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Top 25 Toughest Interview Questions and How to Answer Them – Part 2

Welcome back, job hunters! If you enjoyed Part 1 of our guide on JobHunt-OffCampus.com, you’re in for more valuable insights. As a content creator focused on off-campus job strategies, I’ve seen how mastering these tough questions can make or break your interview. In Part 2, we cover another set of 25 challenging questions, with practical advice to help you respond effectively.

 

These are drawn from common scenarios across industries like tech and consulting. Tailor them to your experience, and practice for confidence. Check out our site for exclusive job alerts and resume tips at JobHunt-OffCampus.com. Let’s dive in!

 

  1. What changes would you expect to make if you came on board?

Ans. You, of course, will want to take a good hard look at everything the company is doing before making any recommendations. Examples: “Well, I wouldn’t be a very good doctor if I gave my diagnosis before the examination. Should you hire me, as I hope you will, I’d want to take a close look at everything you’re doing and understand the process. I’d like to have in-depth meetings with you and the other key people to get a firm grasp of what you feel is working well, and what could be improved.” “From what you’ve told me so far, the areas of greatest concern to you are…” (name them. Then do two things. First, ask if these are in fact the major concerns. If so, then reaffirm how your experience in meeting similar needs elsewhere might prove very helpful). This kind of question can be related to 30-60-90 day planning; if appropriate, share your first-three-month concept after deciding how best to create such plans.

 

  1. I’m concerned that you don’t have … (“x” college degree/ “x” certification or licensure/ as much experience as we’d like in “x” area…..)

Ans. Before going into any interview, identify the weakest aspects and/or missing qualifications from this company’s point of view. Then prepare the best approach possible to shore up your defenses. To get past this question with flying colors, you are going to emphasize your experience and strong qualifications, and while being honest about the missing piece(s), emphasize how this will not diminish your status as the best candidate for the job. More specifically, when the interviewer poses as objection like this, you should… 1. Agree on the importance of this missing qualification. 2. Explain that your overall strength may indeed be greater than your resume indicates because (mention something additional not emphasized in the resume, if it’s there…) 3. Assert that it’s really your combination of strengths and qualifications that’s most important. Then review the areas of your greatest strengths that match up most favorably with the company’s most urgently-felt wants and needs. This is a powerful way to handle this question for two reasons. First, you’re validating (and not avoiding) your interviewer’s area of concern. But more importantly, you’re then shifting the focus away from this one isolated area and putting it on the unique combination of strengths you offer, strengths which tie in perfectly with the employer’s greatest needs.

 

  1. How do you feel about working nights and weekends?

Ans. If you’re a workaholic, embrace it by stating that a demanding schedule aligns with your nature, emphasizing your family’s support. They recognize that your professional satisfaction benefits the family. For those preferring balance, inquire about the norms for top performers in the company. If the hours seem excessive, ask if any successful employees manage to balance family time while achieving high performance. Connect yourself to that group of top performers, demonstrating your commitment to both success and family. Should extended hours concern you, express this positively by highlighting your work effectiveness—mention your key qualifications relevant to the employer’s needs. Stress that you excel not just by working hard, but also by working smart, thereby ensuring productivity. Assert that you value family time, which enhances your happiness and productivity at work. Ideally, you could take on some evening or weekend work, enabling your family to see you more and creating a win-win situation. This approach portrays you as a valuable, high-performing candidate who can manage workloads effectively while maintaining a fulfilling personal life, showcasing exceptional productivity alongside strong credentials.

 

  1. Are you willing to relocate or travel?

First, assess potential relocation locations and travel requirements. If there’s no issue, express excitement. If you have reservations, consider two approaches. One approach is to keep your options open and not disclose reservations initially, saying “no problem.” This allows you to negotiate a better offer before deciding whether relocation or travel is worthwhile. By the time you receive offers, you may have multiple options to evaluate. Avoid shutting down potential opportunities too soon, as you might regret it if you’re still job-seeking later. The second approach is to acknowledge reservations but state your openness to relocating or traveling for the right opportunity, aiming to maximize your financial and benefit package. Your chosen strategy should reflect your eagerness for the job; if you desire to minimize relocation/travel, opt for the first approach. If you want to negotiate for a more attractive offer, use the second approach to maintain leverage.



  1. Do you have the stomach to fire people? Have you had experience firing people when necessary?

Ans. The management process involves hiring the best talent and providing thorough training while fostering team pride and excitement. This collaboration aims to achieve shared goals, minimizing the need for firings. When necessary, firings are approached as a last resort, executed quickly and decisively to minimize the negative impact on team morale. Maintaining a strong team is essential, and poor performers can significantly undermine good employees. Therefore, it’s crucial to act swiftly when relationships aren’t working for the benefit of everyone involved.



  1. Why have you had so many jobs?

Ans. To minimize the perception of being a job hopper, consider removing irrelevant short-term positions from your resume, displaying tenures in rounded years instead of detailed months. For example, instead of listing three specific positions with exact dates, summarize them as broader date ranges to eliminate less significant roles and reduce perceived instability. When discussing job changes in interviews, frame them as part of a pattern of professional growth, avoiding blame and attributing departures to external factors when applicable, such as mergers or economic downturns leading to temporary positions. Highlight longer tenures to indicate stability, conveying that you are now seeking a similar long-term commitment. This strategic approach can help alleviate concerns regarding job history while emphasizing your upward career trajectory and current motivations.

 

  1. What do you see as the proper role/mission of… …a good (job title you’re seeking); …a good manager; …an executive in serving the community; …a leading company in our industry; etc.

Ans. Think of the most essential ingredients of success for each category above – your job title, your role as manager, your firm’s role, etc. Identify at least three but no more than six qualities you feel are most important to success in each role. Then commit your response to memory. Here, again, the more clarity you may have about the position’s requirements, the wants and needs of the interviewer, and the more homework you’ve done to identify the culture of the firm, the more on-target your answer will be. Those encountering these kinds of questions are likely candidates for high positions in an organization.

 

  1. What would you say to your boss if he’s crazy about an idea, but you think it stinks?

Ans. In evaluating ideas, prioritize integrity and remain positive. Identify the merits of an idea before addressing reservations with specific, objective critiques. Honesty is crucial in maintaining trust with your boss, as it ensures credibility for your feedback. Aim to present thoughts constructively, suggesting ways to enhance the idea to address any concerns. If ultimately the boss decides against your suggestions, offer your full support to ensure successful implementation, demonstrating commitment and teamwork. This approach fosters a collaborative environment while upholding your values and responsibilities.

 

  1. How could you have improved your career progress?

Ans. You’re generally satisfied with your career trajectory, acknowledging that earlier knowledge about industry trends or downsizing could have influenced your path. Despite this, you take responsibility for your journey and feel no regrets. Reflecting on past experiences leads to considering future directions, though this isn’t the focus of the current discussion. Addressing where you envision your career heading might prompt further dialogue about your aspirations five years from now, which you may be prepared to discuss or prefer to set aside unless you’re eager to explore your options.

 

  1. What would you do if a colleague at your level wasn’t pulling his/her weight…and this was hurting your department?

Ans. Gauge the firm’s political style and act accordingly, prioritizing effective human relations principles. Address issues directly with the individual involved, seeking their help for a positive resolution. Use persuasive communication to highlight the mutual benefits of collaboration and the consequences of non-cooperation for the company and its customers. If no change occurs, do not ignore the problem, as this could set a negative precedent. Persist in finding solutions by engaging a wider network, including higher-ups and peers, to illustrate the advantages of teamwork and the downsides of resistance. In my experience, this constructive approach typically leads to successful resolutions.

 

  1. You were with your former employer a long time. Won’t it be hard switching to a new company?

Ans. To overcome this concern, you must point to the many ways you have grown and adapted to changing conditions at the previous job. It has not been a static situation. Highlight the different responsibilities you’ve held, the wide array of new situations you’ve faced and conquered. As a result, you’ve learned to adapt quickly to whatever is thrown at you, and you thrive on the stimulation of new challenges. To further assure the interviewer, describe any similarities between the new position and your prior one. Return to the point that their needs and your skills are such a close match, you expect to be completely comfortable in this new environment.

 

  1. May I contact your present employer for a reference?

Ans. Express your concern that you’d like to keep your job search private, but that in time, it will be perfectly okay. Example: “My present employer is not aware of my job search and, for obvious reasons; I’d prefer to keep it that way. I’d be most appreciative if we kept our discussion confidential for now. At the point you’ve decided I’m your favored candidate, and have tendered a job offer, then by all means you should contact them. I’m very proud of my record there.”

 

  1. Give me an example of your creativity (analytical skill…managing ability, etc.)

Ans. Remember from Question 2 that you should commit to memory a list of your greatest and most recent achievements, ever ready on the tip of your tongue. If you have such a list, it’s easy to present any of your achievements in light of the quality the interviewer is asking about. For example, the smashing success you orchestrated at last year’s trade show could be used as an example of creativity, or analytical ability, or your ability to manage.

 

  1. Where could you use some improvement?

Ans. Keep this answer, like all your answers, positive. A good way to answer this question is to identify a cutting-edge branch of your profession (one that’s not essential to your employer’s needs) as an area you’re very excited about and want to explore more fully over the next six months.

 

  1. What do you worry about?

Ans. Redefine the word ‘worry’ so that it does not reflect negatively on you. Example: “I wouldn’t call it worry, but I am a strongly goal-oriented person. So I keep turning over in my mind anything that seems to be keeping me from achieving those goals, until I find a solution. That’s part of my tenacity, I suppose.” OR: “I’ve never been much of a worrier. What I try to do instead is I focus on whatever issues are before me, and put my energy into finding positive solutions for the tasks at hand.”

 

  1. Could you be considered a workaholic? (or) How many hours a week do you normally work?

Ans. If you are in fact a workaholic and you sense this company would like that: Say you are indeed a confirmed workaholic, that you often work nights and weekends. Your family accepts this because it makes you fulfilled. If you are not a workaholic: “I wouldn’t call myself a workaholic, but I have always worked hard and put in long hours when necessary. It goes with the territory. I don’t generally keep track of hours, because my work is a labor of love, and I enjoy nothing more than solving problems.”

 

  1. What’s the most difficult part of being a (your job title)?

Ans. First, redefine “difficult” as “challenging,” which is more positive. Then, identify an area everyone in your profession considers challenging and in which you excel. Describe the process you follow that enables you to get splendid results…and be specific about those results. Example: “I think every sales manager finds it challenging to motivate the troops in a recession. But that’s probably the strongest test of a top sales manager. I feel this is one area where I excel.” “When I see the first sign that sales may slip or that sales force motivation is flagging because of a downturn in the economy, here’s the plan I put into action immediately…” (followed by a description of each step in the process…and most importantly, the exceptional results you’ve achieved).

 

  1. The “Hypothetical Problem”

Ans. Instead, describe the rational, methodical process you would follow in analyzing this problem, with whom you’d consult, generating possible solutions, choosing the best course of action, and monitoring the results. Remember, in all such “What would you do?” questions, always describe your process or working methods, and you’ll never go wrong.

 

  1. The Behavioral Question (“Tell About a Time When….”)

Ans. A P-A-R approach to these answers is recommended: Briefly describe the problem (P) or situation you were facing; describe the Action (A) you took to address it; and always finish with how things turned out – the Result (R). Anticipate the types of behavioral questions you may face in your area of work, and practice keeping the answers to a reasonable length.

 

  1. What was the toughest challenge you’ve ever faced?

Ans. Be prepared for this question, and have a (preferably) recent example that’s job-related; this could also make use of the P-A-R approach mentioned just above. Example: “Bringing the last project we managed in under budget and on time was truly difficult…(tell why, what was done to make a success, and spell out the end result).”

 

  1. Would you consider starting your own business?

Ans. – Gauge the company’s corporate culture before responding.

– Be honest without oversharing personal dreams, like owning a business.

– In formal, structured environments, minimize expressions of entrepreneurial desires.

– Emphasize experience in larger organizations as your preferred career path.

– In more flexible environments, highlight the opportunity to blend personal ideas with organizational resources.

– Stress the excitement of idea implementation in a stable company.

– Indicate that any interest in self-management is part of your past, not present or future.

– Avoid projecting as a failed dreamer or a restless maverick.

– Ensure your aspirations align with the offerings of the position.

– Tailor your answers to fit the corporate culture to present a suitable image.

 

  1. What are your goals?

Ans. Many employers in a position to hire you are strong believers in goal-setting. (It’s one of the reasons they’ve been high achievers.) They like to hire in kind. If you’re vague about your career and personal goals, it could be a big turnoff to many people you will encounter in your job search. Be ready to discuss your goals for each major area of your life: career, personal development and learning, physical (health), community service – and if you wish to branch into more private aspects for whatever reasons – family and spiritual goals as well. Well-roundedness as an individual and value systems are at the heart of the matter. Be prepared to describe each goal in terms of specific milestones you wish to accomplish along the way, time periods you’re allotting for accomplishment, why the goal is important to you, and the specific steps you’re taking to bring it about. (But be mindful of length – do this as concisely as possible.)

 

  1. What do you look for when you hire people?

Ans. Speak your own thoughts here, but for the best answer weave them around the three most important qualifications for any position. 1. Can the person do the work (qualifications)? 2. Will the person do the work (motivation)? 3. Will the person fit in (company culture/ team considerations, positive attitude)?

 

  1. Sell me this stapler (or this pencil…this clock…or other object on the desk).

Ans. Predictably, you already know the most important secret of all great salesmanship – “find out what people want, then show them how to get it.” If your interviewer picks up his stapler and asks, “sell this to me,” you are going to demonstrate this proven master principle. Here’s how: “Well, a good salesman must know both his product and his prospect before he sells anything. In selling this, I’d first get to know everything I could about it, all its features and benefits. Then, in selling it to YOU, I would have done my research on how you might use a fine stapler like this. The best way to do that is by asking some questions. May I ask you a few questions?” Then ask: “Out of curiosity, if you didn’t already have a stapler like this, why would you want one? And in addition to that? Any other reason? Anything else? And would you want such a stapler to be reliable?…Hold a good supply of staples?” (Ask more questions that point to the features this stapler has.) Once you’ve asked these questions, thank the interviewer, and then make your presentation, citing all the features and benefits of this stapler, and why it’s exactly what the interviewer just told you he’s looking for. Then close with: “Just out of curiosity, what would you consider a reasonable price for a quality stapler like this…a stapler you could have right now and would (then repeat all the problems the stapler would solve for him)? Whatever he says, (unless it’s zero), say, “Okay, we’ve got a deal.” If your interviewer tests you by fighting every step of the way, denying that he even wants such an item, don’t fight him. Take the product away from him by saying, “Mr. Prospect, I’m delighted you’ve told me right up front that there’s no way you’d ever want this stapler. As you well know, the first rule of the most productive salespeople in any field is to meet the needs of people who really need and want our products, and it just wastes everyone’s time if we try to force it on those who don’t. And I certainly wouldn’t want to waste your time. But we sell many items. Is there any product on this desk you would very much like to own…just one item?” When he points something out, repeat the process above. If he knows anything about selling, he may give you a standing ovation.

 

  1. Looking back on your last position, have you done your best work?

Ans. To cover both possible paths this question can take, your answer should state that you’ve always given your best in the past, but you expect the best is yet to be done, because a new position usually presents new and intriguing challenges. (Then be prepared for a follow-up question about what you perceive to be the new and exciting challenges.) You can suggest that, like an athlete at the top of his/her game, you are just hitting your career stride thanks to several factors. Then, recap those factors, highlighting your strongest qualifications.




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