The Top 10 Most Difficult Interview Questions for Experienced Workers

By understanding what exactly is being asked, mature workers can adopt a strategy that will allow them to answer almost any tough interview question

Part 2 of a 2-part series on difficult interview questions for experienced workers. View Part 1 here

Employers are becoming more adept at asking the challenging interview question, especially of mature workers who are typically applying for the higher paid positions. To outperform other qualified candidates, you’ll need to understand what the interviewer is trying to learn by asking each difficult question. He or she wants to see how you respond to the pressure, your thinking process, and to learn your underlying motivations and values. Your key to excelling with difficult questions is thorough preparation that will enable you to leverage your experience and wisdom.

In Part 1 we covered the first five questions. Here are five more challenging questions you might be asked, along with suggested strategies to tackle the each question.

Question 6: How does this opportunity compare with others that you considered?

Suggested Strategies:

  • This question is designed to reveal where you are in your job search. Be careful responding.
  • If you believe this to be a great opportunity, be specific in why you believe it to be a great opportunity.
  • If you seem open to any decent offer, the employer will question whether you really want this position, or any good position.
  • If you say you have no other considerations, the interviewer may take that to mean that no one is interested, and that could raise concerns about your candidacy.
  • If you say you have offers, your interviewer may take that as a sign of you wanting to prematurely precipitate an offer, and may discontinue consideration of your candidacy.

Question 7: Why have you been out of work so long?

Suggested Strategies:

  • This question is usually asked of candidates who have current and/or prior employment gaps on their résumé.
  • The interviewer may be trying to learn what is wrong with you and why other employers have passed on you.
  • Talk about how you have filled/are filling any gap through gaining more education, developing your skills, volunteering, contract work, and keeping yourself current on technology and the state of your industry.
  • This question may be followed by, “Why were you let go and not somebody else?” or “Why specifically did you lose your last job?” You must be prepared to answer these.

Question 8: Tell me what was unfair in your last job.

Suggested Strategies:

  • Interviewers who ask this type of question want to learn what you define as unfair, and see the degree to which less significant things annoy you.
  • Whatever you reveal will speak to your approach in dealing with things you believe are unfair.
  • If you say that nothing was unfair, your interviewer may believe you are not being fully forthcoming.
  • Carefully consider what you’ll say, and then briefly describe what was unfair. Spend the bulk of your answer on the positive steps you took to change it, accept it, deal with it, or cope with it.
  • Your answer will reveal your ethics and integrity, where the line is that you won’t cross, and whether or not you’ll compromise your honesty.

Question 9: Suppose we hire you and both of us are sitting here a year from now celebrating your top accomplishment. What will it have been?

Suggested Strategies:

  • This question is designed to reveal what you believe to be the top priorities of the job and what you see as your best contribution to those priorities.
  • The example you choose should be of strategic importance to the employer, which will reveal how well you’ve researched and understand the strategic direction of the employer.
  • Use “we” and not “I” in your answer – it is always about the people, customers, and team.
  • Point to similar past successes as proof you can and have delivered results.

Question 10: Suppose we hire you and you have a terrific first year. You love what you do and are well regarded. What would another employer need to offer you to lure you away?

Suggested Strategies:

  • The interviewer wants to know about your loyalty, motivation for working, commitment, and whether you view this position as a career position or a stepping stone to something bigger.
  • The question reveals how important compensation is to you, or if you are driven by higher purpose.
  • An effective strategy for answering is something like, “I expect to be quite successful here, and put the company in a position to give me more to do. With great results comes greater responsibility, and I’m confident you’ll want to compensate me accordingly as I add value to the organization.”

Bottom line: These aren’t all the difficult questions an experienced worker can anticipate being asked. The key is to understand what specifically they are trying to learn, and be prepared to provide thorough, thoughtful, and compelling answers that show you’re thinking and planning ahead. Realize that the best jobs come with stiff competition, and the only way you’ll land the job is to outperform your competitors on the tougher questions.

Boyer Management Group works with employers, organizations, and job seekers alike to help them become more successful. For employers, we offer world-class talent management, acquisition and onboarding tools and programs to help employees and volunteers achieve consistent, optimal performance. For job seekers and universities, we offer tools, assessments, books, and curricula to help connect people with careers. To find out more, please visit us at, email us at, or call us at 215-942-0982.


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