trait Assessed: Teamwork, conflict resolution

Why It’s Tough: It requires candidates to be honest about any past interpersonal conflicts.

3) Describe the last time you had to give someone difficult feedback. What was the feedback and what was the result?

Purpose: Effective communication is an important durable skill. This question looks at a candidate’s ability to deliver tough feedback with empathy.

Trait Assessed: Communication skills

Why It’s Tough: Not everyone is comfortable with giving feedback, even when it’s necessary.

4) What critical feedback do you most often receive?

Purpose: This question assesses a candidate’s ability to identify and admit fault. Also, it shows how they responded to the person who delivered the negative feedback. Most importantly, their answer reveals their commitment to personal growth.

Trait Assessed: Self-awareness

Why It’s Tough: Candidates must be open about their flaws and show how they actively work towards overcoming them.

5) If you could change one thing about our organization, what would it be and why?

Purpose: This question reveals multiple things. Did the candidate adequately research your company prior to the interview? How well do they know your industry? Can they offer feedback with tact?

Trait Assessed: Strategic thinking, emotional intelligence

Why It’s Tough: Not only does the candidate need to assess your company to offer suggestions for change, but they also need to deliver their answer tactfully.

Ask Tough Questions to Speed Up Your Hiring Process

Remember, asking tough interview questions isn’t about trying to trick candidates or make them feel uncomfortable. This interview technique should spark authentic conversation to give you genuine insight into a candidate’s potential to fill the role successfully.

Interviewing candidates is just one part of the hiring process. If you need to hire quickly and don’t have the time to do it right, Insight Global can help. Our hiring partners have conducted hundreds of interviews, so we know the right questions to ask to find the best talent for your business. And you don’t pay until your new hire starts.

Reach out today to find out what Insight Global can do for you.