4 toughest interview questions you need to prepare for

So you’ve crafted a winning resume …

… written an amazing cover letter …

… and you might have gotten a little ahead of yourself and started clearing out your desk.

Your hard work has paid off though, because you’ve nailed an interview with the job you want. Congrats!

But it’s not the time to celebrate yet. After all, you still need to crush the interview. That means preparing answers for some potentially hard, but common, interview questions.

Luckily, we have a list of five of the toughest interview questions you’ll encounter — and specifically how to answer these interview questions.

4 tough interview questions you need to be prepared for

When it comes to crafting perfect answers to common interview questions, you just need to remember one thing: Always look for the question behind the question.

It’s like when your significant other comes up to you and asks, “Does this outfit make me look fat?” What are they really asking?

They’re not just looking for an honest opinion; they’re seeking validation. They want to feel secure with how they look.

It’s the same with interview questions. Every question that comes your way is really asking a dozen other questions behind it. Your ability to answer all those other questions is what’s going to determine the strength of your interview.

Here are some of the most challenging questions you’ll face, what they really mean, and how you should answer it.

Question #1: What’s your biggest weakness?

What they’re really asking: What are you doing to improve yourself?

This question is to interviews what “Free Bird” is to a Lynyrd Skynyrd concert. You’re DEFINITELY going to hear it come up.

Not only that, but it’s a veritable minefield of potential pitfalls for the person being interviewed. If you’re too honest, you might reveal too much and alienate the hiring manager. If you go with something like, “I work too hard,” they’re going to pick up on your BS and be alienated even more.

You have to remember that the hiring manager doesn’t actually want to hear about each and every weakness. Rather they want to know how you’re working on improving yourself.

This is a great opportunity to leverage the power of storytelling. If you can show the hiring manager how you’re 1) Aware of your shortcomings and 2) How you have been actively addressing those shortcomings, they’re going to LOVE you for it.

Show them how you took a negative experience or trait and turned it into a positive growing experience.

Strong example:

“That’s a great question, and it’s something I’ve spent a lot of time thinking about. What I’ve found is that the majority of my career was spent working for one industry. In many ways, that can limit my perspective.

But, of course, I’ve worked in a variety of departments and been in several different positions. In fact, I was promoted faster than anyone else to lead new projects. But I’m ready to take what I’ve learned from this one industry to a different culture and new industry, and that’s why I’m here today.”

Question #2: Where do you see yourself in X years?

What they’re really asking: Are you just going to jump ship once a better opportunity comes along?

Hiring is EXPENSIVE.

The average cost of hiring just a single employee is typically around $5,000, according to hiring website Recruiter Box. Not only that, but once the company hires you, they’re going to be paying for your salary, training, and benefits. All told, the cost of hiring and keeping you as an employee will stretch at least into five figures.  

That’s why it’s in the company’s best interest to hire and keep you for as long as possible.

So when a hiring manager asks you where you see yourself in five years, what they really want to know is if you plan on staying at the job for a long time or if you’re treating the job as a stepping stone for another role.

To answer it well, you’ll want to remain honest while still showcasing that you’re ambitious and want to do good work for the company if and when you get hired.

Strong example:

“I’m very excited about the junior copywriting position with your company because in five years I want to be working at a director level in the email marketing industry. Knowing your needs for good email marketers, I know that I’ll have ample opportunity for growth and to learn the skills I need to get there.”

Question #3: Can you tell me about your work history?

What they’re really asking: What are your strengths and how have you grown?

When most candidates hear this, they’ll simply walk through their entire resume with the hiring manager and leave it at that.

DON’T be like most candidates.

Your hiring manager already has the resume in front of them. They can already see that you spent that summer interning at that one consulting firm and that you went on to X company to do Y work. That’s not what they want to hear from you.

What they really want to hear from you is how you’ve grown throughout your career so far and the wins you’ve gotten as a result.

That means highlighting key strengths in your background and crafting a story around that that showcases how you’ve grown.

Strong example:

“If you look at my work experience, there are three things that stand out.

First, I have experience with many areas of marketing, including social media, product marketing, and customer relationship management.

Second, I’ve always been fascinated by the analytical side of marketing, which is why I chose to study this in college. My recent social media campaign experience really allowed that passion to flourish.

Finally, I’ve always wanted to take my skills to a larger stage, which is why I moved from A Company, which was a startup, to B Company, which is more established. Now, I’m excited to be here talking with you today because of those transitions and how they fit so nicely with your needs around this position.”

Question #4: Why should we hire you?

What they’re really asking: What value are you going to offer?

Another classic interview question rife with potential pitfalls.

The danger behind this question though is how vague it is — inviting unsuspecting job seekers to ramble on without a point or purpose.

The key here is to remember:

It’s not about you. It’s about the company.

Instead of saying something like, “I’M looking for an opportunity for a job that challenges ME.” Reframe: “I see a lot of opportunities to help YOU.”

Put yourself into the hiring manager’s place and think about what they want to hear.

Strong example:

“Well, based on the things we’ve already talked about, I know there are three main challenges you’re looking at.

The first one is getting new leads, the second is increasing conversions, and the third is retention.

And my experience is in email marketing. I’ve done a lot of work on the conversion side of things and I think could help you guys in AREAS 1, 2, 3.

In fact, the last company I worked with increased their conversions by 26%. I think I can do even better for you.”

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4 toughest interview questions you need to prepare for is a post from: I Will Teach You To Be Rich.