Top Questions Interviewees Despise and Why You Should Ask Them

By Adam Robinson,
October 25, 2016


Interviews are tough, for both interviewees and interviewers. There’s a lot at stake. And when it comes to asking the questions, it’s not exactly a normal impulse to want to make people squirm. Humans, for the most part, are conflict averse. We empathize with other people: we don’t like to ruffle feathers or make people uncomfortable.


But rememberÉ there’s a lot at stake here. Your approach to interviewing-and the hiring decisions you make-has a very real impact on the success of your organization. So don’t shy away from these top questions interviewees despise:


Top 5 Questions 


1. Where do you see yourself in X years?

It doesn’t matter how many years you propose here, nobody likes trying to peer into a crystal ball and predict the future. And if most people were being honest, they’d say ‘a lottery winner living on a tropical island’. People hate this question because they know it’s hard to answer without sounding dishonest, and no matter what they say, it’s kind of a random guess.

Ask it anyway. It will give you an idea of whether or not they plan to stick around for a while. Not at your company maybe, but at least in the industry. And if your candidate is planning to stick it out for the long haul, it’s your job to keep them around anyway. It’s not going to do anyone any good if they’re looking for a long career but end up quitting for a better opportunity across town.


2. Can you sell me this pen?

This one is a classic, and it’ll make even the biggest pro squirm a little. No matter if it’s a pen or a Porsche, it’s hard to sell anything when you’re not talking to a customer, but instead being put under the microscope by a potential employer.

Nevertheless, it’s important to ask. You’re asking the candidate to think on their feet, to show you what kind of demeanor they have, and to see whether they’re confident in their role or prone to buckling under pressure. Those are important traits to consider in any potential employee, from salesperson to porter.


3. Why should I hire you?

Perhaps there’s no more general, open-ended question than this one. And to an interviewee, that makes it a pain. They could say literally anything and still feel it’s an unfair question because the other questions they’re being asked should address it anyway.

But it’s important to ask, for that very reason. A candidate’s answer will tell you exactly the first thing that comes to mind when they’re asked to determine their own worth. Do they think it’s their fancy wardrobe that counts? Or maybe the college they went to? Or their experience? Whatever their answer is, it will be the thing that they want you to think matters most. And knowing that thing should matter to you.


4. What would your last boss say about you?

This question could elicit a range of responses, from ‘my last boss would say I’m the greatest employee in the world,’ to ‘my last boss would say I’m the worst employee in the world.’ But it won’t. Rather, the interviewee will try to split the difference, with the conclusion being positive overall.

So why ask it? Because no matter what they say, the most important thing is not the words the candidate speaks, but how he or she speaks them. The tone of voice will tell you a lot that the words can’t-it will tell you how the candidate really felt about their last boss, which is what this question is really about. Pay close attention the candidate’s tone and whether it sounds like they’re describing a visit to the dentist or a visit to the beach.


5. What were you earning at your last job?

This question is a killer, because no matter what the interviewee says, it could work against them. But they’ll never know if it did. The interviewee knows that a lowball answer could make you think they are willing to accept a lower salary than they really want, but they also know that a number that’s too high might price them out of your budget.

But it’s simpler than that-you do have a budget, and you need to know if you can afford them.


It’s not your job to make interviewees feel comfortable, it’s your job to find the best person for the position. And that means asking questions they may hate. But don’t let that stop you, these questions will tell you a lot of things the softball questions won’t. 


Want more information on interview questions you should avoid and keep? Download our eBook on illegal interview questions by clicking on the link below.

About the Author

Adam co-founded Hireology with the mission to help growing companies make better hiring decisions through data and better technology. Adam is passionate about entrepreneurship, donating time to a number of organizations that support the entrepreneurial cause. Adam completed his undergraduate study at the University of Illinois at Urbana-Champaign, and received his MBA from DePaul University in Chicago, IL.

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