The Core Strategies for Addressing Challenging Job Interview Questions

Written by Mitch Jacobs, M.Ed., LPC
Published on Sept. 18, 2018

You want to land your dream job or make your next career move. Have you been applying to and interviewing for a variety of job opportunities? Maybe, after reading a couple of articles about about how to interview, you’ve still not obtained a job offer. It would be understandable if you’ve been feeling confused and frustrated, and telling yourself, “What will it take to get a job?”

There can be many reasons for feeling thwarted in your goal to obtain the job offer, one of which can be not knowing how to address difficult job interview questions, such as:

  • Why should I hire you?”
  • “What is your greatest weakness?”
  • “Tell me about a time that you made a significant mistake at work and what you did to correct it.”
  • “Who was your best boss and who was the worst, and why?”

There are many challenging interview questions that may be asked, and many strategies to address them about which you can read online. At their root, many such questions are designed to assist job interviewers to learn more about the ways in which you problem-solve, your values and ethics, how you relate to others and fit into the company culture.

Interviewers want to hear examples of how you have used these skills and characteristics in the service of solving the kinds of problems you will be expected to resolve in your potential role for their companies.

So, how do you improve your interviewing skills to the point of being able to meet these expectations? Improving your ability to answer any number of challenging interview questions first requires having a focus, understanding and communicating the value you can provide potential employers.

To accomplish this, use an appropriate strategy in the job interviewing preparation stage, not at the last minute before you participate in a job interview. Here is a strategy and some steps you can take:

a. Sufficiently understand your problem-solving style, values and ethics, along with your skills and competencies in order to better formulate how to communicate these well. Become an expert on yourself and your value to potential employers. This knowledge becomes the basis from which you communicate your most relevant qualifications to job interviewers when asked challenging interview questions, and the most compelling reasons for them to give you the job offer.

b. Identify several job openings in the area for which you are most qualified. Track the skills and knowledge they most commonly seek, and the goals they most often want met so that you can understand the priority needs of employers, in general. Then, evaluate your goodness-of-fit with the kind of position for which you expect to be interviewed.

After this is accomplished, you are ready to prepare specific interview answers to some of the more challenging questions you will probably be asked during job interviews. Many job seekers use the STAR (Situation or Task, Action Steps and Results) Method to structure and develop interview answers. It would be well worth your time and effort to use this kind of method, and you can learn more about it by searching online for “STAR interviewing tutorial”.

So, how do you answer the question, “What is your greatest weakness?”

  1. Identify a skill or knowledge area in which you initially lacked experience, and have since gained the experience to perform the skill or knowledge to obtain desired results.
  2. Structure your answer to include the Situation, Task, Actions and Results you attained. A basic fill-in-the-blank example of a strategy to draft an answer to this question is:


As a ____ working for ____ one of my responsibilities was to _____.


The ____ (assignment submitted had a couple of errors in it, because I had not initially adequately prepared, etc.) and we needed to ____ (recalculate the metrics and revise our findings, etc.). My task at-hand and goal was to _________________________________.


So, I _____, and ______, then ______.

Not having had enough experience yet in addressing ____, it did not initially go as planned.


I learned from that experience to ____ (stay up-to-date on the compliance requirements, reviewing the regulatory and company compliance requirements weekly. By the end of my second month at the company, I had thoroughly updated my knowledge and subsequent, similar assignments were accurate and submitted on time, saving the department staff time and the company money, etc..)

When it does come time for a job interview, beforehand, study the job description:
  1. Research the company web site and press releases and conduct advice interviews with employees or competitors, if possible, to gain insight into industry trends, and employers’ histories, challenges, goals and initiatives.
  2. Identify the employer’s priority needs that you will be expected to meet.
  3. For each of the employer’s top 7 to 10 priority needs, identify which STAR stories you have already developed best communicate how you meet each of those needs. Develop new STAR stories, if needed, to address priority needs that weren’t already addressed by your existing answers.
  4. Rehearse your STAR stories / interview answers until you are comfortable with them in preparation for your interview. Employers appreciate job candidates that are prepared for the interview and can clearly communicate their value using STAR stories.

Many of the interview questions you may be asked will be based on the skills, knowledge and results outlined in the job description, as well as a few of the more challenging questions, some of which were outlined in this article. By having developed and rehearsed interview answers that address these ahead of time, you will have improved your ability to better communicate your value to potential employers.

For more guidance in how to use the STAR method and suggestions on how to answer difficult interview questions, I recommend that you meet with a trained professional Career Coach. Then use the knowledge and confidence gained to develop interview answers that can make the difference, and help you land that job!

Much success to you! Mitch Jacobs, M.Ed., LPC, Career Coach at JFS.

Learn more about the individual coaching, and free employment networking groups, seminars, workshops and PC Literacy Classes provided by expert Coaches in the Career and Financial Services program at JFS, at and

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