The five most awkward interview questions and how to answer them

I spent the early part of my career asking awkward interview questions of job applicants.

And ever since I left that role behind, I’ve been preparing others on how to answer them. 

In a two-part blog, last time I outlined the five most common interview questions and how to answer them.

This time, let’s deal with the five most awkward.

These are the questions most interview candidates fear.

But they all have an answer, and they can all be prepared to give you confidence.

And remember, if you want to learn more, we’ve got an e-learning course on job interviews right here.

1. What are your biggest weaknesses?

This is the worst-answered question I’ve seen.

People pick a strength and thinly disguise it as a weakness.

For example:

“My biggest weakness is how hard I work, people are always telling me to ease off.”

Sick bucket please.

It’s completely see-through and can erode trust (if you’re lying about that, what else have you lied about?)

Better to pick an actual area of improvement, and demonstrate how you’re overcoming it:

“I’ve always struggled with WordPress, so I’m taking classes now to make sure I’m fully proficient by the end of the year.”

You’re now building trust through honesty, demonstrating your self-awareness and desire to improve.

2. Tell me about a time you dealt with a difficult person

This one is a classic ‘SOAR’ question.

Situation, objective, action, result.

Be careful to avoid going into too much detail and criticising someone overtly.

Instead, discuss your process of how you worked things out and what that reveals about your personality.

For example:

“In my first role, I managed a role of students, one of whom was hampering the productivity of everyone in the group.

“It came to a head when he spoke out of turn in a management meeting, which was embarrassing for everyone.

“I arranged a 1-1 meeting to explain what was expected of him, and we got on really well after that.

“If that happened today, I would tackle the problem much earlier to avoid any embarrassment.”

3. Why should we hire you over everyone else?

Ah yes, the chance to talk down your fellow job candidates.

Always avoid criticising the competition. It’s an undesirable quality and may come back to bite you.

Focus on yourself and your own strengths.

“I can only speak for myself.

“I do believe I’m a strong candidate given my sales experience.

“And the fact I’ve been promoted twice this year demonstrates both my focus and my drive.”

4. What would your friends and family say about you?

I got this one really wrong.

I pictured my friends saying terrible things about me and went into far too much detail, revealing my worst traits.

The best answers here pull on soft skills, for example:

“I expect my friends and family would say I’m dependable.

“If there’s ever a problem, I’m the person people call to sort it out.

“My Dad used to call me ‘the diplomat’.

“Sometimes I get it wrong, but whenever I see someone being bullied, I feel the need to step in and sort it out.”

5. What kind of biscuit are you?

This is all about dealing with the off-the-wall question.

“Why are manhole covers round?”

“If you could travel back in time and say three words to yourself, what would they be?”

These questions are far more about how you deal with pressure than giving the perfect answer.

Take your time.

Showing you can handle silence is a real sign of confidence.

Take five seconds to consider the answer, remembering that the time will feel much longer to you than to anyone else.

And feel confident saying something safe rather than having to be quick-witted or quirky.

You’re unlikely to come up with a killer answer there and then, and you might end up saying something controversial instead.

And if you’re really struggling, let the panel know you’ll have to consider it and email them the answer later.

Now you’ve got a direct route into their mailbox hours after you’ve left the building.

Awkward interview questions and how to answer

So there you have it.

The five most difficult questions you can be asked at interview stage – and how to answer them.

If you’d like to know more, you can preview and purchase our Virtual Interview Masterclass.

You’ll learn to prepare effectively, engage a virtual panel and answer any question thrown your way.

And by the way, if you’re still wondering why manhole covers are round, it’s because manholes are round.

Andrew McFarlan runs Pink Elephant Communications.

Read more about him here.

Photos in Awkward interview questions blog by Pink Elephant Communications.
Awkward interview questions blog written by Andrew McFarlan.
Awkward interview questions blog edited by Colin Stone.