- Rob Cancilla’s go-to interview question has gotten him roles at Harvard Business School and Facebook.
- This question presents the candidate as someone who envisions themself in the role.
- It’s a question that also has a proven track record in getting candidates their dream job.
As an executive recruiter and career coach, I’ve prepped thousands of job seekers on interview preparation, and I believe I’ve found the single best question you can ask in almost any interview.
A crucial part of any interview preparation is developing questions to ask the interviewer. The questions you ask in the interview can be instrumental in your ability to move forward in the interview process and ultimately receive an offer.
You should always develop a handful of custom questions to ask specifically about the company, the role, and the interviewer, but there is one single question I always recommend asking:
“What is the biggest challenge for anyone coming into this role?”
I’ve recommended countless job seekers ask this question and it yields consistent success. I’ve also personally used this question for over 15 years, and it’s helped me land roles at Harvard Business School, PwC, and Facebook.
In almost every interview where I’ve used this question, the interviewer’s response is, “That’s a great question.”
This an excellent question for three reasons:
1. You will stand out
This is not a common question you'll find on Top Interview Questions lists… at least not yet.
Hiring managers and recruiters are consistently drummed with the same questions from job seekers. Utilizing the same interview questions as everyone else limits your ability to stand out and be memorable.
2. You highlight that you are ready to take on a challenge
A common interview question found on blogs and articles is, "What does success look like for this role?"
At its core, it's not a bad question, but it's an overused question that every hiring manager has heard before.
When you instead ask, "What is the biggest challenge for anyone coming into this role?" you're signaling to the interviewer, not only do I want to be successful in this role, but I'm ready to take on challenges today.
Hiring managers will be impressed that you're not just asking questions that benefit you personally, but asking real questions about the role and how to be successful, despite the challenges.
3. You are starting to envision yourself in the role
Hiring managers want to know if you are starting to envision yourself in the role and take on the responsibilities needed. By leading with the challenges, as opposed to the successes, you're sending a clear indication that you can see yourself in the role and are excited to jump into the day-to-day, whatever it entails.
Bonus tip:
After you ask the question, be sure and listen very carefully to the answer and, if possible, provide an example of how you were able to overcome or solve a similar challenge in your previous role(s). Even if you can't respond with how you overcame a similar challenge, asking the initial question will allow you to stand out.
I recently posted a video about this interview question on my Job Search/Career Tips page on TikTok (@rob_canilla) and the responses from active job seekers have been amazing. Be sure and utilize this question in your next interview.
Rob Cancilla is an executive recruiter for early-stage venture capital backed companies, an adjunct professor for the Quinlan School of Business at Loyal University Chicago, and cofounder of multimedia resume platform Vibio.