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 1 of a 2-part series on difficult interview questions for the mature worker.

Did you know that experienced workers (those with ten or more years’ experience) will make up nearly two-thirds of the non-institutional workforce by the year 2020? Couple this with people changing jobs an average of eleven times over their working career, and in the next decade or two, you’ll have hundreds of millions of experienced workers participating in over a billion interviews that ask nearly a trillion interview questions!

Employers, increasingly concerned with the high cost of making a bad hire, will turn to more robust interviews as part of the process they use to vet candidates. It’s no wonder that experienced workers can expect to answer more difficult interview questions than ever before.

We’ve assembled some of the most challenging interview questions experienced workers might be asked, along with suggested strategies to tackle the each question.

Question 1: Your current {previous} job exists to help your employer to achieve and maintain profitability. Specifically, how do you accomplish this in your current assignment?

Suggested Strategies:

  • While all jobs exist to enable employers to achieve over-arching sets of objectives, profit is a key measure of how well an employer is doing. Show your profit-mindedness by describing how you directly or indirectly contributed to the bottom line of your employer.
  • Use examples to demonstrate how your actions helped to identify, prevent, and solve problems that interfered with profit creation or mitigated profit loss.
  • Point out how the indirect beneficiaries of your profit-minded actions benefitted – your employer’s customers, community, shareholders, employees, and stakeholders.

Question 2: What did you do to prepare for this interview?

Suggested Strategies:

  • This question is designed to show how well you researched the employer, industry, products or services, your interviewers, and other key information.
  • Bring your research file containing everything you learned during your research, so you can show what you learned, where you searched, and any important conclusions you formed as a result of your research.
  • As you share your findings, connect what you learned with why the position interests you, and how you’d be a good fit.

Question 3: Suppose you won the lottery tomorrow. How would your life change from where you’re heading today?

Suggested Strategies:

  • Interviewers who ask this type of question want to learn your reasons for interviewing – if you are interested in the job out of necessity, or if there are other reasons behind your interest in working for the employer.
  • The interviewer likely wants to better understand your life priorities and motivation.
  • The interviewer may want to see if you play the lottery or engage in other speculative activities.

Question 4: You’ve been at your current {pervious} employer for # years. Why do you want to leave a good position with a good employer?

Suggested Strategies:

  • The interviewer is trying to determine your real reasons for considering a change and to surface any red flag concerns, such as attitude, performance / behavior problems, interpersonal conflict, or other similar issues.
  • The interviewer wants to hear how you speak about your current {previous} employer, and to see whether your answers are consistent with what you’ve already said were your reasons for seeking a position with this employer.
  • Share specifically how your current {previous} position has prepared you for this employer.

Question 5: Who do you know that works for {has worked for} our company, and how do you know them?

Suggested Strategies:

  • This can be a tricky question because you may not know how the interviewer or employer perceives the person(s) you mention. A well-regarded name can be an asset while a poorly regarded employee could reflect unfavorably on you.
  • If you say you don’t know anyone, the interviewer might think you didn’t bother to connect with current or former employees via social media, which may suggest a lack of interest or resourcefulness on your part.
  • Whoever you mention, rest assured that the interviewer will seek that person’s opinion of you.

Bottom line: Understand what the interviewer is trying to learn by asking the 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. The key to nailing the difficult question is thorough preparation.

We’ll cover Questions 6-10 and their suggested strategies next time. Until then, consider how you’ll answer the first five.

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, or call us at 215-942-0982.


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