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Defeating the Dreaded Interview Questions

Erin Rhinehart

Defeating the Dreaded Interview Questions

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Picture this: Tom, an eager 2L, scores an interview at a reputable mid-sized law firm for a summer associate position. This is it. This is the opportunity for which Tom has been waiting. Sporting a freshly pressed navy suit with a starched white shirt and red power tie, Tom walks confidently into the managing partner’s office. He shakes the partner’s hand and introduces himself—making sure that his grip is firm and he makes eye contact. No nerves here. Tom takes in a deep breath, tells himself he has got this, and sits down as the partner shuts the door behind him. The well-seasoned attorney sits behind his desk, removes his reading glasses, and takes a long, hard look at Tom. The lawyer leans forward, looks Tom in the eyes and asks . . .

Here it comes. Is Tom really ready for this? More importantly, are you ready for what comes next?

The dreaded interview questions. Thirty minutes of rapid fire questions that are designed to see how well you think on your feet and test your oral advocacy skills. How do you handle them? Is there a “right” answer? Is there a “wrong” answer? The secret to your best interview ever is preparation. There is no way to know every question you will be asked. Sure, there are the repeat offenders (some of which are discussed below); but, for the most part, you are preparing for the unexpected.

The best interviewees prepare by spending some time thinking about what it is they want to get out of the interview. It may seem obvious that the answer is a job. That isn’t the answer. Your long-term goal may be a job offer, but for this interview you need to set a more immediate goal (e.g., learn as much as you can about the firm or understand what the position entails). Only you can decide what you want to get out of the interview. Here’s how.

First, know yourself. What are your strengths, weaknesses, and professional goals? What makes you the best candidate for the position? It’s soul-searching time. Often, this is the most difficult part of preparing for an interview. The Internet can’t help you here. Only you can answer these questions.

Second, know your audience. What is the firm culture, who will be interviewing you, and what is the interviewing partner looking for in a new hire? This one takes some research on your part. Now, you can hit up the Internet for some answers. Scour the firm’s web page. Does the firm have a blog? Check out some of the recent posts. If you know who you will be interviewing with, then look up their biography. If you don’t know who you are interviewing with, you can always ask—and should. If you have the luxury of meeting with several attorneys of varying practice areas or experience levels, then maximize the opportunity by prioritizing your questions accordingly. After all, you are interviewing the firm just as much as the firm is interviewing you. Come armed with research on the firm. Look for recent cases the firm handled or insider information from websites like

Finally, know how to answer the tough questions. The questions that leave a deafening silence in their wake after escaping the interviewer’s mouth, the questions that you agonize over for weeks after the interview. These questions are obstacles for the most seasoned interviewees. Now is the time to start preparing and cultivating your answers to these questions. But how? Below are five of the most common, and most dreaded, interview questions with tips on how best to prepare your answers. You could take some canned answers off the Internet, but that would not serve your goals. You must be prepared for the topic at hand—you.

The advice that follows each question is designed to be applied not only to the specific question posed, but to similar interview questions that often stump and confound the best of us.

What are three adjectives to describe you?

Good thing you followed preparation step number one know yourself; otherwise, this question could really blindside you. Brainstorm a little and be honest. Start writing any adjective (good and bad) that comes to mind when you think about this question: ambitious, shy, motivated, eager, introverted, loud, sarcastic, meek, outgoing, thick-skinned, sensitive, diligent, reliable, procrastinator, light-hearted, serious, or resilient. Once you have your list, review it, and think about it. Pick your top three and figure out why those adjectives best describe you. Often, the adjectives selected will call to mind a specific situation in which you were [insert adjective here]. Now you’ve got a great start to an answer to this question. The interviewer is not concerned with the specific adjectives you select. The interviewer wants to learn how you think about yourself, and why you think that. So be sincere. Do not ramble off a canned answer to this (and other) questions. Preparation is not the same as rote memorization. Sincerity and thoughtfulness will take you far in an interview. The best interviews are organic and natural. Interviewers know when you’re forcing it—and so do you. Creating personal connections leave the best first impressions. Try to have a conversation with the interviewer.

What is your biggest weakness?

Don’t throw away that list of adjectives you worked so hard to create. Remember all those not-so-great adjectives that didn’t make the cut for your response to the first question? Time to take a hard look at why they made the list in the first place. We all have weaknesses. No interviewer expects you to be perfect. This question is designed to see what you consider a weakness and what you have done to improve yourself. Employers want to know that, when you make a mistake (yes—when, not if), you can acknowledge it. More importantly, you will learn from it.

Where do you plan to be in five years?

You decided to go to law school; good for you. Now it is time to think about what kind of a lawyer you want to be. Where do you want to take your career? Only you can answer this. (Are you seeing a trend here?) If you want to be a rising star in the law firm at which you are interviewing, then tell the interviewer that. But be prepared to describe what being a “rising star” means to you, and how you plan to achieve that goal. Maybe you want to be part of an in-house legal department working on employment law issues. If you are interviewing at a firm to get private practice experience that you hope to leverage into an in-house job in a few years, you probably shouldn’t lead with that. (Remember, know your audience.) I doubt that the managing partner will be motivated to hire someone that intends to leave his firm just when he or she starts to become profitable. However, don’t be dishonest. Instead, focus on the skills you want to develop at this job. Discuss your interest in employment law and how you hope to garner experience litigating discrimination lawsuits. Indeed, honing specific skills is exactly what you will have to do you be able to land the next job in-house. Of course, maybe you really do not know where you want to be in five years. That is okay too. Be honest with your interviewer. Let them know that you are still figuring out your career trajectory and, while you may not know where you want to be in five years, you do know that you would like to start your legal career with this firm. Reevaluating your career goals is normal.

Describe a challenge that you overcame and how you overcame it.

Okay, so this one is not really a question, but it is something that is often asked of interviewees. Dig deep. Show some vulnerability and let the interviewer in here. This question provides the opportunity for you to show another side of yourself to the interviewer—a more personal side. We all have to overcome adversity in our lives; some more than others. Your answer does not have to focus on a professional challenge. While it is great that you finally found the perfect case at the eleventh-hour for your boss last summer, those types of anecdotes fail to offer any real insight into who you are as a person. People hire individuals with whom they have a personal connection. You have (maybe) 30 minutes to make that connection with your interviewer. Use every possible opportunity to sneak a little of yourself into your responses. For example, maybe you found yourself having to put your own plans on hold to care for a sick parent or sibling. Without getting too personal, you can share a story that demonstrates your ability to thrive in stressful and emotionally difficult situations. The interviewer wants to know that you can identify the challenges in your life, overcome the inevitable adversity we all must face at one time or another, and still stay focused and productive under pressure.

Why should I hire you?

The interview is wrapping up and you are feeling pretty good about how it has gone. It is the last few minutes and just when you think the interviewer is going to lob you a softball question about your time spent studying abroad, he smacks you in the face with this question. It all comes down to this. Why should this firm hire you? What can you bring to the table? The key to answering this question is three-fold. First, focus on yourself and your strengths; do not put down other candidates. Second, do not cross the line between confident and cocky. Arrogance will get you nowhere. Finally, reiterate your interest in the firm and emphasize to the interviewer that you want this job. Desperation stinks; but genuine enthusiasm (like flattery) never hurts.

Ten More Dreaded Interview Questions

  • What did you not like about your last employer?
  • How long would it take for you to start making a real contribution to the organization?
  • What have you learned most from your past career?
  • What would you most like not to do in this role?
  • What would your job references say about you?
  • Why is there a gap in your employment history?
  • Tell me one thing you would change about your last job.
  • Explain a complex transaction negotiation or litigation strategy to an eight-year old.
  • What would the person who likes you least in the world say about you?
  • What’s the biggest risk you’ve ever taken?