The Questions That Get the Most Out of Candidates

May 21, 2019 at 3:40 PM Sean Simerly

50 Interview QuestionsInterviewing is tough business – you have but a brief moment to gather your thoughts on not only an individual's aptitude, but also whether or not you think they possess those critical intangibles that lead to success within your organization.

It’s no surprise then that folks are always asking hiring managers about their interview techniques and questions in order to gain an upper hand. Instead of following that path, we're flipping the script and asking YOU for your favorite (and least favorite!) interview questions. By submitting your answers here, you may be included in a resource for recruiters and hiring managers for years to come. To get the ball rolling, I’ve included a few of my own below.

Since I started hiring at Entelo, I’ve interviewed hundreds of candidates, and brought on board north of 40 SDRs. I’ve had stellar interviews with lackluster candidates and the opposite; I’ve been blown away by candidates that in many other organizations would have been stopped at the application screen; and candidates have both told me I’m the easiest, friendliest interview while others have said I’m impossible and brutal. In any case, below are a few questions that I’ve used, and will continue to use, in all of my interviews:

Tell me, in as much detail as you possibly can, what you did to prepare for our conversation today.

Props to one of my first bosses who gave me this one (Psssst: it’s also been the subject of a standalone blog post from back in the day) because I still use it to this day. This question gives those candidates that genuinely care a chance to shine. Preparation is a skill that benefits almost every profession, and the intangibles of grit, collaboration, and diversity are all represented through the act of preparation.

This question is especially beneficial for early-in-their-career individuals. When you can’t ask about past performance or accomplishments, this question lets ability trump pedigree – and trust me – it’s a great indicator of potential commitment.

What are you looking to accomplish in your next position?

This question has a dozen different faces: Where will you be in 5 years, what do you want to be when you grow up, etc. etc.

What those fail at doing is having the candidate focus on the present. By expanding scope, you may receive career pathing insight, but you lose the opportunity to see someone’s ability to plot their path on their own – whether immediate or far-flung.

Tell me about a time when you had to deliver difficult feedback.

Too often interviewers (and interviewees!) think of feedback as a one-way street. A manager gives feedback to their direct reports, and the world spins on.

The truth of the matter however is that the best organizations think of feedback as a dialogue. To foster peak productivity, direct reports need to feel empowered (and confident) in delivering feedback to their supervisors.

This question shows their appetite for challenge, and their tact in delivering difficult feedback regardless of the audience.


So tell us – what are the best, and the worst, questions you’ve been asked in an interview? Take it a step further: Why?

One person’s perspective is a page, but we’re hoping to write a chapter – so let us hear it through this form here. Join the Conversation!

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