Answers to the Top 10 Interview Questions – by Kary York, Insurance Resourcing

The interview process is always intimidating with dozens of questions that you need to anticipate and have answers to in advance of your interview.

I created a ten part video blog series to answer the “Top 10 Interview Questions” that are most often asked during the interview process.

1. Tell me About Yourself?

2. What Are Your Strengths?

3. What Are Your Weaknesses?

4. Tell Me About Your Greatest Success?

5. What Was Your Greatest Failure?

6. Why Did You Leave Your Past Position?

7. Where Do You See Yourself in 5 Years?

8. Why Should I Hire You Over My Other Applicants?

9. How Would Your Supervisor Describe You?

10. Do You Have Any Questions for Me?

“Tell me About Yourself?” Top 10 Interview Questions by Kary York

Question #1 ”Tell me About Yourself?”

People hate this question because it is so open ended and there are too many answers, however, it is probably one of the most asked interview questions, especially in the beginning stages of the interview process.  Knowing how to handle this question can make the difference between advancing to the next stage or being told “we have other candidates that we feel are better fits for the position”—a nice way of being told “thanks, but no thanks”.  
When you are asked “tell me about yourself”, ask the interviewer, “I’d be happy to, where would you like me to start?”  This allows the employer to tell you what aspects of your background they want you to address and most importantly, keeps you from having a long-winded answer that isn’t what the employer wants to hear.  They rarely want to know all about your youth and where you grew up.  They typically want to know about your professional experience but typically won’t ask the question directly.  Remember, this is sometimes used as a “trick” question.  Often times interviewers ask this open ended question because they want to see how you will answer it; personally or professionally, or a combination of both.  What they really want to know is how you can solve their problems.  Remember, you are hired because you either make money, save money, or makes things go more smoothly.

Make sure your answers to “tell me about yourself” have some sort of accomplishment tied to them.  For example, “After graduating from college, I took a job as a salesman at the XYZ insurance company.  I wasn’t experienced in insurance sales, but I worked really hard and became their Rookie of the Year.  After only three years, I was promoted to a Sales leadership role and my team was recognized as the “most improved” sales team in the Western Region”.

So now you are thinking, that’s great if you are a sales person, how do I answer this if I am in an administrative role?  The same principle applies.  Think about the things that you did that made you a “game changer” in the company.  For example, “I started out in the insurance industry as a receptionist and policy clerk.  I didn’t have my license so I studied on my own time and passed my insurance exam on the first try.  My boss, seeing that I had a knack for the business, moved me into an Account Assistant role.  I worked hard to learn the book, and was rewarded with my own accounts in only 12 months; this was a record in my office.  I have since moved up again, and now I’m a Senior Account Manager working with our most prestigious clients.

Your answer to this question shouldn’t be more than 2 or 3 minutes long and should be concise and well thought out ahead of time.  Getting this one right will open the door to the next step; the face to face meeting.

Learn more about the next question:  ”What are your Greatest Strengths?”

“What Are Your Strengths?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #2:  What Are Your Greatest Strengths?

This interview question has many versions but essentially, the employer or recruiter, is looking for you to “sell yourself” to them.  Typically, I hear the following soft skill answers:  I’m a hard worker, good team player, a people person, get along well with everyone, nice, friendly…etc.


Tips to Answer This Question:

The problem with these answers is that the hiring manager expects that of you already, or they wouldn’t be interviewing you!  These answers don’t get you anywhere.  They don’t have “food value” by themselves.  They must be illustrated with examples that demonstrate HOW you have used the skill.  For example, if you think you work hard, say “I am the person who typically is the “go to” person for the team and for my boss”. Then follow that with an illustration: “We were recently working on a very tight deadline renewal proposal for a customer.  There were a number of quotes that we needed to review and one of the people on my team was out on vacation.  I stayed late and worked diligently with the remainder of the team and leadership to make sure that we got the proposal out on time.  As a result, we were able to retain the client and renew the business.

Make sure that your answers show how you contributed to the company’s bottom line. Here’s another example for the “people person” skill: “I have always been told I have really good people skills.  Recently one of our best customers called in with a big messy claim.  She was pretty irate and not happy with how the claims adjuster had treated her.  I calmly listened to her concerns, suggested a couple of ways we could work through the problem, then contacted the carrier’s adjuster team supervisor, explained the problem, and was able to get the claim back on track.  The adjustor called the client, apologized for their rudeness and as a result, the customer called me back and thanked me for getting involved and even wrote a thank you letter to my boss.

The bottom line to remember with the “strengths” question is to not use cliché and tired words that every recruiter and hiring manager has heard a million times.  Make sure to back everything up with a little story that shows your strengths in action.  Watch for “buying” queues from the hiring manager such as head nodding or agreement sounds that give you valuable feedback that your answer is hitting home.

List out your strengths ahead of time and try to come up with 1 to 2 examples that really demonstrate each skill.  This way you will be ready and will be able to easily recall them under pressure.

Learn About the Next Interview Question: “What Are Your Weaknesses?”


“What Are Your Weaknesses?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #3: “What Are Your Weaknesses?”

This is one of the toughest and least liked of all of the interview questions.  The problem with this question is that you have to answer it, if you say, you don’t really have any, and the employer doesn’t believe you or thinks you may be hiding something.  If you say the wrong thing, such as you have a tough time staying on task or being focused, you can be out at first base.  So what is the right answer?  First off, remember that very few people ask this question directly anymore.  Often times it is couched inside of a more positive sounding question, such as “what are some of the areas that you have been coached on in the past?” or “what is an area that you have been working on for self-improvement?”  These are much nicer questions, but don’t be fooled; the hiring manager is asking you to reveal your weaknesses.

Tips to Answer this Interview Question:

The key to answering this question is advance preparation!  Start by thinking about the constructive comments that former managers have given you.  Criticism is never easy to stomach so you need to think about the changes in behavior that you made, if any, as a result of your boss’s coaching. List the behaviors that were pointed out as “areas for growth and development” another nice way of saying weaknesses, and think about how you responded to the advice. Think about how you applied the advice and changed your behavior in the workplace.  What were the results with your peers, with customers, with your supervisors?  For example, if you were coached that you needed to be more focused and less chatty in the office or asked to improve your spelling and written communication, or be on time in the mornings, when you changed your behavior, what kind of feedback did you get from your peers, or your boss?

There is nothing wrong with stating what your weaknesses are, we all have them.  The important thing to do is to demonstrate to the hiring manager that you are “coachable” and not so set in your ways that you can’t take constructive feedback and apply it to improve in the workplace.  Make sure to explain that once you were made aware of the problem that you quickly acted to change the situation.  Then explain how you use the new behavior now in your everyday work.  For example, if you were late a lot due to lack of personal organization, mention how you now get up an hour early or get everything ready the night before so that you aren’t running around frantically in the morning looking for things.  If your spelling and grammar was lacking, talk about how you took some remedial classes to correct the problem and how things improved in your office as a result.

Learn More About the Next Interview Question: Tell me About Your Greatest Success in the Workplace?


“Tell Me About Your Greatest Success?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #4:  ”What Is Your Greatest Success?”

This is a common question and most people like this one.  However, a lot of people don’t take full advantage of the opportunity that this question affords them.  This is your opportunity to shine and to really show the employer why you are the person for the job.



Tips to Answer this Interview Question:

The key to answering this question lies in thinking about the things that you have done in your work life, ideally recently, that really made you a “game changer” for the company.  For instance, did you win a key piece of business, save a huge account, develop a new program, or mentor someone that turned out to be a terrific asset for the company?  Once you decide on what your example is going to be, then you need to think about how you are going to explain the impact on the company or department making sure to quantify your answer by how you made money, saved money, or made things run more smoothly.

Here’s a sales example:  I targeted a prospect that was currently doing business with one of our biggest competitors.  When I first approached them, I got the typical response;” no, we already have a broker we’ve been working with…thank you, good bye”.  I didn’t let this first no deter me; in fact, I started by identifying customers of their business that were also clients of ours.  I also sent the prospect articles that were about his industry and followed up with him on a regular basis.  I also made friends with some of his support staff and other department decision makers.  In time, I was given the opportunity to bid on his business and I’m proud to say, I was able to win the account and have now received two additional referrals from the customer’s vendors and between the three accounts, I was able to put $100K of revenue on the books.

Here’s a non-sales example:  When I joined the ABC firm, they were still using paper files in addition to trying to use AMS.  Because I came from a paperless office, I was able to help teach my supervisor some tricks to automate the business and eliminate some of the redundancy.  She was so impressed that she arranged a meeting with the owner who ended up putting me in charge of automating the office and helping to train the support staff.  As a result, I was promoted to the office trainer and was able to help the firm reduce the amount of time it took to process a renewal by over 25%.

Once you have told your story, make sure that you link the results back to the job you are applying for.  This is where most people fall short.  Say, “I’m sure that when I work for you, I’ll be able to achieve similar results.”  Watch for positive response from the employer.  Your goal is to get them to see you in the role in their mind, then summarize, relative to the job description, that you feel strongly that you can be very successful in the role.

Learn about the next interview question #5: “Tell me About your Greatest Failure”

“What Was Your Greatest Failure?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #5: “What was your greatest failure?“ 

Ahh, the dreaded question. This one is even touchier than the weaknesses question because you have to admit a failure, not just a weakness. The trick with this question is to show how you learned from the failure and how you use the experience to help you make decisions today.


Tips to Answer this Interview Question:

Again, this requires you to prepare an example ahead of time. It should be work-related, but you can discuss a personal experience if it is closely related to a work-like event. For instance, if you didn’t graduate from college, perhaps you feel this is a failure or regret. If it’s unlikely that you’ll one day get a degree, then show how you keep yourself current with changes in the industry and new carrier products, how you have obtained insurance designations, etc.

If your failure example is work-related, make sure you set up the scenario so the employer understands the whole picture and doesn’t assume the worst. For example, suppose you had the idea to reorganize the work flow in your department. You need to show that you studied the problem, decided on a solution, implemented the solution, measured the results, found that it didn’t solve the problem, and decided to abandon the project in favor of a stronger option.

The key here is in the presentation. You do not want to come off as a victim. Do not blame others for the fact that something didn’t work. You must take ownership of the situation. Employers use this question to see how you react to and deal with adversity. Do you take responsibility for your decisions or blame the world for what went wrong? This is especially important since you most likely don’t know about the inner workings and politics of the firm at this point. Take the high road, even if your former company made decisions that derailed your project.
Most importantly, show how you made the decision to change course and quantify those results.  Then, show how you use the experience to guide your decision-making today.

Learn about the next interview question: “Why did you leave your previous position?”


“Why Did You Leave Your Past Positions?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #6: “Why Did You Leave Your Past Positions?”

Almost every employer asks me as a recruiter, “Why did she leave her previous employer?”  This difficult question is always asked, but rarely answered directly.

Part 1:


Part 2:


Tips to Answer this Interview Question:

“It was mutual” doesn’t cut it. Nor does ”I was laid off” if the hiring manager knows someone else is doing your former job. Don’t lie on this question; employers often ask it to see if you will tell the truth, especially if they know your former boss or have friends working at your former company.  Also, don’t gloss over or make up bogus answers for significant time gaps in your résumé. If you were temping, say so. There’s no harm in that. It’s a tough economy; at least you were working. If you have been unemployed for more than six months, and have been diligently looking for work, say so — but add that you have been taking classes to keep your skills current and sharp, and that you keep up on insurance industry news.

If you had to leave your past job due to personal reasons such as medical issues or caring for a family member, say so. Tell the interviewer you had to take care of some personal affairs and didn’t want your work to suffer, so you chose to resign until you could fully commit to a full-time role again. Explain that the situation has resolved itself and you are ready and excited to resume a career, adding that you kept your skills sharp by staying abreast of industry news and trends while you were out.

What if you were fired for cause? Most employers will only give dates of employment and maybe verify your title, but that’s just as bad as saying you were let go. In this case, no news is not good news! Be honest; again, it only takes a couple of phone calls in the industry to uncover the truth. Use the firing experience to show how you learned from it and how your work is much better today as a result.

What if you have had multiple short-term jobs? Everyone is afraid to hire the job-hopper. You have an uphill battle with this one, but you can lessen the climb by talking about how and why you moved from job to job. If the company went out of business, relocated or closed your division, that’s legitimate and not your fault. The important thing is: how long was it until another employer picked you up, and how did it happen? The key thing to focus on is that you were “referred” into the next job. Employers think the best people are always referred to them. Use this to your advantage. If you were recruited away, say so. There is no harm in being recruited away, especially if it is for a better opportunity or career growth. Just make sure you reinforce that you left for opportunity, not just for more money.

If you moved due to a spouse’s job or military transfers, say so, and focus the employer on how fast you were able to learn the new company’s computer systems and procedures. Again, have solid examples and preferably letters of recommendation from past managers.

The important thing when answering the “why did you leave” question is to briefly state the reason, then direct the employer to the reasons why it was a sound decision. If it was a poor decision, take responsibility for the choice, show how you learned from it, and move the conversation forward.

Learn more about the next interview question: “Where do you see yourself in 5 years?”


“Where Do You See Yourself in 5 Years?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #7 - ”Where Do You See Yourself in 5 Years?”

With this question, the employer is asking you to gaze inside your crystal ball and predict the future. It would be nice if that were possible, but with the quickly changing economy, it is not.  This is also a veiled way for the employer to gauge your real interest in being in the position they are hiring for right now.


Tips to Answer this Interview Question:

This question seems to trip people up because they start to talk about the future job they really want and stop focusing on the position they are applying for now.  I’ve heard too often that a candidate who answered this question the wrong way is not pursued because they are “overqualified” for the role.

Don’t follow the employer’s lead when you say you want to get into management, underwriting, etc. They can lead you down the “thanks but no thanks” path if you’re not careful.  If you mention that you would like to become an underwriter in the future and the employer starts asking you questions as to why, the conversation can go way off track.  The next thing you know, the interview is over, and you get a “no” letter in the mail saying they have better fits for the position.  You are left scratching your head wondering what happened because you had all the qualifications the employer was looking for. Has this happened to you before?

Your answer needs to make sense inside the department you’re interviewing for.  If you are interviewing with a brokerage for an account management position, don’t start talking about wanting to be an underwriter.  That’s a company role, and while it’s an admirable goal, the hiring manager is going to think you’re using their firm as a stepping stone to get to what you really want to do.

Instead, make the employer understand that you learn quickly, excel at your job, and have been handpicked for promotions by past managers based on your work performance and peer recommendations. Here’s an example: “In five years, my goal is for you to tell me I have mastered this position, clients really like me and appreciate my hard work, and that my co-workers see me as a good resource for information and the ‘go-to’ person in the department. If I have accomplished my goal, then I hope you would have given me the opportunity to become a senior account manager or maybe even a team lead by that time.”

The key to answering the five-year question is to stay logical, poised and reasonable. You don’t want to be a threat to the hiring manager; you don’t know her internal promotion track record, and you don’t want to come off as uninterested in the job at hand. A good follow-up question for the hiring manager after you answer the five-year question is to ask her how she got to the position she is in now. Her answers will give you clues as to your real promotion opportunities with the new firm.

Learn more about the next interview question: Why Should I Hire You Over My Other Applicants?

“Why Should I Hire You Over My Other Applicants?” – Top 10 Interview Questions by Kary York, Insurance Resourcing

QUESTION #8: – “Why Should I Hire You Over My Other Applicants?”

This is one of those questions that you truly can’t answer because you typically don’t know who else they are interviewing. What the employer really wants to know is: WHY YOU?


Tips to Answer this Interview Question:

This question usually comes up towards the end of the interview but sometimes it is one of the first questions asked. The key to answering this question is to sell yourself based on your understanding of the problems/pain that the employer is encountering by not having the position filled.

For example, if you are interviewing for a Senior Account Manager role, and you know that the job is open because someone who had been there for several years moved away, you know that the pain the employer is trying to avoid is losing loyal customers to their competitors.

You also know that just because the position is vacant doesn’t mean that the work has moved away too. The work load has been dispersed amongst the remaining team members and rest assured, they are probably not too happy about it. The employer has also lost a key relationship with underwriters. Now the trick is to answer the question by making the employer aware that you understand the problems they are facing with the vacancy.

You want to hire me because I understand what it’s like to work in a short staffed office due to a key employee leaving. The producer is lost without his account manager, the work load has been dumped on the rest of the staff who don’t know the accounts very well, and you are at risk of losing the account to your competitors once word gets out that your key account manager left. I was hired into this very same situation in my last position.

I was able to quickly work with the remaining account managers to understand the inner workings of the computer system and office procedures because I am a quick learner and good with computers. I was able to review the files with the Underwriters and make contact with the clients who were up for renewal so that they felt loved and cared for. I’m proud to say that we didn’t lose any business with the transition and I have been able to maintain at least a 93% retention rate on my book since then. I know firsthand, Mr. Employer, what it’s like to be in your situation right now, and that’s why I feel that I am your strongest candidate for the role.

The key to answering a comparison question like this one is to make sure the employer understands that regardless of who else he is interviewing, you “get it”; you understand the problems he is facing, the upset in the office due to the vacancy, the competition internally for the role, and most importantly, you show that you have the confidence to tackle the job head on.

I would follow up your answer with a simple question especially if you are in the wrap up phase of the interview: Mr. Employer, do you see any reason why I wouldn’t be a great fit for the position? Remain silent, and if the employer is truly seeing you in the role, you should hear and see very positive results that get you one step closer to the offer.

Learn more about the next interview question: “Where do you want to be in 5 years?”

QUESTION #9 - ”How Would Your Supervisor Describe You?”

The reason why the interviewer is answering this question is because they are curious in knowing how a former supervisor or manager describes you. This can be a bit tricky, especially if you didn’t have the best relationship with your old boss or current one.


Tips to Answer this Interview Question:

The important thing here is to not badmouth a past manager or the company in general. The insurance industry is a small world and, whether you like it or not, hiring managers will back-check with people they know, such as carrier reps or former coworkers. This might have happened already once they saw your résumé — before they even scheduled the first interview! Do not make up answers here; you will be found out.

First, if you have a job description for the position you are applying for, look at the qualifications section. If it has words you know your past managers have said about you in past reviews or to others, use those words when answering this question. Just be prepared to back them up with concrete examples.

For instance, if the job requires strong detail orientation, and you were praised for your ability to work accurately, say something like: “My managers have often commented that they wished they were as detailed as I am. Last week, my boss came over to my desk and complimented me on the amount of certificates I made and how none of them required any revisions.”

If you don’t have a job description, think about the skills you feel are needed for the role and pick the most vital ones — the “meat and potatoes” necessary to perform the job. Then, share a past experience or two when you were praised for these skills. If you have a letter of reference or a thank-you letter from a customer, bring it out and offer to share it with the employer. The written word speaks volumes, especially if it is on company letterhead.

What if you know your past manager will not have “good things” to say about you and she is a well-known figure in the insurance industry? It happens to everyone at some point; there are just some people we don’t get along with no matter how hard we try.

Typically, people in this situation will try to bypass the question and answer some other version of it that they make up. DO NOT DO THIS! Instead, you can use the question to illustrate how you deal with difficult people and difficult managers.

For example: “My current boss and I have had cultural differences, and at times we have struggled to get along. If you asked her to describe me, she would say I’m not shy and I’m not afraid to voice my opinion. She might also say I am a little too quick to want to change things. However, she will also tell you I always put the customer first. She would say I go the extra mile to make sure my work is done right and on time; that I’m highly organized and extremely dependable.”

The bottom line with this question is to answer it honestly, directly and not give “fluff” answers that the interviewer can see right through. Your candor will be appreciated; it demonstrates that you aren’t afraid to deliver bad news if necessary.

Next in this Series – Question #10: “Do You Have Any Questions for Me?”