The 3 Interview Questions You Can’t Afford to Wing

Most people walk into interviews having prepared their answer to the obvious one: “Tell me about yourself.” And that’s great — you should. But here’s the catch: that’s not usually the question that trips people up.

The questions that derail candidates are the ones they thought they could wing. The ones that sound simple on the surface but reveal a lot about how seriously you’ve prepared, how self-aware you are, and how you handle uncomfortable topics.

I’ve been in recruitment for nearly 20 years, and I’ve interviewed thousands of candidates. These are the three questions that come up time and time again — and they’re the ones you absolutely cannot afford to wing.

1. “Why This Company?”

Sounds straightforward, right? But this is where most candidates give generic answers:

• “I’m looking for a new challenge.”
• “I’ve always admired your brand.”
• “I think I’d be a good fit.”

Here’s the problem: those answers could apply to literally any company. Hiring managers are looking to see if you’ve done your homework and whether you actually understand what they do, what they’re about, and why you’re motivated to join them, not just anyone.

How to answer it properly:

• Do real research. Don’t just memorise the About Us page. Look at recent press releases, product launches, strategy updates, or LinkedIn posts from leadership.
• Connect it to your skills. Instead of “I admire your growth,” say: “I saw you’re expanding into the healthcare market. In my last role, I worked on X project in that space, so I’m excited about contributing to that journey.”
• Show personal alignment. If their values or mission connect to something that genuinely motivates you, call it out. Authentic enthusiasm is a differentiator.

Quick Fix: Before your next interview, write down three specific reasons you want that company — one about the company itself, one about the role, and one about how it aligns with your career goals.

2. “Tell Me About a Failure”

Nobody likes this one. It feels like a trap. And the biggest mistake candidates make? Dodging it. They give a fake failure (“I care too much” or “I work too hard”), or they tell a story that’s actually a success in disguise.

The interviewer can see straight through it. What they’re really looking for is self-awareness, resilience, and the ability to learn from setbacks.

How to answer it properly:

• Pick a real example. Something that didn’t go to plan. It doesn’t have to be catastrophic, but it should be genuine.
• Use the STAR method. Situation, Task, Action, Result. Be clear on what went wrong, what you did about it, and — most importantly — what you learned.
• End on growth. Example: “In one project I underestimated the time needed for stakeholder sign-off. The result was a late delivery. Since then, I’ve built in buffer time and I’ve become much more proactive in chasing sign-offs early. It taught me the importance of stakeholder management.”

Quick Fix: Think of a time where something genuinely didn’t work out. Frame it honestly, but always end with the lesson and how you’ve applied it since. That turns a weakness into evidence of growth.

3. “What Are Your Salary Expectations?”

This one catches people off guard more than any other. And if you wing it, you risk either underselling yourself or pricing yourself out of the process.

Here’s the golden rule: don’t tell them your current salary. It’s irrelevant. The only thing that matters is what the role is worth and what you expect for the value you’ll bring.

How to answer it properly:

• Do your research. Check market ranges for the role, industry, and location. Use multiple sources — job boards, salary surveys, recruiters.
• Be clear and confident. Example: “Based on my research and the scope of this role, I’m looking for something in the region of £55,000–£60,000.”
• Don’t be vague. Saying “I’m open” or “negotiable” makes you look unprepared. Having a clear range shows confidence and market awareness.

Quick Fix: Before every interview, decide your acceptable range. Know your ideal number, your walk-away number, and be ready to state them clearly if asked.

Why These Three Questions Matter So Much

These aren’t trick questions. They’re diagnostic. Employers use them to figure out:

• Are you genuinely motivated to join this company?
• Can you own mistakes and grow from them?
• Do you know your value in the market?

Get these wrong, and you risk undermining all the great answers you gave elsewhere. Get them right, and you stand out immediately — because most candidates wing them, and it shows.

Putting It All Together

Here’s your prep checklist before your next interview:

1. Why This Company?
   • Research three specific reasons you’re excited about them.
2. Tell Me About a Failure
   • Pick one real example. Use STAR. End on growth.
3. What Are Your Salary Expectations?
   • Decide your range in advance. Be clear, confident, and market-aware.

If you can confidently answer those three questions, you’ll already be ahead of 90% of the candidates competing for the same role.

Preparation Is Everything

The biggest mistake jobseekers make is thinking they can wing interviews. The truth is, interviewers can spot a half-baked answer instantly — and those half-baked answers are usually to questions like these.

You don’t need a script. You just need to prepare properly.

And if you’re not sure where to start, my AI Interview Coach can help. Upload your CV and the job ad, and it’ll generate tailored answers for the questions you’re most likely to get — including these three. It’s trained on my 20 years of recruitment experience, so it’s not generic fluff. It’s practical, relevant, and designed to get you through to the offer stage.

Because interviews aren’t about perfection — they’re about preparation. And these three questions are the ones you can’t afford to wing.

Want help with your job search?

Start with these tools that thousands of jobseekers use every week:

• Download my free CV Template – the proven structure I use as a recruiter.
• Get instant feedback with the AI CV Reviewer – trained on 20 years of experience.
• Use the AI Interview Coach to get tailored questions and strong example answers.
• Explore the full Job Search System if you want a step-by-step plan to land more interviews.

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